A few years ago, shortly after I’d left my job and started a software company, I took walk with a friend to chat about work while our dogs chased each other in the woods.
This friend, who had a successful software company of his own, asked me what I thought I would do if the company grew quickly and I was able to sell it for a bunch of money. I said, “probably what I was doing before, just on my own. Coaching and consulting with people about work and leadership, writing more.”
“You should probably just go do that,” he said, “save yourself the headache.”
I’m sure he was going through a low at the time…we laughed about it. Ha! What an absurdly simple idea.
The comment glanced right off of me. But it was such a candid moment that the truth of it still resonates. I never did sell that company for a bunch of money, but I am now coaching and consulting on my own, and writing more.
, who in 2013 was described in Time as, “the best short-story writer in English — not ‘one of,’ not ‘arguably,’ but the Best,” and who has been as present and active a writer in the decade since, wrote not long ago about a time when he almost quit writing:I remember very well almost quitting, back when our kids were small and nothing much was happening for me - or maybe, more precisely, I was trying to think about quitting […] - I was just looking for some power, any power, in the world. But in the end, writing was all I wanted and was what I believed in the most.
In some ways, I think we’re all looking for power in the world.
It’s how we try to mend the feeling of uncertainty and anxiety that we have about what we’re doing, whether we’re doing it well, and whether we’re doing the right thing at all; especially when we’re trying something hard or something new. When the mental meter starts to tip toward anxiety, that’s when we’re prone to pick our heads up and start looking for power.
For me, looking for power usually takes the form of moving toward more tangible signals of achievement - e.g., money, title, prestigious brand names with which to myself - to try to demonstrate that I’ve “made it,” or that I don’t need to be worried about.
I’ve also found that whenever I start prioritizing these things, I can tell almost immediately that I’ve taken my focus off of something essential. That what I should have been doing is managing my discomfort and focusing on the process of pursuing the activities that are interesting and important to me.
I think, years ago on that walk in the woods, I had known what I wanted to be doing the whole time but was reacting against some earning imperative that I’d conjured for myself.
I felt like I needed to do This Other Thing in order to make enough money so that I could then go do The Thing I Really Wanted To Do without having to worry about making money.
This do-this-to-do-that mentality creates all sorts of problems. It fosters a sense that you must have “arrived” somewhere before doing the thing you’re truly interested in. It also forgoes the time between now and your arrival when you could have been doing the thing that might have:
Brought some inherent joy/pleasure/engagement to your life
Created an opportunity for you to get better at that thing
Increased the probability that you could do more of that thing over time
It’s almost like misguided delayed gratification. If I can earn my way into an early retirement, then I can allow myself to do the things I want to do and truly enjoy.
There is a chapter in Matthew Crawford’s still excellent 2009 book Shop Class as Soulcraft in which he addressed this way of thinking:
It is common today to locate one’s “true self” in one’s leisure choices. Accordingly, good work is taken to be work that maximizes one’s means for pursuing these other activities, where life becomes meaningful. […]
There is a disconnect between [one’s] work life and [one’s] leisure life; in one [the worker] accumulates money and in the other s/he accumulates psychic nourishment. Each part depends on and enables the other, but does so in the manner of a transaction between sub-selves, rather than as the intelligibly linked parts of a coherent life (p. 181).
Now don’t misread me as saying you should strive to make your hobbies your job. I subscribe to the avid pursuit of mediocrity and directionlessness in many of my hobbies (and think that’s a good thing). I’m aiming more at the very real vocational interests we often ignore that can (could, should!) inform how we make more fulfilling decisions about how we spend our working years. Even if those decisions include trading “down” on the work front to create more time for less work-related interests.
I suspect we make the do-this-to-do-that trade off because we imagine it will reduce the risks we’re taking. That we’re trying in some way to mitigate the fear of failure - having “proved” ourselves in one domain we can now go into the domain we are actually interested in and the outcomes won’t matter as much.
What I try to remind myself when I’m grappling with this type of thinking: if I’m not trying something because I’m afraid to fail, I’m already failing at that thing. In the end, I’d rather just give it a shot and see what could happen.