The idea of earning a paycheck (and knowing how much it will be for!), speaking to the same people every day, and having a semi-habitual routine (that’s not entirely set by me) seems novel and intriguing when you’ve been doing the opposite for nearly two decades.

There’s something psychologically calming about the notion of not having to be responsible for absolutely every aspect of all the work I do; having other people in the loop, doing their part, hefting their allotment of the workload so I can settle in and focus on mine.

Then again, I really enjoy having full control over how I spend my time and energy. I think it would be interesting and educational to experience the alternative for a while, maybe 5-10 years, but I would absolutely miss my current sense of near-absolute time-freedom and self-guided everything.

Also (and this may or may not actually be a big deal), my skills and experiences do not fit cleanly into the funnels and filters used by the typical work world to determine who would be a good candidate for a given position.

I would probably need to find something specialized, some kind of unusual employer or work situation, as I would almost certainly be sieved-out by the AI or algorithmic systems meant to pare-down the number of applicants for a given position, due to my strangely shaped career.

That latter realization is humbling because I’ve worked hard to build the life I have. Being reminded that core aspects of this life (and the skills, knowledge, and sacrifices required to keep it afloat) aren’t necessarily valued by traditional employers can be deflating.

Then again, having this kind of unusual professional background also unlocks doors that people who have stuck to the traditional employment path would have trouble opening.

I can’t tell you how many incredibly talented, experienced people I’ve met who have tried to leave their jobs to go off on their own, only to find they’re missing a bunch of necessary knowledge and know-how (things that were previously handled by others within their organizations, perhaps), or that they simply lack the mindset to fail and try again, over and over and over, until something eventually works (and maybe imperfectly).

Many of these people have told me they admire and covet the way I live, and the benefits of my time-rich career.

In response, I usually tell them that I wish I had their economic predictability (and thus, stability), their team of collaborators, and a LinkedIn profile that reads as ‘competent, experienced professional’ to the increasingly automated systems that determine whether we’re successes or failures.

It’s possible to do a bit of both, of course.

I sometimes work with clients, and that offers me some of what I miss about the traditional employment world without too seriously impinging on the benefits of the weirdo life I typically enjoy.

That said, I also recognize that it’s human nature to crave that which we don’t have, and there will likely always be a part of me that wants to walk the path I’m not currently on (right up until I start walking that other path, at which point I’ll covet the one I just left).

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To those thus inclined, money is like Pokémon cards or Civil War relics or anything else a person might hoard. And because accumulation feels good, triggering biological reward responses that would have nudged our proto-human ancestors into gathering resources (the better to survive and procreate), some of us keep accumulating money, hitting that ‘get more’ button over and over and over again until we die.

For many of us, though, money actually represents freedom. Or safety. Or the leverage required to accomplish some long-cherished goal. Sometimes the money itself is the point, but sometimes it’s more about what the money symbolizes: the gaps it fills in our lives.

Working out can be similar.

Some people exercise because of the physical and psychological rewards inherent in the act of straining their muscles and circulatory systems. But for others, going to the gym or for a run is a means of staying alive long enough to see their children grow up, or to remain fit enough to continue enjoying long hikes through the wilderness with their partner.

For some people, romantic relationships represent stability. For others it’s love. For still others it represents a certain type of accomplishment or life milestone.

Having kids, investing in our careers, cultivating hobbies, writing books, competing in marathons—all have overt meanings, but also deeper, more specific and personal meanings.

Almost always, our actual reasons for raising children or writing a book will be far more complex than the cursory explanations for these undertakings. In some cases, those default rationales will be just a small part of a larger portfolio of reasons, and in others they’ll be completely orthogonal to our true, us-shaped motives.

Whatever the nature of our ambitions, it’s useful to understand them with as much granularity as possible. Such understanding can help us to aim for ultra-specific aspects of our goals, rather than superficial, iconographic versions of them that kinda sorta look like what we have in mind, but which in practice miss the point entirely.

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You can pick up a hobby—say coloring in coloring books or creating monsters with Legos or playing disc golf or performing interpretive dance—and you don’t have to convince a single person to give you money in exchange for your brick-hydra or your pubescence-inspired tap-dance. You can just do it, and keep doing it, and no one has to like what you do or how you do it but you.

I like to think of hobbies as directional play, as while hobbies tend to be fun (or otherwise enjoyable), there’s also room for growth and development. You can build really simplistic Lego monsters with a few dozen pieces, or you can engineer staggeringly large and complex grotesques. You can have a blast at either end of that spectrum, but you can also choose to progress from one side to the other, and you can stop anywhere you like along the way (and if you find a spot you especially like, you can stay there forever without negative consequence).

That directionality is nice because growth and accomplishment can feel good and be fulfilling.

But ‘play’ is also important, here, because most of us don’t play enough: we don’t just mess around, try and do things just for their own sake. Not as adults, anyway. And it’s liberating to have something in our lives that we don’t have to be good at, and in which we can just fumble around in whichever manner feels right at any given moment.

Hobbies can also, sometimes, evolve into other things, including professions.

There’s nothing at all wrong with this when it happens, but most of us will be best served by periodically reminding ourselves that not everything needs to be monetized, and not everything needs to be purposeful (in the sense of goosing some kind of growth metric, or helping us develop in a quantifiable way).

It’s okay just to do and try things, and to have hobbies that help us pass the time, give us an excuse to be around others, and that stoke and sate our curiosity.

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