Self-employment and freelancing: Have patience, forget ‘perfect’

by Ann Wilkins Jefferson, ‘92

With the COVID-19 pandemic in full swing, many of us find ourselves working from home whether we want to or not. You have a glimpse into how you’d operate as your own boss freelancing or running a business from home – except maybe not with children, a spouse or roommates around all day.
If you have to or want to continue working from home, here are tips to keep in mind:

1. You need to forget about “perfect.”
Finding a perfect time and business plan is counterproductive. Just get the process rolling and the fine-tuning can come later. Of course, you may have to work nights and weekends to do research and build a foundation.
Don’t worry about being perfectly qualified to start advertising your services or product, either. Repeat this phrase often: “Done is better than perfect.” Write it on post-it notes and put it in several places where you’ll see your new motto daily.
If you’re consumed with being flawless, you’ll waste precious time. Simply START. Yes, striving for excellence is a great goal, but as mega-successful entrepreneur Mark Cuban of Shark Tank stated, “Perfection is the enemy of profitability.” It can paralyze you if you’re preoccupied with it.

2. Take advantage of any major life changes (like being quarantined?!).
After graduating college with a degree in Communication – Rhetoric, I held a few very rewarding fulltime jobs for the next nine years. But when my husband, Cal, and I welcomed our third child, we faced daycare payments for three adding up to half my salary and benefits. Rather than both working outside the home, we decided I’d stay with the kids for financial reasons and their well-being. That transition led me to freelancing.

3. Seize opportunity when it knocks.
My first self-employed gig came when the newspaper where Cal worked sought a freelance writer. He volunteered me before I even had a chance to hear details. I almost turned it down, unsure of being exactly what they wanted. Yet I made a key decision in working for oneself: I jumped at the chance to get out of the gate and on the way.
Those first three writing assignments turned into six, then ten, then to about 15. I grew self-assured the more assignments they gave me, gained much-needed additional income, and kept my resume current. Carrie Fisher aka Star Wars’ Princess Leia but also a best-selling author, gave advice to fans along those lines on having courage to begin: “Stay afraid, but do it anyway. What’s important is the action. You don’t have to wait to be confident. Just do it and eventually the confidence will follow.”

4. Have patience and persevere.
If you’re starting a home business and it’s not looking great, remember it takes time to be successful. A helpful motivator: Print out President Calvin Coolidge’s quote on persistence called “Press On” and paste it in your workspace.
Cal, a former editor of Ohio State’s student newspaper The Lantern, earned a bachelor’s in History and then Journalism. In 2012, two decades after his first degree, he launched a “side’ business with two coworkers that grew into fulltime work. None of them have MBAs. But they had vision. After two initial shaky years, patience and persistence paid off!

5. Take calculated risks.
Of course, you’ll also have uncertainties. And if you’re married, starting a home business is a team effort. I stopped freelancing and volunteered for a mobilization to Afghanistan in 2012, as I’m a Navy Reserve officer (we came to that agreement after many discussion and weighing the risks). This way Cal stayed home with the kids and had the freedom to work on the new venture while they were in school. I was able to provide a steady paycheck and medical insurance through my mobilization. Not everyone needs to make a move quite so drastic, though for us it worked.
What could work for you? We are in an era when operating a company or teleworking is possible in various fields due to recent technology and apps, often with little overhead from a home office. You’ve heard before, “Necessity is the mother of all invention” and another ala desperation led to success. But for you it could be neither: Maybe you’d be good at or better at what’s already being done.
Read about those who had successful start-ups and why; Entrepreneur magazine is a favorite of mine. Look up how Sir Richard Branson started Virgin Airlines – it’s a great example about not overthinking, just taking action. Ask trusted colleagues or friends for advice and critique on what you’re planning or take a look at your website or product. Consider joining freelancer sites like Upwork.

6. Don’t forget reaching out to fellow Buckeyes for guidance!
Use your Ohio State alumni connections on LinkedIn, social media and at the Alumni Association for direction and feedback. You’re part of the biggest college alumni group in the world (if that still holds true – if not, it’s the greatest). We’ll cheer you as you go!

Ann Wilkins Jefferson is a 1992 graduate of The Ohio State University with a bachelor of arts in Communication – Rhetoric track. She held fulltime jobs as an assistant press secretary for a U.S. Senate campaign, and communications/ marketing director for a non-profit before starting freelance writing, primarily for two major clients. Aside from her civilian career, Ann is a lieutenant commander and Public Affairs Officer in the U.S. Navy Reserve, a career that takes her around the world. She’s a veteran of Air Force Reserve Public Affairs and a graduate of U.S.M.C. Officer Candidate Course. She and her husband C. Calvin Jefferson, III, ’92, ’95 live in a Cleveland suburb with their four kids (including their oldest graduating from Ohio State in May 2020!). Cal is president of, where Ann assists with operations, editing and events.


Leave a Reply

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