10 Retirement Mistakes I Made (And Why They Didn’t Sink Me), Part 2

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

This post is part two of an article titled 10 Retirement Mistakes I Made (And Why They Didn’t Sink Me). If you missed it, you may want to read it before you dive into this one as it lists the first three mistakes.

Now let’s start this post with mistake #4…

4. Saving Too Much in Hard-to-Access Accounts

When I was working (back in the Stone Age) I had a few things working against me in saving for retirement:

• Pensions were almost non-existent in business then.
• I was making a very high salary and thus needed as much tax relief as possible.
• Retirement savings options were mostly just 401ks (through a company) or IRAs (on your own). Roth IRAs didn’t exist until 1998 and Roth 401ks didn’t exist until 2010 with acceptance/use of both taking many years to become widely used/available.

So I did what seemed reasonable: I plowed as much as allowed into my 401k. The rest I saved in a taxable account.

For this effort I got a nice company match as well as a great tax deduction. Thank you very much.

Now, a few decades from when I first contributed to a 401k (which I then rolled into an IRA when I changed companies — I did this every time I switched organizations) and after ten years of retirement growth, my IRA is our single-largest asset, making up over 40% of our net worth. This is after I have made several Roth conversions in my retirement years.

In addition, my wife has an IRA from her working years and I have a SEP IRA I created for my writing businesses. All told, these accounts make up almost 60% of our net worth.

And yet this money isn’t easily accessible. If I withdraw it (or convert it to a Roth), I pay taxes on it. And as you’ve heard in this series, I’m still earning quite a decent amount, so my tax rate isn’t the lowest there is. I know, cry me a river. Feel free to roll your eyes too.

And while I don’t need the money now (and may never need it), it’s a bit frustrating not to have easy access to it.

If I had to do it all over again, I would have better diversified my retirement savings so I had easier access from the get-go (this a real issue for early retirees…especially if they need their dollars to cover expenses). Yes, I’m aware of Rule 72(t) / Substantially Equal Periodic Payments (SEPP) which allows you to take penalty-free (not tax free) distributions before age 59½. I said “easily” accessible. Dealing with the IRS (and filing just to get my money) doesn’t classify as easy for me. Besides, once you start those distributions, you are locked into those specific withdrawals for five years or until 59½ (whichever is longer). If your life changes or you need more cash for a surprise expense, the 72(t) rule can’t help you.

In the accumulation phase of the ESI journey, many of us focus on maxing out our 401ks (if not to the full amount, certainly enough to get the full match). It’s a great way to lower your current tax bill and build a massive asset. But ten years into my retirement, I’ve realized that following this advice blindly can lead to a significant tactical error: being IRA heavy without desired liquidity in taxable accounts.

If you retire at 65, this isn’t as much of an issue. But if you’re an early retiree — say, someone like me who pulled the trigger in their early 50s — the IRA becomes a locked fortress.

My mistake was focusing too much on the tax deduction now and not enough on the liquidity later. The most successful early retirees are the ones who built a robust taxable bridge — they have enough in their standard brokerage accounts to fund their entire lifestyle for those gap years, allowing their IRA money to compound untouched and penalty-free until the government finally lets them in.

It hasn’t been a big deal for us as we have income to cover our needs. And yes, it’s a “good” problem to have.

But if you’re still in the accumulation phase, consider balancing your tax-deferred savings with a taxable bucket that gives you the freedom to walk away whenever you want, without having to ask the IRS for permission.

5. Investing in Real Estate Syndications

When I started investing in real estate syndications I said that it would be a learning process if nothing else. It certainly has been that…

I also said these (a couple times on the site):

• The money I am investing here is completely AT RISK and ILLIQUID. I would probably never have invested like this earlier in my investing career though others have/do. It depends on the risks you want to take and your goals and I’m not a big fan of either large risk or illiquidity. So before you invest this way, know it’s on the upper end of the risk scale. There’s a reason they want accredited investors for these deals.
• In addition, there’s no control. At least with my own properties, I’m driving the ship. With these investments I am a fly on the wall and along for the ride, which makes these even less desirable.

These were some of the risks people in the Millionaire Money Mentors brought up as to why they were not investing in syndications. They also mentioned their distrust of others managing/investing their money, including stories of incompetence, mismanagement, and even theft.

Turns out I experienced all of these with a side dose of higher interest rates, increasing operational costs, and flatlining rents. Sounds awesome, huh?

Initially, my experience with syndications mirrored the marketing brochures. Several of my early deals did exactly what they promised — consistent quarterly distributions and a nice pop on the backend when the property was sold. But as the saying goes, “Everyone is a genius in a bull market.”

As the economic cycle shifted, the cracks in the syndication model became canyons. My mistake was thinking that diversification into these private deals was safer than the volatility of the stock market. I was wrong. Between interest rate hikes that crushed variable-rate debt, skyrocketing operational costs, and — in the worst cases — gross mismanagement and outright criminal activity, the dream soured quickly. I even had one deal that turned out to be part of a sophisticated Ponzi scheme.

The final tally? At the height I had about $1.6 million invested. Thankfully, I pulled much of that out as the deals ended (I needed the cash to buy our North Carolina house — I paid cash for it before we sold our Florida house — as well as $200k to give to our daughter and son-in-law for their NC home). I can also mitigate some of the losses with tax treatments that I’ll be able to claim (the fact that some was lost in a Ponzi scheme actually gives preferred tax treatment compared to a straight loss), so in the end I’ll be out a few hundred thousand dollars. Not great but obviously not as bad as it could have been.

But as any savvy investor knows, the capital loss is only half the story.

The real killer was the opportunity cost. Those funds, had they simply been sitting in a boring VTSAX index fund during one of the greatest bull runs in history, would have probably doubled. When you add the lost principal to the lost gains, the total hit to my net worth is a staggering reminder that simple is almost always better than sophisticated.

Needless to say, my education in real estate syndication investing has me knowing first hand of their disadvantages including:

• Extreme Illiquidity: Unlike a stock, you cannot sell a syndication when things go sideways. You are locked in for five to ten years, regardless of how poorly the manager performs.
• No Control: You have zero control. If the operator decides to take on risky debt or mismanages the renovation budget, you are just a passenger on a sinking ship.
• High Fee Loads: Between acquisition fees, asset management fees, and the promoted interest (the operator’s cut of the profits), a massive chunk of the returns is eaten before you see a dime. I wouldn’t mind this if the deals had done what they said they would do, but it’s rubbing salt into the wound knowing an investment has stopped distributions while the manager is still getting fees off the deal.
• Tax Complexity: Get ready for the “K-1 wait.” These tax forms are notorious for arriving late (often in March or April, but some beyond that), forcing you to file extensions and adding hundreds of dollars to your CPA bill.
• Capital Call Risk: If the project runs out of money, the operator can demand more cash from you. If you don’t pay, your original investment can be significantly diluted or wiped out.
• Poor General Partners: Who knew that such a group could be so incompetent, inexperienced, and dishonest? But that by and large was the average of them.

In the end, I learned an expensive lesson: Diversification for the sake of diversification is a trap. If you have a solid Invest pillar based on low-cost index funds, you don’t need to chase exotic private deals to win. The boring path won the race, and it wasn’t even close. Of course a bit of this is hindsight (I could beat myself up for not buying Amazon or Apple stock 15 years ago too), but even if the index funds had been flat, they at least wouldn’t have lost money.

Thankfully the lion’s share of my money did remain in index funds which is why my net worth is at an all-time high despite the syndications.

I tried to protect myself from this by diversifying among syndications: by syndicator, type of real estate, area of the country, length of investment, etc. And yet that wasn’t enough to avoid a bad result.

And in the end, out of all the syndicators I invested with, only two so far have had the level of expertise, experience, and trustworthiness I had hoped and expected to find among them all (and these two are still far from the finish line…we’ll see how they end up.)

6. The Sale of Rockstar Finance: A Lesson in Legacy vs. Liquidity

One of the more public mistakes of my first decade of retirement involves a project some of you probably remember: Rockstar Finance. When I acquired the site, it was a thriving hub for the FIRE community — a place that curated the best financial wisdom from across the web. And under my management, it grew significantly. For a while, it was a perfect extension of my Earn pillar. It provided a significant income stream, a platform for influence, and a way to stay deeply engaged with the community.

But as the site grew, so did the maintenance cost of my time. What started as a creative outlet began to feel like a high-pressure executive job. I was spending hours a day managing curations, dealing with various hurdles, and staying on top of the constant churn of the personal finance world. In my quest for time liberty, Rockstar Finance had become an anchor.

My mistake wasn’t wanting out; it was how I chose to exit.

At the time, I was exhausted. I saw the sale as the only way to reclaim my schedule. In my mind, I had a binary choice: keep the job or sell the asset. I completely overlooked the outsourcing option (I tried it a bit with little success anyway). Looking back, I probably could have hired a general manager or a small team to handle the day-to-day operations, keeping the site alive while reducing my involvement to a few hours a week.

Instead, I sold. I found a buyer who talked a good game. I made a significant amount on the sale — money that further fortified my net worth — and I walked away thinking the site was in good hands. I expected the new owner to do it justice and continue the legacy we had built.

But for reasons that remain inexplicable to this day, she simply shut it down. She killed it.

Others tried to buy it from her once it was apparent she wasn’t going to do anything with it, but she wouldn’t even respond to their requests. It was one of the strangest business deals I have ever seen (which is saying a lot).

If I had known she was going to ruin it, I would never have sold. I would have kept it, even if it meant a bit more work, or I would have found a different buyer who actually cared about the community.

The real mistake is that I didn’t buy it earlier (not that it was for sale then anyway). But if it had been for sale when ESI Money was just starting out, I would have added my own personal blog to the site and just written there. Then I wouldn’t have been able to sell it because it was my blog. Hahaha.

If only timing had worked out that way…

7. Took Forever to Launch the Millionaire Money Mentors

One of the biggest wins in my past ten years has been the Millionaire Money Mentors (MMM) — for many different reasons. What took me so long to launch it?

For years people had been asking me if I was going to do “something” with my millionaires interviewed. Many suggested a book but that felt like that had been done a million times.

Then I thought I might do an online class but that sounded like a lot of work. Hahahaha. (See below.)

When I bought Rockstar Finance I added a forums section where bloggers could discuss everything related to the business of blogging. There were several things about that set-up that I liked, so once I sold Rockstar and let the dust settle a bit, it came to me that a similar set-up would work for millionaires to share their experiences with those wanting to grow their wealth.

The best option would have been to launch MMM while I still owned Rockstar Finance. At that time, I had a massive, built-in platform and a level of community momentum that would have acted as rocket fuel for a mentorship program. By waiting until I had sold Rockstar and settled more into retirement (and found pickleball by the way — that started eating up a ton of time, lol), I effectively started from a lower altitude. While MMM has been an absolute home run — providing incredible value to the members and becoming a thriving community of its own — I can’t help but look back and realize it would likely be twice the size today if I had pulled the trigger a few years earlier.

MMM has proven to be exactly what I wanted: a place where real-world millionaires mentor those who are actually in the grind. I’ve also made some really great friendships there (heck, three of the guys there are contacts for my wife to ask for advice if something should ever happen to me.) It’s the most rewarding project I’ve worked on in retirement, but in hindsight, my hesitation cost the community (and the business) years of growth. I wish I had thought of it earlier.

8. The Motivation Gap: Missed Opportunities in YouTube and Courses

A funny thing happens once you become completely financially independent — your motivation to do any extra work, even if it’s for a good cause and could be financially profitable, is pretty much shot.

In the Earn phase of the ESI journey, your drive is often fueled by the necessity of reaching your retirement number. But once you’ve crossed the finish line and your Invest pillar is throwing off more cash than you can spend, your appetite for high-effort projects can start to wane.

Can anyone name a personal finance blogger they used to read a lot from but that blogger has stopped writing because they don’t have to — they have enough and the business of a blog isn’t needed any longer? I can name about 50. Hahahaha.

For me personally, I can look back on several opportunities over the last decade — two big ones being starting a YouTube channel and creating a high-level masterclass or seminar — and realized that I left significant value on the table, both financially and in terms of the number of people I could have helped.

I believe these were winning ideas. I had the data, the millionaire connections, and the platform to make them successful. A YouTube channel would have allowed me to reach a younger, more visual audience that doesn’t spend as much time reading long-form blogs. A structured seminar or course would have allowed for a deep dive into the ESI pillars that a blog post simply can’t match. I believe I would have done very well with both.

So, why didn’t I do them?

The honest answer is that I was too wealthy to care about the grind required to launch them.

Starting a quality YouTube channel isn’t just about talking into a camera (which I think I could do fairly well — I was in drama/speech in high school, worked in marketing, and regularly gave speeches during my career); it’s about editing, lighting, SEO, and consistent scheduling (I can feel myself falling asleep just writing that). Creating a course requires curriculum design and marketing funnels (which are not hard, but do require intense focus for at least some period of time). When you don’t need the money, it becomes very easy to look at that mountain of work and decide to go for a hike instead (which is very easy to do in Colorado!)

When your net worth is in the millions and your expenses are covered, the marginal utility of another $50,000 or $100,000 from a course is effectively zero. This is the paradox of retirement success: the very wealth that gives you the freedom to create also removes the primary incentive to do the hard parts of creation.

I missed these opportunities because I prioritized time liberty over impact scale. While I don’t regret my hikes or my slow mornings, I do see this as a mistake of stewardship. I had tools that could have helped more people, and I let them sit in the shed because I didn’t feel like putting in the sweat equity. If you’re retiring with a lot of ideas but also a lot of money, be aware that your bank account can be the biggest enemy of your next great project. You have to find a “why” that is stronger than the lack of a need.

This said, it’s not too late for me to start something new. We’ll see what happens.

9. Taking Too Long Moving from Being a Saver to Being a Spender

One of the most difficult psychological transitions in the entire ESI journey isn’t the move from working to not working — it’s the move from saving to spending. For thirty years, my brain was wired to view every dollar as a seed to be planted. I was a professional accumulator. That Save pillar was so ingrained in my identity that when I finally reached the finish line in 2016, I didn’t know how to turn the machine off.

I made the mistake of maintaining an unnecessary level of frugality during the first few years of my retirement (and I look like a spendthrift compared to my wife!) Even though the math screamed that I could afford to loosen the reins, I found myself still price-matching groceries, hunting for the absolute cheapest travel options, and second-guessing moderate luxury purchases.

I was rich in assets, but I was still living with a scarcity mindset.

It took me several years to realize that the goal of the ESI framework isn’t to die with the largest possible pile of cash; it’s to use that cash to fund the best possible life. I had spent decades building the Invest pillar so that I could eventually enjoy the fruits of my labor, yet I was treating my portfolio like a museum exhibit — something to be looked at but never touched.

When you spend your entire adult life being disciplined, that discipline becomes a reflex. I felt a strange sense of guilt when I spent money on things that weren’t strictly necessities. I had to literally train myself to become a spender.

Now I’m not a Die With Zero guy either — that would give me too much money stress — but I do need to spend more.

One of my biggest helps in making the switch were the Millionaire Money Mentors. They encouraged me to spend and enjoy. One of our most popular threads is titled “Let’s Spend Some Money” where we all share our purchases to encourage others (and ourselves) to enjoy our money. Why? Because it turns out this is a very common problem with people who are wealthy — they have spent decades being at least moderately frugal and need help learning how to spend.

If you are a hardcore saver, understand that spending is a skill you have to practice. Don’t wait five years like I did to start enjoying the margin of safety you worked hard to build. The Save pillar served its purpose to get you to the summit; don’t let it prevent you from enjoying the view.

The habits that get you to financial independence are often the same ones that can make you a miserly retiree. I had to learn to turn off the extreme frugality and embrace value spending. If an extra $200 makes a trip 50% more enjoyable, the ROI is infinite. I wasted too much mental energy in the early years on small ball savings.

And even my wife is starting to loosen up…a bit…hahahahaha.

10. Failing to Create a Survivor’s Roadmap

This one has been a mistake so far but in 2026 I am resolved to fix it!

If the ESI pillars are the foundation of our wealth, then the survivor’s roadmap is the operating manual for when the lead architect is no longer in the room. I’ve spent the last decade building a fortress of a portfolio, but so far I have made a significant — and potentially devastating — mistake by not having a complete In Case of Emergency (ICE) plan ready for my wife.

This is a silent risk. When you are the one who manages the spreadsheets, knows the passwords to the IRAs, understands the investing strategy, and handles the digital security for the side businesses, you are creating a single point of failure.

I realize that if I were to pass away tomorrow, my wife would be left with a multi-million dollar portfolio but a massive logistical nightmare. She would have the assets, but she wouldn’t have the keys.

This is a big no-no that many high-achieving retirees fall into. We assume that because our spouses are smart and capable, they’ll figure it out. But in the midst of grief, the last thing someone should be doing is playing detective with encrypted passwords or trying to find a hidden safety deposit box key.

It’s even harder when they have little to no interest in it (like my wife does).

I am currently working on fixing this, but it’s a mistake I should have addressed on Day 1 of retirement. Here is what I’m currently detailing for my wife:

• A list of everything we own. This is actually pretty easy — log on to Quicken and it’s all there. It includes every bank account, brokerage, and retirement account.
• Access to our digital lives. Passwords, files, etc. — everything we have digitally (which is about everything we have). This includes codes to my phone and iPad (which she already knows…but just in case she forgets.)
• A letter of instruction. This tells her my thoughts on what she should do, in order, if I pass away, including how to contact my three MMM friends who can help guide her along the way. Gemini is helping me write this.
• All of this is wrapped together with an intro letter of how to get on my computer and a few basic instructions.

We’ll also be “doing drills” where I say, “Find me the email and login for XYZ account” and she has to get to it from ground zero. We did a bit of this a year or so ago but I’m sure it’s not fresh in her mind.

We’ll also take our daughter through all this so there’s a back-up to the back-up. Plus our daughter is more tech savvy and helps run ESI Money, so she’s got insights into the business side of things.

I have started the process by paring down the documents we have on my computer (I saved a ton of stuff we’ll never need and it’s just clutter). I’ve also re-done our online filing system. It made sense when I created it many years ago, but things have changed and it wasn’t very logical for outside eyes…so I’ve fixed that. Currently I’m working on the letter of instruction.

Don’t let your time liberty become your spouse’s logistical prison. I’m lucky that nothing happened in the last ten years while I was getting around to it, but I don’t recommend anyone else take that gamble. A retirement plan is not complete until it’s a plan for both of you — even when one of you is gone.

Why These Mistakes Didn’t Sink Me

Here is the most important lesson of all: None of these mistakes mattered in the long run. Why? Because none of them were that significant — not in comparison to our total finances.

The ESI framework isn’t about being perfect; it’s about being anti-fragile. It’s about building a financial and lifestyle moat so deep that even when you make mistakes — and you will — your fortress remains standing. It’s designed to give you a margin of safety so large that you can afford to be human. You can afford to be a bit too frugal, a bit too planned, or a bit too anxious, and still come out ahead.

Ten years in, I’m a lot smarter than I was on Day 1. I’m more relaxed, less optimized, and significantly more content. My net worth is higher, my health is better, and my mind is clearer. I’ve learned that the perfect retirement doesn’t exist. There is only your retirement — a series of adjustments, lessons, and experiments. If you are still in the grind, don’t wait for the perfect plan. Build your pillars, pull the trigger, and be prepared to make some mistakes. They are the best teachers you’ll ever have.

What about you? For those who are already retired, what is one mistake you made that you’d warn others about? And for those still working, which of these traps do you think you’re most likely to fall into?