Why I (Still) Freelance

Reflections on three years of working for myself

Kelsey Gilchrist
3 min readSep 6, 2023
Photo by Peter Olexa

“Are you still doing that freelance . . . thing?” On family Zoom calls and at holiday gatherings, aunts and uncles inquire with trepidation, as if I’m still working as a lion tamer at the circus (Cirque de Soleil performers: you have my sympathy).

My clients ask me too. Some have even asked if I might prefer to work with them full-time. We have benefits, they say. Generous vacation time! A great team barbeque in the summer!

Yep, I’m still doing this freelance thing. And, against all odds, I’m happy. Happier than I ever was in a salaried job with those perks. Despite the instability and inconsistency, the uncertainty around finding my next paycheque, the challenge of seeking out new clients, and the administrative burden of contracts and finances, this is the best job I’ve ever had.

Why, though?

“Why?” is a reasonable question. The last time someone asked — a great client of mine who wondered if I might be interested in some kind of full-time role with them — I let a beat of silence pass before I answered, reaching deep for the truth.

I think I’m built a little differently, I explained slowly. I like my time to be my own. And I prefer to sacrifice financial security for control — over my…