My 2.0:Women Who Scale: Recent Episodes
Sonali Batish
Sonali Batish interviews Women Who Scale; be it in transitioning careers or scaling their business. You will hear inspiring stories with actionable advice through their challenges of scaling up. My 2.0 podcast aims to build a peer and mentor community of like-minded women who embrace scaling up; be it to transition their careers or to scale up their business!
In episode #65 of My 2.0 Podcast, guest Dolly Oberoi, CEO at C2TI, shares her scaling story at C2 Technologies. Dolly is a true pioneer in online training, sim & modeling, and thought-leader, innovator, and entrepreneur. Through her work at C2TI, she reshaped traditional chalkboards to electronic learning environments and developed transformative enterprise-wide training and talent management solutions.
Dolly talks about the genesis of entrepreneurship as she worked for her entrepreneurial mother in India, in search to bring learning technologies to connect children and learning across the world. She also talks about the initial challenges of entrepreneurship, especially as a female business owner. And how these challenges change as the business evolves over time.
In episode #64 of My 2.0 Podcast, guest Kim Kross, COO At Elevate K-12, shares her scaling story at Elevate-12, where they are on a mission to make zip code free teaching available to all students, irrespective of where they live.
Kim talks about the mission of Elevate K-12, including the opportunities and challenges that the pandemic provided to their stakeholders. While they have achieved tremendous scale, she is forthcoming in the dichotomy of a company’s ability to scale exponentially while most humans scale linearly. how her decisoning framework has changed over the years, incorporating evolution over time with the agility a rapidly scaling company requires.
In episode #63 of My 2.0 Podcast, guest Carolyn Trabuco, CFO At Inclusively, Co-founder/Board Member at Azul, shares her scaling story with Azul, the airline she co-founded with David Neelman, the founder of JetBlue.
Carolyn talks about her background as a Art History major who found a job as a phone rep and eventually through grit and determination, moved on as an equity analyst. She shares her scaling stories at Azul, where she was invaluable with her outsider perspective. She talks about linear v/s bath scaling, about shaping ESG initiatives, and about potentially seeking a path back to art history.
I launched My 2.0 podcast just a little over a year ago; to create a platform through which women could share their experiences of successful career transitions so that we normalize career changes. In reflecting on these profound stories of career changes, I saw close parallels with how we scale ourselves to transition careers, and how we scale businesses. So it seems like a natural transition of this storytelling journey to Women Who Scale; where you will hear from women on how they scale themselves; be it to transition careers and/or to scale their business. Because in the end, the only constant in life is change.
Please stay tuned for new episodes next week!
In episode #61 of My 2.0 Archives, guest Bosky Mukherjee, Founder at PMDojo & Spark To Substance, shares her transition from a career in corporate to entrepreneurship.
Bosky’s life has been a lifelong series of transitions, as she moved across geographies, through various types and sizes of company. The only constants were her love for the product and her desire to always be growing. Motherhood changed her in new and unforeseen ways, as she struggled with the extreme physical challenges with her newborn son. She learned to not settle, to always ask for more from herself and from others around us. But in that process, while she continued to scale the heights of her corporate career, she suppressed the toll that brought on her emotional well-being. And so when her body finally collapsed with burnout, it provided her the tipping point to assess what she really wanted from both her professional and personal lives.
In episode #60 of My 2.0 Archives, guest Justine Evirs, host, entrepreneur and writer, shares her transition from a career in the Military to becoming an Entrepreneur.
Justine walks us through her many transitions starting in her childhood, through to getting into the Military, to becoming a military spouse and finally transitioning out into a higher education, non profit serving the Military and veterans eventually finding her calling in entrepreneurship. She’s never lived in a house for more than three years, and is a first generation college student. And is very open with her struggle with alcohol, including hitting rock bottom three years ago.
Resources:
- Stanford GSB Program
- Protecting Courage Podcast
- Courage To Create
- The Paradigm Switch
In episode #59 of My 2.0 Archives, guest Maxine Cunningham, CEO of Pick My Brain, shares her transition from a career in investment banking to entrepreneurship.
Maxine described her journey of training as an economist, her experiences in the Investment Banking world, then as an environmental economist finally being inspired by the Airbnb founders to create a platform that allows for gifting, buying and selling knowledge in what she believes to be the future of the information/knowledge economy.
Resources:
- Pick My Brain
- Airbnb
In episode #58 of My 2.0 Archives, guest Linda Wenger, Strategy Consultant at Urbaneer, shares her transition from a career in programming to entrepreneurship.
Linda’s first job was at a company called NCR for client support. She went back to graduate school to get her MBA and transitioned to the technical side. She then moved to a consulting company at MCI as a product manager.
Early on in her career, Linda had decided she was going to transition every 2 years to be able to learn and grow most.
Soon after, she had her first child and fully transitioned to motherhood. And that was not an easy transition. It was hard coming from a pretty exciting and changing life to transition into something that was a little bit more sedentary. But as we do as moms, we grow into our roles and we learn every day. About four years later, she had her second child and threw herself into volunteering with the schools, running auctions and fundraisers, to be active with networking.
Linda thought transitioning into and out of motherhood was very difficult. Starting with postpartum depression, losing the sense of freedom, workplace achievements, being physically exhausted all the time. Transitioning back into the workforce was equally challenging. She fought guilt about not being there for the kids. And on missing out being in the industry for 8 years.
And in 2007, she transitioned into helping her husband with his new business in the association industry, in SaaS. Not only did she not know anything about the industry, much less about the work. The world of startups was new and different. And yet, one of the best experiences of her life. It caused her to grow up very quickly.
She went back to school again, to Georgetown, for a leadership program. And is now consulting with a company in the construction industry, one in which she has no experience! But is using her strong skills in finance and strategy to advise them.
She also thinks transitioning is the most challenging, and it’s hard going from stable and known to a new place, one you may not know much about. She also finds that the more mature she gets, the harder it is for her to transition. Because the younger generation is hungry to get things done. And we start questioning our ability to keep up with them, and the learning. But the right answer is for us to continue to have the courage to transition no matter our age.
Her advice to her pre-transition self is to be aware of how easy it is to get stuck in the waiting place. And that there is no such thing as failure, just early attempts at success. And that women are the strongest people on the planet. And always learning is beneficial.
In episode #21 of My 2.0 Archives, guest Dorie Clark, strategy consultant, executive coach, and keynote speaker, shares her transition from a career as a journalist to an entrepreneur.
Dorie thought she was going to be an academic but got turned down for all doctoral programs. Her Plan B was to become a journalist, and she ended up getting laid off after about a year on the job.Eventually she found her way into working in politics, running a nonprofit for two years realized that she wanted to run her own business. And moved on to having her own consulting and executive coaching business.
On the topic of feeling stuck, Dorie felt she didn’t have the luxury of being stuck, and that always needed to figure something out and keep pushing. She decided she was going to exhaust every possible resource, call everyone she knew to hustle and network my way into whatever the next thing is.
Dorie’s advice to her pre-transition self is contained in her book Reinventing You. She interviewed about 50 other professionals who had made career transitions to create a guide that people could use to feel more in control of what can often feel like an out of control process. Her advice was for us to reinvent ourselves in small ways on an ongoing basis and keep ourselves current. The less likely we are to be faced with a situation where we're static for five years or 10 years.
When asked why she wrote Entrepreneurial You, Dorie said it was her attempt to figure out ways to scale her business in developing simultaneous and adjacent streams of businesses.
When asked what it means to have a brand, Dorie answered it needs to start with who we are and what we are able to do, and articulate it to the market. And that when we transition to a different career, we have to be the captain of our narration.
Dorie also talked about her new book coming in September ‘The Long Game. How to be a long-term thinker in a short term world’. Over the last 5 years, she has met a lot of great people and built up a longitudinal perspective and pattern recognition around observations that I've noticed in terms of very smart, very talented professionals in the stressors they face, that come in the way of long term growth. That we don’t know how long it takes to become a successful recognized expert. So this is her attempt to light this dark, long and opaque path.
When asked how we could future proof our careers, Dorie shared that the one thing we do know is that whatever position we're in, we want to be as protected and secure as we possibly can be. So that if disruption is coming down the pike, we are able to pivot with enough time.
On the power of identifying and defending ourselves against our vulnerabilities, Dorie shared that it’s very easy to focus on what you lack, but if we do that, we are accepting other people's frames. The truth is while we are lacking certain things, we are developing new skills all the time.
Dorie also shared the free self-assessment that is tied in the book Revinting You at www.dorieclark.com/reinvent.
Resources
- Home - Dorie Clark - Official Website
- Reinventing You: Define Your Brand, Imagine Your Future: Clark
- Entrepreneurial You: Monetize Your Expertise ... - Amazon.com
- The Long Game: How to Be a Long-Term Thinker in a Short-Term ...
In episode #20 of My 2.0 Archives, guest Sarah Brown, Senior Director Sales Enablement at Health Carousel, shares her transition from a career in counselling to entrepreneurship.
Sarah’s journey started with a Master's in counselling. She worked in juvenile corrections with a superintendent who had been there for 20 years and was very experienced. He had a very robust intervention program that she learnt a lot from. But she was burnt out and was looking to make more money. He suggested that she apply for a training manager position. She first thought she shouldn’t, since she didn’t have the skills. But he convinced her how she had already been doing this job, and so when she got the job, she loved it, and excelled in training and development. Fast forward, she now works in a healthcare system running their leadership programs including coaching their teams and executives.
Sarah always knew that she loved variety. She also got the confidence to move into a consulting role outside the organization for 15 years. And decided to open up a blow dry bar in 2015. She invested money, time, heartache, into this and two and a half years later, she closed it and it was devastating. She had really attached personal value, her self worth to the success of the business. And she was embarrassed that people will attribute her to the failed business. At that time, she decided that she was going to separate her self-worth from what she did professionally.
When I asked her for tips on how to solve this problem, she said to start with being aware of the issue. And to take the time to notice triggers, to pause, to reflect on what drives us to feel positive or negative. She also feels that the universe has a great way of redirecting us when we are not in the right space.
Sarah’s biggest challenges during her transitions were the self-limiting beliefs in her head. And the irony that no one cared. If anything, people were envious of her ability to pivot and rebrand herself.
Sarah’s most recent endeavor is 0.0 Living, which helps people reset their relationship with alcohol. And that could look like containment, abstinence or anything else in between. This comes from a personal struggle Sarah had with alcohol and one she saw manifesting with a lot of people during the pandemic.
She created the Failing Forward podcast so she could touch people with inspiring stories of failures that people learn from, and change from. It started with being local for Cincinatians but just this January, Sarah took the podcast global, telling and sharing stories all around the world.
In debunking transition myths, Sarah thinks that we need to understand the value of our transferable skills, and articulate them into the new/next job. And to understand the importance of EQ and not just rely on IQ.
The advice she would give your pre-transition self is to bloom where you're planted, stay planted as long as you can. And move to a new location when you’re ready.
Sarah then asked me a question about what gifts the podcast has given me. To which I said it connected me to many women I learned from, that I would not have met otherwise. And it teaches me to be a more empathic and curious listener.
Resources:
- Failing Forward Podcast
In episode #55 of My 2.0 Archives, guest Bea Wray, Author and Keynote Speaker, shares her transition from a career as an entrepreneur to an author.
She grew up always knowing that she’d be a psychology major and a psychology researcher. And she went to college for psychology and even did an honors thesis and was on a path to do research and hopefully eventually go to graduate school. But while she presented her thesis, expecting to fail, given it wasn’t statistically conclusive, she was shocked to receive the highest honors. Her own reaction to that was to find another career. And so she went into business, starting and leading many successful companies.
When I asked her how she compared her career with her father’s 30 year career at Ford, she said she has worked with entrepreneurs and startups. She understands imperfections and chaos and problem solving in a way which is different from people working in large corporations.
Bea’s advice to her pre-transition self is for people to always be open and true to themselves. And to be aware of your surroundings and what you want out of life and use all the incredible opportunities that come our way.
Some of the transition myths Bea would like to debunk are that career transitions cannot be done and that the next thing may not be better. She talks about our career being a three-legged stool; each leg representing industry, position and geography. And that we should never try to change all at once.
When I asked what led Bea to write the book, she mentioned that after selling the company, she took six years off spending time with her family. And when she went back to the workplace, she felt intimidated with very low confidence. And she realized she kept receiving thanks and compliments for helping people and when she reflected about her innate skills, she realized all her skills from business schools were honed by her kids. It included empathy, communication and negotiation. And that was making a difference.And one thing led to another and she started writing about it and I published a little article in entrepreneur.com. So at some point she knew a book would come out.
As she lost her confidence and was trying to figure out the next point in her career, she asks us to never let not having confidence get in our way. And if there is something we want to try or do, we owe it to ourselves to try.
She offers her advice on negotiation skills using the BATNA principal they use at HBS; the best alternative to a negotiated agreement. She explains how she has never looked for just one job, but multiple ones at a time.
Her thoughts on whether children should be allowed to fail were that being an entrepreneur, she understands the importance of establishing a culture of failure so it allows for risk taking. Which is similar to our career transitions. Taking that to parenting, we want our children to not have to be perfect, and to accept failure.
Resources.
- What an MBA taught me..but my kids made me learn
In episode #17 of My 2.0 Archives, guest Judy Robinett, Founder of Crack The Funding Code, shares her career transition from social work to a power connector.
Judy calls her career transitions ‘one mistake after another’. She went to college for a Physcology degree and became a social worker after. She transitioned to getting her masters in Economics and started figuring out that she was good at business. Working in Fortune 500, she felt nausea on Sunday nights thinking about going to work on Mondays. After more explorations and reflections, Judy decided to start her own business running a franchise restaurant for 8 years. She maintains that the important thing is to do the hard work. We will hit a wall, but will also figure out a way over it, under it, around it, since there’s always a way.
After selling the restaurant, a friend asked for advice for a biotech company that was broke and in litigation. After she helped them with their challenges, she was asked to be a CEO. She struggled internally with questioning her own competence in being the CEO of a public company but worked through that challenge to successfully raise money and turned it into a success. She thinks that the next level will bring the next devil and as Tony Robbins says, a Golaitah shows up every time but it’s up to us - whether we’re going to get a sling and a rock or run away.
Additional questions for Judy.
- What helps us get through current challenges and be ready for the next one?
In Judy's opinion, asking people for help, and knowing where to find the right people in the right rooms is what helps us get through current challenges and be ready for the next one. She also believes in the right mentors and to always be learning. We should be asking people the three golden questions; How can we help them, what other ideas they have for us and who else they think we can talk to.
- What causes us to break out of our comfort zone?
We should think through all our preconceived notions and assumptions of difficulties. To solicit as much help as we can, to ask for training when we need it. And to understand that if we don’t get out of our comfort zone, we’re stuck.
- Her advice to pre transition self.
To kick fear to the curb. To avail all opportunities and use all the information and ideas we have and are surrounded with. To get into the right rooms with the right people to ask the right questions.
- What led her to write ‘How to be a power connector’?
Judy wanted to write a book about funding businesses. When her agent discovered the types of people she knew, she asked Judy to write a book on networking. And Judy wrote this book to help people like her, shy and unsure. To turn each stumbling block into a stepping stone that makes us stronger, and puts steel up her spine.
- How can women use wisdom through the book in their career transitions?
This book will help us evaluate our current network, and build it out, including helping us find people smarter than ourselves and in different walks of life.
- What led you to write ‘Crack the funding code’?
Judy didn’t want to write another book. But the more people she talked to, she realized how critical and pervasive the problem of funding for startups was. And so through this book, she intends to provide founders the wisdom and resources to show them the right rooms with the right people that can help them with their funding problem.
- How do we make sure we get more women to the starting line of entrepreneurship, and find funding for their businesses?
Judy’s advice is to take baby steps, networking one person at a time. And to leverage resources like the
In episode #16 of My 2.0 Archives, guest Kristy Wallance, CEO of the Ellevate Network,shares her transition from a career in finance and investing to running a networking platform.
Ellevate network is the largest coalition of professional women in all career stages committed to succeeding in the workplace and the world and in lifting communities around us. They have experienced many changes due to COVID. They had hyper local communities and squads which were online peer mentoring groups, with a large opportunity in the middle of both these types of groups. So they introduced weekly executive round tables talking about relevant topics and taking it back to homes and workplaces.
Networking is traditionally a dirty word, and people use it transactionally only when they need to. Women, in particular, don’t invest enough in it. But what we miss out on is timely and intentional relationships. Just like we value our personal networks, we need to value our professional relationships to create that bench of thought partners who can help solve not just the business partners of today, but become a part of our life-long career journeys.
Kristy also hosts the Ellevate podcast. She loved internalizing and learning from other experiences, and improving her own listening skills.
Krist graduated as an English and Sociology major and went into investment banking. But soon realized that Corporate was not the right place. She quickly moved on to startups, in sales eventually leading revenue operations. She was eventually asked to grow her business globally but was pregnant with her first child and felt overwhelmed. She was working long hours and didn’t see a way forward. She took a break to travel and connect with different people, cultures and places, looking for inspiration and creativity. She did a listening tour and eventually moved into a health and wellness startup. Soon after, she met Allie MacDonald who was the founder of 85 Broads, and who introduced Kristy to the Ellevate Network. Kristy’s interest was piqued and within a couple of days, she moved on to her new position at the Ellevate Network.
She believes that we need to explore, to connect with our community to help us realize our vision.
Her advice to those who want to explore stepping back to explore career transitions is to ensure financial stability and to make space to explore options for the next transition. She personally regrets the fact she did not make that time and space for herself. And seemed in a rush to get back to the comfort of a professional identity. She asks us to not be embarrassed but instead to be curious and patient.
Kristy’s rituals and habits for not feeling stuck are to determine our key activities and do them in the most productive time in the day, and to make that a bit. She also likes to keep a list of people that she likes to keep in touch with, and to check in with periodically.
Her pre-transition advice to herself is to not be hard on ourselves, and to identify the things we want to do/enjoy that are separate from our professional lives. .
And in order to embrace our career transitions, she does a quarterly check with herself to see if she is happy in all her roles and is fulfilling her expectations. She also is curious and aware of all the opportunities that are being presented to her.
In episode #13 of My 2.0 Archives, guest Diana YK Chan, Founder and CEO of My Marketability, shares her transition from a career as a consultant to career coach.
Diana experienced multiple pivots along her career path. She started with a rotation program in operations, training, marketing. And eventually pushed to get her MBA and landed a top job as a management consultant. She wasn’t too happy though, with crazy hours, and a feeling that something was missing and that she was a failure. She went on a soul searching journey, including walking on fire! She gained clarity that she was meant to become a speaker, trainer and coach. As she moved into recruiting, she understood it as being one step closer to the dream job. And then she found herself let go of, two months before her wedding. She had been planning to start her own business but that timeline came sooner. She felt like she was an emotional roller coaster, with a feeling of shame that she wasn’t good enough. But the fire in her caught spark and she decided to start her business in a week. And was hired by Google Canada later that month.
Diana talks about the challenges during career transition. She struggled with whether she was doing what she was meant to do. With her career identity and with fitting in.
Her advice to her pre-transition self is to trust yourself. To trust our intuition, to follow our heart and our gut. Even if we don’t know what it is, we should search for it. She feels very grateful for all her career transition experiences since they help her guide her clients.
Some transition myths she would like to debunk are.
- Do we have to start from the bottom?
- Are we going to make less money?
- Do we have enough experience to make the change?
I also talked to Diana about her coaching practice on the topics below.
- Discover our greatness.
Most people are not comfortable talking about their greatness, and in claiming it. We should recognize, believe and convey our value. Diana uses her D.I.S.C.O.V.E.R framework to help clients identify their core values.
- Branding and women.
Diana feels her female clients can lack the confidence required to recognize and own their greatness. She believes that when we start recognizing our own value and appreciating our own value, we are actually being of greater service to the world.
- How does one know when it’s time to stop doing, even at the cost of failure. What are the next steps?
Diana says that deciding is the hardest part. Most people say they wish they’d done it sooner. We need to get clear on where we are going after, including mapping out the vision. And if that vision is clear enough, we will naturally start attracting the right opportunities.
- How do we future proof our career?
We need to be the CEO of our career. We can control how we feel, think and decide on what skills are required. And get comfortable with being uncomfortable.
In episode #51 of My 2.0, guest Alisa Cohn, Global CEO Coach, #1 Startup Coach - T50 Marshall Goldsmith Awards; shares her career transition stories spanning from accounting, corporate to coaching executives across the world.
Alisa talks about her career stories and how she transitioned into coaching. How that was not an aha moment for her but a deep conviction in her ability to mentor and grow executives around her. She also talks about her view on the future of work, how it’s in the process of being written, and will likely need to be adaptive to accommodate ever-changing times. Last, but not least, she talks about her new book ”From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business” with the focus on how critical it is for leaders to manage themselves in order to best manage their business.
Resources:
- From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business
- Alisa Cohn's Website
In episode #50 of My 2.0 Podcast, guest Debbie Millman, Designer, Author, Illustrator, Educator, Brand Consultant, Host of the award-winning podcast 'Design Matters', talks about her career transitions and lessons learned.
Debbie talks about the drawing she did as an 8 year old, that she discovered a few years ago, that seemed to have foretold her entire life and career. She shared her traumatic experiences with abuse and the importance of having open and healthy conversations about mental health. She also shares her view of courage over confidence, and about the value of lead genes and she transformed Milton Glaser’s 5 year plan into a 10 year plan that she has been using with her mid-career design students.
Resources:
- Design Matters
- Why Design Matters: Conversations with the World's Most Creative People
- Brand Thinking and Other Noble Pursuits
- How to Think Like a Great Graphic Designer
- Look Both Ways: Illustrated Essays on the Intersection of Life and Design
- Brand Bible: The Complete Guide to Building, Designing, and Sustaining Brands
- Self-Portrait as Your Traitor
- The Essential Principles Of Graphic Design by Debbie Millman
- Leave Me Alone with the Recipes: The Life, Art, and Cookbook of Cipe Pineles
In episode #48 of My 2.0, guest Poorvi Shrivastav, GM & VP, Product@HubSpot and member of the Forbes Technology Council shares her many career transitions in the product and technology in her search to find purpose.
Starting off in India building a high-end apparel start-up to solve a problem she was facing, Poorvi consolidated her software developer roots in Microsoft, making a physical move to the US and also transitioning to business school. She discovered her love for product and venture, eventually picking her next transition to product at Salesforce. Unlike her peers, Poorvi has chosen to stay longer in each role at her companies and recently moved to Hubspot. In her entire journey, Poorvi never lost sight of her other passions, in serving/lifting others through technology and education. And she remains dedicated, stronger than ever, to align her love for product, technology, passion and purpose.
In episode #47 of My 2.0, guest Joanna Bloor, Founder and CEO of The Amplify Lab, shares her transition from a career as a technology executive to a potentialist, adventurer and fairy godmother.
Joanna came to the US from England in high school and began her discovery of building a future without any rulebooks. She talks about how important it is for us to be able to identify the magic in who we are and what we do to be present in the room where decisions about our future are made. Her take on the classic Cinderella story is not to be missed, it’s what makes her a fairy godmother!
Resources:
- The Amplify Lab
- Joanna Bloor
- LIVE! with Joanna - Every Friday at Noon PST
In episode #46 of My 2.0, guest Joanna Bloor, Founder and CEO of The Amplify Lab, shares her transition from a career as a technology executive to a potentialist, adventurer and fairy godmother.
Joanna came to the US from England in high school and began her discovery of building a future without any rulebooks. She talks about how important it is for us to be able to identify the magic in who we are and what we do to be present in the room where decisions about our future are made. Her take on the classic Cinderella story is not to be missed, it’s what makes her a fairy godmother!
Resources:
- The Amplify Lab
- Joanna Bloor
- LIVE! with Joanna - Every Friday at Noon PST
In episode #49 of My 2.0, guest Melanie Spring, International Keynote Speaker & Professional Speaker Trainer, shares her transition from a career in branding to a speaker trainer.
Melanie started her career in web design and branding, where she always had a side hustle like most entrepreneurs. When she finally bit the bullet to start her own branding agency, she felt like she created another job for herself. While business boomed, her hustle and stress took its toll on her to the point that she closed down her agency to figure out who she was and what she wanted from life.
In episode #45 of My 2.0, guest Michelle Lim Warner, CEO and CoFounder at DCanter, shares her transition from a career in healthcare innovation to wine retail.
Michelle and her husband loved wine. Not just consuming it, but exploring the many grape varieties and the associated culture and traditions. Since they didn’t have an endless budget that allowed them to explore the world for wine, they tried to find local wine stories that would combine the discovery, exploration, learning and consumption. And when they didn’t find any, Michelle, who is a self-starter, decided to take on the solution through DCanter!
Resources:
- DCANTER - A Wine Boutique
In episode #44 of My 2.0, guest Asha Aravindakshan, VP Customer Delight and Operations at Sprinklr, shares her transitions starting in middle and high school through non-profit, government, the private sector and finally to becoming an author.
Asha thinks she was meant to have career transitions since she seemed to have lined up jobs and internships even in middle and high school to align her longer term career goals and personal interests. As she goes through her career transitions, she realizes the value of transferable skills, and the power of networking. She them embarks on the journey of publishing Skills: The Common Denominator to provide a strategy for making successful career transitions.
Resources:
- Skills: The Common Denominator
Re-airing Dorie's original episode #21 of My 2.0 to celebrate her recent book The Long Game: How to be a long term thinker in a short term world.
Dorie thought she was going to be an academic but got turned down for all doctoral programs. Her Plan B was to become a journalist, and she ended up getting laid off after about a year on the job.Eventually she found her way into working in politics, running a nonprofit for two years realized that she wanted to run her own business. And moved on to having her own consulting and executive coaching business.
On the topic of feeling stuck, Dorie felt she didn’t have the luxury of being stuck, and that always needed to figure something out and keep pushing. She decided she was going to exhaust every possible resource, call everyone she knew to hustle and network my way into whatever the next thing is.
Dorie’s advice to her pre-transition self is contained in her book Reinventing You. She interviewed about 50 other professionals who had made career transitions to create a guide that people could use to feel more in control of what can often feel like an out of control process. Her advice was for us to reinvent ourselves in small ways on an ongoing basis and keep ourselves current. The less likely we are to be faced with a situation where we're static for five years or 10 years.
When asked why she wrote Entrepreneurial You, Dorie said it was her attempt to figure out ways to scale her business in developing simultaneous and adjacent streams of businesses.
When asked what it means to have a brand, Dorie answered it needs to start with who we are and what we are able to do, and articulate it to the market. And that when we transition to a different career, we have to be the captain of our narration.
Dorie also talked about her new book coming in September ‘The Long Game. How to be a long-term thinker in a short term world’. Over the last 5 years, she has met a lot of great people and built up a longitudinal perspective and pattern recognition around observations that I've noticed in terms of very smart, very talented professionals in the stressors they face, that come in the way of long term growth. That we don’t know how long it takes to become a successful recognized expert. So this is her attempt to light this dark, long and opaque path.
When asked how we could future proof our careers, Dorie shared that the one thing we do know is that whatever position we're in, we want to be as protected and secure as we possibly can be. So that if disruption is coming down the pike, we are able to pivot with enough time.
On the power of identifying and defending ourselves against our vulnerabilities, Dorie shared that it’s very easy to focus on what you lack, but if we do that, we are accepting other people's frames. The truth is while we are lacking certain things, we are developing new skills all the time.
Dorie also shared the free self-assessment that is tied in the book Revinting You at www.dorieclark.com/reinvent.
Resources
- Home - Dorie Clark - Official Website
- Long Game Strategic Thinking Self-Assessment
- Reinventing You: Define Your Brand, Imagine Your Future: Clark
- Entrepreneurial You: Monetize Your Expertise ... - Amazon.com
- The Long Game: How to Be a Long-Term Thinker in a Short-Term ...
In episode #42 of My 2.0, guests Melissa Boatwright, Global Insights and Technology Leader at LinkedIn, and Sarah Roberts, Head of Military and Veteran Programs at LinkedIn, share their personal stories of career transitions from the Military into Civilian space, including insights from their recently published Women’s Veteran Opportunity Report.
Melissa served as a broadcast journalist in the Air Force, transitioning out of the military to spend time with her mother while her father was deployed in Afghanistan. Her transition, she says, was atypical. She went to school and then quickly got the jobs she applied to. And how that seems to be different for the vast majority of female veterans.
Sarah served as a finance officer in the army and talks about the challenges of leaving the military at the same time as her husband, and how they were told they’d have to pick one of their careers to follow, and that it wouldn’t be hers.
Resources:
- Women Veteran Opportunity Report
- Veteran Opportunity Report
In episode #41 of My 2.0, guest Kara Goldin, Founder and CEO of Hint, Inc., shares her transition from a career in ecommerce to launching a new product category through Hint water.
Kara started her career in journalism at the Time magazine and later CNN and found her way into becoming a technology executive at America Online. As she took some time off to care for her four young children, and started looking at what she was putting in her body, specifically through diet sodas, she started to solve a problem; that she wanted to drink water for health reasons but found it too boring.
Resources:
- Undaunted: Overcoming Doubts and Doubters
- Hint Water
In episode #15 of My 2.0 archives, guest Seema Alexander, Founder and Chief Strategy Officer of Disruptive.CEO and Creator of the U.N.I.Q.U.E Method shares her career transition from the corporate world into entrepreneurship.
Seema grew up in a small business environment, since her parents ran the first Indian vegetarian restaurant in the DC area. She started working there when she was 12. But her experiences from that time took her away from entrepreneurship, and into the Brand and Business Strategy world in NYC.
She worked at Prudential for 13 years in 5 of their businesses, including in their historical rebranding effort—where she learned the importance of how repositioning your brand can be a huge lever in growth.
Over time, she didn’t feel authentic in corporate America. And as she experienced her first pulmonary embolism at age 36, she came to a mid-life awakening for the desire to go back to entrepreneurship.
She had been helping a client on the side for a while, who then asked her to join him full time. She got pregnant with her second child, took an extended maternity leave so she could explore her entrepreneurial options deeper and never looked back.
Seema is very passionate about amplifying the businesses and brands she believes in.
In debunking transition myths, Seema points out that entrepreneurship has its freedom because you are able to work on things you love. However, it takes time to build a reputation and more importantly—a profitable business—and you will make mistakes along the way. You will feel financial constraints, have moments of overwhelm, and second guess yourself (as impostor syndrome is real).
That’s why it is really important to surround yourself with people who believe in you, in your vision—because not everyone will understand your move from stability to instability to follow your passion and dreams.
Additional questions I asked Seema.
- What were the challenges she experienced through her clients?
- She said it was the process of discovery of the ideal client, the founder’s passion, conviction in their expertise and in understanding what the market wants.
- Why did she pick the name Disruptive.CEO? Do we have disruption porn like failure porn?
- She thought people like to reimagine the future and hence the name. She acknowledges that disruption gets used a lot but a lot of times it is what is required to reposition to grow and to become better.
- What do you know now that you didn’t before you started your business?
- She understands the value of self care, and how it contributes to major personal growth.
In episode #14 of My 2.0 Archives, guest Anita Moorthy, CEO and Founder of The European Startup Show, shares her transition from being a computer engineer to product marketing and podcasting.
Anita has experienced several transitions in her life, starting from when she was studying computer engineering at the University of Waterloo, working in their coop programs when she realized at the end of her term that she really didn’t want to become a programmer but instead chose to become an IT consultant, focussing on the bigger picture in business. She wanted to understand the power of IT as an enabler melding it with business.
She thinks her experience of living in so many countries around the world has made her personality and experiences more complex and richer. While she does not have roots that people have when living in the same place for a long time, she wouldn’t trade her rich experiences for it!
Resources:
- Managing Oneself
In episode #12 of My 2.0 Archives, guest Jessi Hempel, Host of the Hello Monday podcast and Senior Editor at Large at LinkedIn, shares her personal transition story as well as what she has experimentally learnt through her podcast.
Jessi has wanted to be a writer since 3rd grade, and went to college to become a journalist. She wrote for Time Asia, Business Week, Fortune and Wired. She was always seeing clearly the next rung of the ladder and was able to climb it. But that started to change as she got to Conde Nast in 2018. While her position was secure, she knew the company was in financial trouble and that she was a part of a dying industry. She also knew she was at the top of her food chain and that it was time to move on.
She has always been interested in and fascinated with technology. So when LinkedIn approached her in 2018 to start their podcast, giving her all the resources, smart people and freedom to further her career, she didn’t very long to make that decision.
She does not think we need a full skill set to transition to a new career but she feels that women in particular feel the need to.
Some transition myths she would like to debunk are that there is a right time to transition. In her opinion, there is not. They should happen when they are supposed to happen. She further mentions one of her guests Bruce Feiler who thinks transitions will be lifelong, happening one every 7 years.
Below are some of the topics we talked about from a few of her episodes at Hello Monday.
Reinventing ourselves. Dorrie Clark.
- Conducting experiments/soft launching or plan B. Women don’t give themselves enough credit about hard things. Plan B with Plan A is hard but is very possible.
- Branding. Women find it hard to talk about themselves. But branding is simply featuring our differentiators contained in our personality.
Burnout. Emily and Amelia Nagosky.
- Stress and stressor. They are two different things that should be treated differently. While identifying and solving for the root cause is critical, it is equally important for us to deal with the stress as well. Especially if we can’t do anything about the stressor.
- Self care of the individual and through the community. We need to take care of ourselves individually but also responsibly lift the community around us.
Designing your life. Bill Burnett and Dave Evans.
- Circumstances/Gravity. We need to understand what we are capable of and design a life with goals we can achieve. It may feel hard and unfair, but that’s what life is.
- Separating career and passion. The notion of combining career with passion is 20th century and applicable to Gen X. But we need to be open to the fact that the two may not intersect and that it’s ok for them to diverge.
Career change. Robin Arzon.
- Discomfort in career is not the same as athletic discomfort. It seems easier to push ourselves more physically than it is intellectually.
What does it mean to have it all?
- This is also a 20th century notion to have it all. And it doesn’t work. What works is our ability to make a choice from options we have, and to feel solid in our choice.
Jessi’s question to me. What’s the one thing I didn’t know that I know now.
To which I responded that transitions are hard, take their own time and are best when planned and gradual. And we don’t need a full skill set to turn to a new career and definitely need cheerleaders along the way.
Resources:
- Hello Monday
n episode #38 of My 2.0, guest Carol Fishman Cohen, CEO and Co-founder of iRelaunch, shares her transition from a career in finance to entrepreneurship.
Carol took a career break from 1990 to 2001. As she contemplated her return to work, she socialized the idea with business school classmates and ex-colleagues and landed a job much more quickly than she thought. She then started to co-author her first book on career breaks and relaunching that was also the beginning of kicking off iRelaunch, a platform that connects employers with relaunchers - people who are looking to come back to work after a career break.
Resources:
- iRelaunch
- Jessi Hempel's podcast featuring Carol
- How To Get Back To Work After A Career Break
- How The Pandemic Created Demand for Older Workers
In episode #37 of My 2.0, guest Kaitlin McCulley, Founder & CEO at Outlet, shares her transition from a career in news channels to building a media platform as an entrepreneur.
Kaitlin started working as a TV anchor and journalist and through her years at many TV channels, realized that she wanted to do more than shaping news in the way the channel needed it to be shaped so as to grasp audience attention to sell ads. That led her to starting her podcast Outlet which she then turned into a media platform.
Resources:
- Outlet Media
In episode #36 of My 2.0, guest Caroline Vaquette, Executive Partner OurOffice, and a changemaker for a more inclusive workplace, shares her transition from a career in business to HR.
Caroline is French, born and raised in France. But was ready for an adventure when she and her husband decided to move continents to China. And decided to do it all over again when they moved to the US. Throughout this time, she worked to learn about the culture and people that helped her integrate much better and faster, as she transitioned within the many corporate domains eventually into entrepreneurship.
Resources:
- Our Office
In episode #35 of My 2.0, guest AdaPia d’Errico, Principal & VP of Strategy at Alpha Investing, Real Estate Investor & Entrepreneur and author of Productive Intuition shares her transition from a career in banking to real estate investments.
AdaPia decided at an early age that she’d need to sacrifice her childhood dream of becoming a paleontologist to a more respectable career choice as an attorney, to win her dad's approval. That journey kicked off a series of career transitions from banking, through hedge funds and entrepreneurship in the arts. She eventually came back to Fintech and struggled with the loneliness and incompletenss on the inside, causing her to commit career suicide and taking time off to find herself. And she wrote about that experience in her book Productive Intuition and found her calling in real estate investments.
Resources:
- Productive Intuition
In episode #34 of My 2.0, guest Karen Laos, communication expert, keynote speaker, podcast host, shares her transition from a career in corporate to entrepreneurship.
Karen started her career in HR, serving in large corporate retail like the Gap and moving on to other large corporations. She started training and developed but moved on to mastering communication skills at her last position at Decker Communications. Karen’s passion is coaching high achievement women in business who are over forty to overcome self-doubt and speak with confidence & clarity.
Resources:
- Karen Laos Consulting
- Ignite Your Confidence
In episode #33 of My 2.0, guest Allison Shapira, CEO and Founder of Global Public Speaking, LLC,shares her transition from a career in opera singing to running a public speaking business.
Allison trained to be an opera singer through school and college but when she was provided with harsh feedback that she wasn’t good enough to compete, she felt disrupted, unfocussed and she began her transition journey to determine how best to leverage her core skills into her new vocation.
Resources:
- How a small business owner saved her public speaking firm during the pandemic
- Speak With Impact
- Public Speaking Tools
In episode #32 of My 2.0, guest Irene Koehler, Personal Branding and Social Media Specialist shares her transition from a career in corporate to entrepreneurship.
Irene started her career in HR, working through the ranks to run the function at a Director level working with global operations. But she was itching to experiment being a consultant to get rid of office politics and to get flexibility in her schedule. And she realized she was quickly filling her pipeline with referrals. With the launch of LinkedIn, she gravitated towards mastering it to build and advertise one’s personal brand.
In episode #31 of My 2.0, guest Cecilia Hahn, Co-founder of Coder Kids and Product Manager at Farmstead, shares her transition from a career in entrepreneurship to corporate.
As a Software Engineer, Cecilia was determined to expose young children to all the coding options she herself didn’t have the opportunity to learn before college, which resulted in her first business Coder Kids. Guided by her three principles of keeping family first, providing joy and value to people’s lives and to always be learning, Cecilia moved on from Coder Kids to have a baby, and start her next business in Chile, before finally returning back to corporate life through Farmstead.
In episode #30 of My 2.0, guest Danielle deShaw, Mindset and Confidence Coach, TV Host and Speaker, shares her transition from a career in corporate to entrepreneurship.
Danielle started her career in manufacturing, in microbiology, since that was her education and background. Over the years, she moved to human resources and at age 40, decided she was going to take a step back to figure out who she was and where she wanted to go next. Given she was surrounded by entrepreneurs, she decided to try that path even though it was vastly different from her career choices up until then. Two and a half years into entrepreneurship, she felt she had big learning gaps and wasn’t much closer to finding herself. So she went back to manufacturing, but kept one ‘shoe’ in entrepreneurship!
In episode #29of My 2.0, guest Pat Hedley, Investor, Advisor and Author (Meet 100 People), TedX speaker, former Managing Director at General Atlantic, shares her transition from a career in intrapreneurship to investing.
Pat had a steller, and exciting career at the General Atlantic where she took on multiple ‘blank paper’ opportunities i.e. she didn’t know much about the work but knew that she had the skills of collaborating with experts to get their wisdom, and synthesize it to make it her own. And it’s this simple philosophy that has brought many exciting and unexpected new career opportunities to Pat. Pat is also a strong proponent of building social capital through relationship building and credits her insatiable curiosity to form new and exciting relationships all the time.
In episode #10 of My 2.0 Archives, guest Lina Zdruli, Founder and CEO of Dafero, shares her transition from being a consultant at the World Bank to becoming an entrepreneur.
With her background in international relations and focus diplomacy and small and medium enterprises from a trade perspective, she worked at the UN, merging international relations with environmental conservation. While doing her Masters at Georgetown in transatlantic relations, she learned about forced displacement and refugees. And was interested in how the private sector could support this issue for long term change. She then started working at the World Bank, doing exactly that work.
She had a very intensive travel schedule and found that she loved eating all sorts of foods all over the world but got a stomach ache every time she returned to the US. She tried to practice the elimination diet to resolve the issue, but to not avail. After one of her trips, she started baking with dates and found they were delicious and healthy. As she tried to find dates spread in the US, she discovered there wasn’t one that didn’t have any additional sugar. The need to stick to natural ingredients and yet maintain taste, gave birth to Dafero. She also tried to solve the forced displacement labor problem by using them as the workforce at Dafero.
The transition was gradual, and she didn’t realize how much what once was a weekend passion was taking over her life. She started to go deep into learning about food science, and other things about starting and running a food business. She loves combining tradition with trend and loves that her energy is flowing where her attention is.
Lina talks about feeling stuck all the time. About being covered in date explosions, burning blenders and food processors. Scaling up was hard; getting the manufacturing right for the new production levels was very hard.
Lina used the following resources to unstick. She tapped into fellow entrepreneurs. She also absorbed ideas about packaging, branding and taste from her travels and conversations around the world.
She would like to debunk the following transition myths. That one has to be 100% sure else to not do anything new. And that it will be very expensive to start a new venture.
She is very excited about the Dafero 2.0 rebrand. They are revamping the look and feel of the brand in the labeling and packaging. And making sure it represents a fun, happy, colorful and inclusive brand. They are also celebrating overcoming their manufacturing challenges as a result of scaling up.
Her last words were for us to detach ourselves from our company. Because even if the company fails, we will live on to do bigger and better things!
Resources:
- For food-business specific
- For mission-based companies
- Understanding business and human behaviour
- Marketing
- Dafero referral link
In episode #9 of My 2.0 Archives, guest Liza Rodewald, Founder and CEO of Instant Teams, shares her transition from being a computer programmer working as an employee to a 4x entrepreneur building scale.
Liza talks about loving her early career but facing challenges in being an involved mother at the same time. It was this passion, in the ability to build careers with a flexible lifestyle, that set brought out her accidental entrepreneurship. Further, as she became a military spouse, she saw the challenges that came with these qualified women not being able to secure stable jobs because of the demands of their military spouses. And how there was a potential to make this a win-win, in using this untapped and qualified pool of labor, and matching with companies who needed this talent.
She recommends having a group of mentors to guide through transitions and progressions. She learnt everything she needed to know about scaling a company from the Founder Institute, and recommends resources like that for all entrepreneurs looking to scale.
Her recommendation for encouraging entrepreneurship in girls is to invite female entrepreneurs to schools and colleges so they set a role model and are able to provide mentorship opportunities early on.
Some transition myths she would like to debunk are that we think we need a full skill set for our new job. She thinks we don’t, but that we identify our core, transferable skills, so that we can forge a path to get better skilled at the new job.
Resources:
- Founder Institute
In episode #28 of My 2.0, guest Patrice Williams Lindo, People and Change Manager at KMPG, shares her transition from a career in consulting to coaching.
Patrice started dabbling in teaching in her early years through child play, moving on to a career in teaching and training. She was always looking for that next challenge, those new skills to learn and grow in. When she landed her first consulting job at Accenture, she was surprised. She continued to chalk up her success to luck with her second consulting job but when she was offered her third, she decided to share all the learnings and knowledge she had accumulated in positioning herself to the best possible career opportunities so she could help others around her, specifically women.
In episode #27 of My 2.0, guest Amy J. Wilson, bestselling author, CEO, and keynote speaker, shares her career transition from public relations to empathy.
Amy started in public relations and communications but moved on to strategy and innovation, working with the Obama White House in setting the Better Government Movement and kicking off Innovation.org. She experienced a huge mismatch of values during the transition to the Trump administration, leading to her being fired from the position.
Resources
- Empathy For Change
- The Better Government Movement
In episode #26 of My 2.0, guest Joya Dass, founder of LadyDrinks, an events driven leadership development platform, shares her transition from a career as a journalist to an entrepreneur.
She has a successful career of 20 years as a journalist covering financial markets of which she ran a leadership platform for women in the last 7 years. And what started as a side hustle, developed into bigger than anything she had done on television.
Joya talks about the importance of building an ecosystem of people we hold ourselves accountable to, about her worthiness journey.
Resources
- Ladydrinks
In episode #25 of My 2.0, guest Bosky Mukherjee, Founder at PMDojo & Spark To Substance, shares her transition from a career in corporate to entrepreneurship.
Bosky’s life has been a lifelong series of transitions, as she moved across geographies, through various types and sizes of company. The only constants were her love for the product and her desire to always be growing. Motherhood changed her in new and unforeseen ways, as she struggled with the extreme physical challenges with her newborn son. She learned to not settle, to always ask for more from herself and from others around us. But in that process, while she continued to scale the heights of her corporate career, she suppressed the toll that brought on her emotional well-being. And so when her body finally collapsed with burnout, it provided her the tipping point to assess what she really wanted from both her professional and personal lives.
Resources:
- Spark To Substance
- PM Dojo
In episode #24 of My 2.0, guest Justine Evirs, host, entrepreneur and writer, shares her transition from a career in the Military to becoming an Entrepreneur.
Justine walks us through her many transitions starting in her childhood, through to getting into the Military, to becoming a military spouse and finally transitioning out into a higher education, non profit serving the Military and veterans eventually finding her calling in entrepreneurship. She’s never lived in a house for more than three years, and is a first generation college student. And is very open with her struggle with alcohol, including hitting rock bottom three years ago.
Resources:
- Stanford GSB Program
- Protecting Courage Podcast
- Courage To Create
- The Paradigm Switch
In episode #23 of My 2.0, guest Maxine Cunningham, CEO of Pick My Brain, shares her transition from a career in investment banking to entrepreneurship.
Maxine described her journey of training as an economist, her experiences in the Investment Banking world, then as an environmental economist finally being inspired by the Airbnb founders to create a platform that allows for gifting, buying and selling knowledge in what she believes to be the future of the information/knowledge economy.
Resources:
- Pick My Brain
- Airbnb
In episode #8 of My 2.0 Archives, guest Anya Fasolyak, Founder and President of Studio Fasol, shares her transition from being a graphic designer to running her own design studio.
Anya talks about knowing the need for change given her desire to have the freedom to choose the work she wanted to do, with when she wanted to do it. She decided to share this with her boss, and they mutually agreed to a long transition so they could find the right replacement and for Anaya to hone her skills.
Anya talks about being very clear when it was time to move out. And it’s because she couldn’t stay. It was more an impulsive and emotional decision given she didn’t have a client list for her new business but that did not stop her from moving on.
She talks about how different the mind of a business owner is, from that of an employee. How the work may be the same, but the positioning, the need to know sales and marketing is paramount for a new business owner. She also credits this transition to her identity shift, and thinks it will be hard for her to go back to being an employer.
In the rituals and habits she developed, rising early, having some still self time every morning before the craziness of the work day starts was very important. She tries to meditate, do yoga as well. Not always successful but always tries!
In her recommendation for a transition toolkit are books and advisors. She understands it is hard to get the right type and number of advisors when you’re a young business owner, but she recommends being open, teachable and try hard to reach out to people.
Her advice to her pre-transition self is to know sales, to have a plan of how to build the list of potential clients.
She is passionate about encouraging girls and women to entrepreneurship. And thinks having women in business as influencers will help. Along with Shark Tank like business programs in high schools.
Her advice to her millennial peers is to not stay in unhappy jobs. But to act on the situation, to develop skill sets and opportunities that allow them to explore new career paths.
Resources:
- Pricing Design by Dan Mall
- Predictable Prospecting by Marylou Tyler and Jeremy Donovan
In episode #6 of My 2.0 Archives, guest Jenn Stofferahn, Vice President and Co-owner of TFN Training shares her transition from major gifts fundraising in the non profit world to barbells, strength training and personal training. While her transition may have been facilitated by meeting her future husband, who was an established expert in the powerlifting space, she had been ready for a transition. She negotiated with her then employer to work part time, while she went to fitness school to study the science and hone her skills.
Jenn draws the similarities between her two careers in how they both require to build deep, personal relationships. With a long view on end goals. And how they both require creativity and flexibility to stay in step with the client and their goals.
She talks about the uncertainty that comes with transition, and how, if possible, we want to make sure the other people and things in our ecosystem remain stable as we journey through our transition.
The challenges she experienced with transition with feeling the imposter syndrome. And struggling with the chicken and egg situation of experience v/s skills gap. And she advises we bridge that gap through self-confidence.
She goes on to debunks common transition myths that:
- We need to have a complete skill set for the transitioning domain. She describes that as a chicken and egg situation that we bridge using our self-confidence.
- Certain domains are more women-friendly than the others. She went from a traditionally male-dominated field to a male-dominated one.
Resources:
- “3D Muscle Journey”
- “TFN Training”
- ““Everyone Should Lift Weights” By Elliot White
- “Start With Why” By Simon Sinek
In episode #22 of My 2.0, guest Linda Wenger, Strategy Consultant at Urbaneer, shares her transition from a career in programming to entrepreneurship.
Linda’s first job was at a company called NCR for client support. She went back to graduate school to get her MBA and transitioned to the technical side. She then moved to a consulting company at MCI as a product manager.
Early on in her career, Linda had decided she was going to transition every 2 years to be able to learn and grow most.
Soon after, she had her first child and fully transitioned to motherhood. And that was not an easy transition. It was hard coming from a pretty exciting and changing life to transition into something that was a little bit more sedentary. But as we do as moms, we grow into our roles and we learn every day. About four years later, she had her second child and threw herself into volunteering with the schools, running auctions and fundraisers, to be active with networking.
Linda thought transitioning into and out of motherhood was very difficult. Starting with postpartum depression, losing the sense of freedom, workplace achievements, being physically exhausted all the time. Transitioning back into the workforce was equally challenging. She fought guilt about not being there for the kids. And on missing out being in the industry for 8 years.
And in 2007, she transitioned into helping her husband with his new business in the association industry, in SaaS. Not only did she not know anything about the industry, much less about the work. The world of startups was new and different. And yet, one of the best experiences of her life. It caused her to grow up very quickly.
She went back to school again, to Georgetown, for a leadership program. And is now consulting with a company in the construction industry, one in which she has no experience! But is using her strong skills in finance and strategy to advise them.
She also thinks transitioning is the most challenging, and it’s hard going from stable and known to a new place, one you may not know much about. She also finds that the more mature she gets, the harder it is for her to transition. Because the younger generation is hungry to get things done. And we start questioning our ability to keep up with them, and the learning. But the right answer is for us to continue to have the courage to transition no matter our age.
Her advice to her pre-transition self is to be aware of how easy it is to get stuck in the waiting place. And that there is no such thing as failure, just early attempts at success. And that women are the strongest people on the planet. And always learning is beneficial.
In episode #21 of My 2.0, guest Dorie Clark, strategy consultant, executive coach, and keynote speaker, shares her transition from a career as a journalist to an entrepreneur.
Dorie thought she was going to be an academic but got turned down for all doctoral programs. Her Plan B was to become a journalist, and she ended up getting laid off after about a year on the job.Eventually she found her way into working in politics, running a nonprofit for two years realized that she wanted to run her own business. And moved on to having her own consulting and executive coaching business.
On the topic of feeling stuck, Dorie felt she didn’t have the luxury of being stuck, and that always needed to figure something out and keep pushing. She decided she was going to exhaust every possible resource, call everyone she knew to hustle and network my way into whatever the next thing is.
Dorie’s advice to her pre-transition self is contained in her book Reinventing You. She interviewed about 50 other professionals who had made career transitions to create a guide that people could use to feel more in control of what can often feel like an out of control process. Her advice was for us to reinvent ourselves in small ways on an ongoing basis and keep ourselves current. The less likely we are to be faced with a situation where we're static for five years or 10 years.
When asked why she wrote Entrepreneurial You, Dorie said it was her attempt to figure out ways to scale her business in developing simultaneous and adjacent streams of businesses.
When asked what it means to have a brand, Dorie answered it needs to start with who we are and what we are able to do, and articulate it to the market. And that when we transition to a different career, we have to be the captain of our narration.
Dorie also talked about her new book coming in September ‘The Long Game. How to be a long-term thinker in a short term world’. Over the last 5 years, she has met a lot of great people and built up a longitudinal perspective and pattern recognition around observations that I've noticed in terms of very smart, very talented professionals in the stressors they face, that come in the way of long term growth. That we don’t know how long it takes to become a successful recognized expert. So this is her attempt to light this dark, long and opaque path.
When asked how we could future proof our careers, Dorie shared that the one thing we do know is that whatever position we're in, we want to be as protected and secure as we possibly can be. So that if disruption is coming down the pike, we are able to pivot with enough time.
On the power of identifying and defending ourselves against our vulnerabilities, Dorie shared that it’s very easy to focus on what you lack, but if we do that, we are accepting other people's frames. The truth is while we are lacking certain things, we are developing new skills all the time.
Dorie also shared the free self-assessment that is tied in the book Revinting You at www.dorieclark.com/reinvent.
Resources
- Home - Dorie Clark - Official Website
- Reinventing You: Define Your Brand, Imagine Your Future: Clark
- Entrepreneurial You: Monetize Your Expertise ... - Amazon.com
- The Long Game: How to Be a Long-Term Thinker in a Short-Term ...
In episode #20 of My 2.0, guest Sarah Brown, Senior Director Sales Enablement at Health Carousel, shares her transition from a career in counselling to entrepreneurship.
Sarah’s journey started with a Master's in counselling. She worked in juvenile corrections with a superintendent who had been there for 20 years and was very experienced. He had a very robust intervention program that she learnt a lot from. But she was burnt out and was looking to make more money. He suggested that she apply for a training manager position. She first thought she shouldn’t, since she didn’t have the skills. But he convinced her how she had already been doing this job, and so when she got the job, she loved it, and excelled in training and development. Fast forward, she now works in a healthcare system running their leadership programs including coaching their teams and executives.
Sarah always knew that she loved variety. She also got the confidence to move into a consulting role outside the organization for 15 years. And decided to open up a blow dry bar in 2015. She invested money, time, heartache, into this and two and a half years later, she closed it and it was devastating. She had really attached personal value, her self worth to the success of the business. And she was embarrassed that people will attribute her to the failed business. At that time, she decided that she was going to separate her self-worth from what she did professionally.
When I asked her for tips on how to solve this problem, she said to start with being aware of the issue. And to take the time to notice triggers, to pause, to reflect on what drives us to feel positive or negative. She also feels that the universe has a great way of redirecting us when we are not in the right space.
Sarah’s biggest challenges during her transitions were the self-limiting beliefs in her head. And the irony that no one cared. If anything, people were envious of her ability to pivot and rebrand herself.
Sarah’s most recent endeavor is 0.0 Living, which helps people reset their relationship with alcohol. And that could look like containment, abstinence or anything else in between. This comes from a personal struggle Sarah had with alcohol and one she saw manifesting with a lot of people during the pandemic.
She created the Failing Forward podcast so she could touch people with inspiring stories of failures that people learn from, and change from. It started with being local for Cincinatians but just this January, Sarah took the podcast global, telling and sharing stories all around the world.
In debunking transition myths, Sarah thinks that we need to understand the value of our transferable skills, and articulate them into the new/next job. And to understand the importance of EQ and not just rely on IQ.
The advice she would give your pre-transition self is to bloom where you're planted, stay planted as long as you can. And move to a new location when you’re ready.
Sarah then asked me a question about what gifts the podcast has given me. To which I said it connected me to many women I learned from, that I would not have met otherwise. And it teaches me to be a more empathic and curious listener.
Resources:
- Failing Forward Podcast
In episode #19 of My 2.0, guest Bea Wray, Author and Keynote Speaker, shares her transition from a career as an entrepreneur to an author.
She grew up always knowing that she’d be a psychology major and a psychology researcher. And she went to college for psychology and even did an honors thesis and was on a path to do research and hopefully eventually go to graduate school. But while she presented her thesis, expecting to fail, given it wasn’t statistically conclusive, she was shocked to receive the highest honors. Her own reaction to that was to find another career. And so she went into business, starting and leading many successful companies.
When I asked her how she compared her career with her father’s 30 year career at Ford, she said she has worked with entrepreneurs and startups. She understands imperfections and chaos and problem solving in a way which is different from people working in large corporations.
Bea’s advice to her pre-transition self is for people to always be open and true to themselves. And to be aware of your surroundings and what you want out of life and use all the incredible opportunities that come our way.
Some of the transition myths Bea would like to debunk are that career transitions cannot be done and that the next thing may not be better. She talks about our career being a three-legged stool; each leg representing industry, position and geography. And that we should never try to change all at once.
When I asked what led Bea to write the book, she mentioned that after selling the company, she took six years off spending time with her family. And when she went back to the workplace, she felt intimidated with very low confidence. And she realized she kept receiving thanks and compliments for helping people and when she reflected about her innate skills, she realized all her skills from business schools were honed by her kids. It included empathy, communication and negotiation. And that was making a difference.And one thing led to another and she started writing about it and I published a little article in entrepreneur.com. So at some point she knew a book would come out.
As she lost her confidence and was trying to figure out the next point in her career, she asks us to never let not having confidence get in our way. And if there is something we want to try or do, we owe it to ourselves to try.
She offers her advice on negotiation skills using the BATNA principal they use at HBS; the best alternative to a negotiated agreement. She explains how she has never looked for just one job, but multiple ones at a time.
Her thoughts on whether children should be allowed to fail were that being an entrepreneur, she understands the importance of establishing a culture of failure so it allows for risk taking. Which is similar to our career transitions. Taking that to parenting, we want our children to not have to be perfect, and to accept failure.
Resources.
- What an MBA taught me..but my kids made me learn
In episode #18 of My 2.0, guest Nancy Payne, Entrepreneur in Residence at WeWork Labs, shares her transition from a career in new and media to entrepreneurship.
Nancy’s life has been a lifelong series of transitions. She had an early start in news media, working in multiple firms and then moved over to a small government agency working on global development and social impact. Moving on to become the COO of a non profit that used technology for peace building. She took a break 2 years ago to travel the world with her husband coming back to become a mentor to early stage entrepreneurs and to volunteer.
In Nancy’s opinion, careers are not linear and neither are career transitions. Her life and life decisions prompted her transitions. The change from corporate to a government agency was not as radical because the agency was small and run more like a company and also served the private sector. The move to non-profit was definitely different, since there was no longer a focus on profit but more on the mission.
She has been fortunate to build on current skills, starting with writing and communications pretty early on. Moving on to managing; people, time, projects, way of thinking and doing.
Nancy feels it’s easy to feel stuck. She feels so in her current transition and the reason is the struggle between competing ideas to fully immerse herself in a role as opposed to continuing to find time for new and interesting roles including volunteering. She also feels that feeling stuck in her late stage career is different from what one might feel in early stages of career.
She also talks about her identity shift. From being a Mom to have a clear and defining title. To one where she no longer has as definitive a title as she had in the past. And how it’s taken her about 6 months to be OK with the new shift.
The transition myths Nancy would like to debunk are:
- You have to know what’s next. This seems to be a common assumption, though she doesn’t think that we always need to.
- Transitions are really hard or easy. She thinks they are generally neither.
Her advice to pre transition self. Is to follow the V, like one does in river rafting. It leads you downstream riding currents and keeping you out of trouble!
Her recommendation in encouraging female entrepreneurs is to reward their curiosity. And to make sure they know it’s great to ask questions and pursue different lines of thinking.
She wanted to share her notable failure, and what she learned from it. She thinks she was more focussed on what she wanted to get to, rather than enjoying the journey.
Resources:
- VIA Character
- Practice What You Preach
- Technical.ly
- Michelle Obama’s podcast
In episode #17 of My 2.0, guest Judy Robinett, Founder of Crack The Funding Code, shares her career transition from social work to a power connector.
Judy calls her career transitions ‘one mistake after another’. She went to college for a Physcology degree and became a social worker after. She transitioned to getting her masters in Economics and started figuring out that she was good at business. Working in Fortune 500, she felt nausea on Sunday nights thinking about going to work on Mondays. After more explorations and reflections, Judy decided to start her own business running a franchise restaurant for 8 years. She maintains that the important thing is to do the hard work. We will hit a wall, but will also figure out a way over it, under it, around it, since there’s always a way.
After selling the restaurant, a friend asked for advice for a biotech company that was broke and in litigation. After she helped them with their challenges, she was asked to be a CEO. She struggled internally with questioning her own competence in being the CEO of a public company but worked through that challenge to successfully raise money and turned it into a success. She thinks that the next level will bring the next devil and as Tony Robbins says, a Golaitah shows up every time but it’s up to us - whether we’re going to get a sling and a rock or run away.
Additional questions for Judy.
- What helps us get through current challenges and be ready for the next one?
In Judy's opinion, asking people for help, and knowing where to find the right people in the right rooms is what helps us get through current challenges and be ready for the next one. She also believes in the right mentors and to always be learning. We should be asking people the three golden questions; How can we help them, what other ideas they have for us and who else they think we can talk to.
- What causes us to break out of our comfort zone?
We should think through all our preconceived notions and assumptions of difficulties. To solicit as much help as we can, to ask for training when we need it. And to understand that if we don’t get out of our comfort zone, we’re stuck.
- Her advice to pre transition self.
To kick fear to the curb. To avail all opportunities and use all the information and ideas we have and are surrounded with. To get into the right rooms with the right people to ask the right questions.
- What led her to write ‘How to be a power connector’?
Judy wanted to write a book about funding businesses. When her agent discovered the types of people she knew, she asked Judy to write a book on networking. And Judy wrote this book to help people like her, shy and unsure. To turn each stumbling block into a stepping stone that makes us stronger, and puts steel up her spine.
- How can women use wisdom through the book in their career transitions?
This book will help us evaluate our current network, and build it out, including helping us find people smarter than ourselves and in different walks of life.
- What led you to write ‘Crack the funding code’?
Judy didn’t want to write another book. But the more people she talked to, she realized how critical and pervasive the problem of funding for startups was. And so through this book, she intends to provide founders the wisdom and resources to show them the right rooms with the right people that can help them with their funding problem.
- How do we make sure we get more women to the starting line of entrepreneurship, and find funding for their businesses?
Judy’s advice is to take baby steps, networking one person at a time. And to leverage resources like the
In episode #16 of My 2.0, guest Kristy Wallance, CEO of the Ellevate Network, shares her transition from a career in finance and investing to running a networking platform.
Ellevate network is the largest coalition of professional women in all career stages committed to succeeding in the workplace and the world and in lifting communities around us. They have experienced many changes due to COVID. They had hyper local communities and squads which were online peer mentoring groups, with a large opportunity in the middle of both these types of groups. So they introduced weekly executive round tables talking about relevant topics and taking it back to homes and workplaces.
Networking is traditionally a dirty word, and people use it transactionally only when they need to. Women, in particular, don’t invest enough in it. But what we miss out on is timely and intentional relationships. Just like we value our personal networks, we need to value our professional relationships to create that bench of thought partners who can help solve not just the business partners of today, but become a part of our life-long career journeys.
Kristy also hosts the Ellevate podcast. She loved internalizing and learning from other experiences, and improving her own listening skills.
Krist graduated as an English and Sociology major and went into investment banking. But soon realized that Corporate was not the right place. She quickly moved on to startups, in sales eventually leading revenue operations. She was eventually asked to grow her business globally but was pregnant with her first child and felt overwhelmed. She was working long hours and didn’t see a way forward. She took a break to travel and connect with different people, cultures and places, looking for inspiration and creativity. She did a listening tour and eventually moved into a health and wellness startup. Soon after, she met Allie MacDonald who was the founder of 85 Broads, and who introduced Kristy to the Ellevate Network. Kristy’s interest was piqued and within a couple of days, she moved on to her new position at the Ellevate Network.
She believes that we need to explore, to connect with our community to help us realize our vision.
Her advice to those who want to explore stepping back to explore career transitions is to ensure financial stability and to make space to explore options for the next transition. She personally regrets the fact she did not make that time and space for herself. And seemed in a rush to get back to the comfort of a professional identity. She asks us to not be embarrassed but instead to be curious and patient.
Kristy’s rituals and habits for not feeling stuck are to determine our key activities and do them in the most productive time in the day, and to make that a bit. She also likes to keep a list of people that she likes to keep in touch with, and to check in with periodically.
Her pre-transition advice to herself is to not be hard on ourselves, and to identify the things we want to do/enjoy that are separate from our professional lives. .
And in order to embrace our career transitions, she does a quarterly check with herself to see if she is happy in all her roles and is fulfilling her expectations. She also is curious and aware of all the opportunities that are being presented to her.
In episode #15 of My 2.0, guest Seema Alexander, Founder and Chief Strategy Officer of Disruptive.CEO and Creator of the U.N.I.Q.U.E Method shares her career transition from the corporate world into entrepreneurship.
Seema grew up in a small business environment, since her parents ran the first Indian vegetarian restaurant in the DC area. She started working there when she was 12. But her experiences from that time took her away from entrepreneurship, and into the Brand and Business Strategy world in NYC.
She worked at Prudential for 13 years in 5 of their businesses, including in their historical rebranding effort—where she learned the importance of how repositioning your brand can be a huge lever in growth.
Over time, she didn’t feel authentic in corporate America. And as she experienced her first pulmonary embolism at age 36, she came to a mid-life awakening for the desire to go back to entrepreneurship.
She had been helping a client on the side for a while, who then asked her to join him full time. She got pregnant with her second child, took an extended maternity leave so she could explore her entrepreneurial options deeper and never looked back.
Seema is very passionate about amplifying the businesses and brands she believes in.
In debunking transition myths, Seema points out that entrepreneurship has its freedom because you are able to work on things you love. However, it takes time to build a reputation and more importantly—a profitable business—and you will make mistakes along the way. You will feel financial constraints, have moments of overwhelm, and second guess yourself (as impostor syndrome is real).
That’s why it is really important to surround yourself with people who believe in you, in your vision—because not everyone will understand your move from stability to instability to follow your passion and dreams.
Additional questions I asked Seema.
- What were the challenges she experienced through her clients?
- She said it was the process of discovery of the ideal client, the founder’s passion, conviction in their expertise and in understanding what the market wants.
- Why did she pick the name Disruptive.CEO? Do we have disruption porn like failure porn?
- She thought people like to reimagine the future and hence the name. She acknowledges that disruption gets used a lot but a lot of times it is what is required to reposition to grow and to become better.
- What do you know now that you didn’t before you started your business?
- She understands the value of self care, and how it contributes to major personal growth.
In episode #14 of My 2.0, guest Anita Moorthy, CEO and Founder of The European Startup Show, shares her transition from being a computer engineer to product marketing and podcasting.
Anita has experienced several transitions in her life, starting from when she was studying computer engineering at the University of Waterloo, working in their coop programs when she realized at the end of her term that she really didn’t want to become a programmer but instead chose to become an IT consultant, focussing on the bigger picture in business. She wanted to understand the power of IT as an enabler melding it with business.
In her second transition, she started a company in Boston focussing on doctors and nurses, and how they could use technology as a platform to be more savvy with information from consumers. She took on product development as her responsibility and enjoyed building a business so much that she went on to pursue her MBA at the Sloan school of Management. She then moved on to Siebel as a product manager, where she was the CEO of her product, managing all aspects of it, bringing together business, management and engineering. And it was when she realized her passion to be the go-to-market aspect of a product. In her personal life, she experienced a lot of transitions by virtue of her husband moving across the globe for his career.
Anita feels that the way to find out what we’re going to be good at is by moving through a series of experiments. To understand and embrace curiosity about people, cultures and the unknown. To tap into what is accessible and leverage that to build current or new skills.
For any new careers we transition to, she does not feel that we need to have the full skill set for our new career. But that we build on the core skills, using self learning, and by learning through our network, and subject matter experts.
She started her podcast as she was transitioning from her last company and learning a few new things about herself - how she learns and communicated. And as the pandemic struck the world, and she immersed herself in the world of podcasts, she realized there wasn’t a podcast based on startups in Europe. And hence the birth of her show!
Her advice to her pre-transition self is to grow and learn in every aspect of the job and not take it so seriously. To enjoy the journey and not just the goal. To reflect on the growth and not be stocks in the weeds.
Her transitions have always been supported by people, her family, her husband and her network.
To be better prepared for future transitions, it’s best to have an idea of what we are good at and what we would like to be good at. And of not being afraid but have the confidence of doing new things successfully.
As for encouraging entrepreneurship in girls and women, she feels the US does a great job at providing the right opportunities, rewarding both successes and failures and building a culture of risk tolerance. She also thinks we should encourage our children to solve abstract problems so they are viewed as fun and not fearful.
She thinks her experience of living in so many countries around the world has made her personality and experiences more complex and richer. While she does not have roots that people have when living in the same place for a long time, she wouldn’t trade her rich experiences for it!
Resources:
- Managing Oneself
In episode #13 of My 2.0, guest Diana YK Chan, Founder and CEO of My Marketability, shares her transition from a career as a consultant to career coach.
Diana experienced multiple pivots along her career path. She started with a rotation program in operations, training, marketing. And eventually pushed to get her MBA and landed a top job as a management consultant. She wasn’t too happy though, with crazy hours, and a feeling that something was missing and that she was a failure. She went on a soul searching journey, including walking on fire! She gained clarity that she was meant to become a speaker, trainer and coach. As she moved into recruiting, she understood it as being one step closer to the dream job. And then she found herself let go of, two months before her wedding. She had been planning to start her own business but that timeline came sooner. She felt like she was an emotional roller coaster, with a feeling of shame that she wasn’t good enough. But the fire in her caught spark and she decided to start her business in a week. And was hired by Google Canada later that month.
Diana talks about the challenges during career transition. She struggled with whether she was doing what she was meant to do. With her career identity and with fitting in.
Her advice to her pre-transition self is to trust yourself. To trust our intuition, to follow our heart and our gut. Even if we don’t know what it is, we should search for it. She feels very grateful for all her career transition experiences since they help her guide her clients.
Some transition myths she would like to debunk are.
- Do we have to start from the bottom?
- Are we going to make less money?
- Do we have enough experience to make the change?
I also talked to Diana about her coaching practice on the topics below.
- Discover our greatness.
Most people are not comfortable talking about their greatness, and in claiming it. We should recognize, believe and convey our value. Diana uses her D.I.S.C.O.V.E.R framework to help clients identify their core values.
- Branding and women.
Diana feels her female clients can lack the confidence required to recognize and own their greatness. She believes that when we start recognizing our own value and appreciating our own value, we are actually being of greater service to the world.
- How does one know when it’s time to stop doing, even at the cost of failure. What are the next steps?
Diana says that deciding is the hardest part. Most people say they wish they’d done it sooner. We need to get clear on where we are going after, including mapping out the vision. And if that vision is clear enough, we will naturally start attracting the right opportunities.
- How do we future proof our career?
We need to be the CEO of our career. We can control how we feel, think and decide on what skills are required. And get comfortable with being uncomfortable.
In episode #12 of My 2.0, guest Jessi Hempel, Host of the Hello Monday podcast and Senior Editor at Large at LinkedIn, shares her personal transition story as well as what she has experimentally learnt through her podcast.
Jessi has wanted to be a writer since 3rd grade, and went to college to become a journalist. She wrote for Time Asia, Business Week, Fortune and Wired. She was always seeing clearly the next rung of the ladder and was able to climb it. But that started to change as she got to Conde Nast in 2018. While her position was secure, she knew the company was in financial trouble and that she was a part of a dying industry. She also knew she was at the top of her food chain and that it was time to move on.
She has always been interested in and fascinated with technology. So when LinkedIn approached her in 2018 to start their podcast, giving her all the resources, smart people and freedom to further her career, she didn’t very long to make that decision.
She does not think we need a full skill set to transition to a new career but she feels that women in particular feel the need to.
Some transition myths she would like to debunk are that there is a right time to transition. In her opinion, there is not. They should happen when they are supposed to happen. She further mentions one of her guests Bruce Feiler who thinks transitions will be lifelong, happening one every 7 years.
Below are some of the topics we talked about from a few of her episodes at Hello Monday.
Reinventing ourselves. Dorrie Clark.
- Conducting experiments/soft launching or plan B. Women don’t give themselves enough credit about hard things. Plan B with Plan A is hard but is very possible.
- Branding. Women find it hard to talk about themselves. But branding is simply featuring our differentiators contained in our personality.
Burnout. Emily and Amelia Nagosky.
- Stress and stressor. They are two different things that should be treated differently. While identifying and solving for the root cause is critical, it is equally important for us to deal with the stress as well. Especially if we can’t do anything about the stressor.
- Self care of the individual and through the community. We need to take care of ourselves individually but also responsibly lift the community around us.
Designing your life. Bill Burnett and Dave Evans.
- Circumstances/Gravity. We need to understand what we are capable of and design a life with goals we can achieve. It may feel hard and unfair, but that’s what life is.
- Separating career and passion. The notion of combining career with passion is 20th century and applicable to Gen X. But we need to be open to the fact that the two may not intersect and that it’s ok for them to diverge.
Career change. Robin Arzon.
- Discomfort in career is not the same as athletic discomfort. It seems easier to push ourselves more physically than it is intellectually.
What does it mean to have it all?
- This is also a 20th century notion to have it all. And it doesn’t work. What works is our ability to make a choice from options we have, and to feel solid in our choice.
Jessi’s question to me. What’s the one thing I didn’t know that I know now.
To which I responded that transitions are hard, take their own time and are best when planned and gradual. And we don’t need a full skill set to turn to a new career and definitely need cheerleaders along the way.
Resources:
- Hello Monday
In episode #2 of My 2.0 Archives, guest Kristina Bouweiri, the President and CEO of Reston Limousine, shares stories of her career transition. On how she embarked on a non-profit career in Somalia, transitioning into a commission-only Sales position in the US. On how she joined Reston Limousine with her then husband, and eventually took over running the company from him.
Listen in as Kristina opens about how she dealt with imposter syndrome, and her insecurities with being the only female CEO in rooms crowded with male founders and CEOs. And how she worked with a slew of business coaches in growing her ability and confidence to solve complex business problems, including becoming a master speaker, as she scaled the business exponentially. And the importance of self-care and cheerleaders, including the struggles of being a successful business woman, while being a single working mother.
In episode #1 of My 2.0 archives, guest Melissa Boatwright, a Global Insights Leader at LinkedIn, shares stories of her career transition. From the Military to the civilian world. And from communications to engineering. She talks about her journey from a small town in Wyoming into the Military, and then transitioning out into the civilian world.
Listen in as Melissa opens about how she dealt with imposter syndrome, and her work with being vulnerable, and shining the light on shame. Melissa also talks about the transition challenges experienced by a female vet, and the part we as an individual, corporate America and the society at large can play to make these transitions smoother. Melissa proposes her transition toolkit, the advice she would give her pre-transition self and what she and her partner do to be better prepared for their next transition.
In episode #11 of My 2.0, guest Lauren Maffeo, Civic Tech Service Designer at Steampunk, shares her transition from a career in content and media to design in technology.
Since high school, Lauren was focussed on an education and career in journalism, and did a major in media studies. She oriented her internships around digital news writing. As she was finishing college in a period of recession, she saw the ad spend drop from news to technology. And her options to pursue a full time career as a journalist seemed low. After completing her masters in media theory and communication in London she spent a year working as a freelancer in web reporting for startups in London. And then moved back to the US, working in a content-based company in Silicon Valley, followed by a Research Analyst position at Garneter, working on tech trends, and AI. Her most recent transition was to Steampunk involving work that focuses on human-centered design in technology.
As Lauren transitioned from media to technology, she didn’t understand all the concepts but was curious and eager to learn more. She thinks journalism has hard, immediate deadlines which are different compared to the tech world she operated in, that uses Agile methodology to deliver projects. While deadlines continue to be important, the provision of a roadmap in her technology projects allows to focus on the long view with the ability to be flexible in the short term.
Lauren’s transition was over a period of 2 years. Marketing was a natural progression from journalism but she knew she didn’t want that. She was looking to combine her user research experience with product management, including integrating feedback from the end users.
Lauren often felt stuck in her transition. And she applied to a lot of jobs, outside of her regular work hours, which seemed to be a full time job itself. She says the working world is not always honest about the time that it would take to get something that’s the right fit for you and your skill sets.
In terms of developing rituals and habits to get through transition, Lauren says she maintained the ones she already had. She made sure to get her required sleep, to continue running, long walks during lunch time.
What she found most challenging about transition is that she didn’t know how long it would take. And it took longer than she thought. She also felt she didn’t have all the skills required in the new job. But she focussed on understanding what the new job required from her, what her core skills were, and designed a path to build that bridge.
She says it would have helped to have known how long the transition would take. And while she was sure she wanted to do something different, she wasn’t going to leave for anything. She is also a strong believer of things working out the way they are supposed to.
Some common transition related myths she would like to debunk are:
- She doesn’t think transitions should happen quickly.
- And it is useful for us to learn how to now just evaluate the skills required of the new job, but also assess the culture fit in the new company.
As someone who is an example of bridging STEM with liberal arts, Lauren feels that not only is technology all-pervasive now, but also that it is no longer a niche in education but instead the combination of allows us to not use/build technology in a vacuum, and instead allows us to think the bigger picture clearer.
Resources:
- Hello Monday with Jessi Hempel
In episode #10 of My 2.0, guest Lina Zdruli, Founder and CEO of Dafero, shares her transition from being a consultant at the World Bank to becoming an entrepreneur.
With her background in international relations and focus diplomacy and small and medium enterprises from a trade perspective, she worked at the UN, merging international relations with environmental conservation. While doing her Masters at Georgetown in transatlantic relations, she learned about forced displacement and refugees. And was interested in how the private sector could support this issue for long term change. She then started working at the World Bank, doing exactly that work.
She had a very intensive travel schedule and found that she loved eating all sorts of foods all over the world but got a stomach ache every time she returned to the US. She tried to practice the elimination diet to resolve the issue, but to not avail. After one of her trips, she started baking with dates and found they were delicious and healthy. As she tried to find dates spread in the US, she discovered there wasn’t one that didn’t have any additional sugar. The need to stick to natural ingredients and yet maintain taste, gave birth to Dafero. She also tried to solve the forced displacement labor problem by using them as the workforce at Dafero.
The transition was gradual, and she didn’t realize how much what once was a weekend passion was taking over her life. She started to go deep into learning about food science, and other things about starting and running a food business. She loves combining tradition with trend and loves that her energy is flowing where her attention is.
Lina talks about feeling stuck all the time. About being covered in date explosions, burning blenders and food processors. Scaling up was hard; getting the manufacturing right for the new production levels was very hard.
Lina used the following resources to unstick. She tapped into fellow entrepreneurs. She also absorbed ideas about packaging, branding and taste from her travels and conversations around the world.
She would like to debunk the following transition myths. That one has to be 100% sure else to not do anything new. And that it will be very expensive to start a new venture.
She is very excited about the Dafero 2.0 rebrand. They are revamping the look and feel of the brand in the labeling and packaging. And making sure it represents a fun, happy, colorful and inclusive brand. They are also celebrating overcoming their manufacturing challenges as a result of scaling up.
Her last words were for us to detach ourselves from our company. Because even if the company fails, we will live on to do bigger and better things!
Resources:
- For food-business specific
- For mission-based companies
- Understanding business and human behaviour
- Marketing
- Dafero referral link
In episode #9 of My 2.0, guest Liza Rodewald, Founder and CEO of Instant Teams, shares her transition from being a computer programmer working as an employee to a 4x entrepreneur building scale.
Liza talks about loving her early career but facing challenges in being an involved mother at the same time. It was this passion, in the ability to build careers with a flexible lifestyle, that set brought out her accidental entrepreneurship. Further, as she became a military spouse, she saw the challenges that came with these qualified women not being able to secure stable jobs because of the demands of their military spouses. And how there was a potential to make this a win-win, in using this untapped and qualified pool of labor, and matching with companies who needed this talent.
She recommends having a group of mentors to guide through transitions and progressions. She learnt everything she needed to know about scaling a company from the Founder Institute, and recommends resources like that for all entrepreneurs looking to scale.
Her recommendation for encouraging entrepreneurship in girls is to invite female entrepreneurs to schools and colleges so they set a role model and are able to provide mentorship opportunities early on.
Some transition myths she would like to debunk are that we think we need a full skill set for our new job. She thinks we don’t, but that we identify our core, transferable skills, so that we can forge a path to get better skilled at the new job.
Resources:
- Founder Institute
I took a break from recording over Thanksgiving, so I could pause, reflect and just be. This is not easy for me, since my comfort zone is to drive and to do. But just like you, I have been inspired by the amazing guests who are singularly focussed on doing the right thing, even if it means getting out of their comfort zones.
And so I give my thanks to these courageous women who come forth to share their stories of inspiring career transitions. And I give my thanks to you, for giving me the opportunity to share these stories with you and to build a community of women who embrace career transitions.
We will be back to the usual programming next week!
In episode #8 of My 2.0, guest Anya Fasolyak, Founder and President of Studio Fasol, shares her transition from being a graphic designer to running her own design studio.
Anya talks about knowing the need for change given her desire to have the freedom to choose the work she wanted to do, with when she wanted to do it. She decided to share this with her boss, and they mutually agreed to a long transition so they could find the right replacement and for Anaya to hone her skills.
Anya talks about being very clear when it was time to move out. And it’s because she couldn’t stay. It was more an impulsive and emotional decision given she didn’t have a client list for her new business but that did not stop her from moving on.
She talks about how different the mind of a business owner is, from that of an employee. How the work may be the same, but the positioning, the need to know sales and marketing is paramount for a new business owner. She also credits this transition to her identity shift, and thinks it will be hard for her to go back to being an employer.
In the rituals and habits she developed, rising early, having some still self time every morning before the craziness of the work day starts was very important. She tries to meditate, do yoga as well. Not always successful but always tries!
In her recommendation for a transition toolkit are books and advisors. She understands it is hard to get the right type and number of advisors when you’re a young business owner, but she recommends being open, teachable and try hard to reach out to people.
Her advice to her pre-transition self is to know sales, to have a plan of how to build the list of potential clients.
She is passionate about encouraging girls and women to entrepreneurship. And thinks having women in business as influencers will help. Along with Shark Tank like business programs in high schools.
Her advice to her millennial peers is to not stay in unhappy jobs. But to act on the situation, to develop skill sets and opportunities that allow them to explore new career paths.
Resources:
- Pricing Design by Dan Mall
- Predictable Prospecting by Marylou Tyler and Jeremy Donovan
In episode #7 of My 2.0, guest Nan O’Connor, a Business Coach for Business Owners and Their Teams, shares her transition from running a communications company for 15 years to becoming a business coach.
Nan explains how she built a business that didn’t take into account what she loved doing. And how terrifying it was to rediscover her identity without the business. She built two separate lists, things she was really good at, and things she loved to do. And she landed on becoming a business coach, which had just started to become a thing.
Once she could visualize becoming a business coach, she executed her plan of action. Which was to take her academic training, and build a client list.
She talks about the concept of cheerleaders and their importance in the transition journey and recommends applying discernment to differentiate real from misled (yet well-intentioned) cheerleaders.
She talks about her practice of meditation, journaling and reflection causing her to be a lot more meaningful when grounded in being.
Her transition toolkit comprises imagination and vision, resilience and tenacity.
Her advice to her pre-transition self would be to believe in herself, that things will work out as long as we apply ourselves. And to have more trust in ourselves and less fear.
Some of the transition myths she debunks is that people feel like the grass is greener on the other side (of the transition). She asks us to explore that for ourselves, that it may be greener. And if it’s not, then if not, then we simply course-correct.
Resources:
- The First 90 Days
- Pivot
- Clocking Out
In episode #6 of My 2.0, guest Jenn Stofferahn, Vice President and Co-owner of TFN Training shares her transition from major gifts fundraising in the non profit world to barbells, strength training and personal training. While her transition may have been facilitated by meeting her future husband, who was an established expert in the powerlifting space, she had been ready for a transition. She negotiated with her then employer to work part time, while she went to fitness school to study the science and hone her skills.
Jenn draws the similarities between her two careers in how they both require to build deep, personal relationships. With a long view on end goals. And how they both require creativity and flexibility to stay in step with the client and their goals.
She talks about the uncertainty that comes with transition, and how, if possible, we want to make sure the other people and things in our ecosystem remain stable as we journey through our transition.
The challenges she experienced with transition with feeling the imposter syndrome. And struggling with the chicken and egg situation of experience v/s skills gap. And she advises we bridge that gap through self-confidence.
She goes on to debunks common transition myths that:
- We need to have a complete skill set for the transitioning domain. She describes that as a chicken and egg situation that we bridge using our self-confidence.
- Certain domains are more women-friendly than the others. She went from a traditionally male-dominated field to a male-dominated one.
Resources:
- “3D Muscle Journey”
- “TFN Training”
- ““Everyone Should Lift Weights” By Elliot White
- “Start With Why” By Simon Sinek
In episode #5 of My 2.0, guest Kim Weinberg, Founder of Coach In Motion LLC, talks about her linear career path, when she forced her college to ‘create’ her major in ‘Organized Communication’, a passion she discovered there. That set her off on a path in HR, starting with training, moving to Organization Development and finally finding her juiciest spot yet - YPO forum facilitation.
She loves working with people to uncover and resolve what causes them to be stuck. She describes it as flatlining, experiencing pain of being cooked like a frog in the pot. And that if we don’t want to suffer that fate, we want to pay attention to our itches.
She recommends starting by making sure we know our core values. Then asking the hard questions as we explore what brings us joy, what we are good at and what we can make money in. Keeping in mind the long game of life, and breaking our goals into byte sized journeys.
She is a proponent of having a coach, whether formal or informal. Someone who knows our core values, potential and blinds spots. And is a non-judgemental partner every step of the way.
She talks about the importance of the morning ritual. For her it’s hot water with lemon, stretching, meditation. It’s taking in the quiet that she won’t get once she hits the day running.
She also talks about the importance of mantras. They are the guiding start as we form new habits and rituals and keep us on track.
Her recipe for a successful transition path is to:
- Know our core values
- Live by our core values
- Design and implement supporting rituals
- Have a team of people who support you on the journey
Resources:
- “From Psychological Safety To Organizational Performance” By Amy Edmondson
- “Working Identity: Unconventional Strategies for Reinventing Your Career” By Herman Ibarra
- “Start with Why: How Great Leaders Inspire Everyone to Take Action” By Simon Sinek
- “What Color Is Your Parachute? 2020: A Practical Manual for Job-Hunters and Career-Changers” by Richard N. Bolles
- "So Good They Can't Ignore You" by Cal Newport
In episode #4 of My 2.0, guest Melissa Qazi, Associate Director, Healthcare Professions and Emerging Markets at Kaplan talks about a year long process while at medical school, where she questioned her prescribed path to becoming a practicing physician. On what seemed like a long year of being alone with her guilt and self-doubt questions and the clarity of purpose that came to her through intense work on her personal development and unwavering support from her friends and family.
She talks about the importance of clarity of purpose that helped her find her new domain, to explain her new career path to others. And the importance of her supporting ecosystem that helped her find her new calling in healthcare education and product management.
She goes on to debunks common transition myths that:
- We need to have a complete skill set for the transitioning domain. Instead, she feels we need to be clear about the why, and use it to build a clear narrative on the relatedness of the transitioning domain.
- That we need to have existing relationships in the new domain. She thinks given how intricately socially connected we already are, we simply need to build a relatedness with person(s) in the new domain.
Her recommended toolkits for transition are:
- Support system that allows us to share our thoughts and questions without fear of shame or judgement
- A forum/channel for personal development work
- A morning ritual focussed on the whole personal development
Resources:
- “The Landmark Forum”
- “The Miracle Morning”
- ““Reinventing You” by Dorie Clark”
In episode #3 of My 2.0, guest Aurelia Flores, Managing Member at Athena Digital Media Group, shares stories of her career transition. From a successful corporate attorney for nearly 20 years, to an entrepreneur, as she fulfilled her lifelong dream of running her own business. She found her passion and calling when she started playing with the digital marketing media world on the side. And the transition was propelled by the birth of her daughter, and Aurelia’s desire to seek more freedom and flexibility with her time. It did not take the risks away from her, being the sole provider of her family. But she was determined to take this chance on herself, for her own personal growth.
Listen to Aurelia talk about the importance of a sound financial cushion, a full sales and marketing pipeline and a strong cheerleading network as the must-haves for making career transitions.
She describes the trials and tribulations of being an entrepreneur; that you are in a constant push-pull with your self in being an optimist and a realist. From being the chief cook to the bottle-washer! And how the process makes you humbler, wiser and instills more confidence in yourself.
She ends with debunking these transition myths:
- I could never do that (career transition)
- It’s easier to stay (in current career)
Resources:
- “Designing Your Life: How to Build a Well-Lived, Joyful Life By Bill Burnett and Dave Evans”
- “Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones By James Clear”
- Citrine Angels: Angel Investing for Women by Women
- Pipeline Angels: Creating Capital for Women and Non-binary Femme Social Entrepreneurs
In episode #2 of My 2.0, guest Kristina Bouweiri, the President and CEO of Reston Limousine, shares stories of her career transition. On how she embarked on a non-profit career in Somalia, transitioning into a commission-only Sales position in the US. On how she joined Reston Limousine with her then husband, and eventually took over running the company from him.
Listen in as Kristina opens about how she dealt with imposter syndrome, and her insecurities with being the only female CEO in rooms crowded with male founders and CEOs. And how she worked with a slew of business coaches in growing her ability and confidence to solve complex business problems, including becoming a master speaker, as she scaled the business exponentially. And the importance of self-care and cheerleaders, including the struggles of being a successful business woman, while being a single working mother.
In episode #1 of My 2.0, guest Melissa Boatwright, a Global Insights Leader at LinkedIn, shares stories of her career transition. From the Military to the civilian world. And from communications to engineering. She talks about her journey from a small town in Wyoming into the Military, and then transitioning out into the civilian world.
Listen in as Melissa opens about how she dealt with imposter syndrome, and her work with being vulnerable, and shining the light on shame. Melissa also talks about the transition challenges experienced by a female vet, and the part we as an individual, corporate America and the society at large can play to make these transitions smoother. Melissa proposes her transition toolkit, the advice she would give her pre-transition self and what she and her partner do to be better prepared for their next transition.