Here’s a Sign That it Might Be Time to Quit Your Job

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Written By Colin Graves

If you look closely at your boss’s job and think, “I would never want to do what they do,” it’s a good sign that it might be time to move on.


I worked in banking for 24 years. And for about 17 of those years, as I moved through the ranks, I was motivated to get to the next level. I was “climbing the corporate ladder”.

That doesn’t mean that I was never happy in my current roles; I was. But once I became proficient at my job, it wasn’t long before I would start looking for the next challenge, aka my boss’s job.

I would observe my boss’s daily routine and responsibilities and wanted to do what they were doing.

But all of that changed in 2015.

At the time, I had been in the same role for a few years, and I still enjoyed it. But I was also starting to get bored and felt like I needed a new challenge.

But when I looked at what my boss was doing, no matter how much I tried to convince myself otherwise, I didn’t want their job.

It was an executive position. Lots of money – company car, stock options, and plenty of “prestige” within the organization.

What I couldn’t reconcile was the trade-offs. If I took this job, I would be expected to:

  • Work 50-60 hours a week (essentially give my life to the company)
  • Regularly attend community events (photo-ops) – galas, fundraisers, etc. – mainly in the evenings and on weekends
  • Declare myself 100% mobile and willing to uproot my family and move around the country when asked
  • Return to school and get my Executive MBA (a significant financial and time commitment)

Laura and I wrestled with the idea for over a year but never felt at peace about the decision. Ultimately, we decided that no amount of money or prestige was worth the sacrifice.

I also considered other career opportunities within the organization, but nothing interested me more than what I was doing. And because I knew that I didn’t want to stay in the job I was in for another 15-20 years, something had to give.

So I started to take action.

  • In 2016, I started my personal finance blog.
  • In 2017, I tested out a couple of side hustles.
  • In 2018, I started the side hustle that would allow me to quit my job.
  • By 2022, my side hustle exceeded my 9-5 income, and I quit my job.


Do you want your boss’s job?

If you’re reading this and you’re in your 30s or 40s and staring down another 15 or 20 years before retirement, and you have no interest in continuing to climb the corporate ladder, it’s not too late to make a change.

I was 46 when I left the corporate world. Married, with three kids, on a single income. It took me four years to build my side hustle into a six-figure remote business. But knowing what I know now, I could have done it in less time.

If you’re reading this email and it resonates with you, I share strategies for escaping the 9–5 in my weekly newsletter. Details below. πŸ‘‡πŸ»

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Hi! I’m Colin Graves, a financial writer and editor based in Winnipeg, Manitoba. In 2022, I walked away from a 24-year banking career after building my side hustle into a six-figure business.

Every Tuesday morning (6 AM CST), I email an idea, story, or tip that helped me escape the 9–5.

If your 9–5 is keeping you from living the life you dream of, sign up for my newsletter and begin the journey to getting unstuck.

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