Leaping into Freelance as a 40-Something Single Mom

May 5, 2016


As we ramp up to Mother’s Day, a special guest post from freelance writer Lorraine Sommerfeld. She shares her inspiring story of pivoting to a freelance career at 40, as a divorced single Mom.

Freelance job. Single mother. Those four words can look a little dangerous, but I’ve made it work for nearly 14 years. I could say it’s because I’m a rockstar at what I do or I’m a trust fund baby who works for kicks, but neither would be true. I work hard every day, I worry about my kids and go to bed each night hoping I’ve pulled off enough good to offset the mistakes.

I’m not sure which came first, the freelance writing career or the basketball to the face. I was plugging away at my office job when the call came in from my then 10-year-old son’s principal. He’d taken a basketball to the face and was bleeding all over the office floor, something they seemed to think I could staunch over the phone.

If you think working and having children can be a bit of a juggle when you’re married, doing it while you’re single isn’t about even dropping a ball. It’s about the balls just crashing to the floor while you sit there helplessly. Sometimes crying. After the divorce (the family owned business – and my job – went with it), I was working a string of desk jobs that mostly left me just enough time in the day to wonder if I had enough gas to get home. I got paid by the hour, but only the hours my butt was in the chair. One sick kid meant a day off I could hardly afford; illness for myself was a luxury, like a restaurant where you didn’t order off the wall.

It was the bloody nose that made me become a freelancer, an idea I’d been fiddling with for years. I wanted to be a writer and I thought I could actually make the writer thing happen. I finally realized I could be broke and unhappy, or broke and happy. I was about to turn 40 and my sons were 9 and 12. My parents, whom I’d adored, had passed away when the boys were really little. I had nobody to step in every time the school called.

Which isn’t to say I woke up one morning able to support my kids while I chased my dreams with a butterfly net. I gave myself one year and $20,000 into my line of credit to make a go of it. If I couldn’t make it work within that frame, I had to go back to one of those jobs I usually got fired from. Having no choice is a wonderful motivator, and looking back, I think the only way I actually made it was by never looking down.

There was a time when working freelance made you an outlier, a renegade, a fool. The goal was always to get in with a good firm – a big one – and take care of your family with benefits and a guaranteed paycheque. Predictability, for all the negative connotations it brings up, is a good thing when you have children.

That was then, this is now. Today, some of us are forced to do some form of freelance work in a world economy gone haywire. I doubt I could have assuaged my parents’ fears, if they were alive, that this would be a viable way to raise my sons. But for me, it has always been the allure of the unknown, not the fear of it, which has wooed me away from gold watches and dental plans. While my sons had benefits, I learned early on how to barter my talents for things I needed, like working on websites in exchange for home repairs.

The biggest myth (and obstacle) about working from home is that people think you’re hanging around all day because everybody knows those television shows don’t watch themselves. Establishing boundaries, both for my kids and myself was a challenge. I started working from my kitchen so I could be here for my boys more, but ended up I was shoving them out of the room and warning them to respect that I was working. I’d always had a wonderful network of moms who all helped each other out when I’d worked outside the house; we continued to use our village to raise a passel of kids. Everybody understood that my hours at the keyboard were as surely work as any of theirs in boardrooms or behind a bar. I never denigrated what I did, because if I didn’t consider it work, how could anyone else?

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The money may have been a little fragile, especially in the early years. But I never had to send a child to school who was really too sick to go, and I could line up doctor’s appointments and errands in the day to free up those valuable evening hours for those with less choice. I’d suffered migraines all my life, and the reduced stress of not having to push my productivity into someone else’s idea of face time saved me a lot of pain, and even more on drugs.

Freelancing is very much like that other ‘f’ word: flexibility. I’m sure I work twice as many hours as I ever did, but they’re my hours. The only staff meetings I have are with my cats. My sons have had to see up close epic deadline freak-outs, but they have also always known and understood what I do for a living. There is no mystery. They know what I earn, they know what it costs to run the household. They know gigs can end with no notice, and they know you can survive it.

I used to say freelancing isn’t for the faint of heart, but as more people are forced into a decision I willingly made, it’s better to talk about what it really is. It’s hard work, it takes a plan, and it takes a ton of discipline.

Good qualities for any of us, come to think of it.


about the author

Freelance Contributor Lorraine Sommerfeld is a Drive columnist for Postmedia, television host of the Lemon Aid Car Show and Motherlode columnist for the Hamilton Spectator. She’s made a living writing about her sons. They remind her of that every day. Follow her on Twitter @tweeetlorraine.