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Self-Employment: Three Valuable Lessons Learned

What I discovered about being a solo entrepreneur

Many of us dream about leaving our jobs for self-employment. Working from home and controlling our schedules sounds appealing — no more useless meetings. We can go to the gym in the middle of the day. Plus, there’s no cap on the amount of money solo entrepreneurs can earn.

That was me six years ago. I filled my head with positive stories of people who worked for themselves. Not to mention, I was miserable in my job. So I snagged the first chance I had to become self-employed. It was a huge mistake.

My first round of solo entrepreneurship lasted ten months. By the end of it, I was broke and desperate for a steady paycheck. But the experience wasn’t wasted time and effort. Instead, it was a valuable learning experience that’s prepared me for my next go at self-employment.

Some who try and fail at working for themselves realize it’s not for them. These folks gladly leave solo entrepreneurship behind. Others of us regroup, learn, and give it another go. After all, if we all gave up another trying something once, much of the technology and science we have today wouldn’t exist.

After getting married last year, I joked that having planned my first wedding, I’m better prepared to do it a second time. But there’s indeed no replacement for personal experience. The key is to learn from your mistakes.

It’s been six years since my first bout of self-employment. In a couple of weeks, I’m giving it another try. But I’ve learned from what I did wrong the first time around. Having tried, and failed, at solo entrepreneurship once, I’m more prepared than I was before.

There are three essential lessons I learned from the first time I worked for myself. I cover each item below. You can’t replace personal experience, but you can grow through others’ insights.

If you’re thinking about self-employment, these three lessons may help you prepare for being your boss.

Pick a focus

I started freelancing before I went into full-time self-employment. My freelance clients hired me to do social media marketing for them. But then I met some people at an agency. The firm was looking for someone to provide search engine optimization (SEO) for their client’s websites.

Photo by Stanley Dai on Unsplash

While I had SEO skills and experience, it wasn’t the kind of stuff I’d planned on doing in self-employment. But the agency would provide steady work. And I needed clients. So I agreed.

Signing with the agency gave me enough of a client base to justify leaving my job. Going full-time, though, meant I needed more clients. So I hustled, leveraging my network to meet potential clients.

And there wasn’t a potential client’s need that I couldn’t meet. Do you need social media help? I do that. Do you want an SEO expert? That’s me. Are you looking for someone to write website copy? I’m your guy. If I thought I could deliver whatever a prospective client asked of me, I took the job.

Before long, I had many clients and plenty of work. But I had no specialty. This lack of focus created a couple of issues.

First, it was difficult to improve. We improve the more we do something. And when you specialize, you hone in on getting good at your specialty. Yet my client offerings were too diverse. Instead of offering one thing done well, I delivered many things done averagely.

Secondly, I had trouble marketing myself because I offered no special sauce. Was I an SEO guy, a social media marketer, a freelance writer, or something else? I tried to be whatever a prospective client wanted me to be to win their business. But when you’re everything to everyone, you’re no one to anyone.

Don’t be your bad boss.

Some of us who try self-employment do so because of the cult of entrepreneurship. Many cultures champion entrepreneurs. Especially in the 2010s, people who made and grew businesses were celebrities. Entrepreneurship was sexy. I wanted in.

Plus, I wanted to be my boss. I was miserable at my job before self-employment. Part of the reason for my disillusionment was a poor relationship with my manager. So I thought working for myself was a way to drop my bad boss problem.

That wasn’t true, however. Yes, you’re your boss when you’re self-employed. But you can be a bad manager, as I was. I was my bad boss. I failed to set goals and didn’t hold myself accountable.

Another name for self-employment is self-management. I’d spent my whole professional life having someone manage me. Now that I was solo, I lacked the discipline that a manager provided me.

Working for someone else can hide your shortcomings. Your teammates and manager can make up for your deficiencies. But this support disappears when you’re self-employed.

Working for yourself magnifies your flaws. That’s why it’s essential to shift your mindset from being an employee to being a manager. You have to manage yourself and your business. And you don’t want to be your bad boss.

Solo entrepreneurship isn’t a solo decision

Self-employment will expose your flaws, including those in your relationships. The first time I jumped into self-employment, I believed my then-partner was supportive.

I wanted to work for myself, and I had clients willing to pay me. Plus, as I mentioned, I was miserable in my job. Going into self-employment should have been a joint decision between my partner and I. Instead, it was a demand I placed on him.

At the time, I didn’t realize my partner wasn’t supportive of my move. But it’s easy to convince ourselves of what we want to believe. And I convinced myself that my partner was OK with my self-employment.

Yet he wasn’t comfortable with my decision. My partner and I split up a few months into my solo entrepreneurship. Any number of factors play a part in a relationship’s success or failure. My boyfriend and I didn’t break up because I started working for myself.

But self-employment magnified the cracks in our relationship. The issues were too significant to ignore. And so we went our separate ways.

The breakup gave me essential issues to confront. First, because we lived together, I had to find a new home. Secondly, I needed to deal with my emotions. And I now had financial pressures because my plan had been for my partner to subsidize me while I grew my business.

Being self-employed is hard enough without having to deal with emotional turmoil and money problems. I didn’t handle the breakup well, which cost me precious money and clients — my work dried-up. My money ran out. It wasn’t long before I needed a salaried job with insurance.

Now I’m married and embarking again on solo entrepreneurship. This time I’ve engaged my husband throughout the process. From the moment I considered self-employment through today, we speak almost daily about my move. Plus, we both feel we have a healthy, happy, and strong relationship.

It can be easier to go into self-employment if you have a spouse or partner. They can help support you while you ramp-up your business. And, at least in the U.S., you may need the health insurance that having a spouse can provide.

But make sure your choice to go into solo entrepreneurship isn’t a solo decision. You don’t want your relationship to end. (Or, if you do, make sure to finish it before becoming self-employed.) And the last thing you need to deal with when starting out working for yourself is a breakup.


Self-employment is exciting. There are fewer limits to your potential. You can control your schedule and work environment. But it’s not without pitfalls.

Six years ago, I started working for myself. I thought it would last the rest of my working life. It lasted for ten months. That time wasn’t a failure, however, but a learning experience.

And the three most valuable lessons I learned about solo entrepreneurship are:

  • Pick a specialty for your work.
  • Don’t be your bad boss.
  • Make sure your spouse or partner is on board.

What about you? If you are or have been self-employed, what did you learn through the experience that you think can help others?


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