Building something on the side while you still have a job is, without question, the safest way to start. It’s how I did it. By the time I handed in my notice I had already run the full loop once: a service, a price, a few paying clients. That’s what made the decision possible.
But this piece is less about the method and more about what I actually think of this path.
Full-time job on one side, your own thing on the other, looks prudent, and it is. There’s also a trap in it that very few people will describe honestly. The trap is that a lot of us treat the side business, or the dramatic resignation, as a way out of work we’ve come to hate. Which is entirely understandable. You’re worn down by the internal friction, the politics, the faces of people you don’t like, and the sense that none of it means anything. So you think, I’ll build my own thing and slowly get myself out of this system.
Then there’s the picture of the one-person company: glamorous, free in time and place, working only with clients who fit you perfectly. You’ve seen the posts, someone with a laptop in Bali. I think anyone loudly selling that side of it online is being dishonest. It isn’t the whole truth.
The other side of the truth is that going solo drops you into the market with nothing between you and it. Product, sales, marketing, aftercare are all yours. You can hire a business coach, and I have had one the entire way. You still do the work. You still make the call. You still carry the result. A lot of the time nobody can tell you what the right answer is. A lot of the time it’s try, get it wrong, take the feedback, correct, try again.
That process can be very lonely, and it does sharpen a person.
I finished my coaching training and got certified in 2022. There were forty or fifty of us in that cohort. Just after we qualified everyone was full of energy, building, visible on social media.
Four and a half years on, as far as I can tell I’m the only one still doing this on my own. Some went back to a nine-to-five. The rest, honestly, I don’t know.
I’m telling you the other side of it because of a specific trap in the build-it-on-the-side route: if your why isn’t clear, you’ll quit at the first serious difficulty and go back to the familiar nine-to-five. Or you’ll never start at all, because starting takes energy too.
If the only reason is to get away from a job you hate, here’s what happens. Working for yourself also gets hard. It also has parts you’ll hate. And in that moment, if the only thing driving you is escape from pain, it’s very difficult to keep going.
One fix. Don’t run on relief from pain, run on the picture. Spend time every day imagining, in detail, what it looks like once your business exists. Then each time you hit something hard, let that picture pull you through it.