Moving from Employment to Self-Employment

Patchen Barss
Photo by hay s on Unsplash

“Patchen, either you’re 85 years old, or you can’t keep a job.”

Neither is true, but I understand why an old boss of mine had that reaction when he looked at my CV. Like many writers, I’ve spent 20 years moving between jobs in the media, the non-profit sector, and the corporate world, often punctuating these transitions with years spent working as a full-time, self-employed writer and author.

It’s always shocking to give up a steady paycheck, benefits and security for the hustle-or-starve world of freelance and contract work. With discipline, though, self-employment can provide the freedom to pursue projects of uncertain remunerative merit (like writing a book, for instance), while still taking on enough paying work to maintain the glamorous lifestyle to which we freelance journalists have become so accustomed. Every time I’ve moved from structured office life to the sweet freedom of being my own boss, I initially experience equal parts exhilaration – “I could spend this afternoon at a café just writing whatever comes!” and panic – “I could spend the next 20 years living in a cardboard box and then die alone!”

Panic tends to win the day, and I get down to work. Here are some of the things that have worked for me over the years:

Put a lot of pressure on yourself…

… But only if you’ve given yourself a break beforehand. Currently, I am very excited about my next book project, but I have also just moved into a new house and my partner and I are expecting our second child at any moment. I could make myself miserable trying to hammer away at the book while keeping up with child care and bill-paying writing. Instead, I made a deal with myself: take a break from the book until the new year, and then go back at it with a vengeance. This deal requires the discipline, both to take the pressure off myself now, and to reapply it in a few months to ensure I make time to work on it.

Write something terrible…

… But get it done a day or even a week before deadline. It doesn’t work for everyone, but I find it much more helpful to get the right number of words on a page for an assignment, even if it is just blather, as long as I have time to go back and turn it into something intelligible. I give myself permission for the first draft to suck, because I know that the final product will be better than if I tried to craft a single draft just in time for deadline. And even if your first draft turns out to be great, it’s amazing how it can improve even more if you allow enough time for it to sit for a few days before you take another pass at it.

Ignore your financial situation…

… Because you have excellent records that tell you how you’re doing. I used to think about money every moment of every working day. Now I keep a simple spreadsheet that tells me what I’ve earned, what I’m owed, what I’m promised in future work, my monthly expenses, and how much I need to set aside for taxes. I check in a couple of times per month to update and asses my situation. The rest of the time, I can put financial concerns out of my head and focus on writing.

Goof off every day…

… But don’t do it alone. The freelance life is amazingly isolating – when I first started working from home, I found that when I was around other people, I would babble uncontrollably, so excited was I to be around other beings. Ultimately, I determined that it is highly valuable to interact with humanity at least once per day. Find other freelancers, go for a coffee or a walk. When you’re paid by the job, it always feels like a luxury to leave your desk, but human interaction not only keeps you sane, but it also makes you more productive.