Do I Regret My Early Retirement?

Do I Regret My Early Retirement?

This question came from a commenter on YouTube. The short answer is no. I don’t regret retiring in 2022 after 25 harsh years in the teaching profession, which in my case had become harmful to my health. Early retirement also helped me to escape an unsafe housing situation. But more on leaving teaching and relocating later. The question I received from this commenter was specifically rooted in the financial aspect of risk involved with retiring early, so let me get into that first.

The financial risks.

Yes, I face some real financial risks. Outside of around 10k in a Roth IRA and several thousand in a high-yield savings account, I don’t have any retirement savings. I do have a partial pension, but without a cost-of-living adjustment, its value erodes with inflation. Fortunately, for now, I have a newer house and newer car. Neither of them needs any major work right now—but let’s face it—the car will eventually need brakes and tires. The house will one day need the roof replaced, the driveway repaved, the deck rebuilt. I have a plan to address the upcoming gaps in my finances that I've already identified, but no matter what, there will always be risk.

I’m able to work side hustles right now and squirrel away a few thousand each year that I can hopefully draw upon during any years I come up short, but who knows? Those side hustles could dry up—I’ve had side hustles in the past I thought would last forever that suddenly dried up. Also, I could get sick or incapacitated in some way, preventing me from working the side hustles. Or a situation could happen that wipes out whatever little bit of money I do have. Yes, there is definitely risk involved with my decision to retire early.

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What I left behind.

I still don’t regret it, though. When I think about where I'd be if I had kept the teaching job and stayed in NJ, I realize I wouldn’t have been better off. Maybe I would’ve been more comfortable financially, but I was very unhappy with my living situation. I was stuck with an uncooperative homeowners’ association and a couple of neighbors who made me feel unsafe just simply coming in and out of my home.

Even though, at the end of my career, I was finally earning in the low six-figure range, it wasn’t enough for me to move somewhere better in NJ. Everything was just too expensive. I was looking for an escape. Since the value of my NJ house peaked around the same time that I qualified for early retirement, I used the opportunity to escape both the stressful work and housing situations. I also unexpectedly found more freedom to focus on self-care and precious time to spend with my family that I wouldn’t have had if I had continued working full time as a teacher.

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Teaching is a misunderstood occupation.

A lot of people think it’s simple—you get to have fun all day interacting with children, you have the summers off, you get out of work at 3 o’clock each day.

It was refreshing and rewarding to work with children every day. The younger ones especially had uninhibited creativity, and it was so exciting to watch them learn and grow right before my eyes. However, it was also extremely challenging. Kids are people, too. Not only are they capable of hurting others, but when they do, they’re usually given a pass to keep right on doing it. Don’t get me wrong. Out of the hundreds of children I worked with, only a small handful caused me distress, but that distress was piled on by politics, baggage, and pressure from aggressive and sometimes mean-spirited parents, colleagues, and administrators.

On top of the ordinary stress teachers face, I was also dealing with racism coming from multiple directions for the entire 25 years. Apparently, I wasn’t what certain people expected a teacher to look like. That caused friction, not only from those who wanted to stereotype me, but also from within, by some folks who looked like me. I didn’t follow their established societal rules, therefore, I didn’t fit in.

This all caused an enormous amount of stress that I don’t regret leaving behind by taking an early retirement. The effects of stress are real. I believe that taking an early retirement has helped to prevent my life from being cut short due to the effects of stress.

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The original plan was to transition careers.

I was hoping for a while to get a six-figure salaried tech job. I studied hard for a few years, earned several certificates, joined a few organizations and built networks. I was even accepted into two competitive academic programs related to coding, and I worked for over a year in paid tech-education roles.

But through the process, I realized that it was becoming very difficult to enter the field. There was a brief window when someone like me, with basic skills and without formal training or a computer science degree, could get an entry-level tech job, but by the time I was ready, that window was almost closed. And honestly, I wasn’t willing to do what it would’ve taken to get through it before it fully closed. I wasn’t aggressive enough. I just didn’t want it enough.

And especially after I relocated to DE in 2024 and got a full taste of the peace I could have in retirement, I let go of that dream of starting over in a new career at the age of fifty plus. I embraced the idea of allowing myself instead to rest, focus on self-care, and be more present in my own children’s lives, even though it means that I might struggle financially.

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For me, it’s worth all the risks.

As I continue brainstorming how to get myself onto more stable financial footing, I'm keeping in mind that all of this is temporary. Things can and will change. I’ll have ups and downs in my life, just like always. There were health risks involved with staying in the teaching job, and there were safety risks involved with staying in that living situation. Life is risky, no matter what. The best I can do is face the challenges that come my way, prepare as best as I can, and most importantly, stay prayed up.

So, I don't regret taking early retirement. For me, it’s worth all the risks because it's giving me a more peaceful life on my own terms.

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For more conversation on this and other early retiree topics, be sure to browse the playlists on my YouTube channel and visit my podcast on Spotify.

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