When the Ground Moves

I’ve been working for myself, running a collection of publications and small businesses and “weird internet projects,” since 2009.

That’s a long time ago! Smartphones were still a new thing, the world was still recovering from a global financial crisis, and I was 24-years-old, trying to figure out how to convert my experiences up till that point and small arsenal of skills and know-how into something that might sustain the sort of life I wanted to live.

As it turns out, while stubbornness and sturdiness can help, it’s often more valuable to have the sort of wobbly resilience that comes from not being too precious about any particular way of doing things.

When I started traveling full-time way back then, I mostly survived on freelance design and branding projects I could take on from the road.

Then I transitioned, not without trepidation and some amount of initial financial pain, into writing books and doing some freelance writing projects on the side.

I started to attract some small speaking opportunities not long after that, and was able to cobble together a few small publishing-focused business efforts.

I taught some online classes and some in-person workshops.

I consulted on various things.

I wrote more books, presented more talks, and started up some podcasts, propping the latter up with a combination of membership offerings, ad-slots, and sponsorships.

I’ve at times done pretty well with donations through PayPal and Buy Me a Coffee, and in some blessed moments paid most of my bills with Patreon and Substack, alone.

But these sorts of things ebb and flow, controlled by complex variables far beyond my reckoning, much less influence.

It’s possible to sustain an unusual, you-shaped lifestyle with just one thing, one primary project, but that generally requires that you also spend the majority of your time and effort on just that one thing, and ideally it’s one thing that has mass-appeal potential and that will not collapse around you as trends and preferences shift and evolve.

The 1,000 True Fans theory posits that you can survive with a relatively small number of supporters, but that theory requires all of your fans pay you a certain amount of money on a regular basis and never leave (“churn,” to use the industry parlance)—which is not realistic for almost every “creator” making almost every type of thing: fans change, creators change, and the economy (and a fan’s concomitant ability to support creators whose work they enjoy) changes.

I’m incredibly fortunate to do what I do, to have the globally dispersed audience I’m able to share with, engage with, and learn alongside.

But the reason many people taste-test this sort of lifestyle before ultimately returning to the paycheck-predicated world is that it can be a stressful scramble, a tumultuous ride bounded by uncertain prospects, worrying trends and projections, and roiling, rock-strewn rapids that can knock even the most-veteran of makers from their seemingly stalwart, cozy perch.

It’s not boring, that’s for certain.

And it requires an unusually high tolerance for unknowns, risk, and failure.

It also requires that one always keep five or so other irons in the fire, just in case the heating element under one’s primary iron(s) starts to fizzle and disappear.

This isn’t what people like to hear, as the dream of running one’s own thing, turning a side-gig into a full-time gig, is supposed to be difficult, but in a fun way—and believe me, it often is fun and rewarding and all the other things you imagine.

But the satisfaction of doing non-standard, passion-centered work almost always comes at the cost of some amount of stability because of how the economics and incentives are built and oriented, because of how difficult it can be to stand out (and continue to do so), and because of how easy it is to lose your footing when the ground starts to move and your heretofore firm foundation becomes anything but.





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