Non-Feral Free Agency

I started a single-person company to simplify my life.

And all I got was extreme loneliness. Bad health insurance. Tidal waves of anxiety. Neverending paperwork. And constant mental churning on how to make ends meet.

I was beyond stressed out.

Somehow, I had stumbled into a lot of clients for my business, which was supposed to be a good thing, but I couldn’t handle it.

There were multiple balls in the air that seemed destined to come crashing to the ground: a massive consulting project that was going off the rails, a pile-up of inbound sales requests I couldn’t get to, and a half-finished curriculum for my upcoming cohort course launching the following week.

I remember looking at my girlfriend and saying, “I don’t know how I’m going to make it all work. I don’t think it’s possible,” as I curled into the fetal position on our couch and felt an anxiety so strong it numbed my entire body.

But I wouldn’t trade the solopreneur experience for anything.

Because amidst all the anguish, the banality, and the loneliness of running a single-person company, there are some incredibly beautiful things: the freedom to experiment; an opportunity to structure alternative working norms; the ability to choose who you work with; and a sense of personal ownership that is both humbling and inspiring.

But I wish someone had warned me before I got started on this path of the vast array of psychological traps in running your own solo Internet business, which is now more doable than ever, but also fraught with extreme challenges.

The tales of building hyper-growth startups that become billion-dollar unicorns or fast-burning dumpster fires are well-told. These are the success stories and failure porn of Silicon Valley. But what about the lone person at their home desk? The person who wants a little more from work than the corporate superstructure but isn’t interested in raising venture capital, conquering the world, and giving a lobotomized Ted Talk on how you just need to learn how to code? What does this parallel, smaller, more approachable entrepreneurship path look like?

The rosy promises for wannabe solopreneurs are clear from online discourse: when you start your own company, especially something as small as a single-person Internet business, you are setting off on a path paved in freedom, unilateral passion following, 4-hour work weeks, and $30k/month in passive income while you surf off the coast of Bali. 

There is some truth to those promises. But to get there, it takes extreme discipline, consistency, luck, and a radical deprogramming (especially if you’re coming from the corporate world) that is hard to fully articulate. The self-employed path is laden with self-imposed traps and external pressures everywhere. The ability to grind from sunup to sundown; to say yes to any opportunity that crosses your desk, no matter the personal sacrifice; to scroll Twitter and compare yourself unrealistically to someone further on the path—if you’re not careful, you’ll find yourself constructing a perfect self-torture device. And in a company of one, no one is there to tap you on the shoulder and tell you you’re creating the very thing you left behind.

So how did I end up in the fetal position on my couch, numb to the core with anxiety? How did I, at one point, fuck up the perfect paradigm of solo employment? 

I applied an old playbook to my new vocation. 

I worked ten years in the corporate world, and that way of working, a constant sense of “on-ness”, low-grade performance anxiety, and a debilitating need to people-please, was etched into my bones. My new boss (my literal fucking self) was just as big of a jerk as my old one: equally demanding, uncompromising, and disrespectful to my personal boundaries. 

It takes intention to develop a personal way of working that inculcates you from the modern corporate tradition of grinding, competing, and growth-at-all-costs mindset. Simply starting your own thing won’t intrinsically fix your relationship with work, and in some cases, it will amplify them. I have to remind myself daily to not fall into the work tempo traps of my own making—to slow down, to do less, to create space. And I’ve been at this for two years.

There’s a gift self-employment gives you, if you’re willing to take it, that’s not as readily available in the corporate world—the ability to say no; to turn down things that don’t serve you in favor of things that do. That muscle was so atrophied in me, it's taken years to learn how to use it again.  

I’m not even close to figuring this thing out, I’m constantly stumbling in the dark along this vocational path, but I wouldn’t change one second of the experience. It’s painful. It’s lonely. It’s stressful at times. But there are moments when I’m doing it right, when I go on long walks with my girlfriend in the middle of the day, or when I’m working on exactly what my soul wants to work on, that it’s worth it. It can be both—challenging and beautiful.