When I first went freelance, I was still tethered to my old job. Not by a contract or a desk, but in my head.

Every decision went through an imaginary sign-off.

Would Kevin from HR think this project made sense?

Would my old design director nod approvingly?

Would it look “on brand” in the tidy portfolio I was still building, just in case I needed to crawl back to full-time?

I stuck to the same kinds of clients, the same safe deliverables, the kind of work that wouldn’t raise eyebrows in an appraisal meeting.

It was freelancing, but with a boss who lived rent-free in my imagination.

For some people, that tether is important. It keeps you close to steady pay and familiar work. And that’s fine: you can keep it tight for as long as you need.

But for me, the tether started to slacken over the years. The more I realised I could just try things — without permission, without worrying how they’d look on a CV — the lighter it felt.

One of those experiments started with a small newsletter I was writing about business concepts for designers. The research led me to a course, which I took and enjoyed. That turned into a relationship with the founders, and now part of my work is helping to shape that course, doing some of the teaching and coaching. I love it. But I never would have designed it into my CV.

Another time, I designed a one-day workshop. I marketed it, built the materials, got everything ready… and hardly anyone bought a ticket. Commercially, it went nowhere. But I loved the process. It showed me I can design and package something like that, which means I can do it again, with a different subject that might land better.

That’s the thing about a loose tether: it lets you take on small, sideways projects that might turn into major income streams. Or, it might simply give you skills and confidence you can use later. Coaching, speaking gigs, building a course, prototyping a product… these are often the things you dreamed of trying when you were perm, but never had the space for. Freelancing gives you that space.

My dog stretched out on the rug, finished the last bit of a chew, looked over at me and said, “You’re making this very deep for someone who’s essentially just avoiding a boss.”

The less you start wondering what that boss-you-don’t-really-have would think about your choices, the more freeing it gets. You stop curating every move for an imaginary line manager. You start choosing projects because they make you curious, not because they make sense to someone else.

Freelancing lets you decide when to keep the tether tight and when to let it out.

Tight when you need security or you’re eyeing a return to perm.

Loose when you want to explore, take risks, and follow your nose into the unknown.

There are more lucrative options back in full-time land. But I’d be trading away the slack, and I’m not reeling it in any time soon.