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I just finished reading Morgan Housel’s The Art of Spending Money, and it hit a different nerve than most financial books.
Most of us spend years talking about how to earn more, save more, invest better, and retire sooner. All of those matter. But Housel pushes a harder question:
What is the money actually for?
Is it buying back time? Peace? Family memories? Health? Independence? Or is it quietly being used to chase status, comparison, or applause?
One line I keep coming back to is this:
A raise that becomes a payment is not really a raise anymore. It is a new obligation.
That made me think about retirement, lifestyle creep, debt, and how easy it is to look successful while feeling trapped.
For me, the bigger lesson is that spending is not automatically good or bad. The real question is whether the purchase supports the life you actually want — or the image you feel pressured to maintain.
So, here’s the conversation starter:
What is one purchase you made that genuinely improved your life — not because it impressed anyone, but because it gave you more peace, time, health, family connection, or freedom?
And on the flip side:
What is one purchase you thought would make life better, but later realized it was mostly about status, pressure, or keeping up?
Having recently retired, I’m spending on experiences. I’m still frugal when purchasing food and clothing (love shopping second hand stores), but don’t think twice about spending money on family experiences. My one son lives in New Orleans and I will be buying 7 Saints / Packers tickets for a December game ($4k) in NOLA that brings my two sons and their families together (the other son and family and I live in Pennsylvania) to enjoy a shared love of football and have an early Christmas together with the grandkids.
Another purchase I have made recently with no regrets? A prescription to Wegovy (the pill). Not covered by insurance of course and costs me $300 a month. Insurance is only willing to pay after you go into cardiac arrest. I have high cholesterol, had to start taking blood pressure medication in the last year, moved into the “pre-diabetic” zone, and was near an obese BMI. I started taking Wegovy in January and have lost 25 lbs. Ten more pounds to go and I’ll be “normal” weight and weigh as much as I did in high school. I have so much more energy, I drink less alcohol, and feel and look great. I know i’ll be taking that pill for life…best damn money I ever have, and will continue, to spend. And I get to save the insurance company future health care costs! LOL.
A 22-foot, used camper-van greatly improved our lives in our early-mid retirement years. We set off on numerous trips across the US and Canada typically for a couple of months. The little van had a diesel engine and we averaged about 23 miles per gallon (versus the 10 mpg a bus-size RV gets.) Though other people embrace the RV approach to “go wherever the road takes you,” I preferred researching, planning, and reserving destinations and campgrounds to maximize our time.
We visited dozens of national parks and historic sites, and had too many adventures to detail. As examples, we followed Lewis & Clark’s route and the California Mission Trail. We found each lighthouse along the coast of Maine, and slept beside Ancestral Puebloan ruins at Chaco Canyon. We stayed in peaceful campsides by the water in the Florida Keys, booked a campsite by the Albuquerque Balloon Fiesta’s launch field , and had dinner with a view of the North Rim of the Grand Canyon (in the lodge that sadly burned to the ground last year). Often I wrote magazine articles about our trips, which provided a little extra retirement income. My husband supplied some of the photos, a fun collaboration. In between the van travels, we visited with family members and made trips to places you can’t drive to. After 8 wonderful years, we sold our “magic carpet” just before the Pandemic hit. I spent those shutdown months making photo books of our travels, and we still look at them constantly. I’m gladly we didn’t end up with a long “someday” list. Our travels are now limited by my spouse’s health, which makes that investment priceless.
We did most of that as well- in a car and hotels though 😁
We started out that way, as did many of our friends, but found we spent a lot on hotels and restaurants, and we both had grown up in frugal households. After buying the van, which doubled as our second household vehicle, we kept detailed records and realized we could travel that way for around $100 a day inclusive, which suited our budget. Of course, that was in 2011!
I am beyond purchasing much, these days I’d rather use money to help family members when they have a problem, to help fund college costs, to overtip servers who have way less than I do.
Two purchases come to mind. The first was our Peloton bike at the beginning of 2021. I’ve completed over 1500 rides and over 4000 classes (including strength, stretching, and later rowing) in the five-plus years since, and it was a great investment in my health and to a lesser degree my husband’s. I’ve never been great about actually leaving the house to go to a gym, but I’m very good at working out at home. We actually offset the purchase of the bike and later rower with an annual wellness credit his company gives—didn’t cover the whole thing but took some of the sting off the price tag.
The other was our 2018 Audi TT Roadster convertible. It’s the most indulgent thing we’ve ever bought for ourselves. Yes, it impresses people, but it’s also made us very happy. When my job got very stressful, a weekend drive in the convertible quite literally helped me breathe, and it was like a mini-vacation. We’d always wanted a convertible; that was even the title of one of my husband’s albums! It still only has a bit over 30K miles on it, so I think we’ll have it until we’re no longer able to climb in and out of it!
Sorry, I answered the first question earlier but missed the second question until more readers had commented! When I was living in Italy in my 20’s I bought a classic Italian sports car. While it did get some approving looks and comments from older Italians, it didn’t get me many dates and was a maintenance hassle.
Good topic Jeff.
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Love this idea, Jeff. Thanks for posting.
My answer would be my home. Actually all my homes along the way, but this house, bought out of desperation during the 2021 housing craze and way too big for the two of us, has been the best of all. When we finally got my wife’s entire family out of China, this place was big enough for everybody. All five bedrooms full, clattering in the kitchen until 8pm, and I loved it. Now it’s quieter, a place for Mama to live out her life and for Sarah and I to have a sense of comfort and security in an increasingly weird world, and it’s a priceless feeling.
As to the second question, the brand-new 1985 Cougar XR-7 I bought to impress my dates as a hot sporty guy still makes me wince in recollection.
Thai is a great thought exercise, Jeff. The time invested in my daughters bought me more fulfillment than anything I have ever purchased for myself. Teaching them to swim or ride a bike, vacations, school work, touring prospective universities all come to mind.
The home we built in the 55+ community has improved our lives. Having all the essentials on a single floor makes housework more manageable. No lawn mowing or snow shoveling is sweet as well. More time for fun stuff, or to do nothing at all.
Regarding your second question, keeping up with the Jones doesn’t seem to be one of my dominant genes. Whenever we make a more upscale purchase, it’s because the quality of the widget has value in the form of longevity or performance. Examples for me might be a quality watch or my ‘vinyl resting place’, Chrissy might say nicer clothing that fits and feels better.
Jeff, great book you referenced. Like Greg, the purchase of our Condominium at the NJ Shore was the best (and scariest) purchase we ever made, 9 years ago. At the time, we were still working (in the office 5 days a week) and had two young granddaughters, ages 5 and 3. We used part of our retirement 401k funds to come up with the 20% down payment and took on a large 2nd mortgage, albeit at a great 3.5% rate.
In the years following, this 2nd home, just an hour from our primary home in North Jersey has become the center of our social and family’s lives. From Memorial Day through Labor Day, our daughters, SILs and now 4 grandchildren (ages 3-14) come down and spend the weekends with us enjoying, beach, pool and the NJ shore summer vibe. We are blessed that our family lives close enough to spend this time with us and enjoys coming down often. We are now retired and spend much of the summer here at the beach (when not returning to North Jersey for Drs. Appointments, etc.) getting together with the many friends we’ve made here and having other friends visit from North Jersey (during the weekdays) to spend time at the shore. Besides all the great times and leisure activities the home provides, the increase in value has made it one of the best investments we’ve ever made.
Thanks Jeff. I also very much enjoyed Housel’s book.
Our best purchase was a holiday (vacation) house we purchased with some inheritance money. It was very cheap, very basic. But it gave our family a wonderful reason for so many weekend getaways, time spent on the lake, pub meals, Saturday morning community markets. The house wasn’t actually the main thing, it was the amazing family memories that it helped to create.
With regards the second question, I’ve been pondering what we have bought for status, prestige or keeping up. But I think the truth is we just never cared enough to make these types of purchases. We didn’t invoke any great self control to stop ourselves buying fancy stuff, it just has never interested us.
Paradoxically, the same purchase answers both sides of your question: an engagement ring.
In the short term, it was pure status, a financial stretch driven more by social pressure and the unspoken rule that the size of the stone somehow measured the depth of the commitment. Looking back, a more modestly priced ring would have meant exactly the same thing to the person who mattered.
But in the long term? That single purchase indirectly bought me everything on your list: peace, happiness, stability, and family connection. The ring wasn’t the point, of course. What it set in motion was.
It’s a strange thing to reflect on: the most meaningful investment of my life was also the one I made for partly the wrong reasons.
My wife was overseas visiting her parents on our 5th wedding anniversary, and she’d left her engagement ring home because she didn’t like to travel with her jewelry. So I thought I’d surprise her by doubling the size of the diamond.
When I gave it back to her, she didn’t even notice.
I certainly married the right girl, but it was a pretty dumb investment.
🤣
We got engaged at unusual time so I hadn’t bought a ring. When we talked about one my wife said she didn’t need one, but I insisted that she have one for it’s symbolism. We found one at an upscale craft fair with a 1/5 carat diamond.
Fourty years later when I was going through our papers I stumbled upon the receipt and googled the artisan and he still was in business in San Francisco. I emailed them a quick Line just to let them know we were still married. This goes to show me that perhaps the size of the diamond doesn’t mean anything, or perhaps it may mean the opposite.
The first thing that comes to mind, and still the top one after thinking about it for a bit:
Freedom and peace of mind, purchased through monthly payments to myself over many years.
Ditto! To be blessed with freedom and peace of mind is so very precious.
On the keeping up side, apparel purchases during my working years would top my list. The extended wearspans of retirement clothes are much more to my liking.
Two purchases improved my life – a right knee replacement as I retired in 2020 and (two years later) a left hip replacement. Both purchases eliminated daily pain, plus they restored my desired activity level.
Other thoughts: adding a master suite to our home made it so much easier to live in our home. Adding a front porch to our home increased our social engagement with our community.
On the flip side: many years ago, my then-wife convinced me that purchasing a vehicle with a certain level of status would be beneficial. That Saab lasted a long time, but finding a qualified mechanic was difficult, and the vehicle was expensive to repair. I no longer own that car and I’m also no longer married to that woman.