If I could get a do-over on my retirement, there’s one thing I would change.
I wouldn’t have retired.
Or more accurately… I wouldn’t have quit my job at 56.
At the time, it felt like the right decision. I was burned out, dealing with health issues, and ready for something different. Walking out that door felt like freedom.
But what happened after that is something I didn’t fully think through.
🎥 Watch the full video here
What Led Me to Quit
I had worked at the same company for 14 years, and it was actually my second time working there. When I first started, it was a family-owned business, and it was a great place to work.
But over time, the company was sold… and then sold again.
Eventually, it ended up being owned by large corporations, and everything changed.
The people changed.
The environment changed.
The way things were run changed.
And slowly, it became a place I didn’t want to be anymore.
At the same time, I was dealing with knee problems. We had moved to a new location, and the job required me to be on my feet a lot more than before. Physically, it was getting harder.
So now it wasn’t just that I didn’t like the job…
It was that I didn’t feel like I could keep doing it.
The Moment Everything Changed
I remember the exact moment I decided to leave.
I was sitting at my desk out in the plant. The door was propped open, the sun was shining through, and my car was parked just outside.
And I don’t really know how to explain it…
but it felt like that door was pulling me toward it.
Like everything in me was saying, “Just go.”
So I did.
I sent an email to HR telling them I had some good news and some bad news.
The good news was I was retiring.
The bad news was… it was effective immediately.
Walking out that door felt incredible.
For a moment, it felt like I had solved everything.
Why I Thought It Would Work
I didn’t leave without a plan.
At least, I thought I had one.
I had started a side hustle with LegalShield, and my intention was to go all-in on it. I believed I could build it into something that would replace my income and give me the freedom I was looking for.
And to be fair… I did make some money with it.
But not enough.
Not enough to replace a full-time income.
Not enough to feel secure.
When Reality Set In
It didn’t take long before things started to feel different.
The money wasn’t coming in the way I expected.
At the same time, my savings were going down faster than I thought they would. My 401k, which wasn’t unlimited to begin with, was shrinking.
That’s when the reality of the situation really hit.
I had left a stable job… without a stable replacement.
Selling My House
At that point, I had to make another big decision.
I sold my house.
It was a house I had built, and it was a great place to live. I’ve talked about it before in my downsizing regret article, and it’s something I still think about today:
👉 Downsizing in Retirement: How to Avoid the Biggest Mistakes
But I couldn’t afford to keep it.
So I sold it and moved back into a condo I had bought years earlier and had been renting out.
What I Have Now
Fortunately, the timing worked out in one way.
The real estate market was starting to rebound, and I was able to make enough from the sale of the house—after paying off the mortgage—to also pay off the condo.
So what I ended up with is what I still have today:
- No mortgage
- A maintenance fee
- Very low property taxes
Financially, that helped stabilize things.
But it also came with trade-offs.
I still miss that house.
What I Would Do Differently
If I had a do-over, I would not have quit my job when I did.
I had great benefits.
I could have had my knees replaced while I was still working, and those benefits would have covered me—even while I was off recovering.
I also likely would have continued working.
Full retirement age for me is just a few months away now.
And here’s something else that stands out when I think about it…
A lot of the people I didn’t like working with ended up leaving the company not long after I did.
So the situation I felt like I had to escape…
might have changed on its own.
And the biggest realization?
If I had stayed…
my house would be paid off in just a few months.
That’s a completely different situation.
But That’s Not the Whole Story
Even with all of that…
I don’t regret everything.
Leaving that job removed a lot of stress from my life.
And in many ways, that was a big positive.
I’ve also been able to spend time with my grandkids in ways I never could have if I was still working.
And that’s something you can’t really measure financially.
And the truth is…
living in my condo is just fine.
In fact, learning to live simpler has been part of this journey too:
👉 Why Less Really Does Feel Like More After Retirement
Final Thoughts
I tend to look at things from a financial point of view.
But retirement decisions aren’t just about money.
They’re emotional.
They’re personal.
They’re about how you want to spend your time.
If you’re in a position where you’re hating your job and thinking about leaving…
just take the time to really think it through.
You might also want to think about what life actually looks like on the other side:
👉 How to Live Well on A Retirement Budget
Sometimes your situation will change if you just wait.
Other times, you may make the decision anyway.
And if you do…
you move forward, deal with what comes next, and make the best of it.
Because at the end of the day…
that’s what most of us are doing.
We make the best decision we can with what we know at the time…
and then we live with it.