One year later: The benefits and tragedies of self-employment

Almost exactly a year ago today, I quit my full-time job to pursue my passion — writing. It was one of the proudest moments of my life, but it was also terrifying. I had spent the last six years working alongside my husband, a mortician, in the funeral industry. My job certainly wasn’t perfect; but it was stable, well-paying, and sometimes fun. I also loved the people that I worked with and was extremely attached to a few. On the other hand, I knew it was time. I had been working full time and writing on the side for so long that I no longer knew what a “real life” was like. In fact, my “real life” was a mess.

Everyone talks about how lucrative and exciting having a “side hustle” can be, but no one talks about the toll it can take on your life. Since I worked 9 to 5 and had two small children, the only time I could write was at 5 a.m. before work or at 8 p.m. after the kids went to bed. This meant that I was working 16 hours a day at times — actually all the time. And the weekends? I worked those too.

But, like I said, one year ago today was the day I finally snapped. It was a Saturday afternoon and I had worked over 70 hours that week, yet I was stuck working late at my job … again. I called my bosses and asked if I could talk to them. And when I showed up at their home, I nervously put in my three weeks’ notice and hoped they would forgive me. Then I called my husband.

“I did it,” I said. “I quit my job.”

We had been talking about it for months. I always said that I would quit when my side income surpassed what I earned at my full-time job. But saying it and actually doing it were two entirely different things. Ironically, leaving my mortuary job felt like a death in itself. I knew that once I left, there was no going back.

“Awesome, Babe,” he said. “You’re self-employed now. It’s all you.”

The Benefits of Self-Employment

Once my final three weeks were up, I hit the ground running and started looking for writing jobs to fill my 40- hour work week. And it didn’t take long. Soon I was working 40 hours per week, or more just to keep up with the various writing jobs I had acquired and my own two websites. But the work wasn’t draining me the way my old job used to. In fact, I felt like I had a whole new lease on life — like I had rediscovered myself. The fatigue and exhaustion I felt when I quit my job had been replaced with inspiration, creativity, and passion. Some of the other benefits I noticed right away:

  • Flexible schedule — I quickly found that one of the best parts of self-employment was the ability to create my own schedule. And since I was no longer tied down to 9 to 5, I began working 7 to 3, which is my ideal.
  • Less time primping — I absolutely hated doing full makeup and hair every weekday, so abandoning that ritual was fine by me. Doing so also freed up at least 45 minutes of my day, which allowed me to start work earlier.
  • Normal lunch routine — My old job made lunch time nearly impossible some days, either because a funeral was going on or the phone was ringing off the hook. But now that I was working at home, I could make a healthy meal and eat it without interruption.
  • Less stress — I was constantly teetering on the edge of insanity at my old job, usually because there was so much going on. It was stressful. Once I started working from home, the stress instantly melted away. I no longer had to juggle 500 things at a time and make small talk incessantly. I only had to focus on work.

The Tragedies of Self-Employment

Self-employment seemed like the perfect gig at the beginning; but as with most things, the disadvantages of my new arrangement began to show once the newness wore off. First things first, I never realized just how high taxes are for self-employed individuals. Basically, because the self-employed work for themselves, they have to pay twice the amount of Social Security and medical taxes. It’s understandable, but it doesn’t make it any easier to write the check.

And about those checks. I hated paying quarterly taxes at the beginning. When I worked in my 9-to-5 job, I just had extra money taken out via payroll to account for the extra taxes I would owe. But now I had to part with my money the old-fashioned way, and it was painful. For some reason, it’s an entirely different feeling when the money is quietly deducted from my paycheck compared to actually having to pay taxes as if they were a bill. I wrote about how paying cash hurts a few months ago, and it’s true!

No Employer, No Benefits

Another big issue we’ve encountered is a lack of options when it comes to health insurance. Since my husband works for a small employer who doesn’t offer coverage, we’re basically on our own. We hoped that the passage of the Patient Protection and Affordable Care Act (PPACA) would help us, but found that we make too much money to benefit at all. In fact, the cheapest health insurance plan available to us is almost twice what we pay now (we currently pay $393 per month), and it carries a $12,000 family deductible.

Our current plan expires later this year, and we’ll have to decide if we want to pay nearly $800 per month for a plan we’ll likely never use or try something unconventional. And when I say “unconventional,” I mean that we’ve considered joining a healthcare sharing ministry, something that Get Rich Slowly writer Lisa Aberle wrote about last year. But for now, our healthcare situation is up in the air.

In addition to those gripes, here are some other disadvantages I’ve noticed since becoming self-employed:

  • No 401(k) match — My previous employer generously matched the first 4 percent we contributed to our company-sponsored 401(k) plans, and I really miss it. Now I have to save more to reach the same retirement savings goals I had when I worked for someone else.
  • No social interaction — I really miss having co-workers to talk to and spend time with, and spending all my time home alone can get boring. This past winter was particularly rough since it was so cold and miserable outside. I felt completely isolated from the outside world at times.
  • Work becomes “work” — Even if you start doing something out of passion, it seems like almost anything becomes “work” at a certain point. I still enjoy writing, but it’s different now that it’s my full-time job.
  • No paid vacation — I got 20 days of PTO at my old job, all of which I forfeited when I left. Now I get zero paid vacation days, which means that I typically work on vacation. I miss having that carefree time off, and the paycheck that came with it, of course!

The truth is, no job is perfect. I certainly lost some perks when I quit my job, but I gained some awesome benefits too. I suppose it’s all about balance and finding a situation that is as close to ideal as possible. I miss my old job and my old identity, but I’m loving my new-found freedom and the responsibility that comes with it. Now I can only hope that, when all is said and done, I made the right decision. Because, like I said, there’s no going back now.

Have you ever considered self-employment? Do you think you would like it? What is your ideal working situation?

More about...Side Hustles, Insurance, Taxes

Become A Money Boss And Join 15,000 Others

Subscribe to the GRS Insider (FREE) and we’ll give you a copy of the Money Boss Manifesto (also FREE)

Yes! Sign up and get your free gift
Become A Money Boss And Join 15,000 Others

Leave a reply

Your email address will not be published. Required fields are marked*