Justin's Podcast: Recent Episodes
Justin Harter
A semi-regular review of the books Justin’s read, writing, and other musings. Sadly, another white guy with a podcast.
David Brooks calls it the “second mountain”, I call it “struggling with above average mediocrity in lieu of a mid-life crisis.” As my generation ages into their 30s and 40s, there’s a struggle — particularly among men — of how to deal with being “merely average”. I think it’s slightly worse recognizing you might be “slightly above average” in many things, but still not good enough to be great at anything.
Transcriptions for this episode are generated by automatically AI. A copy of the transcript follows.
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It’s probably no surprise that as people get older they tend to question their averageness, right?
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Sometimes I think about all of the people who have ever lived in the history of the world, in the history of civilization,
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and thinking about all of the things that most people did day to day that are completely forgotten.
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There are a handful of people that maintain sort of a vaulted status in our society.
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And a lot of them are the kinds of people that you would expect.
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Titans of industry like the Rockefellers or great rulers or great military leaders like Napoleon and that sort of thing.
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Queens, Cleopatra for example.
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But there are so many people who even get to positions similar to that
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Like there are plenty of presidents that most people have really never heard of or have almost no information about
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And I think about that and it sometimes depresses me a lot that there’s this
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lack of longevity to a person’s life and
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I think that I think about that more
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precisely because I
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Don’t have kids
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I’m probably not going to have kids if I do have kids. It’s almost certainly not going to be biological and
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as a result of my being an only child
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there’s something that bothers me about
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the fact that
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I’m the end of the line for this branch of this tree and
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genealogists would tell you that trees are very complicated and that branches
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have all sorts of sub branches and other things and that this doesn’t mean that this is sort of the end of
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the gene pool of my descendants are
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But at the same time it doesn’t feel great
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and I think about this too from
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An early age of my academics, right? Like I was always
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above average
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But I was never the top of my class. I was never the very top of my class. I was never
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the best at
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anything, except maybe, you know, here and there, maybe in elementary school, you know,
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I was the first kid in my third grade class to complete my multiplication tables.
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Whoop-de-doo, right?
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At the same time, I was 10th, or no, excuse me, 11th place in my fifth grade spelling
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bee.
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And so I feel like most of my life has been shockingly average, but only slightly above
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average.
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about how some people overcome this, right? David Letterman famously always had a scholarship that
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was offered to students at his alma mater at Ball State that was awarded only to a communication
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student, which he was, but also the most C average communication student because he himself was
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almost a straight C average student. And I don’t know that there’s a way that a person can overcome
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that, right? Like I feel like people can master certain things and we know a lot about mastery
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of topics or subjects or activities like athletics for example, or learning how to play an instrument.
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But it’s also true that a lot of people just don’t have quite what it takes for one reason
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or another, right? That, you know, to be a Michael Phelps-level swimmer requires that
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you have a wingspan like Michael Phelps, right? He has a biological advantage. And we can
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argue whether that’s fair or not, and I think a lot of people would argue that the equity
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of that is unfair, and inherently we should just sort of do something about that. I’m
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not one of those people. I tend not to think that it’s inherently unfair that some people
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have more money than me or that I have more money than other people or that some people
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are more physically attuned to certain things better than me than not.
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I think that the world has to recognize that sometimes there’s just luck, right place,
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right time, biological factors, economic factors, placement of things that just are in so many
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ways unfair but just the way they are.
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And as I’ve gotten older and I’ve gotten to a part of my life where I start working professionally
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with people, for a long time, for many years over the last six, seven, eight years, it
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has been really hard for me to think about how to make websites better, right?
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I make websites for a living.
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Now I sort of consult a little bit in a different capacity and I write for websites in various
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ways.
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And I don’t know how to make them
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World class right like I don’t I don’t I don’t know how to make them
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excel I can only seem to do about as well as
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It’s not budget right like
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There are some things in this world that no amount of money will make a big deal right you can’t take a small client or an author
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or an organization or something and
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and make them into a big deal globally known
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simply by virtue of a great website, right?
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There are so many other factors in that,
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including the team that they have in place
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and sort of the work that they do
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and where they do it and the geography of that.
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And that reminds me of this notion that Aaron Ren has,
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who’s a writer and podcaster here in Indy,
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where he talks about superstar cities, right?
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Where that there are places in the world like the London and New York and
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Hollywood and L.A. of the world where people there are just better, right?
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Not all of them, but that superstars in their fields will go to these places
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and just sort of be elevated to new heights.
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And I don’t know that a person can reasonably do that
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from within the confines of most other cities.
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Certainly every city has their celebrity du jour.
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Indianapolis likes to hang its hat next to Kurt Vonnegut,
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as well as others, Dave Letterman being another.
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But I don’t know that that works for everyone.
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I don’t think that a person in my position
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that a website consultant can sort of become
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a world-class website designer, developer, consultant, writer,
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whatever, but even being here or by being any place outside of some major agencies that
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have already attracted talented organizations and clients that they themselves are already
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a big deal.
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You think about Mad Men, for example, and Don Draper starts talking about Mohawk Airlines
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in this, which was a small airline for, and so as a small ad agency, they got this small
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airline having an airline was the big deal.
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And the famous quip in there was that we don’t need a big airline
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because we’re going to make Mohawk Airlines a big airline.
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And did they know?
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Is it possible to do that?
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Maybe it is somebody
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capable in sort of that anti-heroic way like Don Draper is to be able to elevate
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something like Mohawk Airlines into something from nothing.
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Maybe, but probably not.
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And again, it’s coming to terms with the luck and the randomness of it
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and recognizing that not every client can light the world on fire,
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that not every organization can light the world on fire.
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Not every person can light the world on fire.
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And therefore, there’s just a level of mediocrity and average
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that you just have to come to accept in life.
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And that’s really hard to do.
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And I don’t know that I know how to do that quite yet.
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I think about success inflation, right?
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Where there’s this notion that obviously
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if a person was successful that they need
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to have more success and whether they measure that
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in dollars or whatever is somewhat irrelevant.
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Although I would argue that money is a neutral indicator
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of value by and large.
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And so if a person is giving a person more money,
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then therefore they’re producing more success or more results, right?
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And I know lots of people can take lots of quibbles with that,
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but by and large, that’s a pretty good indicator, right?
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Like we’ve got a pretty good system in place in the United States
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to be able to sort of finagle that and figure that out.
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And that having one thing leads to wanting something else
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and leads to sort of a snowball effect of success.
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And some might argue that that’s a bad thing.
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And I don’t know that it’s necessarily a bad thing.
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I don’t think it’s a bad thing to always be reaching
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for the stars, right? You know, we think about just human navigation, right? That humans crawled out of a cave and
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we walked across the prairie and then we walked across the mountains and then we walked across
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the landmass and then
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we sailed across the ocean and then we made
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machines to do all these things faster and then we took to the skies and then we took to space and we landed on the moon
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And the next step is Mars, right?
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And so why do we have to go to Mars?
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Because it’s next.
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Because it’s the thing.
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We walked out of the cave and we saw where we could go.
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And so Mars is just next.
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And I don’t think that squashing that ambition
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is good for anybody.
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I don’t think it’s good for a nation.
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I don’t think it’s good for society.
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I don’t think it’s good for humanity.
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And so why would we do that and pigeonhole ourselves
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into those sorts of things?
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Why wouldn’t we always be wanting to reach
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for the next thing?
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Why is it not good to always be thinking about what’s next?
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What’s the best next thing that I can do?
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I think a lot of people look at that
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and they feel that this is sort of the rat race
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sort of a thing where you climb the corporate ladder
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and it’s all just sort of bleak and miserable or whatever.
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And maybe that is.
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It’s not a bad thing that some people don’t wanna do that.
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I don’t wanna do some of that stuff, right?
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I don’t want to climb a corporate ladder
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and become a big executive vice president or whatever,
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at some big corporation.
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But at the same time, I don’t think it’s a bad thing
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to be thinking about how to make things better,
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how to make my life better, how to earn more money,
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how to do it sustainably,
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how to live a more comfortable life,
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how to be more efficient and productive,
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and how to produce things that people care about
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and write things that people want to read
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and produce things that people want to watch
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or listen to or whatever.
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I don’t think that’s a bad thing.
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And so success inflation can be good fuel for that.
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And by that rationale, you get back to this notion
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of superstar cities.
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And so if you live like me in a place like Indianapolis,
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by default, shouldn’t I want to move someplace else
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in order to be able to produce things that are better,
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to be able to be in an environment
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or in a community or a location
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that just has more built-in success to it
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by some virtue or by some rationale, right?
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Or by just being a slightly nicer place to live, right?
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That it could be some place that just has weather
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that you like more or that it’s some place that’s just
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more visually beautiful.
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Because I don’t think anybody would describe Indianapolis
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as a beautiful city.
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I don’t think it’s the worst, but I don’t think it’s the best,
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right?
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And so success inflation would dictate
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that we just kind of have to keep moving forward in a way that pursues something better.
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And Thomas Jefferson put that right there in the founding of the country, right there
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in the Declaration, right there in the pursuit of happiness, right?
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And all of this could come down to me having a midlife crisis, right?
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that there is stress over being merely average,
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that there is stress at being maybe even above average
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in some things and not being the best person on the planet
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at some thing.
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And I have given a lot of thought over the years
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about what is something that I can do
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that I can be the best person on the planet at doing.
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And I don’t know that there is an answer to that
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because we have an answer to that
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for so many other things, right?
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have an answer to who is the best swimmer on the planet, who is the best golfer, who
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is the best speller, who is the richest man, who is the richest woman, who is the best
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person at any number of things.
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And you can probably come down to somebody, even like who makes the best pizza, right?
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There are Netflix specials about this, about who makes the best kind of margarita pizza,
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or who makes the best pizza crust, or the best pizza sauce.
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Amazon even has lists of all these different things, right?
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If you write a book or produce something that gets into the Amazon store, there are so many
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categories and subcategories of best sci-fi thriller with leading female characters, right?
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Or best such and such with this other subcategory defined by the weather, right?
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And so it’s almost impossible not to become a bestseller in some subcategory someplace.
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And so I’m always thinking about how to get to that spot, how to become the best, most
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recognized known person about some thing.
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And I don’t know that a lot of guys would talk about it, certainly not men.
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I think it probably also impacts women, but I think it certainly impacts men, particularly
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in their 30s and 40s, where they start recognizing that maybe the peaks of things have come,
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right?
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no more mountain to climb, right? David Brooks talks about this in life as being sort of
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the second mountain, right? That the first mountain is sort of education, job, family,
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and that the second mountain is what happens as you climb what you… The second mountain
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is what you do after you’ve sort of raised your family and you’ve, you know, peaked in
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your career in some fashion and that now you start sitting around and looking at what is
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next, right? And it’s not retirement, it’s the thing that happens in midlife right before
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retirement, that second mountain of being able to have connection and community and
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a sense of belonging and purpose and place. And that the second mountain is so much harder
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than the first because the first is so well defined, right? It’s very obvious that you
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go from high school into a college or some sort of career path, maybe the military even,
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an apprenticeship, that the learning paths are very step stone oriented.
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But the second mountain is just this giant thing that you have to scale and you have
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to sort of define your own toe holds along the way.
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And then when you get to the top of it, how do you know that you’re even at the top?
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Because the second mountain, unlike the first where there’s gradations of things like top
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of the class by grades or top of the performance by sales or whatever, the second mountain
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doesn’t have that.
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And so as a guy in his mid-30s, I’m starting to look at this second mountain in my life
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and I’m starting to think about the averageness of things and trying to come to terms and
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being comfortable with that.
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And I don’t have any sage advice for it.
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I don’t have good opinions about any of this yet.
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I don’t even know how to feel about that yet.
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Because I also recognize that for a lot of people,
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that this is the time of their life
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when they actually have a little bit of money
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to be able to do some things
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and they have a little more flexibility
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and that things kind of free up in ways
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that they never had opportunities to free up before.
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And that enables them to accomplish great things.
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And so I can only hope that I have great things
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that are ahead of me.
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But I worry about it a lot.
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It takes up a lot of space in my brain
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to think about this sense of malaise,
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that I could die and that the only thing left behind
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would be some things that I owned
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that would all be distributed to who knows where,
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hither and thither, and that would be it.
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I even think about sometimes recognizing
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I’ve always thought that I wanted to be cremated when I die, but then recognizing that most people
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who are cremated don’t have headstones, and that headstones are at least this long-lasting marker
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of a person’s presence on this earth, and that yes, it too will crumble and fall away given,
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you know, a billion years or whatever. But not having even that strikes me as troublesome in
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my mind, which is kind of a bleak and depressing thing.
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I recognize that.
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People who are older than me may tell me that they themselves continue to fight with this
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problem.
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People may tell me that people get over it.
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Maybe it impacts some people more than others.
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I really don’t know.
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This is sort of where I am in my life and I recognize at least to the extent that everyone
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else probably also has these same questions and quandaries and problems and also don’t
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know what to do about it.
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And I don’t know what to do about it either.
After dedicating nearly my entire career to the endeavor of growing a business and counting on the talents of so many people over the years, I sold a business in 2020. But no one ever tells you how you’re supposed to feel or what to do, look for, or figure out in the lead-up to that process. So much of selling a small business boils down to, “Well, you look like you have money.” Here’s what I learned.
Transcriptions for this episode are generated by automatically AI. A copy of the transcript follows.
Every time I told somebody I was selling my business, they would say, “Congratulations!” And I would think, “What are you talking about?” I just screwed everything all up. Nobody ever tells you how you’re supposed to feel when you sell a business. Because from the time I started my freelance business, which in earnest sort of started in the blink. I don’t know, 2003-ish, 2004.
I grew that business steadily for literally my entire career. And it was a hard-fought thing. I didn’t never have money for large advertising schemes or grand marketing plans or whatever, which is ironic considering I ran a website design and developed as a marketing advertising agency.
But I did it one client at a time, doing it the way that people who have been doing it for a long time will tell you is the best way to grow a business, which is that you just provide a really good product or service, and the rest should just sort of take care of itself. I still sort of believe that, but that’s not entirely true, of course, advertising certainly makes things go a lot faster, and if you have the money to be able to do that, you can sort of turn that success dial up a lot faster.
From my experience, though, I had been putting everything into this business, and particularly around 2009, or excuse me 2007 rather, when I really started in earnest, there was a time when I made the commitment to leave what was then my full-time job that had benefits and steady salary and start this business. And I think that year that I made something like $7,500. I think actually my tax returns that you reported something in the neighborhood of like $74, $1,700 in revenue and profit really. And the amount of money that can revenue that I managed to bring in was something like $13,000. It was like $13,000 or $14,000. And in retrospect, I don’t even know how I did that, but I did it through not spending a lot of money. A lot of tuna salads in, which is, I remember that.
There were a lot of those for lunch. I’d have a half a can for lunch, and then the other half, which would make the other sandwich for dinner. And over time, I got a few more clients here and there. And then somewhere along the way, things went off the rails. Things changed when I got an office space because somehow the expense scheme changed. I got more clients as a result of that. It generally was a good thing for the business to have the office space because it allowed me to be near other people, other business owners and sort of give the ability to meet new people and that networking had a useful effect based off of the office space that I was in. It was affordable space by all measures. But in that time, I also managed to bring on interns and staff, I had contractors. I was trying to scale up in useful ways. And most of that scaling was just sort of churning around and around and around with clients all day all night on stuff that truly just kind of didn’t matter for a lot of people in a lot of ways. I had a lot of clients that just took up a lot of time. They were high touch, they needed a lot of handholding, they wanted everything explained to them in a way that most businesses just can’t quite scale.
Certainly not at the rates that I had been charging. And so I had agreed this business and I continued to grow this business in a way that was really great for one person, but not great for a lot of people. And once I sort of was approached by this idea of like, “Well, maybe you should consider selling somebody that I knew and trusted had a connection that they knew and trusted who might have been interested.” And so there were actually a couple of suitors who had proposed Bids to buy the book of business that I had made. And by this point in time, the business was making some place in the neighborhood of about $150,000 a year.
I wasn’t pulling that much money out of it. A lot of it was kind of going right back into the business in ways that paid for other people and paid for help and other office space and that sort of stuff. And so I wasn’t realizing a lot of it. And I felt like I was working a lot to not really have a whole lot of benefit from it. And around 2018, things had been off the rails for a while. The number of clients that we had was just a little bit too much. I used to call it the hump problem, because if you imagine that if, if, say, for example, as a business, you’re able to maintain 10 clients of a certain size and scope, and then you want to keep growing, you need another 10 clients pretty quickly in order to pay for another person, right? And so if you have 11 clients, that’s really hard because you don’t have the money from those 11 people to pay you and somebody else. And it’s difficult to find, you know, talented, young people, talented juniors or talented part-time people, particularly in the web design development industry that are loyal to those sorts of things because they themselves are probably trying to do other things. And so even if you had 12 or 13 clients, it’s still not enough to sort of get you over the hump. You need probably 16 or 17 clients to in order to pay for yourself and most of of somebody else or at least to break even in that. And then you really want 20 clients because that’ll make it comfortable for you and the other person. The problem then is that when you have 20 clients, well, then you’re in the exact same hump all over again where it’s like, well, now we got 21 or 22 clients because somebody referred somebody else or somebody came in the door or whatever.
And then the result is that you’re always fighting this hump where it’s like I just need a little bit more money to afford this XYZ thing over here or this person over here. And I was constantly in that struggle. It was incredibly stressful for me. I think I’ve probably aged more in the years between like 2017 and 2020 than just about any other period of my career so far. I enjoyed having a lot of long-term clients that were still good for customers of ours. We increasingly had other clients that we would occasionally recognize that we should turn down or turn away. But by large, we did what a lot of businesses do, which is that you just sort of take people on because at least within a service business like ours, you just don’t know quite what you’re getting into with people until you’ve worked with them for a while. And no amount of interviewing or vetting or anything like that is really going to change that dramatically.
And so by the time 2018, 2019 rolled around, I was just burnt out and I just did not know what to do until somebody came along and said, “Hey, maybe you should consider selling the business.” And I had never thought about that before. It just, I was kind of in this mindset of like, “This is just what I’ll do until I die, I guess.” ‘Cause I just didn’t know what else to do. And if it didn’t seem like, I certainly couldn’t walk away. I couldn’t leave all those people hanging, right? because there were some people who I genuinely liked very much and were relying upon us to do a job that’s very important to them, represents them in their organizations and their businesses.
And part of it too is that in addition to being burnt out on all that sort of business administration stress and sort of the constant grind around the hump of always getting over the next problem, I was also kind of bored with a lot of the work because a lot of it was is just so repetitive. It’s like, oh, this person’s got their golf outing again this year. This person’s got the such and such event. This person’s doing this thing. And it’s not even like the themes of these things changed very much, right? It’s not like they’re like, I’ve had some clients that have like nonprofit fundraisers, for example, or big galas every year, but it’s a different theme so you kind of get to do different interesting things with it. In my case, a lot of the work was just like, no, but it’s the same golf outing.
It’s the same expo that we’ve always done, the same conference we’ve always done, same this that and the other the same father’s day say all the same mother’s day event the same everything right it’s always kind of the same routine and so for a lot of clients that was both a blessing and sort of a stickiness of us because we mostly me just deeply understood the patterns of things I knew what they liked and if they didn’t like I knew what they couldn’t couldn’t say based off of policies or internal preferences or laws or whatever and so there was never a moment where they had to run out and like onboard some other agency or whatever or some other person or freelancer and then have to explain all that to them all over again because we just knew it, right? We could anticipate their needs, we could anticipate what problems they were going to run into, we just got better and better every single year.
But even though we got better and better at providing a service to them every year, it didn’t necessarily mean that we got faster at it every year. Sometimes it just took up a lot of time. And a lot of times, that time was consumed doing things that just weren’t that interesting. Even like month to month sort of things, where it’s like, well, here’s their monthly meeting or their quarterly whatever, and just sort of producing all the material that goes with it, because now they need a social media graphic because they want to put something on Facebook.
And we need a webpage for it and a registration for it. And we need to email campaigns for it. And that there’s whole big strategy for this thing that to them is very important. and I don’t belittle it and I don’t begrudge them for doing what they were doing. And I think that’s sort of what makes the world a rich and interesting place. But after you do that for three or four years, five or in my case, close to 10 or 12 years with some people, you just kind of want to know, it’s like, was there anything else that I can do?
And sometimes you try to pass the stuff on because I can hear you out there, I can hear people saying like, well, you should delegate these things. If I had spoken to a business coach at some point, I’m sure they would have told me the same thing as occasionally. I would have brief conversations with business coaches who would always tell me these things like, “Oh, well, you have to delegate these things out so you can go on and do these other things.”
But I didn’t really want to do that. They took me a long time to realize that is that I actually liked creating the stuff to an extent that I liked being the person who was actually making things even though I got tired of doing the same things over and over again as opposed to being the person who just sort of ran a business, right? to each their own, but took me a long time to figure that out. And by 2019, I was in a pretty bleak place. I was tired all the time. I was irritable a lot. I probably wasn’t a very compelling person to be around a lot of the time. And quite frankly, I just didn’t want to do it anymore. And I didn’t know how to get out. And so when this opportunity came up to consider selling, late in 2019, I ran the summer actually I guess July or August of 2019. Started having conversations with a couple of people. The numbers just pretty much break even, right? Like the business just wasn’t that extravagant. It wasn’t like I was gonna be a millionaire. I wasn’t gonna be able to retire off of it. I didn’t even know what I was going to do afterwards.
It’s like, well, if I sold it, then what would I do tomorrow? I just didn’t have an answer for that, but I also didn’t care. I was at that point almost willing to do any number of things, But I had a few rules about it. I wanted to know that everybody was well taken care of. I wanted to make, it was important to me, and I wanted to make sure that all of my clients were well taken care of. I wanted to make sure that my team was well taken care of, that they would carry on, that they would have the ability to be involved, that they would have improvement from it, that they would advance as a result of it.
And I wanted to know that, you know, I wasn’t being totally fleeced, right? And those are the things that you can’t Google for. Nobody ever talks about that when you sell a business. Nobody ever talks to you about how you should feel leading up to it, about what your rules are for selling. It’s usually a very transactional sort of a thing, particularly in big business, where it’s just, well, how much money do you make? What’s your revenue? What’s your profit? Multiply some of that out over about three years. That’s probably the approximate value of the business.
And if somebody’s gonna offer you a check, it should be about three times your revenue or maybe your profit depending on who you’re negotiating with. And there was no guidance for this. This is not the sort of thing they teach you how to do in school, right? And there aren’t a lot of books that I read about it that were very good. I don’t remember any actually at this point that were very good topics about it. But I had my three guiding rules, right? I had my three guiding principles. Take care of the clients, take care of the team, and take care of myself mostly in that order. And by the time the conversations started going around with a few other people, it finally came across a group that was more interested in making a more substantial offer. And part of that offer included that I would continue to work for them for some period of time. And the contract protected them in ways in case I wanted to leave. And I don’t really recall thinking about it that much at the time, I knew that it satisfied two and a half of the rules. Right?
I knew that my team was well taken care of. I knew that my clients were going to be well taken care of, and that I was going to continue to be there. And so by and large, you know, it’s sort of, I guess, took care of me. But then the problem started to arise, which is that after we finally finalized the deal, which just sort of coincidentally happened right ever on the time that COVID-19 was happening, But it didn’t solve my problem. It didn’t solve my burnout problem. It didn’t make my life easier. There wasn’t like some extravagant amount of resources that suddenly appeared, like I didn’t have a new staff. Even though I think in my head there was this point where I thought, okay, I’m going to sell this business to this group over here.
They’re going to have all these people that are already there. And I can just kind of sit back and sort of help guide these people on autopilot for a little while and I don’t have to work as much that I can work like, you know, an 8 to 4, kind of a 9 to 5 thing, even, maybe I’ll just work 6 hours a day or something, right? And that didn’t happen. In fact, things actually got worse because then I was sort of thrust into this higher level director-ish position where not only was I managing more people and then I had to hire more people, but the stark realities of differences in business style came about, right?
That when you sell a business, like you have your way of running things and you have your tolerance for what’s good for you or your clients and you have sort of your ethos about like, well, we’re going to do what’s best for the client and the circumstance and therefore that’s what we’re going to do because that’s how we’re going to do it, right? Whereas you can demand and other businesses that are like, well, that’s not good for the business so we’re not going to do that. And you kind of run into those collisions a little bit. And that’s normal.
But again, not something that anybody really prepares you for. And it’s not really something that at least I at the time was not equipped to figure out how to navigate. I couldn’t interview my way through that. I couldn’t investigate my way through that. I didn’t know the questions to ask. I didn’t know how to suss out a sense for that. I couldn’t sniff that out to determine in advance, it’s like, well, I’m going to sell to these people, but we’re going to disagree on X, Y, and Z. I just didn’t know.
And so we finalized the deal and it was about, I think, June or July of 2020 when the whole deal was finalized and we made an outspest to people and I said, “Yeah, pretty much, I’m going to continue doing this all over here.” So there’s really no change for the clients. The team was in a better position. In fact, they got increases in their pay that was more commensurate with where they really should have been at the time anyway. And I ended up getting more money out of it. I started to make more money out of it. But part of the contractual obligation, which was reasonable from the standpoint of the purchasers, was that I sort of had to protect that book of business, right? I had it be the one that maintained some of that in order to get paid out because it wasn’t a immediate payout. It wasn’t the sort of thing where they just said, “Okay, we’re going to buy this and here’s a big fat check.”
And then, you know, good luck. It was paid out over a period of years on a monthly basis, based on the percentage of the book and various other factors, which again was totally reasonable. Not something that in HipHoney really ever teaches you or prepares you for. I wasn’t really prepared very well for it either. But it was fair. I could understand that at the time. I still understand that. I still think it’s fine. I still think it’s fair. But it didn’t solve my problem. So I had solved two and a half of my rules, but the last half that wasn’t solved was the part where I was supposed to not feel so burnt out anymore. And that didn’t change. In fact, it got worse. And eventually, what triggered a change in all of this was that, as a prodigious wearer of my Apple Watch, I would look at some of the data about my heart rate variability and my heart rate at night and sleep tracking and I always make sure that I exercise. And so here I am, a young person, in my, you know, barely 30 years old, I’m sleeping enough, I’m eating exceptionally well, certainly compared to the average. And there’s just anomalies, right?
My heart rate is just too high sometimes. In fact, just sitting at my desk, my heart rate would be as high as a person who maybe had just walked up the stairs, right? Like, if you sat on the couch and then you walked up the stairs and your heart starts to pump a little bit to catch up with that. Imagine that it stayed at that higher sustained level. That’s what my heart was doing kind of all day. And realizing that maybe the Apple Watch was wrong. I started to look into it a little more closely, a little more carefully, and I realized that there was definitely something wrong. That for the brief period of time that I could take a few days off on a vacation, or particularly on Sundays, which were usually my calmest days, that there was markedly lower, right? It was, you could plot it on a graph.
You could be like, well, here’s Justin at work and sitting on a desk just being stressed out and angry and sort of anxious about lots of different things. And here he is where he’s not any of those things. And I was like, I wanna be that more often than not, right? And further complicating all of this is that as I’ve discussed, my mother died at a relatively early age and sometime around the age of 30 or 31, I started to realize too that I was approaching an age where I would be the same age as my mom when she was initially diagnosed or that I potentially could outlive her. But also, maybe I wouldn’t, that maybe I would end up dying in early death too. And maybe it wouldn’t be a heart problem, maybe it wouldn’t be a brain tumor like what she had, But maybe it could be something that could be fueled by a lot of these things. Whatever it was, some part of my health was not optimal.
In fact, it was sustainably not optimal. It was unsustainable, right? It was consistently not where it should have been. It’s consistently not great, right? And I thought, I have to do something about this and I don’t know what to do. And so I thought the only thing that I can do is I just have to stop. I just have to stop this. I just have to leave this part of my life behind. And at the time, it did not seem like a hard decision to make. It was very obvious, right? It’s like, well, this is not going to work. It obviously cannot work. There, and nothing else is going to change about it that’s going to dramatically improve it. Therefore, I just have to be done. And I was very at peace with that. And so that’s what I did. I walked away from all of that. and just woke up one morning and didn’t have to do all that stuff anymore. And then I was like, “Oh crap, what am I going to do?” And so I ended up getting some smaller jobs and decided, “Do you know what I really would like to do?” Is that for all these years that I’ve done design development stuff, I really enjoy the copyrighting part of it. It’s like, am I able to just create a whole new business and learn from all those experiences in the past and create a new sustainable business that I could limit to like seven or ten clients depending on the scope of them and just be done.
Recognize that I don’t want staff, I don’t want to hire people, I don’t want to have part-term contractors, I don’t want to do any of that. I just want to have a loyal base of clients that I do exceptionally good work for because at some point over those last few years, I feel like no matter how much I tried, it was not possible for me to deliver the same level of work that I had been. And that bothered me to no end. And so I decided that I would do that. And I started with getting a couple of larger part-time contract gigs, one of which was with a school and another which was with a couple of other smaller businesses. and that sort of came out of nowhere that I had approached that I knew. And I thought, hey, we’ve talked about this in the past. Maybe you’d like to just do this copywriting thing. Here’s what I can do for you. And so suddenly I had my base again, right? Except this time, unlike the time when I started this in 2007, I actually had a little bit of a network to fall back on. And so I actually knew some people. And so those connections helped.
And maybe it’s just sort of spin up a business that would allow me to live comfortably almost overnight. And I’ve continued on that path, and now I’m maxed out. And now that I’m sort of in a different place in my life and in my career, I sort of reinvented what it is that I do, and I’m trying to be exceptionally good at that at the things that I do do, and that I’ve diversified the kind of work that I do from teaching and writing and a few other things, working on my book, for example.
That now I sit and I think, how should I have felt throughout all that? And then every time initially when I told somebody, it’s like, yeah, I sold a business or I’m selling the business or whatever, they would always say, oh, congratulations. Like they were very excited about it. And I felt like I had just screwed everything up. I was like, I just built a business that was just terrible. Like I did all the wrong things, all the wrong ways. And anything that I did do right, I probably screwed it up in no time at all. And I felt bad about that. I felt so intensely bad about leaving people. I felt like I abandoned some people a lot of cases, particularly people that I’d worked with for a very long time. And ultimately, I got to a point where I just made peace with that and realized that the way that I felt was driven in large part by that abandoning them, by that abandonment.
And I still feel a little bad about that. But in retrospect, looking back now, connecting some dots over the last few years since all this has transpired. interesting to me, although I still tell people that, oh yeah, I ran a business doing XYZ for so long, and then I sold it in 2020, and then I almost immediately put a subordinate clause in there to say, “Eh, that was pandemic unrelated.” Right? Because it almost feels like, “Oh, the pandemic came along, “and then you lost all your business and then you went out.” It was actually completely coincidental.
And so I feel like I always have to say that. Like, I’m trying to make it sound like I was successful, and I guess in some ways I was. Right? I had a successful exit. I did a thing that a lot of people strive to do in some way and never make it, right? Because they just lose all sorts of money and they never, they’re in debt up to the eyeballs and I never had that. I never had a lot of debt, never had any debt, really. Personal or private. And it worked out. And what the future holds, I don’t know. But recognizing now that when you prepare to sell a business or that when you do sell a business, nobody ever prepares you for how you’re supposed to feel about that. And I don’t know that it’s written in any place that there’s a specific feeling that you should feel. I tend to think that in some ways, most small business owners find it a pretty bittersweet experience.
The sort of thing where it’s like, well, you know, I came to this conclusion for one reason or another, and I’m going to do this because it’s good for whatever reason. It’s also recognizing that you’re letting go of a thing that you built a part of yourself, right? And then somebody else picks that up or carries it on and then whatever happens happens, right? Maybe in the case of a lot of customers, maybe they just don’t stick with you for very long as certain people who purchase large international global social media organizations might a test that sometimes when new ownership comes along a lot of people don’t like that and they just leave and I guess that’s part of it and that’s how the market works. And that’s the system that we have. But I don’t regret that period. In fact, there’s time progresses. I look back and I think, wow, that was all a really good learning experience. It was challenging. It was incredibly challenging. Was it super successful? No, but did I die? No, did other people die? No. Did people get a good service? I think so.
Did people get value out of it? I think so, otherwise why would they have kept paying me all that time? And I’ve managed to create a level of connections and skills that have allowed me to transform into a slightly different career path. And now I have learned from those mistakes. I’ve learned when to say no to clients. I know how to suss out quite when something’s not right or when a person might be a flight risk or their payment might be a problem. I know how to feel about these certain things, and I have a level of control that kind of only comes with experience and wisdom, right? And I now see and I mentor young people who are where I was 20 years ago or so in 2007, and they are struggling with these same sorts of things, and I recognize that even when I tell them, my experience are kind of how to feel, why they feel the way they feel that it’s not a satisfying answer, right? Because you just have to live through it. [BLANK_AUDIO]
It’s an odd thing, telling people who you want to have sex with. But, we humans do that a lot.
There’s a lot that I remember about the day my mom suffered a seizure, including the weather. And the day she died, and what happened at strange intervening moments in between. But what I don’t remember is what happened at the funeral. It seemed like the most unimportant thing in the entire 732 day affair.
Episode 2 of this season’s podcast, wherein I remember the time I picked up a random man at Wal-Mart. He gave me the low-down on Amtrak’s real plans and vaguely remembered where his sister lived.
Welcome to Season 2 of my award-self-nominated podcast. This season is more personal stories and anecdotes. If you didn’t like last season, good news! It’s not about books. If you like books, bad news! It’s not about books this time around.
To kick off this season of Justin’s Podcast, I’ve got a list of 21 things I learned while teaching Photoshop at IU last semester.
Here’s the summary:
- Asking pointed questions elicits pointed answers.
- Having two tracks makes double the work for me, but seems worth the cost.
- Need to discuss logos with clarity early in the semester. It comes up a lot.
- Having uniform rubrics is impossibly hard for visual arts. And devolving to technical criteria risks making everything too easy — like repeating a flower 20 times for sake of hitting a “minimum layer target”. Better to let people run with their instincts and trust they’ll rise to the occasion.
- I wish I had a better way of recording and editing more visually interesting videos.
- The first week’s swipe file assignment is probably too easy and not considered by anyone later in the semester, despite being a truly useful way of collecting good ideas. Probably just isn’t vital to most people, most of the time, though.
- Creating a newspaper ad would be an interesting challenge due to color restraints. But maybe not super applicable.
- It’s not clear to me that it’s clear to most students on the business track that most of the requests, files, ideas, and “emails” are, truly, from client interactions I’ve had over the years.
- Canvas stats show many people aren’t viewing the videos, suggesting they’re too long or boring. Not sure if the value of “real world” demo versus “tightly edited like a cooking show” is worth it or not.
- Almost no one takes advantage of office hours or focus times, despite being a problem most readily admit to needing help with. Not sure if that’s because of timing or not.
- A shockingly high percentage of students will wait until the last few hours before a deadline to submit. I don’t recall this from my time as a student at IUPUI.
- Halloween week was probably the most fun, despite not being particularly common for sake of future career use.
- There should probably be more opportunities to post in the forums, but without a point penalty no one will. Also conflicts with my student experience of assuming the forums were shallow and people just reply for sake of replying with banal comments. But many students do exceptionally good work — and having others see that level of quality is valuable. Everyone in this class will be competing against everyone else for work someday very soon.
- I wish more than I thought I would that I could talk and interact with students more, if only via Zoom.
- Most students need the weekend to work on projects. Regardless of when or how the semester starts and ends, try to permit a schedule that allows for two weekends instead of one for projects.
- There is a significant gap — perhaps from mere lived experience — between thinking about what a project needs and what a project demands.
- Some students will face challenges in their lives that I can’t do anything to help with. But sometimes, just asking seems like more than most people do.
- Messaging students directly is vitally important to better understand students’ careers, hopes, and needs. Can tailor work for them while class sizes remain modest.
- The price students pay for this class must live up to that cost, even if they may not realize it until months or years later, if ever.
- Students who aren’t self-directed, or aren’t sure if they’re self-directed enough, should be advised early this class might not be for them.
- It’s incredibly hard to teach or even relay what is good taste, style, and panache.
I like parts of this book and not others, but it's probably the most "aggressive" of any book I've read on what it takes to achieve some kind of life satisfaction.
This book is seemingly everywhere lately, or at least the author is. I listened to the audiobook version of "Stolen Focus" and found it holistic, compared to many other books on the same topic. Though there are some things in here—like treating Facebook as a public utility and all the regulatory trappings therein—downright absurd.
The Dust Bowl probably got a fleeting mention in your elementary education. I knew it as a time a bunch of dust blew around sandwiched between poodle skirts and Hitler.
A good book for individuals lacking guidance, clarity, or focus. And an even greater book for companies. But my attention here was paid solely to ... Read More
I read "The Everything Store" several years ago and found it fascinating. I always like to peek inside large companies that really change industries, for better or worse. "Amazon Unbound" is the follow-up to that book.
Ikigai is a Japanese word that roughly translates to "the reason you get up in the morning" and the researchers (I assume they're researchers anyway) follow the advice and lives of Okinawans. Supposedly, there are more 100+ year olds living there than anywhere else in the world.
A well-written and well-documented look inside the U.S. Secret Service, largely from the time of Kennedy up to the Trump Administration. It's an easy read with excellent storytelling, including of breaches and issues I had never heard of before.
If you’re constantly put off by books encouraging you to make the most of your time on this precious earth and that every day is ... Read More
But it's loaded with data on surveys about things most people already recognize, like working less reduces stress, and eating better is...better. No one needs a study to tell them that.
You’ll like this book if you’re interested in history of work, urban planning, technology, and hard truths about focusing on our lives and not just our work.