Why Leaving Employment Feels Scary (and What to Do About It)

Let’s stop pretending: leaving a job to go freelance isn’t just exciting—it’s terrifying. The glossy LinkedIn posts and “be your own boss” slogans skip over the part that keeps most people stuck: fear.

I’ve been through it myself, and I can tell you—fear is normal.

Here’s what it looks like up close.

What were your biggest personal fears when you thought about leaving employment?

When considering going freelance, I was concerned about a few things: Is it safe? Is it even a good idea? Where will my income come from? Where will I find customers? It was like staring over the edge of a cliff and wondering if the parachute would open.

Why do you think fear is such a common theme in the transition to freelancing?

Because the unknown is scary. It feels like stepping into a tunnel where you don’t know how long it is—or what’s waiting on the other side. When you’re employed, at least you know what your salary looks like. As a freelancer, you don’t know if you’ll earn enough—or if you’ll earn anything at all. Leaving your comfort zone is rarely a comfortable experience.

Can you share a specific moment when you overcame one of these fears?

Honestly, it didn’t happen on day one. It took a few months. Once I started landing clients and money was actually coming in, the fear of “What if I don’t earn?” began to shrink. Having a savings buffer was key too—it gave me breathing room. That safety net made the leap feel less like freefall.

What practical steps can someone take to reduce fear before they quit their job?

Talk to freelancers who’ve already walked the path. Don’t just read generic advice—get real stories from real people. Ask them what they wish they’d known, how they found their first clients, and what surprised them most. Those conversations strip away the mystery and make the unknown feel navigable.

How do you personally manage fear today as a freelance consultant?

Fear doesn’t vanish—it just changes shape. Today, it’s less about survival and more about growth: losing a client, stagnating, or missing new opportunities. I manage it by reflecting regularly—what’s working, what could be better, what I need to change. And I use Tim Ferriss’s “fear-setting” exercise: naming the worst-case scenario, planning for it, and realising it’s rarely as catastrophic as your brain makes it out to be.

The worries never go away; they just change.

Fear isn’t a red flag telling you not to freelance. It’s proof you’re human. The key is not to eliminate fear but to shrink it into something manageable. Prepare enough, talk to the people who’ve been there, and build yourself a safety net.

Because on the other side of fear isn’t just risk—it’s freedom.