Am I the Boss or the Secretary? A Year of Working for Myself


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


  1. Steve Togasaki

    I was self employed for 14 years in a family business, and 2 years later, worked with a partner(my brother David) for another 18 years. Two completely different industries, import/expert with Japan, and sales/installation/service in the window covering industries. While one dealt with merchandise, complex financing, and projecting 6-9 months into the future, the other dealt with interior designers, distributing, craftsmanship, and homes. There were constant themes running through both.

    Self employment requires working knowledge of so many areas including sales, marketing, finance, accounting, project management, customer service, quality control, management, and collaboration. It almost guarantees lost sleep, always taking work home(especially if you work out of your home), stress when you’re too busy and stress when you have idle time, and the pressure of being a generalist.

    But there are some great benefits. The variety of tasks means you’re seldom bored. You’re always trying to learn and improve is different areas. And you are indeed your own boss. Which means you can determine the ethics of how you run your business, what standards of quality and service you decide to adhere to, and what kind of client base you want to deal with.

    Like all things, there are the ups and downs. At time you feel like (as by brother-in-law so succinctly put), the phone’s never going to ring again, we’ll never have another order, and we’re all gonna die. Then there are the times when, like Hannibal Smith of the “A Team”, you get to say “I love it when a plan comes together”.

  2. Ann Hasse

    I love your comment about people who are not self-employed straddling the fine line between hopeful and delusional! I worked for a small firm for six years, and it was in many ways like working for myself although I did have an office to go to and didn’t have to do all rain making. But many of your comments ring quite true for me, nonetheless. It’s a very nerve-wracking situation in many ways, despite the alleged flexibility — it is hard to take a vacation! I enjoyed your piece very much!


  3. steph

    Thanks Steve and Ann both for sharing your experiences! Not being bored and being able to run your business (and grow yourself) in the ways that you want are so wonderful.

  4. Having freelanced almost all of my working life, there’s no doubt about the roles anxiety and inertia can play. When I taught, briefly, on an adjunct basis, I told my cinematography students that ‘free’ time is the greatest challenge. The times that are not defined by paid work confront us with our innate creative potential. This is made difficult but not knowing what’s on the horizon. It’s an act of faith that challenges and defines us. Profoundly.
    So, it’s easy to romanticize the idea of being your own boss. But being your own boss calls on us to be the kind of boss we’d like to have/be.
    Thanks, Steph.

  5. Emily

    Steph, I so appreciate this piece and can sympathize on so many levels. For the first time ever, I am currently spending part of my year (8 months) working remotely for my company – and from home, alone. Although I have a boss to answer to – which is where our experiences differ – I find structuring my day to often be very difficult. I, too, am ruled by “shoulds!” I find the flexibility wonderful, but the loneliness that comes alongside it (in my situation) often very challenging. Sometimes I daydream about celebrating a co-workers birthday in an office environment, or slipping over to a coworkers desk to share a funny work-related (or personal!) story. Ultimately, I agree – one straddles a very fine line when working remotely, or from home, or for him or herself. Like most things in life, it’s all about balance!

  6. steph

    Emily– thanks for your comment. I love the daydreams about celebrating coworker’s birthdays– amazing! I certainly agree that balance is the key (to this and the rest of life)!

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