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It took TEN coding jobs to learn this hard lesson

How I was finally forced into following my own path.

Tom Gregory
Tom Gregory
Jun 19, 20253 min read

Change jobs every couple of years. Build up your CV. Gain valuable new skills.

That’s the advice we’re given as software developers.

But what if that common advice won’t actually get you what you really want from life?

After changing jobs 10 times, I realized that no matter how many times I switched, I was looking for something in a software development job that I was never going to find.

In this article, I’ll break down why that is — and what you can do to get out of that cycle so you don’t spend your whole career searching in the wrong place.

The job hopping trap

Some developers are happy turning up at their 9–5 to do what’s necessary to pay the mortgage and support their family.

If that's you, no problem.

But some of us want more meaning from our work: to have a bigger impact and feel like we're making the most of our talents.

That's exactly how I felt in each of my ten jobs.

After a while, you've learned the systems. You know the required technologies. You stack skills on your CV and feel like you're making progress.

After a year or two in a job like this, I always got bored.

Normally I was working on products I didn’t care about. Every time, I thought "this isn’t the job I was looking for. It must be somewhere else.".

I would start the job-search again.

Recruiters loved my CV. They always said they had a role that would be perfect for me.

The cycle repeated. 13 years. Ten jobs.

Although I didn’t hate any of those jobs, by the end I was just treading water.

I asked myself — am I going to keep repeating this cycle for the next 30 or 40 years?

Or can I use my skills and experience in a different way?

The desire for autonomy

After pondering that question for a few years, I realized what I really wanted was autonomy.

Control over the kind of work I do. Control over when I work, and even where I work.

Today, I’m writing this in a park on a rare sunny day. I get to choose to be here. I’m not glued to a screen from 9 to 5 waiting for my boss to call.

Since I quit my 9–5 four years ago, I’ve been building an audience online — mainly through YouTube.

With this audience, I've launched courses, written ebooks, freelanced, and earned ad revenue. I still haven’t fully replaced my old salary, but I know now that it’s possible.

It’s easy to look at creators online and think they’re lying about their revenue, or that the only way to earn a living is through a job.

That’s not true.

Open your mind to the fact that this opportunity is right under our noses. We’re all consuming content online — so why not create it too?

It doesn’t have to be YouTube. It could be software, or anything you can create yourself instead of for someone else.


How long are you planning to stay in software development? How many jobs will you go through? Do you honestly believe that’ll give you the life you want?

If yes, that’s fantastic.

If not, then use this article as inspiration that an alternative lifestyle is possible. Start thinking today about what option could work for you.

Want to build an audience on YouTube? Check out my free course Dev Creator KickStart and publish your first video in the next seven days.