‘What Was I Thinking?’ The Big-Ticket Items People Regret
People spend a lot of money on all sorts of things, only to later ask themselves: Why?
5 min
While it may be true that money can’t buy happiness, that doesn’t stop people from trying.
And then wishing they hadn’t.
Many of us have had a big-ticket expenditure that we later come to regret. Maybe it’s something meant to convey status, which we realise later did nothing of the sort. Maybe it was to fulfil dreams of a luxury lifestyle, only to discover that we’ve bought a bottomless money pit.
We asked Wall Street Journal readers to share their stories of pricey purchases that ultimately led to disappointment. Below are some of their stories and reflections—with some free advice to their younger selves.
The wristwatch of his dreams
“It was back in day of wingtip shoes, white shirts and red ties,” says Bryan Desloge, who began his career at IBM in 1984. And like many rookie employees, Desloge wanted to fit in. “I bought suits. I took my earring out. I cut my hair and I registered in the Republican Party,” he says. To complete the look, he paid over $7,000 for the wristwatch of his dreams—a Rolex Submariner. It was a hefty sum, considering he was making roughly $18,000 a year.
Now 64 and retired, Desloge says his younger self saw the stainless-steel watch as a status symbol. “The older guys had nice dress watches already, while I wore a Casio or a Timex.” Just two years after buying the Rolex, however, Desloge realised the timepiece was impractical for him. “The Rolex is great, but I don’t want to look at a clock face,” he says, “and the glow-in-the-dark hands are hard to read at night.”
Desloge, who lives in Tallahassee, Fla., recently tried to give the Rolex to his son, who turned him down. So it remains tucked away in favor of a Garmin smartwatch, which has a fitness tracker, alerts and email, among other features. Purchased for about $500, the Garmin can multitask in ways his Rolex cannot. “I will probably wear that watch for the rest of my life,” Desloge says.
Cabin fever
The family called it “the little brown house,” says Michael Kotas of his vacation cabin in the mountains overlooking Tucson, Ariz. In 2005, Kotas and his wife paid $120,000 for the 1950s cabin, and it needed a lot of work.
“We bought it from an older couple, who had dark rugs and wood paneling,” says Kotas, who is now in his mid-60s and retired from a job in technology sales. He redid the cabin “with a cool Manhattan vibe,” updated the electrical wiring and corrected a flooding issue in the basement. In all, Kotas estimates he spent $60,000 in upgrades.
But his financial headaches were far from over.
Even though Kotas owned the cabin, the federal government owned the land it sat on, since it was located within the Coronado National Forest. Leasing the land cost $800 a year when the cabin was purchased, but eventually grew to $3,600 a year by the time it sold.
During that time, two fires came within 100 yards of the cabin, jacking up Kotas’s fire-insurance premiums. Then, a species of bark beetle attacked ponderosa pines there, and the Forest Service required cabin owners to remove infested trees around their property, costing $1,000 to $1,200 a pop. “I counted all my trees around my house and thought, ‘I can’t afford this.’ ”
Over time, Kotas’s children didn’t want to go to the cabin anymore, saying “there was nothing to do,” he says. “We ended up spending about five nights a year there for the last several years.” Kotas, whose year-round home also is in Tucson, came to the realisation that he wasn’t getting his money’s worth. “It became an albatross,” he says.
The tipping point came when a man parked his truck just 100 feet from the cabin and lived out of his vehicle on the side of the road. Kotas sold the cabin in 2022 for $195,000.
“I would probably never buy a vacation home again,” he says. “It was a tough lesson to learn. I wish the [new] buyers well, but all I can say is, ‘Good riddance!’ ”
RV to nowhere
After retiring from a career in ophthalmology, Gordon Preecs bought a large pickup truck in 2013 and a 22-foot travel trailer in 2017 with the dream that he and his wife, Connie Preecs, would visit national parks around the country. Combined, the new vehicles cost around $50,000.
Living in Seattle at the time, the couple started out by taking the RV on short trips, such as an event for woodcarvers in Washington state. It didn’t take long for them to feel pinched in a 120-square-foot RV. “I thought we’d have our own hotel” with an RV, says Preecs, who is now 75 and living in Round Rock, Texas. “But we had to just shove things in there. The kitchen counter was hand’s breadth wide, and the bathroom was like a phone-booth shower. If I dropped the soap, I couldn’t pick it up.”
Three years after purchasing the trailer, Preecs and his wife relocated to Texas to be closer to their grandchildren. Still, they were able to visit Grand Teton and Yellowstone national parks in the Northwest. That’s when they felt the financial pinch of RV ownership.
“At 6 miles per gallon and $60 to $80 a night at RV parks, the expenses really added up,” he says. “We found it was an inefficient way to travel.” Some of the RV parks are located in funky, backwater places, he says. And setup and breakdown at every stop became a hassle. “You want to be free, but you’re not.”
In 2020, they sold the trailer, which had less than 5,000 miles of use, and the pickup for a combined $32,000. With the proceeds, Preecs bought a Tesla.
Outfitted and outwitted
As a vintner in California, much of Pam Starr’s work takes place outside among the grape vines. “I live in jeans and winemaker vests, T-shirts and sometimes boots,” says the 63-year-old. “So I can tear my clothes on a vine or get barrel slime on me” and it doesn’t really matter.
A few years ago, a well-heeled friend with an eye for fashion convinced Starr, who lives in Napa, to join her in San Francisco for a meeting with her couturier—a person who creates luxury clothing to the client’s specifications. The friend had told Starr that she wouldn’t have to buy anything, but this particular couturier was very persuasive, Starr recalls.
For example, the couturier held up a gauzy swimsuit coverup with white sequins and said, “You have to wear this swimsuit coverup by the pool.” Starr paid $1,800 for a custom coverup, but later it hit her: “I don’t wear a coverup when I’m at the pool because I’m actually in the pool.” To this day, it has never been worn. Starr says she spent another $1,800 for an off-the-shoulder silk shirt with three-quarter length sleeves.
The quality of the clothing was low, Starr says. “That silk shirt turned out to be my most disappointing piece,” she says. It didn’t clean well, and hasn’t retained its shape. Many of the pieces she purchased haven’t held up well, she says, even though she rarely wears them. “Out of the 15 items I had made for me, I loved maybe three,” Starr says. “That’s more than $20,000 worth of clothes, and I should have gotten more out of them.”
If she could go back in time, Starr says, she would say to herself, “ ‘Listen, Pam. Pick two things and start slowly. If you like them, you can expand into other things.’ ” Also, she would pause to ask herself how often she would actually wear the clothing.
“Because of a friend, I ended up in a couture shop,” Starr says. “In that world, it’s uncharted territory for me. The couturier pulls you in really hard.” Knowing what she knows now, Starr says, “if I needed someone to design a gown for me, I wouldn’t go back there. I would go to a seamstress locally.”
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From early financial mistakes to hard-earned habits, five high-performing leaders share how they spend, invest and think about wealth.
9 min
Five minutes doesn’t sound like much. But it’s enough time to tell whether someone really understands money or just talks about it. Because once the gloss is stripped away, what’s left is instinct. The early mistakes. The bad calls. The quiet pivots that no one brags about but shape everything that follows. Making money is one thing. Living with it, and not mishandling it, is another. Here, five executives talk about what they got wrong, what they’ve learned, and how they now actually spend, invest and think about wealth.
Andrew Raso: Founder, Online Marketing Gurus
Self-made millionaire Andrew Raso grew up in an ethnic household with a father in construction. Investing was not a priority, he recalls.
The co-founder and CEO of Online Marketing Gurus, a digital marketing platform that generated more than $30 million in revenue in the 204/25 financial year, admits he’s had to learn about handling money as his wealth has grown.
“If I had my time again, I would change my spending habits and would probably be a lot more wealthy as a result,” the Sydneysider tells Kanebridge Quarterly.
Raso, in his mid-30s, says that his biggest lessons have come from his losses.
Buying the wrong property and copping the losses upon sale. Feeling FOMO when buying crypto and making a purchase that lost money.
“I’ve learned a lot from the errors that I’ve made,” he says.
Raso admits that he gets more of a thrill out of working than watching money hit his bank account.
“I’ve had the cars, I’ve had the property, I’ve had the watches. Once you’ve had them, they’re not that exciting, but the process of earning money is pretty cool.”
What he won’t forget is being $45 million in property debt a few years ago.
“I’d never want to be in that position again,” he says.
“My investing strategy is a lot safer these days. I’m very cautious. I’d prefer to invest in things that don’t take as long to be realised so my family can be financially secure.
“Once you have a house paid off and a few investments, it then becomes about enjoying your money, rather than hoarding it. Giving back gives me a much bigger kick than spending these days.”
Daniel Wessels: CEO, Jacaranda Finance
Fintech founder Daniel Wessels knows only too well that money remains a taboo topic in Australia with many people.
He points to consumer surveys that reveal people are more likely to talk about their sex life with friends than their finances.
It’s a major concern for the man who founded Jacaranda Finance in 2013, which has helped countless people lift their credit scores and get their finances back on track.
“If people aren’t learning money habits at school and they aren’t discussing it with their friends, learning new strategies and better habits is difficult,” says Wessels, who is based in Brisbane.
He wants to see more people take the time to proactively understand where and why they are spending money.
“Everyone needs to have a financial strategy and a plan to measure if it’s working,” he says.
The father of two young children admits his week can be pretty fast-paced. Pomodoro clocks, sleep optimisation techniques and saying ‘no’ keep him on task during the week.
“I used to think I was fairly decent at managing time, but the whole game changed when we had kids,” he says.
“Now, I’ve got to get out of the house at a certain time and leave the office at a certain time for daycare pickup. I’ve got to be really specific about my tasks to maximise my week.”
Before he had a family, he loved heading out to one of the trendy new restaurants popping up in Brisbane.
But that happens less these days. He’s saving to build his forever home but admits that price rises have resulted in rising costs.
“It’s such a big project with so many variables that change quickly,” he says.
These days, Wessels likes to optimise his professional and personal life. “With only a finite amount of money, time and energy, you’ve got to be really good at deciding what you want to be good at,” he says.
He calls this ruthless prioritisation. He has a very specific focus on activities that prioritise health and wealth, adding experiences into the mix more recently. This has meant the addition of micro-holidays to his annual calendar.
Wessels works with a couple of financial advisers. That said, he also does his own due diligence before agreeing to investments.
“One likes private equity investments that pay cash every month and another prefers to focus on the NASDAQ Stock Exchange for buying shares because he’s bullish about that.” he says. “They’re each experts and really good at what they do.”
Jim Penman: CEO, Jim’s Group
He may have invested a lifetime building a franchise juggernaut that is reportedly a $1 billion a year empire, but Jim Penman insists he’s a frugal guy who prefers to spend time planting a tree in his garden than contemplating his wealth.
What started out as Jim’s Mowing back in 1989 became Jim’s Group. Today, there are 5,700 franchisees across Australia and New Zealand in the business that has become ubiquitous for being the local handyman company that households could rely on.
He may have built a successful business empire, but the Melburnian insists he’s stingy when it comes to money.
“I wear my clothes even today until they wear out. I’ve always had a very lean and mean attitude. I live a simple life. My personal needs are very modest and my finances are simple,” he says. Jim reveals he’s usually in his garden these days and rarely eats out or takes holidays.
He is also running for state politics in the November Victorian election.
“I’m not particularly money focused. I could tweak the franchise contract to put more fees in and double my profitability, but that’s not my goal or my aim. To be honest, I often make decisions that go against my financial self-interest,” he says.
Jim purchased his first brand new car three years ago, opting for an electric Volvo.
“Being rich is not my aim and it never has been. People think I’m a lot richer than I am. They think I’m a billionaire, which is kind of ridiculous,” he says.
In fact, he insists he carries debt, which is common for anyone in business. “If I wanted, I could pay it off in 18 months.”
While his competitors were spending on fancy office space, Penman was running his franchise from his basement, keeping business costs low. “When I started out, I didn’t have any concept of how big this business could be. But there has never been a plan to grow franchisee numbers.
“Our attrition rate is far more important, and how to reduce complaint rates and drive more enquiries through new software.”
He believes people these days worry too much about impressing others, which leads to spending on superficial things.
“I would rather than offer people advice on how to be happy, rather than how to become rich. It’s important to have a good income so you can support yourself. But life is more about purpose.”
Jim doesn’t bother with stocks or bonds. He only invests in his own business. “My rate of return on my business is substantial. I could buy back a regional franchise when they come on the market and get a 20-25 per cent annual rate of return, plus capital gains. There’s nothing like that available in the investment space.”
Nicola Beswick: Founder, White Rabbit Advisory
Rabbit Advisory founder.
A clothing allowance provided by her parents and then a part-time job during high school was the first taste of financial freedom for Nicola Beswick.
She quickly became a spender rather than saver, but she’s changed her tune over the years.
The founder of financial advice firm White Rabbit Advisory left behind a successful career in intellectual property law a year ago to become a financial adviser because she realised the potential that financial education could have on someone’s life.
Her journey began after coming across the book Rich Dad Poor Dad some years ago, which opened her eyes to the power that money could have on her life. This marked a time when she became serious about her finances.
“Financial education and investing over time can have a huge impact on a person, and that book got me thinking about money and financial education in the first place,” she says.
Nicola says years ago, her father was diagnosed with multiple sclerosis. When dealing with the devastating news and an uncertain future, her father discovered he was eligible to receive an income protection payout.
“This was the stone that rippled his pond and mine. A new complex world of finance opened up and I discovered my calling – helping people plan for a financially secure future.”
She hasn’t looked back. “Commercial law was very transactional. I don’t regret quitting at all. I’m much happier now helping people get their finances in order. Financial planning helps people change their lives. That was a really big driver for me.”
The Melburnian admits she’s learned plenty of lessons along the way as she embarks on the process of building wealth. She uses superannuation as an investment vehicle, favouring its tax advantages.
“I also built a nest egg outside of super, because you never know when the rules will change,” she says.
She prefers to set a financial goal and save up for something specific over time than rush out and make a purchase.
“It’s a really powerful thing to wait before making a purchase,” she says.
Her current financial goals involve renovating her heritage-listed home. “We will keep the façade and gut it to rebuild. That’s a major expense for us on the horizon.”
While holidays are rare, she will spend on overseas trips on occasion. “I’m terrible at taking time off. I’m always working.”
Sam Riley: CEO, Drova
Sam Riley was in his 20s when he set out to amass enough money to be able to retire by the age of 40 if he wanted to.
“The goal was always to be doing something by 40 that kept me engaged enough that I didn’t actually want to retire because I was happy,” he says.
An entrepreneur at heart, Sam started a juice and espresso bar when he was 21, which didn’t work out. His next venture was a technology business, Ansarada, an ASX-listed company he ultimately sold nearly two years ago for $250 million.
The sale set him up for life, but he’s not one to rest on his laurels, launching into the complex world of artificial ntelligence with his next technology play, a company called Drova.
The technology startup simplifies risk, compliance and resilience for small businesses. Sam believes it’s got potential to become a tech juggernaut in time.
Having early financial success has meant he has the luxury of slow mornings and working in short bursts throughout the day, problem solving, experimenting with what works and figuring out how to harness AI.
“I favour a more sustainable approach to working these days. More frequent breaks. Making sure not to deteriorate my capacity,” he says.
It was a hard slog. He admits he touched the fringes of serious burnout when he was younger, which he works hard to avoid these days.
“Every business venture has exposed a gap in my skills that I’ve worked to close. Whether that’s marketing or managing people, closing those gaps along the way is how you get more effective at generating wealth,” he says.
The secret to his success has been finding ways to bolster value in the corporate world, finding ways to bring more to the table. Sam admits he spends too much money on travel, food and niche vinyl audio equipment, like turntables. He prefers to invest in experiences rather than things.
But it can get expensive. Like a recent trip to Antarctica to stay in a lodge for a week. “The thing is I didn’t like having these experiences on my own, so I have to bring family or other people and then pay for them.”
Sam describes his investment portfolio as balanced. While he continues to invest in entrepreneurial ventures, he admits he has a safe foundational platform to his investment approach.
“Over the years, I’ve added a lot more dividend stocks and protective assets like gold and silver, and some index funds.
“When I was younger, I didn’t appreciate the value of being safe and boring in the investment world.”
He says a lot of his investments used to be leading edge and visionary. “Some of them work, and some of them don’t. I didn’t really have much balance in my portfolio. I still invest in entrepreneurial things, but am much more conscious of taking a more even-handed approach,” he says.
This article appeared in the Winter 26 issue of Kanebridge Quarterly, which you can buy here.
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