I spent over 10 years working in HR, eventually leading the People & Culture function for a growing business and sitting on the senior leadership team.
A couple of years ago, I left to pursue a business I’d been building on the side.
There wasn’t some dramatic fallout or career disaster behind it. The business had simply grown to the point where I couldn’t realistically do both anymore. I had a young family, I was leading a department at senior level, and I’d reached the point where something had to give.
So I had a choice:
- stay in the secure role I’d been in for nearly 8 years
- or take a risk on something I’d built myself
At the time, staying felt like the “safe” option, but also the complacent one. I’d started getting restless, frustrated, and honestly a bit too comfortable. Nothing catastrophic, I just knew I needed a change.
So I took the leap.
Now, nearly two years later, I genuinely don’t regret it. Running your own business teaches you things you simply don’t experience in employment. You wear every hat. You carry the pressure constantly. You learn quickly because you have no choice.
But I’ve also learned a lot about myself.
I’ve realised self-employment can be incredibly isolating. I miss collaboration. I miss being part of a team. I miss building something alongside other people instead of carrying absolutely everything myself.
So earlier this year I started looking to move back into employment.
And honestly, the experience has been far more draining and demoralising than I expected.
I completely understand that after stepping away from traditional employment for a couple of years, I may not be able to walk straight back into the same level role I had before. I’m realistic about that. Careers aren’t always linear and I knew there was risk attached to the decision I made.
But what’s surprised me is how negatively self-employment can sometimes be viewed by recruiters and employers.
The most genuine feedback I’ve received so far is essentially that my decision to go self-employed is now seen as a risk.
And that’s been difficult to process because it can feel like the experience before it suddenly counts for less.
I sometimes get this passive-aggressive undertone of:
“Why would you leave a secure career?”
or
“What’s stopping you doing it again?”
As if trying something entrepreneurial was somehow irresponsible.
Beyond that though, I think the whole process of job searching itself is just exhausting.
I’ve had interviews stretched over weeks with little communication, recruiters openly admit they don’t understand the field they’re recruiting for, companies ghost after multiple stages, and rejections arrive after hours of preparation with little or no feedback.
And after a while it becomes mentally draining constantly trying to package yourself into the “right” answer for every application.
Especially questions like:
“Why do you want to work here?”
Because obviously you try to answer professionally and thoughtfully, but the reality for most people is also:
“I need a job. I need stability. I need an income.”
That doesn’t mean you can’t care about the company or the role. But sometimes the process feels oddly performative on both sides.
I’ve only been searching since February, which I know is nowhere near as long as some people on here. Honestly, I really feel for people who’ve been dealing with this for much longer because even after a relatively short time, it’s surprisingly easy for the process to wear you down.
Curious if anyone else who’s gone from employment - self-employment - back into the job market has experienced something similar.
EDIT: TLDR - Left a senior HR role to pursue self-employment, returning to the job market has been surprisingly exhausting and I’ve been shocked by how negatively some employers view self-employment.