10 Retirement Mistakes I Made (And Why They Didn’t Sink Me)

In 2026 I hit a milestone that seemed like a distant, foggy dream back in my corporate days: the ten-year anniversary of my retirement.

If you want to go to the beginning and get the details on that blessed event, check out I Retired! There are some fond memories for me in that post!

Anyway, my plan to celebrate this momentous occasion is to write several “10 Things” posts about retirement.

So far, here are the articles in this series:

• 10 Things I Love About Retirement: Reflections After a Decade of Freedom
• 10 Things People Hate about Working (That Retirement Fixes)
• 10 Things People Love About Working (That They Want to Keep in Retirement)
• The 10 Best Financial Moves I’ve Made in 10 Years of Retirement

Retirement Mistakes

In the last post in this series, I patted myself on the back for making some great money moves. This post will be the opposite of that.

Yes, we’re going to cover my retirement mistakes…10 mistakes I made heading into or during retirement.

I’ve shared money mistakes previously on more than one occasion. Consider this another article in that fine tradition.

And since I share in so much detail, I’m going to break this massive post into two parts. Let the record reflect that I spent one post on what I did right and two on what I did wrong. Hahahaha.

I’m listing these so you know that I’m not perfect (like anyone would think that anyway) and understand that even with the many mistakes I’ve made, things have still turned out great.

There is a silver lining in this list. Because I built a massive margin of safety through the ESI framework, none of these mistakes were fatal. In fact, many of them were first-world problems that served as valuable lessons for the second decade of my freedom.

That’s the real key in both growing your wealth and hanging onto it…you can make mistakes (and you will), you just can’t make large, fatal, lose-everything mistakes.

If you are currently in the grind or just starting your retirement journey, I hope my candid reflections on these ten mistakes will help you navigate your own path with a bit more grace (and a lot less stress) than I did.

Here’s my list of 10 in no particular order…

1. The One More Year Syndrome

Haha! I wish!

It was more like the ten more years syndrome. Ugh.

Many years ago I went back and calculated when I was actually financially independent. Turns out it was when I was 42. Yes, I could be celebrating two decades of retirement this year.

I fell victim to one more year syndrome times ten. But I was clueless about FIRE — geesh, 60 was “early” retirement most of my working career. So I stayed in the corporate grind for many years longer than necessary.

Now in my defense, I would have been barely financially independent at that point and I am most certainly more of a Fat FIRE guy. Plus the idea of very early retirement was quite novel then and not many were doing it. It wasn’t the “thing” it is these days.

But even so, I could have retired five years earlier and done really well. FIVE YEARS! And those years were in my 40’s and early 50’s. Years when my kids were at home. Don’t be like me, boys and girls!

If I could go back to 2006 and have a serious talk with my younger self, I would tell him to pull the trigger sooner. My biggest retirement mistake wasn’t a bad investment or a spending spree; it was working waaaaaaaaay longer than I mathematically needed to.

The mistake here wasn’t the extra money — it was the opportunity cost. I traded several years of my peak health and energy for security that I already possessed. We who take one more year (or ten!) to retire trade our most precious asset (time) for an asset we already have enough of (money). It’s a bad trade, and it’s one I’ll never be able to undo.

By the way, as I was writing this section I started to wonder about one more year (OMY) syndrome…whether it’s a literal period of time or if it’s more common for pre-retirees to wait two, three, or more years before they pull the trigger.

I asked both Gemini (Google’s AI that I’ve been using recently) and the Millionaire Money Mentors this question to see what they thought. Here’s Gemini’s response:

It is rarely a literal, one-time extension of exactly 365 days. While it starts as a one more year plan, in practice, it functions more like a rolling mindset or a psychological loop.

For most people, it isn’t a single, discrete decision to stay for 12 months; it’s a recurring decision that can stretch into two, three, or even five extra years.

The term One More Year is more of a shorthand for the inability to stop. Here is why it usually lasts longer than a single year:

• • The Moving Goalpost: If you stay for “one more year” to reach a certain portfolio milestone, and the market has a great year, you might think, “If I stay just one more, I’ll hit the next million.” If the market has a bad year, you think, “I can’t retire now; I need one more year to recover.”
  • The Bonus Cycle: Many corporate roles are tied to annual cycles. Once you finish “one more year” to get your March bonus, you’re already three months into the next year. It feels wasteful to leave that pro-rated money on the table, so you stay for the next one.
  • The Comfort of the Known: Work provides a social circle, a schedule, and a steady stream of attaboys. Retiring requires stepping into a vacuum. It is much easier to re-commit to one more year of the status quo than to face the “identity crisis” of retirement.

Statistically and observationally within the retirement community, it is very common for “one more year” to turn into three or more. Why it happens:

Literal 1 Year: Usually driven by a specific, tangible goal (e.g., “I want to vest my final stock options” or “I want to reach 25 years of service for the pension bump”).

2–3 Years: Often caused by Sequence of Returns Risk anxiety. People want to see how their portfolio handles a full market cycle before they stop contributing.

5+ Years: This is usually full-blown OMY syndrome, where the individual is no longer working for the money, but because they are terrified of who they will be without the job.

The danger isn’t the first “one more year”—that year often does provide a nice extra cushion. The danger is that the psychological fear that kept you working this year is rarely solved by having more money next year. If you don’t address the underlying anxiety or have a clear plan for what you are retiring to, the one more year signpost just keeps moving down the road.

In short: It’s a syndrome because it’s a recurring symptom, not a one-off event. Most people who fall into this trap end up staying significantly longer than the twelve months they originally promised themselves.

Hahaha. Well, I guess that was what I was looking for. FWIW, that took about 30 seconds to spit out. I’m doomed as a money blogger. lol

But the response did make me feel better. Maybe I’m closer to normal than I originally thought. 😉

The Millionaire Money Mentors basically said the same thing…though they were a bit shorter and more nuanced in their responses.

2. Not Having a Plan for My Life (Time)

If there is one mistake that has the potential to turn a multi-million dollar retirement into a psychological disaster, it is this: entering the freedom phase with a solid money plan but zero plan for your life.

I thought that once the money issue was solved, the life part would just happen. I assumed that because I was a naturally curious, active person, I would figure it out as I go. After all, how hard could it be to spend 16 waking hours doing whatever I wanted?

Now, to be clear: I was fine. Because of my natural curiosity and my drive to stay busy, I managed to navigate the transition without the crash and burn that many experience. I didn’t fall into a depression, and I didn’t go crawling back to a corporate headhunter. But looking back ten years later, I realize that going into retirement without even a general time plan was still a massive mistake — and it’s one I absolutely do not recommend anyone make.

According to recent retirement surveys, while over 50% of financial planners think their clients are monetarily ready, only a small fraction (11%) believe they are emotionally prepared for the day-to-day reality. 

When you don’t have a plan for your time, you are at risk for three specific retirement fails:

• The Fading Honeymoon: You spend the first six months traveling and sleeping in, but by month 7, the novelty wears off. You realize that vacation only feels good when it’s a break from something. Without the something, the vacation just becomes a boring, unstructured existence. (BTW, I did experience this a bit living in The Villages — after all, it’s basically a vacation resort on steroids.)
• The Identity Crisis: Your professional title was your social shorthand for 30 years. Without it, you can feel invisible.
• The Un-Retirement U-Turn: This is the most common failure. Because the void of time is so uncomfortable, people retreat back to the only structure they know — work. They aren’t going back for the money; they’re going back because they didn’t have the discipline to build a life of their own and they don’t know what to do. You’ll see stories of these people pop up now and then. They generally claim that retirement was “boring” or something similar. I get it. It’s soooooo boring to do whatever you want. Hahaha. You know what’s boring? These people — for not having enough interest in life that going back to work in desperation is their only solution. Ugh.

Thankfully, I did have enough interests to form a basic framework for my new life: exercise, blogging, and some small hobbies like reading, video games, and walks with my wife. I eventually found pickleball. That absorbed much of the remaining free time I had and I was completely good to go from there.

I was lucky that my personality and interests allowed me to bridge the gap, but going into retirement without a plan is a high-stakes gamble. If you are within a few years of your exit, stop looking at your 401(k) for a moment and start looking at your Tuesday morning at 10:00 AM. What are you doing? Who are you with? If you don’t have a concrete answer, you aren’t ready to retire — no matter how many zeros are in your bank account.

What should you do if you’re getting close to retirement and are not sure how you’ll spend your time?

Preparing for your time is essentially lifestyle R&D. You wouldn’t invest $1 million in a stock without a deep dive; you shouldn’t invest 2,000+ hours of annual free time without a plan.

To develop a plan, I suggest you do the following, beginning a couple years before you plan to retire:

• Identify possible retirement activities. I’d begin with my list of the best retirement activities as these are often vital to a successful retirement.
• Test them out. Use nights, weekends, and vacations to try out your potential new activities (you’ll be able to add these to your existing activities that you want to keep/expand in retirement — assuming you have any). 
• As you start to narrow down your list to activities you want to keep (and getting closer to retirement), create a mock weekly schedule of what an actual week (and month) would look like in retirement. Then you can adjust as needed to design the life you want.
• Try it out. Use your vacation time to test/try out a “normal” week of your retired life. From here you can make more adjustments as needed. The more of these weeks you can do, the better. And the longer you can make them (longer than a week), the better too as these will give you a real sense of what retirement life will be like.

By the way, you don’t need/want to plan every minute of every day or you run the risk of burning yourself out. I’ve found that if you have about 3-4 hours a day of planned activities (at least in your mind) and then a general sense of what the rest of the day can look like, you’ll be fine.

For me, I take two hours in the morning to work out. Add in time for reading and doing my puzzles and some time for writing/desk work and you have four hours at least. From there I can add in things like a shopping trip, yard work, dinner with family, a movie with my wife, and so on for what turns out to be a pretty successful day (on many fronts). String a bunch of those together with bigger events here and there (like a trip, family reunion, and so on) and you have the formula for a great retirement life.

By treating your time with the same rigor as your financial planning, you ensure that the day you walk out of the office isn’t just an exit, but a successful launch into a life you’ve already vetted.

3. Moving from Colorado to Florida

This is a painful one. It worked out in the end but I still wonder what our lives would be like if it hadn’t happened.

In the corporate world, moves are often dictated by the job. In retirement, moves are dictated by the “dream” — but dreams have a way of changing once you actually wake up in them. We were living in Colorado, a place I loved, but we were curious about a different kind of lifestyle. We decided to try out The Villages in Florida to see if the active adult community vibe was for us.

What started as an experiment (a 2.5 month stay there with my dad) turned into a series of small but irreversible decisions. One step led to another, and before we had truly vetted the Florida lifestyle in all its humidity and glory, we had moved there and sold our Colorado home.

This was a massive strategic error. Retirement isn’t a static state; it’s a series of experiments. My mistake was turning a pilot program into a permanent corporate merger. Once the Colorado house was gone, our Plan B evaporated. Shortly thereafter I found out I disliked Florida — primarily the heat/humidity (too hot for too long). But there was a significant complication: my wife loved it.

This created a lifestyle deadlock. I wanted to move back to the mountains, but she didn’t — partly because she found Colorado too cold. If we had kept our Colorado home, I would have moved back in a heartbeat. Without it, we were stuck in a high-stakes compromise that lasted for a difficult year or so.

By selling our primary residence in a state I loved before I was 100% sure about the new one, I eliminated my margin of safety.

We eventually found our way to North Carolina, which has been a fantastic middle ground for both of us. As I said, it all worked out in the end, but the path here was unnecessarily rocky. We spent two years in a state of geographic friction that could have been avoided if we had just rented out the Colorado house for a year or two while we test-drove Florida more extensively.

While numbers are hard to pin down, various sources report that a large percentage of retirees who move eventually regret the decision or move again within five years. People move for the “hard” reasons — taxes and temperature — but they often move back (or move on) for the “soft” reasons: social isolation, lack of specialized healthcare, or simply the realization that they don’t actually like the lifestyle as much as they liked the idea of the lifestyle.

My advice to anyone looking to relocate in retirement: Don’t burn your bridges until you’ve spent a full four seasons on the other side of the river. Real estate is expensive to trade, but the emotional cost of being homeless from the place you love is even higher. We survived it because our ESI foundation was strong enough to make the move to NC, but in hindsight, I wish we hadn’t been so quick to sell in Colorado. It worked out for us in the end because North Carolina turned out to be the Goldilocks zone — not too cold, not too hot, and a great place for a number of other reasons. But those two years of rough patches were a high price to pay for a lesson I could have learned for the cost of a six-month rental agreement.

If you’re considering a move in retirement, don’t make the same mistake I did by burning your bridges before you’ve spent enough time in the new place. Here are my suggestions for a successful relocation:

• The Worst Season Rule: Never buy a home in a new state until you have experienced its worst season. If you love a place in the spring, go back in the dead of winter (for the north) or the peak of August (for the south). If you can’t stand the weather at its worst, you shouldn’t live there at its best.
• Rent Before You Repent: This is the #1 tip I give to anyone. Before you sell your current home, rent a place in your target destination for at least six to twelve months. This allows you to experience the daily reality — the traffic, the neighbors, the local politics — without the one-way commitment of a real estate closing.
• Test the Social Infrastructure: Before you move, identify at least three hubs where you will build your new community. Is there a church, a gym, a hobby group, or a volunteer organization that fits your lifestyle? If you can’t find your tribe within the first six months, you will likely fall into the social isolation which we know is a retirement killer.
• Try the Two-Home Bridge: If your finances support it, consider keeping your original home as a rental for the first year (or even let it sit empty if you have someone who will look after it for you). This preserves your plan B and gives you an exit ramp if the new location doesn’t work out. It’s better to pay a bit more in carrying costs for a year than to be stuck in a state you dislike because you sold your refuge.

By the way, let me make it clear that I don’t hate The Villages or Florida. I have many friends who LOVE both of these places. I personally like much of what The Villages offers and would live in a similar community if it was located elsewhere. And Florida itself has a lot to offer (we loved being Disney annual pass members and just visiting for a day with friends). It’s just the weather is not my cup of tea (again, too hot for too many months in the year). For others this isn’t a concern, it’s a benefit. So please take my thoughts generally and don’t just limit them to a “Colorado good, Florida bad” summary.

Funny side note: as I write this, I’m wearing a t-shirt with Colorado’s flag on it. I have one similar for North Carolina. I don’t have one for Florida. 😉

Well, that’s it for this time. How am I doing so far? lol

Stay tuned…the next seven will be shared soon.