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
- 10 Retirement Mistakes I Made (And Why They Didn’t Sink Me)
- 10 Strategies for Staying Socially Connected Without an Office: The ESI Guide to Avoiding the “Loneliness Trap”
An Expert Saver
When I walked out of my corporate office for the last time in 2016, I was a black-belt in saving. I had spent three decades viewing every dollar as a soldier that needed to be protected, hoarded, and sent out to invest for my eventual freedom. (For details, see We Spent 17% of Our Income where you can see that we saved 36% of our income over many years.)
My wife was even better. When people ask how we retired so early I sometimes tell them, “My wife can stretch a penny into a quarter.” Hahahaha.
Like many people, in the early years of retirement that frugality didn’t just disappear; it lingered like a saver’s shadow. I was still price-matching groceries, second-guessing the premium oil change, and living as if I were one bad month away from having to go back to work.
But ten years into this journey, the math has finally won the argument. My Invest pillar has compounded substantially and my Earn pillar continues to provide a margin of safety I never anticipated.
The biggest change, however, isn’t in my bank account; it’s in my mindset. I’ve moved from frugality for the sake of freedom to value spending for the sake of happiness.
The change wasn’t accomplished on my own — far from it. The Millionaire Money Mentors helped me see how ridiculous I was (as well as the same for many others) when we have millions and yet fret over something costing $25!
Today I’m going to share some victories — 10 places I intentionally spend more money on today than I did when I first retired. Woo hoo! This feels like a breakthrough! lol
The Psychological Shift: Moving from Saver to Spender
Before we dive into the list, I have to note how much of an issue this is for retirees. And why wouldn’t it be? We spend three or four decades saving to get to retirement so that stuff is hard-wired into us by the time we quit working. It’s difficult for many to turn that off and start to loosen up the purse strings.
If you have spent 30 years being the “frugal guy,” spending money feels like a betrayal of your identity.
For the first few years of retirement, I still held onto the “S” in ESI like it was a vital part of life. I remember complaining to the Millionaire Money Mentors when the price of a breakfast sandwich at my gym went from something like $6.25 to $6.99. They slapped me into reality (electronically, of course) and let me know I’d be fine and it was ok to spend that extra 74 cents a day. Hahahaha.
I had to realize that the Save pillar has a shelf life. Its purpose is to get you to the summit. Once you’re at the top, continuing to save at the same rate is unnecessary and it slows you down. I had to learn that value spending isn’t lifestyle creep. Lifestyle creep is spending money to impress people you don’t like; value spending is spending money to improve the lives of the people you do like.
This is a vital point — I still don’t spend willy-nilly as I don’t like to be wasteful. And I certainly don’t want to spend on anything that makes my life worse! So the focus is to spend like I want as long as what I’m spending on brings joy/happiness/value to our lives.
Sound good? Ok, let’s get into my list now…
1. Eating Out and Grilling: Buying Back Family Time
A decade ago, I viewed eating out as a luxury that was often wasteful. My wife was even more on alert about it. She would often say something like, “We could make this at home for $12, so why are we paying $30?” This was a remnant of the early ESI days when every nickel saved was a nickel that could be compounded. We treated restaurants as much as a failure of planning as an opportunity for connection.
Today, that calculation has been replaced by a focus on time and family. We spend significantly more on restaurants and high-quality grilling foods because of the environment it creates. In retirement, your kids are adults with their own busy lives. We’ve found that being the hub for Saturday grill sessions or mid-week dinners is a great way to stay connected.
When I spend $100 on steaks for the grill, I’m not just buying protein; I’m buying a several-hour visit from our daughter and son-in-law. We aren’t just eating; we’re experiencing. Whether it’s trying a new restaurant or hosting a family cookout, the money spent on food is actually an investment in our family. We’ve intentionally shifted our budget to favor these shared moments.
To be more specific, we have dinner every Saturday together and we rotate — one Saturday we grill out (sometimes we cook inside but that’s rare) and the next we eat out. We usually follow the food with a movie and a walk around the neighborhood. We supplement Saturdays with simple get-togethers like buying a rotisserie chicken when we go to Costco together or stopping at Culver’s when my daughter and I are out shopping.
The joy of watching my family enjoy a meal I prepared on a top-tier grill (Traeger FTW) or the ease of a long dinner where no one has to do the dishes, is worth every penny of the increased expense. We’ve traded the cost of calories for the value of memories, and the ROI is off the charts.
2. Subscriptions: Paying for Time and Sanity
Ten years ago, I prided myself on having the basic version of everything. I’d suffer through ads, navigate the clunky free versions of software, and spend hours trying to find a workaround to avoid a $15 monthly fee (remember using people’s passwords?) I thought I was being efficient, but I was actually just being cheap with my most limited resource: my time.
Now? I am a subscription maximalist. If a service saves me ten minutes of frustration, provides a seamless experience, or brings me joy in some way, I pay for it. A few examples:
- YouTube Premium to avoid ads.
- Quicken to manage finances (25 years of data now)
- ChatGPT and Google Gemini — Learning AI and seeing how it can simplify life
- Amazon Prime (including no ads on video) — Saves time (home delivery and not watching ads)
- Chess.com — My daily chess puzzles and games
Anyway, you get the idea.
In retirement, time is your most precious asset. Spending money on various subscriptions that remove friction and make my life more enjoyable is an awesome trade-off for me. I’m no longer willing to pay with my patience to save a few dollars.
If you’d like more specifics, check out Why I Love Subscriptions for all the gritty details. 😉
3. Giving: Helping Others Brings Joy
I’ve talked a lot about giving on ESI Money so I won’t detail it too much again here.
As I noted in The 10 Best Financial Moves I’ve Made in 10 Years of Retirement, we’ve upped our giving in retirement. That plan is detailed in my post about IGE (Invest, Give, and Enjoy), but the short version is that we’re at the end (in 2026) of a 5-year plan to give away $100k a year.
Giving is a primary line item in our budget — and it has grown significantly in both percentage and raw dollars. In fact, it’s our largest “expense” by far. Our second largest is taxes. Hahahaha.
We spend more on charity because it brings us more joy than any physical purchase ever could. There is a unique psychological high that comes from being able to make a significant contribution to a non-profit or a church project without having to check the bank balance first.
We’re thinking through what happens as our five year plan is fulfilled this year. That’s still TBD but it’s likely that we’ll continue on with it for at least a few more years.
4. Clothing: The Post-Florida Restock
This one is a bit more practical but reflects a major shift in how I value my daily comfort.
When we moved to Florida a few years back, I aggressively downsized my wardrobe. I had to do this for two reasons. First, our Florida home was much smaller and could only handle so much. Second, I got rid of a big portion of long sleeves and anything warm — I thought I’d live in two pairs of shorts and three t-shirts forever. I was trying to embrace a minimalist vibe that felt right for the tropics but turned out to be too restrictive once we moved back to North Carolina.
I’m spending more on clothing now because I’m rebuilding a wardrobe that fits my actual lifestyle. I’ve traded beach bum attire for the more sporty and comfortable stuff I had in Colorado. Plus I needed to gear up on items supporting our local teams — Panthers, Hurricanes, Blue Devils, Tar Heels, etc.
A few of my focus areas:
- Cotton t-shirts. I love how these feel but in Florida they are little more than sweat collectors — you sweat in them and it sticks with you — so I got rid of most of them. Now I’m making up for that.
- Long-sleeve shirts. Can you ever have too many quarter-zip athletic shirts? I’ll let you know if I ever get to that point. Hahahaha.
- Brooks Ghosts shoes. I love Brooks Ghost shoes (or at least I have up until now.) I tried the latest version and they aggravated my back (they have changed the design), so I went on ebay and Amazon and bought all the Ghost 14s and 15s I could find. They are at least two model years ago, so it wasn’t easy, but I stocked up with six pair…which should last me a good amount of time…enough for Brooks to revert to their previous design or for me to find a suitable replacement.
- Black cotton shorts. I wear these every day. They are comfortable and go with everything I have. They are also pretty affordable so I bought 10 pair more to go with the ones I brought from Colorado to Florida.
Those are the highlights for now, but I’m on the hunt for a few good jackets, so the spending is not over by far.
5. Home Upgrades and Furnishings: Making Our Home the Place to Be
Our home in North Carolina is a significant asset, but it’s also our sanctuary. Ten years ago, I would have done the bare minimum to make a house livable, always with an eye on the resale value. I looked at every renovation through the cold lenses of “Do we really need it?” and “Will I get this money back when I sell?”
With this house, we are making it exactly what we want for us. We’ve invested in new flooring, fresh paint, furnishings that actually fit our style, a redesigned garage, and more! We even painted the kitchen cabinets — a project that a younger, more frugal version of me would have balked at due to the purely aesthetic nature of the cost.
The enjoyment ROI is massive. We spend 90% of our time in this house. Making it a place where we actually want to be — rather than just a place to store stuff — has a significant impact on our daily mood. We’re not fixing it up for the next buyer; we’re fixing it up so that every morning we wake up in a space we love. The peace of having a finished home that reflects your personality is worth far more than any equity we might lose on the upgrades (if we even lose anything).
Just today we got back from the mall and when I walked in the house I had a sense of peace and happiness to be here. Now that’s what I’m looking for!
And since simply thinking about traveling starts to give me the hives, why not make your home a place you’d prefer to anywhere else in the world?
6. Landscaping: Fighting Mother Nature in the Woods
Living in a wooded area of North Carolina is beautiful, but it’s a constant battle against the elements. Ten years ago, I would have spent my Saturday mornings doing all the work myself. I viewed the sweat equity as a way to save money. I thought, “Why pay someone $200 when I have the time to do it myself?”
Now, I pay the landscaping tax gladly.
Our town is 50% covered by tree canopy. Our house is about the same.
Our backyard is woods. We have trees on one side of the house and a small one on the other (we just had a couple trees there cut down as they were threatening our HVAC unit and foundation.) In the front yard we have two trees taller than the house — one maple and one oak (FYI, they are so large and massive that we can barely grow any grass since our front yard gets little sun). Then we have a smattering of smaller trees here and there — a crepe myrtle about as tall as the house and a holly tree almost as big. Plus some bushes in the front of the house.
I think you get the point…we’re living in Sherwood Forest! Hahahaha.
So to take care of all this, we’ve had to do some spending — on a tree service to take down some trees and prune others and on equipment so we could do some of the upkeep ourselves. We’re fighting for our lives trying to keep the woods at bay. lol
We’ve also had some landscaping done — including a wall built around a front garden area and some ground leveled there too.
And while it’s not landscaping (but it is outside), we did have our house, walkway, and driveway power-washed last year. The house needed it as we get some green “growth” on the side of the house when it’s hot and humid (which it was for several months last summer) on places that don’t get much sun (because of the trees). The walkway and driveway were simply needed after 20 years of grime building up.
And it’s not over. Depending on how aggressive we want to be (and what I can convince my wife to agree to), I wouldn’t mind a major yard upgrade that puts stone around our two big trees in the front along with some nice lighting. But we’ll see if I can get that through the budget committee. Hahaha.
By spending more on professionals when needed to handle the heavy lifting, I preserve my back and my Saturday mornings. I get to enjoy the view of the woods without the work of the woods.
It’s a perfect example of spending money to buy back my physical health and leisure time. My time wealth is too valuable to spend it on tasks that someone else can do better and faster. Plus I like to support local businesses. It allows me to be a steward of the woods rather than a servant to them.
7. Transferring Money to Kids: The Warm Hand Inheritance
This is perhaps the most significant shift in our financial strategy. Why wait until we’re 90 to give our kids an inheritance when they’ll likely be 60 and financially stable themselves? This is one part of the Die With Zero philosophy that I’m actually putting into practice.
We are intentionally transferring wealth to our adult children now.
So far it’s been helping with house down payments and a new car, but in the future it could be funding a grandchild’s 529 (we hope!) or anything else worthwhile that pops up. We want to see them enjoy the money while it can actually change their trajectory.
By giving now we get to witness the impact of our ESI success in real-time, strengthening our family bonds and helping them build their own pillars.
It’s an investment in their future that we get to watch grow. This isn’t a loss on our balance sheet; it’s a transfer of utility to the people we love most. By giving now, we are providing them with the Invest foundation they need to eventually achieve their own ESI freedom.
But a word to the wise. If you are planning on doing the same thing, be sure you transfer the money in the right way. Or else you may run into trouble (like I did with Chase). Hahahaha.
8. Christmas: Spreading the Wealth
A decade ago, Christmas was about staying within the budget. It was a seasonal exercise in disciplined spending. I’d look for deals and try to keep things reasonable. Today, Christmas is about spreading the wealth. We spend significantly more on gifts for our family (and others) than we did ten years ago.
It also makes it less of a hassled time of year. Instead of buying 10 gifts for everyone, we buy a few and then give them a check. The amount has gone up and down through the years, but let’s just say it’s large enough for them to buy themselves a really nice gift. 😉
It’s not about being extravagant for the sake of show; it’s about using the holiday as a catalyst for generosity. We love being able to surprise our kids with high-value items or experiences that they wouldn’t necessarily buy for themselves.
We also like to give gifts to those around us at Christmas. This year we gave $25 Amazon gift cards to all the lifeguards at the pool and some of the employees at the YMCA.
This makes a joyous time of year even more joyful. We’ve found that being generous provides a level of satisfaction that no index fund return can match. It makes the season more about “What can we give?” rather than “What did we spend?”
9. Small Giving: The Micro-Blessing Strategy
This is a new category for us that has grown in importance. We’ve started keeping an eye out for “micro-opportunities” to bless people we run into on a day-to-day basis. I call this by several names: small giving, spreading kindness, etc.
This one is a bit all over the map as there are a number of ways you can go with it. We just basically look for opportunities to bless people, then make them happen. A few examples:
- Buying birthday and Christmas presents for a person with an intellectual disability at the gym. We have the staff give them to him so it’s anonymous.
- Putting toys into the Little Free Library at the YMCA. They always disappear quickly. 😉
- Tipping generously when we eat out.
- Buying an item (often a book) when you run into a person who has a need for it (interest or it may help them).
- Providing snacks for the lifeguards at the pool.
- Giving Amazon gift cards as “tips” to people who come to our house to do a service (check the HVAC system, do landscaping, etc.)
- Offer Gatorades to delivery drivers in the summer. It’s hard to catch them as they are in and out quickly, but Amazon sometimes does a good job of telling you when the delivery will happen, so those drivers are catchable with a little effort.
You get the idea. These are small ways we can bring kindness/happiness into others lives.
These small acts of giving keep us grounded and remind us that our wealth is a tool for kindness. It’s value spending that has a 0% financial return but a 100% spiritual one.
It turns an ordinary day into an opportunity to make someone else’s life slightly better. It keeps the scarcity mindset at bay and reinforces the idea that we have enough.
We supplement this with larger (but still small compared to our main giving) gifts to those in need. Examples: sending a $1,000 check to a cousin who had her husband pass away and giving a widow we know is on a tight budget $500 for Christmas.
10. Medical Insurance: The Reality of Medicare vs. Sharing
Finally, one expense that has increased purely due to aging and the shift in healthcare systems. Ten years ago, we started using Samaritan Ministries, a healthcare sharing ministry. We’ve used them for a decade (I still do) with great success. It was incredibly cost-effective — we were paying roughly $500 a month for our entire family when we started and were just under $500 for the two of us ten years later — and it fit our lifestyle perfectly when we were younger.
Now that my wife has transitioned to Medicare, our healthcare costs have actually increased. What a shocker, huh? Higher costs from the federal government. Who knew? lol
Between the Medicare Part B premiums (which for high-income earners like us include the IRMAA surcharges), a Medigap supplemental plan, and Part D drug coverage, we are spending significantly more than we did on a sharing ministry.
While it’s more expensive, Medicare provides a level of set it and forget it security that is valuable in this second decade of retirement. We are trading lower premiums for higher certainty in case of a major health problem. It’s a classic example of paying more for peace of mind. We view this increased cost not as a burden, but as a success tax that comes with having a high net worth retirement. We’ve been dealing with that a long time when it comes to taxes. Hahaha.
The Shifting ROI of the Dollar
If you looked at my budget from 2016 and compared it to 2026, you might think I’ve lost my way as an ESI practitioner. My spending is higher in many discretionary categories. My younger self, still in the grind, would have looked at this budget and been terrified of lifestyle creep.
But I would argue that I am practicing as good ESI now as I was then.
I’m certainly enjoying the spending we’re doing, so that’s what really counts.
The goal was never to see how little we could live on; the goal was to buy back my life. Now that I have the time, I’m using my money to make that time as rich, connected, and significant as possible. The value spending of today isn’t a drain on my future; it’s the realization of the goal I set thirty years ago.
What about you? As you’ve moved through your own retirement (or as you plan for it), what are the categories where you’ve intentionally given yourself permission to spend? Have you found that moving from saver to spender is harder than you expected?
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