I’ve been a self-employed independent creator for 10 years. I don’t recommend it.

Today marks my 10th year as a self-employed independent creator. I don’t recommend it.

It all started when my boss called me into a conference room. As I followed her down the hall, I noticed she was carrying a manila envelope. I could sense what was coming.

It was a short meeting. She told me I was terminated, and I felt relieved. I got up and thanked her. “July 17, 2007 will be a special day in my life,” I told her, smiling genuinely. I rode the antique elevator and stepped out onto Market Street, walking confidently one more time past the tourists in line for the street car. I descended into the Powell Street BART station.

I felt sure that I’d never work for someone else again. My will to “work” was gone. I cashed out a big chunk of my retirement fund to buy myself some time. After all, I had spent years eating 80-cent Banquet® meals for lunch, saving for this moment.


The next morning, I opened my eyes to vastness. There was nothing but time to be filled, like I was just floating in space. I could do anything I wanted with that vastness — build a startup, write a book, or play Guitar Hero and eat nachos. That was every bit as scary as it was exciting. My mission was to reconnect with my curiosity — that feeling that I had had so many times, alone in my room drawing or reading, the time passing so quickly I’d forget to eat.

I wanted to find that again. If I could just find a little snowball of curiosity, I imagined that I could keep rolling it, it would get bigger and bigger, and it would fill up the vastness. Eventually maybe I’d have my own planet to stand on.

That was ten years ago. I’ve stuck with my mission, but I never imagined it would take this long.


In the beginning, I was convinced I would become a billionaire within six months — nevermind exactly how that was going to happen, or why I would even want such a thing. When I cleared out my apartment in Nebraska to move to Silicon Valley, I dreamed that I might “make it” in some big city. At this point, I merely hope to find a way of making a living that doesn’t have me scared on a regular basis.

It’s not that I’m on the verge of bankruptcy. The most valuable lessons of my upbringing were to strive to be financially secure — if not financially paranoid. I’ve recouped the $40,000 of stock I cashed out initially, and then some. Heck, I have savings, which puts me ahead of most Americans. I live a pretty comfortable life. My strange health problems are even more affordable now that I’ve moved to Colombia to reduce my expenses for the next stage of my plan.


On New Year’s Eve, as 2008 turned into 2009, I stayed home, alone, in my drafty apartment in Chicago’s Ukrainian Village. After a year on my own, and a failed startup attempt, I had fled Silicon Valley. I felt pressure in my skull, as if my brain were going to hatch. I felt restlessness in my fingertips. I needed a cold winter, cheap rent, and some space to figure out what it was all about.

On my knees on the hardwood floor, on an $11 piece of tileboard from Home Depot, I sketched this plan.

This was how I would bootstrap my way into making a living following my curiosity. The plan was to make as little money as I needed, with as little of my time as possible, and use the rest of the time to discover and pursue what gave me that feeling of “flow” I had experienced as a child.

Since I had spent as much of my savings as I was comfortable with for now, first, I would freelance. My goal was ten billable hours a week.

With the rest of my time, I would explore ways to make passive revenue.

As I made passive revenue, I would reduce freelancing hours, and spend time on whatever I was curious about.

Eventually, what I was curious about would make money. I would use that money to explore the next thing. And, I’d repeat.


That’s exactly what I did, and the timing was fortuitous every step of the way. Shortly after moving to Chicago, I landed oDesk (Upwork) as a client, for roughly ten hours a week. As that contract ended, I started earning passive revenue from one of my experiments. As that revenue stream dropped, I got a book deal, and another revenue stream popped up to supplement my meager advance payments. This all took about three years.

Now, six years after Design for Hackers, I’m hoping that the timing is good again. I supplemented D4H with some online courses, I spoke all over the world, and traveled. It was an amazing experience, and I made some good money for a few years — enough that I almost felt like I was making as much as I would have if I had stayed on the career track as a designer in Silicon Valley.

I had the opportunity to scale D4H. I turned down so much freelance work I could have started a design firm. I toyed with the idea of expanding the courses and training. I turned down an opportunity to work full-time at a company that eventually sold to Google. But ultimately, none of it was what I wanted. It wasn’t what I was curious about.


I recognized early on in the D4H success (it debuted in the top 20 on Amazon), that I didn’t want to juice it. I wanted, instead, to use that freedom, and the lessons learned from the experience, to be a better writer. More importantly, to be a better thinker, so I could be a better writer. I didn’t want the distractions of building a larger business around it.

A couple of years ago, I was in Mexico on a retreat with some entrepreneur friends. We dedicated a whole week to discussing each other’s directions in life — where we wanted to go, what we wanted to stand for, what we wanted to do next. It took that long to dig through the accumulated years of my own bullshit and admit it to myself. It was hard to say it out loud: “I just want to read about things that interest me, have conversations, use it all to inform my understanding of the world, and share what I’ve learned.”


During that first year of self-employment, I had watched the Steve Jobs Stanford Commencement speech over and over. Every idea in that speech resonated so deeply with what I believed, and the way I was trying to live my life, it brought me to tears regularly. In fact, it’s bringing me to tears as I recall it. One such idea is that you should “have the courage to follow your heart and intuition. They somehow already know what you truly want to become.”

I think what touches me so much about that idea is that I know now better than ever the forces of heart and intuition. They’ll lead you to do things that don’t seem rational. They’ll make you pass up opportunities a rational person would take. They’ll make you take risks that don’t make sense at the time. They’ll lead you to scary places. They’ll make you question your own sanity.

As I tell this story, it’s nice and neat. Past decisions line up to future outcomes. The reality is much messier. I didn’t know why I was eating 80-cent microwave lunches. I didn’t know why I was socking away money in the stock market. I didn’t know why I was leaving Silicon Valley, with job offers nipping at my tail.

Each of these actions created future opportunities that I never foresaw. My heart and intuition knew what I wanted to become. Even when I sketched that plan on my living room floor — though I ended up following it exactly — I didn’t know why I was doing it.


So, when I finally said those words in Mexico, I realized that I had already set the wheels in motion. I was already editing the first episodes of Love Your Work. I already had a one-way ticket to Colombia. I had already spent years honing my writing, building an audience, and taking voice and storytelling classes.

I had been afraid to admit what I wanted because I knew it would be scary. Heart and intuition — and for me, curiosity — will make you do scary things. By the time you discover why, it’s too late to go back.

It’s true that we tend to rationalize things after the fact. It’s quite possible that there’s some parallel universe where I stayed in my hometown with my friends and family, or I somehow mustered the strength to to remain a designer in Silicon Valley. Maybe I’m even happier in those worlds. That’s hard for me to imagine.

I remember early on in my quest, my dad asking me “so, at some point will you decide to get a job?” It’s the kind of question you’d expect from a guy who held onto the same job for 37 years. I thought about it for a minute. A complex web of potential causes and effects unfurled in my mind. Every day, I was learning something new, and each one of those things would branch off into three more things. My answer was a clear “no.”


There are plenty of practical ways for me to make a living. I can design, and write. I could probably still dig a ditch, and I oddly fantasize about becoming a plumber.

But as things stand now, I’m still at the whim of my curiosity. It makes me churn out Love Your Work episodes every week, growing along with my listeners with each conversation I have. And since it’s been six years since my last book, it’s ironic that I’m writing a book called Getting Art Done.

Are these things lucrative? No, that’s why I’m scared. Yes, there’s money to be made selling more courses, or coaching, or I could spend my mental energy trying to capture tiny bits of attention by hacking Facebook’s bewildering feed algorithm or by creating the most controversial content I can. Maybe I should have arguments with my podcast guests?

I want to make a living creating. I don’t want creating to be merely a marketing strategy for other things. Is that completely insane?


While I agree that Real Artists Don’t Starve, the models for making money as a creator don’t really suit my sensibilities. People are beginning to support Love Your Work on Patreon. It seems inevitable to me that the blockchain will bust down some of the barriers to value flow, with sites such as Steemit. Love Your Work is starting to get sponsorships, but it needs more listeners to be sustainable that way. Books are probably the most honest exchange of value out there (a bargain, really), so Getting Art Done, once I get it…done…could bring in anywhere from a thousand dollars to a bajillion dollars.

I’m strangely comforted by stories of other creators, such as comedians like Louis CK, who struggled for decades before suddenly growing exponentially in success and skill. This is a dangerous comfort, as for every one who made it, there are probably hundreds who drank themselves to death, or—perhaps worse—wound up teaching Level I improv classes at Second City.

If I reflect on my own growth as a creator, I can see exponential growth in my own skill in certain areas, the same way a skyscraper quickly rises slowly after the foundation is set. Growth in the commensurate success, however, tends to happen in tiny explosions that are hard to engineer, and impossible to predict.


So, I’m still committed to this. I sense that I’m close, though I’ve sensed that many times before. It’s possible I’ll end up achieving some tamer version of my vision, where I’m making creative compromises to pay the bills. It’s possible life will get in the way, and I’ll hang it up. It’s possible the sunk-cost fallacy will lead me to ruin, and I’ll be found rambling and incoherent on the streets of Baltimore, only to die a few hours later. I really don’t know.

But take it from me, a ten-year veteran self-employed creator: If you are looking for security or reassurance, I do not recommend this line of work. However, if you are burning with curiosity — if your heart and intuition lead you to do things that don’t make sense—well, then you don’t really have a choice in the matter, do you?


If you’re picking up what I’m throwing down, support my work on Patreon, because you’ll get cool stuff and you’ll feel great.