How Risky Is Freelancing?

In the interest of full disclosure, I have to point out that I’m the kind of person who has an optimistic view of the nature of risk, which is why I’m not a financial advisor and you wouldn’t want me to be.

But I also think we are too certain that some actions are “safe” – like having a staff job. I scroll through my LinkedIn feed and all I can say is that I don’t think that’s safe at all. Not a single day passes where I don’t see a ton of people reporting massive layoffs in every industry and a ton of profiles newly sprouting the “open to work” banner.

I’ve been a freelancer for more than twenty years. And I’ve had my ups and downs, but I’ve always managed to make it work out. I’ve had to pivot from one thing to another, but that makes my work interesting and fresh.

“You will always find a way” is something my daughter tells me whenever I face a challenge, and I think if that’s the lesson she has learned from all of this, it’s a hell of a good lesson to learn.

I don’t experience freelancing as risky. I’ve always felt that freelancing has meant my future is in my own hands, not someone else’s. Being in charge of your own life is a lot less risky than being at the whim of some faceless conglomerate or toxic boss.

In fact, a staff job is the kind of thing I would experience as a terrifying risk. I would only do it if I had a side gig that I could ramp up to full time if needed.

So … how risky is freelancing? It depends on what you think risk is.