The 10 Best Financial Moves I’ve Made in 10 Years of Retirement

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)

Retirement Moves

If you’ve followed ESI Money for any length of time, you know that I am a firm believer in the power of a simple, repeatable system. We talk about Earn, Save, and Invest because those are the levers that get you to the finish line. But what happens after you cross that line? What are the moves that keep you on the right side of the wealth curve for the next decade?

Retirement is the ultimate stress test for a financial plan. During your working years, a bad market year is just a buying opportunity (anyone remember 2007-2009?). In retirement, a bad market year combined with a withdrawal schedule is a threat to your survival.

As I look back on ten years of retirement, I’ve realized that my success so far hasn’t been just about the money I had on Day 1. It was as much about a series of decisions I made along the way to protect and grow that wealth. Some of these were moves I planned for years, while others were audibles I called as the economic landscape shifted.

Here are the 10 best financial moves (in no particular order) I’ve made in a decade of freedom…

1. Doubling Down on the “Boring” Index Fund Strategy

When I retired in 2016, there was a lot of noise in the market. We were in the middle of a long bull run, and people were constantly trying to find the next big thing to juice their returns. It’s tempting, when you have millions of dollars sitting in a brokerage account, to think you can beat the market with just a little bit of cleverness.

The best move I made was refusing to play that game. I stuck to a low-cost, broad-market index fund strategy (primarily Vanguard’s VTSAX). Over the last ten years, we’ve seen incredible volatility — including the 2020 crash and the 2022 bear market. By staying boring, I captured the massive recovery that followed those dips without the stress of wondering if my specific stocks would survive.

I’m not the only one. In my Millionaire Interviews, the vast majority of successful retirees cite index funds as their primary investment vehicle. One interviewee told me he spent years trying to pick stocks, only to realize his “lazy” 401k index fund was outperforming his active account by 3% every year. That 3% difference, compounded over a decade of retirement, can be the difference between a growing net worth and a shrinking one. I didn’t need to be a genius; I just needed to be a passenger on the most reliable ship in the ocean.

Over the last ten years, I’ve been approached by plenty of “wealth managers” who wanted to help me optimize my portfolio (basically everyone at all the seminars I’ve attended plus everywhere I have any sort of investments). But as they are “experts” who are often short on expertise, I have passed. I’m more than content with letting the index funds ride.

2. Building a Cash Buffer (The Bucket Strategy)

One of the most stressful parts of retirement is the “What if the market crashes tomorrow?” thought. To combat this, I implemented a bucket strategy — keeping three years of living expenses in cash.

If you want to survive a decade of retirement without losing sleep, you need a moat around your investments. For me, that moat is cash.

BTW, the amount I have is about three years of expenses at a pretty high level of spending. It’s more like 5 years of spending at what we’ve spent recently or several years more if we really needed to make it last (like we did when we were accumulating wealth). Hahaha.

This strategy is common among the retirees I interview. Having a cash moat is the ultimate psychological insurance policy. It turns out that cash isn’t trash — it’s the fuel that keeps your emotional engine from overheating.

Mainstream financial advice often scoffs at holding too much cash, citing opportunity cost and the drag on total returns. They’ll tell you that money should be in the market working for you. But they are thinking like accumulators, not retirees. In retirement, the greatest risk isn’t missing out on a 10% gain; it’s being forced to sell your index funds during a 30% market crash to pay for groceries.

Plus I think those who are trying to maximize every single financial activity are on a fool’s errand. I’m way past that and am now content with protecting what I have. If I give up a percentage return here and there, I think I can live with that. 😉

By having a multi-year cash buffer, I’ve given myself the gift of time. When the market tanked in early 2020, I didn’t have to look at my brokerage balance with fear. I knew my living expenses for several years were already sitting in savings accounts. (I actually bought more then…picking up some dividend stocks). While the world was reeling and the market was down 30%, I knew my bills were paid for the next few years. I didn’t have to touch my investments at all. This allowed my investments to stay fully intact, allowing them to capture the entire V-shaped recovery that followed. The drag of cash is a small price to pay for the insurance of never being a forced seller.

3. Creating a Retirement Income

I didn’t start ESI Money to get rich. I started it to share what I’d learned to help others and to keep my mind sharp (we’ve discuss the need for challenging your mind in retirement many times). However, one of the best financial moves I’ve made in retirement was creating this platform to become an income-producing asset.

Sure, based on my experience at Free Money Finance I assumed I’d earn something, but I didn’t think it would be a meaningful amount.

But ESI Money grew and did well…which then led to Rockstar Finance…which then led to the Millionaire Money Mentors. Between these three (plus some other income — see below) we not only covered our expenses, but had extra left over to add to our investments.

This income in retirement was a game-changer. Because our income covers our costs, we don’t have to touch our core savings. By leaving the principal intact, I’ve allowed my Invest pillar to continue doing what it does best: compounding. The results of this strategy over the last ten years have been staggering. Because I haven’t been forced to sell shares during downturns, and because I’ve allowed my dividends and extra earnings to be reinvested, my net worth today is significantly higher than it was when I retired in 2016.

And in addition to the monetary benefits of these businesses, they provided all the other benefits of working that people want to keep during retirement. This is why I’m such a big fan (and recommend to people) developing a side hustle you enjoy while you’re working…so you can take it with you into retirement.

And while these have been a great thing retirement earnings, they haven’t been the only source of income…

4. Creating Several Income Streams

As you can probably tell from the comments above, I’m a big fan of retirement income.

In the traditional retirement model, you are either “working” or “retired.” It’s a binary switch. This is the definition of the Retirement Police.

But ten years of living the ESI lifestyle has taught me that the most resilient retirees are the ones who play in the gray area by maintaining some level of income. And apparently everyone else is catching on as the definition of retirement is changing.

There are three main reasons retirement income is a great thing…

First, even if your income doesn’t cover all your expenses, having some income in retirement helps provide in case of surprise expenses. No matter how perfect your spreadsheet is, life will throw you a curveball. Whether it’s a $15,000 HVAC replacement, a sudden family need, or a spike in healthcare premiums, having a consistent Earn pillar in retirement means you can absorb these shocks without selling shares of your index funds at an inopportune time. Income is your first line of defense against the sequence of returns risk that destroys so many portfolios.

Second, it allows you to retire earlier because you don’t need to save as much. Having even a small income stream dramatically lowers your retirement number — the total amount you need to have saved to walk away. Think about the math of the 4% Rule. To safely withdraw $25,000 a year from your portfolio, you need $625,000 invested. If you have a retirement job or a side hustle that brings in that same $25,000, you have essentially added the equivalent of $625,000 to your net worth without saving another dime. If you’re aiming for a $100,000 lifestyle and you can generate $40,000 in semi-passive income, you only need a portfolio that supports $60,000. That’s a difference of $1 million in required savings ($1.5M vs. $2.5M).

Third, there is a massive psychological benefit to seeing new cash hit your account every quarter. I love the beginning of each month when a new deposit “magically” appears in my account. 😉

By keeping the Earn pillar active, you aren’t just working in retirement — you are buying back years of your life that you would otherwise spend in the corporate grind trying to hit a higher number. Whether that income covers 100% of your expenses or just 20%, it provides a level of flexibility and security that a static pile of cash simply can’t match.

Over the last ten years, I’ve had several sources of income including:

• Rental Income. My original non-work income source. I knew I could retire at 52 in part because my rental properties brought in $60k in profit every year. If I had to, I knew I could live on that (given I had a paid off house).
• Side Hustle Income. As noted above. ESI Money, Rockstar Finance, and Millionaire Money Mentors. I wonder what is next…
• Private real estate lending. This started with a friend (which went well) and then morphed into real estate syndications (which did fine with several investments before turning south.)
• Dividend Income. This includes dividend stocks (most of which I still have) and dividends from my index funds (if I wanted to take them…I usually reinvest them). I made a deliberate move in retirement to carve out a specific portion of my portfolio for dividend stocks. The goal here wasn’t to beat the market, but to create additional cash flow that didn’t require me to sell shares to pay for my life. By focusing on high-quality, dividend-growing companies and funds, I created new streams of income that flow regardless of whether the S&P 500 is up or down in a given month.
• Interest Income. This was almost non-existent the start of retirement as rates were nothing, but the last few years it’s been nice for my cash sitting in accounts to earn at least something decent.

Many people pooh-pooh retirement income (which is poo-poo IMO…hahahahaha) and opt for a pure asset withdrawal strategy. That’s certainly a valid strategy and if it works for them, that’s great. I may even use that as my primary retirement funding method one day. But for early retirees, and for me especially, I prefer having cash flow.

5. Investing in My Health

Ten years ago, I decided that I’d make sure that having an abundance of time would translate to better health. I invested in high-quality food, a gym membership (with trainer), appropriate supplemental gear for home use, and preventative healthcare.

Money is a tool to buy time, but health is the tool that makes that time worth having.

Why is this a financial move? Two reasons.

First, health is wealth. If you don’t have your health, all the money in the world is useless. Plus I feel better being healthy so the years I have left are better.

Second, because healthcare is the largest x-factor in a retirement budget. According to Fidelity’s 2024 estimates, the average couple retiring at age 65 will need approximately $315,000 to cover healthcare expenses in retirement. By staying fit, maintaining a healthy weight, and being proactive with my health, I am essentially self-insuring against the most common (and expensive) chronic lifestyle diseases. By staying fit and healthy, I’ve avoided the massive hidden costs of retirement: chronic illness and prescription drug costs. Of course you can only do what you can do and problems may still hit, but at least I’m making an attempt to head them off.

Every hour I spend in the gym and every dollar I spend on nutritious food is an attempted hedge against a $100,000 hospital bill or the exorbitant costs of long-term care later in life. In the FIRE community, we talk about ROI on stocks, but the ROI on physical fitness is infinitely higher. You can’t enjoy your retirement if you’re stuck in a hospital bed.

6. Selling My Rental Properties at the “Perfect” Time

Buying my rental properties in 2012 was among the best financial moves I made toward building wealth. Though I was financially independent before I bought them, once I purchased them I was completely independent with room to spare.

They provided cash flow, tax advantages, and appreciation. But as I moved deeper into my first decade of retirement, I realized that the return on equity and the return on hassle were no longer in balance. I had moved to Colorado and my properties were handled by a management company. My initial manager had moved on and the replacement was less than stellar. I was being killed with this cost after that cost — both in quantity of charges as well as the size of them. And what was I going to do about it? I lived 1,200 miles away.

So I sold them.  I sold them when valuations were high, allowing me to capture a decade’s worth of appreciation in a single transaction.

This was a strategic shift from active investing to passive freedom. This move simplified my life and reduced the hassle factor of living (my worst time every month was getting my rental management reports and having to sift through them). In retirement, simplicity is an asset class of its own. I traded a complex, labor-intensive asset for a simple, liquid one — without sacrificing my lifestyle.

7. Timing the Real Estate Market in Colorado and Florida

Did someone say it’s better to be lucky than good? Hahahaha.

Real estate is often a large component of a millionaire’s portfolio (especially in HCOL areas), and I’ve been fortunate with mine. Over the last decade, I made two major moves that significantly boosted my net worth: selling my homes in Colorado and Florida at the right time.

In Colorado, I captured the massive appreciation that came with the mountain-state boom. It’s still an “ok” market there, but I don’t think we’d get today what we did then.

In Florida, the market was strong in The Villages as well — especially for the type of house and location we had (which is why we bought the place). We made almost 50% on our investment in two years, so it was a decent return for sure. Since then, The Villages has started a major building expansion further south which has limited sales prices “up north.” My dad recently sold his home too and was lucky to get what he paid for it several years ago.

By selling these properties when we did, we made nice profits on both. Colorado was complete luck and timing, neither of which I had that much of an impact on. In The Villages, we knew if we bought a nice home in a great location we would do well whenever we sold, so that profit was much more our doing. But they both sold well which allowed us to further fortify our cash buffer (plus take the next step in this list…)

8. Investing in the Next Generation: Helping Our Kids Get Established

In the corporate world, we talk about Succession Planning. In retirement, I’ve realized that the most important succession plan I’ll ever manage is the one involving my children. One of the best financial moves I’ve made in the last decade was choosing to help our kids get a solid foothold in their adult lives — at a time when it actually makes a difference.

Traditional wealth transfer usually happens at the end of a parent’s life, often when the children are already in their 50s or 60s. By then, the money is nice, but it isn’t life-changing. They really need the support while they are in their 20s and 30s.

So once we set their inheritance amounts (what they would get when we pass), we also set a rule that they could withdraw from that amount for “worthy” causes (which we both agree to) like down-payments on a home, a new car, and so on.

Now we get the advantages of helping them when they most need it as well as seeing them enjoy their inheritance. It’s a win/win!

9. Spending for Maximum Happiness

In the Save phase of the ESI journey, the focus is almost entirely on efficiency — how little can I spend while still maintaining a reasonable lifestyle? But in the last ten years of retirement, I’ve made a deliberate financial move to shift the metric from cost to “joy ROI.” I’ve started spending more money specifically to increase my daily happiness, and just as importantly, I’ve stopped spending money on things that would detract from it.

This isn’t lifestyle creep; it’s lifestyle optimization.

So what sort of things am I buying now that I used to eschew? Here are a few:

• Subscriptions. Back in the day I avoided these like the plague. These days I have to keep an on-going list just to remember what all I have (and if I don’t use something, it’s out — though I add about three net subscriptions per year to the list.) I have YouTube TV, Disney+, Amazon Prime, YouTube Premium, a couple AI subscriptions, and a handful of others. And yes, I use them all. 😉
• High-quality fitness gear. This includes weights, a fitness box, and an assortment of bands and mats for my (mini) home gym, the best running shoes for my feet (Brooks Ghost), and a gazillion pairs of swim goggles (hahahaha). These aren’t just expenses; they are investments in a higher quality of life. If a piece of equipment or a specific service makes my daily workout more enjoyable or my sleep more restorative, I buy it.
• Eating and grilling out. We get together with our daughter and son-in-law every Saturday. One week we’ll order out and the next week I’ll grill out (steaks, hamburgers, ribs, etc.) These are great times and the spending here for the joy it brings is a no-brainer.
• Home upgrades. I can’t list all the things we’ve done to this house since we purchased it or this post would be way too long. But some of the highlights are new floors in the kitchen, sanding and restaining all the wood floors (which is about everything but the bedrooms and bathrooms), repainted the entire downstairs, and upgraded the garage (paint, new openers, and floor coating.) We still have a few projects left but we’re nearing the end of the road here.

Equally important in this joy ROI has been my refusal to buy things that would make me less happy.

I think we all know that spending for the sake of spending does not bring joy. So many people seem to try that and all it leads to is a low net worth and more misery. So I’m careful to make sure whatever spending I do is something that adds value to our lives.

Let’s take a couple examples of what this might look like.

Example 1: We have two cars. They both work well and serve our needs, but they are getting older (one is a 2011 and one is a 2016). So we’ve thought about buying a new car. It would most likely replace my car, the 2011 Toyota Highlander.

Would this make me happier, having a new car? Maybe. For a while. But in the end, would the new car be as comfortable as my current car (which is very comfortable)? Would it do everything the old car does? And would I worry about dings and scrapes with the new car (yes, I would) whereas these days I have zero concerns about those.

As such, we’ve decided no new car for now. We may even go for a one-car + UBer solution when my car does finally give up the ghost.

Example 2: travel. Ugh. I shudder thinking of it.

I can’t name a single place in the world where the cost of getting there (in frustration and stress) is lower than the joy you get from being there. Travel is just so horrendous these days even if you go first class, have access to clubs at airports, etc. As a result, most travel for me is a “no.” Besides, I just had 10-years worth of resort activity by living in The Villages for two years. Hahaha.

My answer to this is to create a home I like more than any trip anywhere. Why travel when home is so much better?

That said, I am up for short trips and we’re currently considering options for a couple local North Carolina trips — one way to the beach and the other to the mountains.

By spending to increase happiness and not-spending to avoid misery, I’ve reached a state where every dollar leaving my account has a clear purpose. Ten years in, I can tell you that the best financial move isn’t always the one that grows your bank account — it’s the one that grows your satisfaction.

This said, I’m a pretty easy person to please. It must be that Iowa upbringing. Hahaha. Anyway, even our joyful spending is well below what we could spend on ourselves, so we’ve found another source of “spending” that does bring lots of joy…

10. Spending More by Giving

Four years ago I wrote about IGE (Invest, Give, and Enjoy) and committed to giving away $100k a year for five years. 2026 is the final year of that plan and so far it’s gone quite well.

It took us a long time to sort through charities and find ones that had good data on their effectiveness. But once we got those, we have been set, giving to 4-5 organizations a year in a major way (there are a few smaller gifts here and there but those aren’t very substantial).

We do the vast majority of our giving through our donor-advised fund. This way, the government is a partner of ours in giving as we skip taxes owed on appreciated funds, get a tax deduction, and maximize the amount the charity receives. A DAF makes giving efficient, strategic, and sustainable.

Once we’re old enough, we’ll do Qualified Charitable Distributions (QCDs) from retirement accounts which will help us support causes we care about while simultaneously reducing our taxable estate and future RMD (Required Minimum Distribution) obligations.

There is a happiness plateau in retirement where more personal spending yields almost no extra joy. However, the ROI on giving is massive. Studies from the Greater Good Science Center at UC Berkeley show that “prosocial spending”—spending on others—actually releases more sustained dopamine and life satisfaction than spending on yourself. In addition, there are a whole host of other benefits associated with giving.

Helping our church, local charities in our town, and individuals in need throughout the world has turned our wealth into a tool for significance. I’m spending more now than I did ten years ago, but because a huge chunk of that is giving, it feels like I’m finally putting my money to its highest and best use.

By the way, the big run-up in the market has allowed us to contribute to our DAF every year without losing any value in our taxable account. When I retired, our Vanguard taxable account (from where we fund the DAF) had $580k in it. Today it has almost $100k more. We’ve given $100k out of it the past five years and smaller, but still substantial, amounts prior to that. And we’ve made very few additional contributions to the account. Pretty nice, huh? 😉

This has brought us both a lot of joy…much more than we would have received if we’d spent the money on ourselves.

Conclusion: The ESI System 10 Years Later

As I look at these 10 moves, I realize they all come back to the same core principles: Keep it simple, keep it low-cost, and stay disciplined.

Financial freedom isn’t a set it and forget it state. It’s a series of small, intentional choices that build on one another over time. If you’re still in the accumulation phase, take heart: these habits you’re building now are the same ones that will protect you once you cross the finish line.

The last ten years have been a wild ride for the global economy, but by following these moves, my net worth is substantially higher today (more than double) than it was on the day I retired — even after a decade of spending. That is the power of the ESI system in action.

If you are 10 years away from retirement, or 10 days away, I hope these moves give you a roadmap. Wealth isn’t about one lucky decision; it’s about a hundred small, smart ones made over a decade of freedom.

What about you? For those of you who have been retired for a while, what was the best financial move you made after you quit your job? And which ones do you think is the most important for the second decade of retirement?