Reflections on Self-Employment

On Thursday, April 7^th, 2005, in a fit of frustration with my employer, I started doodling on my yellow legal pad instead of paying attention in a late afternoon meeting.

Specifically, I was coming up with a brand name and logo for my own software development business. I’d had enough of working for the small mom-and-pop shop, and I felt I could make it out there on my own.

At the same time, my boss was starting to zero in on a particular line of business, and starting to ignore the customers who had got him to where he was. I knew all I'd have to do was scoop up some of the business he was turning away. I hadn’t signed a non-compete agreement, and I was entirely transparent about what I was doing. My boss even supported the effort, happy to have someone to refer his long-time clients to.

The business started as a side-hustle; I’d work my day job then come home to start my second shift. I was easily working over sixty hours a week.

Eventually, I had enough steady work coming in from multiple clients that I could take the leap and quit my day job.

Becoming an independent consultant meant I could work on client projects during the day, freeing up my evenings to work on products of my own design. To help stay focused on my own products, I committed to releasing minor updates of at least one free product each week as a way to slowly grow my intellectual property while also bringing in revenue to feed my family.

But it wasn’t all rosy. I quickly learned some hard facts about being your own boss. Not only was I in charge of producing the software, I also had to be sales rep, marketer, tech support, and accountant.

Another lesson I learned was that being in business for oneself means that you have to pay the bills first, and yourself second. While I my gross income broke six figures for the first time, I was bringing home the same meagre salary I had with my previous employer. I had to fully fund all of my benefits, which were more costly than I had anticipated. Taxes alone ate about 25% of my income.

I was humbled by the realities of managing a small business. I came to respect my previous employer on a deeper level.

But there was something to be said for the excitement of it all; I was flying by the seat of my pants and would enter into lucrative contracts where I didn’t know if I could deliver in time.

I look back on this period of high-risk, high-reward a bit in awe that I was able to accomplish as much as I did. I feel proud that I was able to support my growing family while going my own way—although it was a bit like walking a tightrope without a safety net. I had some scares along the way, but I continually brought home the bacon.

At the same time, looking back now through the lens of my diagnosis, I see something else: hypomania.

I was incredibly productive, but, honestly, the quality of my work wasn’t the best. I was self-confident to the point of arrogance: starting a small business requires incredible faith in oneself and the world. You almost have to be somewhat delusional to go for it.

Hypomanic or not, I reflect on that version of myself and almost envy the bravado.

Eventually, the business ended—a victim of the great recession. One of my clients offered me a job and, having newborn Hunter at home, I jumped at the opportunity.

I learned many lessons by being in business for myself; if nothing else, it has made me a more appreciative employee.

Today, I work for a Fortune 50 organization with over fifty thousand people on staff, the exact opposite of a sole proprietorship. There’s some safety in numbers, and distributing the work across that many people means we can deal with a volume of transactions that I couldn’t have imagined handling in the past. My team and I address software development problems that are more interesting exactly because of their scale. I’m happier now than I ever was working on my own.

 What size company fits you best?