Lessons I’ve learned as an accidental solopreneur

6 min read
Sally McGraw

The term “solopreneur” wasn’t a thing then, but I can remember the day I decided to be a writer. Actually, I can remember the moment. It was in my third grade language arts class, and Mrs. Esrick was handing back the poetry assignment we'd submitted a few days previously. We were on our way out the door, poems in hand, when she stopped me and said, “You're really good at this, Sally. REALLY good.” (OK, I'm paraphrasing. Sue me. I was 10 at the time.) And I remember thinking to myself, “I'm good at this. And it's as easy as breathing. I think I'll do it forever.”

Solopreneur Sally McGraw
“I never thought I'd be happy as a solopreneur, but even with all the ups and downs, I can't imagine any other life for myself,” says Sally McGraw (above).

Fast-forward to college at Binghamton University, where I was a giddy creative writing major bent on putting my own stamp on the Arthurian legends. It quite literally never occurred to me that penning a few fan-fic pieces as a pre-teen and some truly lousy short stories in high school wasn't quite enough to prepare me for the novelist's trade. Two weeks into Fiction 101, and I knew: I'd have to make my living another way.

Fast-forward to my seventh job in marketing and communications in 2007. By this point I've written 1,200-word front-page feature stories for local papers that paid me $45 for my work, attempted to totally switch gears and study animal behavior (what?), and settled into a new desk job that I can do in my sleep. I jot down some style advice for a fashion-challenged coworker, and she says, “This is great! People would love this. You should put this on a blog.”

Solopreneur Blog Already Pretty

Fast-forward to present. My style and body image blog will be nine years old in September. I've been livin' la vida freelance for five years, and I've recently shifted focus to ghostwriting and editing.

I am an incredibly stubborn, anxious, routine-loving person, so I'm still thunderstruck to find that the unpredictable ebb-and-flow existence of a solopreneur suits me ... but it does. And I can't imagine ever going back to a 9 to 5.

Here's what I do to make sure I won't ever have to.

Solopreneur lesson No. 1: Diversify, diversify, diversify

Admittedly, I was forced down this road: My blog never made obscene amounts of money and there is zero chance I could ever live off my ad and affiliate revenues alone. But as we enter the era in which Instagram stars can make more than bloggers ever dreamed possible, I'm grateful for my instinct to keep multiple irons in the fire.

Solopreneurs who do only one thing are at a much higher risk of expiring during fiscal dry spells.

Over the past five years I've held down a paid weekly TV spot on a local Fox affiliate, taken on in-person and online style consult clients, taught community ed classes, hired myself out for private speaking engagements, written books, syndicated my content, and written for everyone from to Goodwill. Solopreneurs who do only one thing are at a much higher risk of expiring during fiscal dry spells than those who do multiple things. (And do them all well.)

Solopreneur lesson No. 2: Keep an eye on those quarterlies

Taxes are a bear when you're a solopreneur, especially when you're transitioning from traditional employment to working for yourself. All those shiny checks roll in sans income tax deductions, but many of us forget (or ignore) the fact that a percentage of our dollars technically belong to Uncle Sam.

Take it from someone who learned the hard way: Dealing with taxes once per year in the spring will make you a miserable mess.

Set yourself up with an accountant to calculate quarterly payments, and send them in diligently. That way, you won't have to give the entirety of your savings account plus your firstborn child to the IRS come April 15.

And if you really want to ease your worried mind, set aside those deductions each time you're paid. I can't quite believe it, but 2016 is the first year I've just taken 30 percent off the top of every single check I receive. And it has made my life SO much easier.

Solopreneur lesson No. 3: Network your pants off

Hate this advice? So did I until I realized that any networking activities you hate never pay off anyway. The kind I'm talking about involve being open to meeting and talking with interesting people about their work, letting your friends and colleagues connect you with their friends and colleagues.

I'm talking coffee and lunch dates that end with, “If you know anyone who needs X, I hope you'll keep me in mind! And I'd love to connect you with my friend who is fabulous at Y.” Forget business card exchanges in hotel conference rooms. Focus on talking with acquaintances about the work you do, and offering to help them in kind.

Solopreneur lesson No. 4: Don't panic during lean times

I've had $10K months and I've had months in which three-quarters of my clients have all bailed at once. The former is a helluva lot more enjoyable than the latter, but I've learned to ride the waves as they come. You wouldn't think that freelance writing and editing would be seasonal, but absolutely everyone stops thinking about work in July and August so summer is typically light on work. And money. But September rolls around, the entire world taps the back-to-school mentality, and projects begin appearing again.

Ride the waves as they come.

If my monthly income ever dwindles to the point that I can't pay my share of the bills and mortgage, I'll consider a barista gig. But so long as I'm solvent, I'm fine with a few dry spells.

I would love to say that I've become admirably thrifty and socked away $50K so I never have to worry, but I just plain love shoes too much. And I wish I had some magical hustle-driven formula for drumming up wealthy, easygoing clients to share, but from what I can tell such things are equal parts myth and B.S.

I will say this, though: I never thought I'd be happy as a solopreneur, but even with all the ups and downs, I can't imagine any other life for myself. I'm lucky and grateful, in love with the work I do ghostwriting nonfiction books and editing stellar book proposals, and so glad I took the leap into self-employment.

Here's hoping these tips might help a few of you who are standing on that ledge yourselves.