Regret That Big Purchase? Here’s How to Splurge Smarter
Gene Caballero thought he’d made a smart upgrade when he bought a Tesla. But it didn’t take long to realize he’d overlooked a major issue — finding an apartment in Nashville, Tennessee, with enough EV chargers.
“It’s become a headache constantly worrying about access,” says Caballero, co-founder of the lawn care platform GreenPal. “I wish I would have stuck with something more traditional.”
Ashley Carroll, CEO of Operations House, a business consulting firm in Philadelphia, learned a similar lesson after spending $12,000 to join a high-end country club. She and her husband hoped to network and make new friends — but only visited twice.
“It was mostly empty both times,” Carroll says. They ended up canceling their membership, forfeiting the deposit, and joining smaller local groups that felt more meaningful. “That $12,000 could have funded a year of business retreats or padded our emergency fund. Instead, it evaporated with zero return.”
When you’re earning well, it’s natural to indulge — but not every splurge pays off. Here’s how to avoid post-purchase regret and make smarter luxury spending decisions.
Why We Regret Big Purchases
Most regrettable splurges have something in common: they’re unplanned, emotionally driven, hard to undo, or simply don’t align with your lifestyle or goals.
Alexandra Rooney, a certified financial planner in Greenwich, Connecticut, sees this often. One of her wealthy clients nearly bought a million-dollar rental property — five hours away from home.
“She has significant assets, but she’s not a DIY type,” Rooney says. “It just didn’t suit the lifestyle she’s living right now.”
Not every purchase will be perfect. But if you’re going to treat yourself, there are ways to do it wisely — and still feel good about it the next day.
Budget with Splurges in Mind
“High income” doesn’t mean you can skip budgeting. You still need a plan — especially when indulging.
“It’s important to cover your needs before your wants,” says Glenn Downing, a certified financial planner in Miami. Once your essentials — like housing, food, and savings — are covered, then you can plan for extra spending.
Downing recommends setting a rule for windfalls. For example: one-third goes to savings, one-third to retirement, and one-third for enjoyment.
Rooney advises her clients to only use money they already have — not future income — for big-ticket items. “We don’t want to spend money we haven’t received yet,” she says. Without a clear plan, it’s easy to mentally “spend” your future earnings multiple times.
Some clients even create a separate savings account for big purchases. “It’s about having a long-term annual plan and saving up for those splurges,” Rooney says.
Reflect Before You Spend
Before buying something expensive, ask yourself: does this really fit into your life?
Downing says clients often want to buy vacation homes — and he walks them through all the logistics. “Who’s maintaining it? What happens in an emergency? If you want to rent it out, does the area even allow that?”
Rooney urges clients to think about how they’ll actually use a luxury item. “If you buy a mink coat but never wear it, what was the point?” she says.
One of her clients booked hundreds of thousands of dollars in cruises without ever taking one. She eventually realized cruising wasn’t for her and lost around $10,000 in deposits.
“The marketing we’re fed today is extremely persuasive,” Rooney says. “It’s crucial to help people understand their emotions and their habits before they invest too heavily in something that doesn’t truly suit them.”
Give Your Money Purpose
Jack Heintzelman, a financial planner in Boston, encourages clients to align their splurges with their values. “Ask yourself, ‘What’s important to me?’ and put your dollars toward that.”
This approach helps avoid the “luxury spiral,” where one splurge leads to another and spending quickly gets out of hand.
“The key isn’t doing everything that looks nice,” Heintzelman says. “It’s about identifying what’s meaningful and going deep on that.”
Rooney recalls one client who frequently flew for work and was offered first-class flights — but opted instead to fly private. “It added enormous, unnecessary costs to his financial plan,” she says. “It was a perfect example of spending for ego, not value.”
Just because you can afford something doesn’t mean you should buy it. “You can do anything you want,” Rooney says. “But you can’t do everything, and you definitely can’t do it all at once. Think about where your dollars will make the most impact — and where they’ll bring the most joy.”
The Bottom Line
High earners have more room to indulge, but that doesn’t mean they’re immune to regret. Whether it’s a flashy EV with limited charging access or a lavish club membership that sits unused, even six-figure spenders can feel buyer’s remorse.
According to a recent Creditvana survey, being intentional with your money — even when splurging — is what separates satisfying indulgences from costly regrets.
Before you make your next big purchase, take a moment to plan, reflect, and ask yourself what really matters.
