Every couple of years I begin to yearn for the relative predictability and camaraderie of a more conventional work-life.

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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