This as-told-to essay is based on a transcribed conversation with 34-year-old Jay Wallace, from England. The following has been edited for length and clarity.
I got excited about the sales world when I landed a recruitment job in 2013.
I spent years in sales roles, both as a self-employed sales contractor and as a company employee. I really enjoyed talking with people and making sales that directly correlated to my earnings.
I started a new job as a self-employed sales contractor in June 2023, but quickly became frustrated with the role. As a contractor, I’d tell the company my available hours and they would share sales leads with me. I’d make sales and get commission for products installed.
I felt I had too much freedom and not enough clarity. Because I couldn’t tell whether I was succeeding, I felt like I was failing.
After three to four months of frustration, I decided to leave the job in March 2024.
I didn’t really know what to do next. I’d always wanted to go solo traveling and I also had a loose plan in mind for new business ventures in content creation and coaching.
But chasing freedom didn’t turn out the way I’d hoped. I’ve since struggled to navigate the job market and find work that I can do to support myself while building up my business and YouTube Channel. I realize I left my job too hastily.
Spending time abroad didn’t go to plan
I’d considered leaving sales before in 2020 because I no longer felt challenged. But COVID felt like a bad time to be moving careers.
When I left my job in 2024, I planned to spend a few months in Southeast Asia, mostly living off my savings and passive income from an investment property I partnered with my father on in 2020.
I hoped the lower cost of living in Thailand could help dramatically reduce my bills while I worked on my business idea.
The loose plan was to put more time into the YouTube channel I’d been running for a few years and also facilitate some kind of coaching business.
Thailand wasn’t as I’d expected. It was nice for about two days, and then I sat there thinking, “What am I doing?” It was lonely — I’d left my family and my girlfriend behind to travel.
I wasn’t in the right headspace to run a business, so I ended up coming home after a few weeks.
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Back in the UK, the job market has been tough
I went through a period of real darkness. My last sales role knocked my confidence, I’d failed to find freedom in Thailand, and then felt like I’d failed my relationship when I came back.
I wasn’t mentally in a good place, so I wasn’t making a concerted effort to grow my YouTube channel.
I still had savings because I’d come home earlier than expected, but I didn’t want to go back into sales. I enjoyed manual work before my sales career, so I started applying for trade jobs.
The market was more difficult to navigate than I expected. When I was younger, I moved easily from job to job. I don’t know if it was my age — I was in my 30s, trying to do trade work — or the current economy, but I applied for hundreds of jobs and only heard back from a handful.
By the end of 2024, my savings were coming to an end and I needed more income than my property was providing. I found a job at the Royal Mail post service in late 2024.
Previously I was trying to find a new career, I’m now focusing on paying my bills so I have space to grow my channel on the side.
I’m working five days a week through an agency as a postman. I make less than I did in sales, and feel like I have to work weekends because it pays more.
I’m in a much better place than when I went traveling. I was putting a lot of pressure on myself to be successful. Now, I’ve learned to take that pressure off and enjoy exploring different avenues.
I’d consider going back into sales, but I’ve realized how important community is to me. As an contractor, you spend a lot of time on the road or alone.
I was too rash when I decided to quit my job
With hindsight, I was too hasty quitting my last sales position. I should’ve tried to get some clarity from the company, so I felt happier in the role.
Being self-employed, I had enough money and time to build my coaching business and channel alongside working. I could have waited until my business income matched my sales income and then slowly transitioned.
Before leaving sales, I saw so many people making content on social media about quitting their jobs, saying it would all work out. Lots of creators were encouraging people to go full-time on YouTube and pointing to their own courses on how to make that happen. I didn’t know their backstory, like how they financially supported themselves.
It made me think quitting and starting a business would be easier than I found it.
If you’re committed to leaving your job, there’s nothing stopping you from working on your CV and or applying for interviews while employed. If you’re starting a business, work on it in the evenings and on weekends.
In my experience, the stress of not having money far outweighs the stress of being in a job you don’t like.
I want to warn others to really consider what they’re doing before they commit to quitting their job. There’s a lot of online content out there that can make you believe the grass is greener on the other side, but it isn’t always true.
Do you have a story to share about quitting your job? Contact this reporter at [email protected]
