Behind The Curtain: Why Being Your Own Boss Can Sometimes Suck

Back in 2011, I decided that I was going to try to do something I’d wanted to do my whole life: be a full-time writer.

Unlike other small children, my answer to “What do you want to be when you grow up?” didn’t change from week to week. I wanted to be a writer. Full stop. That’s it.

So I went hunting for writing jobs. Some paid well, some were laughable. An editor friend of mine reached out and asked me to write a post for this new site and it would pay me $250 for roughly 500 words. (To put it in perspective, I regularly write 500-word posts here at least four days a week.) I accepted any assignments she gave me, and for a while, it seemed like I was well on my way to replacing my lost income from my PR job.

One day, the CEO of that site called me directly. Asked me to become a contributing writer, paying me $100 per article, and I would get a guaranteed 10 articles (of my choosing) per month. At the time, I was very happy to get it because I got kids, yo, and it was the highest paying writing job I could find. Plus, the CEO asked me. Lil’ ol’ me from Ohio, receiving a phone call from the CEO while he lounged poolside in LA. Consider my ego stroked. I accepted.

All went well for two months.

In June, I sent my invoice for $1000 for 10 articles written in May. A full month and a half goes by before they send me a check. Only the check is for $250. WHERE IS MY $750, THOUGH? Had me looking at my check like,

ice cube gif

I email and email and get no response. At this point, I’ve also got my June invoice and a few articles from July pending with them. Their accounts payable department finally responds, saying my rate and the rate of all the other writers had been slashed to $25 per post and we just had to accept that the rest of our money wasn’t coming.

Now they’ve made me mad.

justin timberlake gif

I called and emailed the CEO (who was the one who asked me to write) and he was dodging my phone calls like a pro.

I would call and get angry with his secretary. “I KNOW HE’S RIGHT THERE, TANISHA! PUT HIM ON THE PHONE!”  She, of course, refuses, even though I can practically hear him sitting there.


They owed me $1500 for May and June and $300 for July. I needed my money. That was a mortgage payment I was missing. I kept this up for weeks. I tried to get the other writers to organize with me for some type of collective suit, but they weren’t interested. “Just accept it as a loss,” they said. “We’re moving on.”

The website has since gone out of business and I would be lying if I said I wasn’t happy about that. They played me to the left, meanwhile my bills still kept coming. How you gonna change payment terms AFTER the work is completed? We had a contract! An agreement. Freelancing is wack sometimes.

Lesson Learned: Sometimes, people will not pay you. Do as much as you can to guarantee at least a deposit for your services, add strictly worded language in your contract about refusal to pay and pad your bank account for the lean times.

There is so much faith that goes on behind the scenes. You have to believe the work will continue to come, or that you will be nimble enough to adapt if it doesn’t. You have to believe that the person on the other end of that accounts payable email address sees those emails and understands that the quicker you get your check, the faster it hits your check, the faster your mortgage company can get their share. You have to believe you are fulfilling your life’s purpose and that the small (and large) setbacks are worth the headache in the long run.

I do hope to share more stories of my life as a small business owner—the good, the bad and the ugly. Now only will it help me gain perspective about my career (I still had enough money to pay my mortgage after this incident, thankfully) but it is my hope that it will also help you all as you decide to branch out and create side hustles and small businesses!

Have questions about business, working from home, balancing motherhood? Hit me up on my page and your questions might spark a full blog post!