If you poll Americans, 72% say that they would like to work for themselves. Only 7% actually do. I imagine the remaining 65% sitting at their mundane jobs and thinking, “oh, if only I worked for myself! I could sleep in, take time off whenever I want, and make lots of money!” As someone who worked for myself for a year, I think these people are straddling the fine line between hopeful and delusional.
Before I took my current (full-time, salaried) job, I was self-employed as a consultant. I picked up a few paying jobs, did some work for free and constantly wondered what I should be doing with my life. I had fallen into this at the end of grad school when someone saw my masters thesis presentation and offered me some part-time work. This became my main client, and I looked for opportunities for additional work, not to mention more income. I also spent the whole year worrying about money, cooking a lot, buying few things and generally being cheap.
Figuring out my days was a constant challenge. Should I take the day off, or should I always be working? I truly wanted to take advantage of my flexible schedule, yet also felt that I should always be doing something productive. I was ruled by my “shoulds”: I should be networking, I should be learning more, I should be more aggressive, I should…. Although I had a good home office set up, I never got into a productive routine. Often, I would start my day in my pajamas with a 9am conference call and a French press full of coffee. I liked the 9am calls because it made me accountable in the morning, but after a few calls and some emails I was still in my pjs, often cold and going stir crazy.
I also felt alone. One of the things I love most about work is having colleagues and that magic that happens when you are brainstorming and the result is better than either of you could have come up with on your own. Instead, I spent days by myself, making infinite choices about what to do, how to spend my time, and trying to figure out what was right. I always felt that it wasn’t enough, I wasn’t doing the right things, and I would never get anywhere. Since my work was both remote and part-time, I could have taken advantage of this arrangement and traveled. Why not work from New York or Mexico? This wouldn’t have solved the question of what I was doing with my life, but could have made the uncertainty of self-employment worthwhile. In the end, I didn’t use my flexible schedule to do anything that I couldn’t have also done with a regular salaried position.
The hardest part about working for myself was the identity shift. I had fallen into self-employment and felt ambivalent about it. When people asked me what I did for a living, I had a really hard time answering. I would literally physically shrink down, mumble a few things about working on some projects, and shrivel into a pathetic ball that no one in their right mind would hire. I didn’t feel confident in what I was doing, and never developed a good elevator pitch. I thought I had to be doing something in order to tell people about it, but I think I had it backwards. When I was drafting my personal essay for college applications, I remember my dad advising, “You just need to create a story about who you are. The trick is, once you’re there, remember that it was only a story and you don’t have to stick to it.” This time, I needed to create the story — my brand and business plan, really — to convince myself rather than anyone else.
Mostly, I was impatient. I’ve heard that when starting a business, the first year stinks, the second year gets a little better, and by the third year you are finally getting somewhere. By the end of my first year, I could see that this might happen — when I gave up my independence for the safety of full-time employment, I had to turn down what could have been a really interesting new project. In the end, I made $50,000 in the year that I worked for myself, which was unexpected – and impressive to me. If only I had known that I would actually make a reasonable amount of money, I thought at the end of the year, then I could have relaxed and enjoyed it.
In retrospect, although I’d have liked to have traveled and taken advantage of the flexibility, mostly, I wish I’d learned to be easier on myself. I wish I had let myself do the things that I wanted to in the moment (even napping), with fewer shoulds. Seeing now that it could have been ok, I’m not as intimidated to try it again. If there’s a next time, I’ll try to be gentle with myself about how I spend my time and experiment to find a good system that works for me. I know that building a new business takes a while and will plan on that. Until then, I’m feeling grateful to go into an office, have coworkers and a steady paycheck.
Image: Detail of Detroit Industry mural by Diego Rivera, 1933