You know the saying: Hindsight is 20-20.
The misguided cut corners, the impulse splurges gathering dust, the subsequent debt—all of these money missteps can bring on a serious case of financial regret.
And the truth is that we all have such moments in life—moments that can provide some invaluable money lessons learned.
To pool that knowledge, we asked people across the country (and as far as Australia!) to share how they’d do things differently if they could—a so-called “dollar do-over.”
From lessons learned from buying a first home to welcoming home a first pet, here’s hoping their hindsight insight can help you better navigate the financial road ahead.
“I’d Think Twice Before Investing in a Timeshare”
Maura Sweeney, 57, author, Clearwater, Fla.
“As newlyweds, my husband and I were eager to travel. But a weekend in the Poconos cost more than we bargained for, when we were sold on a timeshare condo.
The location didn’t really interest us—we had our sights set on going abroad—but we were persuaded by how timeshares could be swapped among locations, inspiring us to pay into an international timeshare exchange program.
In reality, we never used the condo ourselves. We swapped it only twice, realized most travel dates were blacked out and required upcharges—and were beset with thousands of dollars in maintenance fees.
Then plans for future development at the resort never materialized, and it eventually went into bankruptcy. We were eventually able to opt out of our ownership, and take the loss on our taxes.
The lesson learned? Don’t fall for someone else’s grand sales idea—unless it truly resonates.”
“I’d Pay Up for a Pro Wedding Photographer”
Whitney Schott Taylor, 34, realtor, Newtown, Conn.
“I planned my California wine country wedding on a budget and thought we didn’t need to splurge on photography.
So I hired someone for $1,500 (most people were charging $2,000 to $3,000). He had a cool, edgy style, and I liked his sample work—although it wasn’t from weddings.
Our photos definitely came out cool and edgy, but there are more shots of scenery, including the church’s cemetery, than of guests! And there’s not a single reception family portrait.
Wedding photos are for reliving the experience—and sharing it with future generations. I’m still very disappointed and emotional about mine, not to mention a huge advocate of you get what you pay for.”
“I’d Resist a Status Symbol Splurge”
Dave Parker, 48, radio talk show host and columnist, Virginia Beach, Va.
“A door-to-door Kirby salesperson gave me a convincing spiel for the Cadillac of suction devices. It was $1,500—and I had to have it.
Why? Because my parents had not one‚ but two.
When I called my dad to announce that we had joined the elite Kirby family, he laughed in a way I hadn’t heard in years. It was humiliating.
As he’d found out, and I now appreciate, you can buy a lot of devices that suck the dirt out of your carpet for about one sixth of the price. We still have that Kirby—and plan to get every last cleaning out of it!”
“I’d Give Each Kid an Allowance”
Patty Gibbons, 56, business owner, San Antonio, Texas
“We have six kids, which made for a busy household—and things weren’t always even or fair.
You were expected to do your part of the cleaning, laundry, lunch-making and yard work. In return you had a nice home, fun activities, birthday parties and such.
As the older kids left home, there were fewer people to help. So we began to give the remaining kids some allowance, which bred resentment among the older ones. And the younger kids grew to expect financial support from mom and dad.
Looking back, I’d have started them all with allowances at a young age, so they could pay for things they wanted, like after-school lessons or lunch at school.
A better planned system would have taught the value of earning money.”
“I’d Spend More Cautiously When Expanding My Business”
Jason Mudd, 39, C.E.O. and president of Axia Public Relations, Amelia Island, Fla.
“In 2006 my company had incredible growth. So we confidently reinvested 100% of our profits, and took out a small business administration loan.
Initially, it looked like a wise strategy—by mid-2007, we produced more revenue than in 2006. But by the third quarter, we began to see the impact of the Great Recession. Forty percent of our clients ran out of marketing funds. And many are now no longer in business, so we never collected past due balances.
We entered the recession without any cash reserves or much liquidity—and, at 30, I almost lost my company.
I’ve since learned to operate more like a C.E.O. and strategically manage our growth. Before, we just answered the phones, and could make money without paying attention to financial statements.
All in all we’re a smarter, more efficient and financially conservative organization. We’re actively paying down debt, and building up our cash reserves, so that our company becomes 100% debt-free within the next six to 12 months.”
“I’d Buy Pet Insurance on Day One”
Brandi Stupica, 31, developmental psychology professor, Alma, Mich.
“We paid $1,200 to adopt Charlie, a purebred St. Bernard, and we didn’t take out pet insurance because she had a terrific pedigree and breeder. Plus, she was guaranteed not to have hip dysplasia, a condition that’s common in the breed.
But we had no clue that St. Bernards are susceptible to other problems. Charlie had 11 bladder infections, and ultimately needed corrective plastic surgery. And, at 18 months, she got wobbler syndrome.
Her neurosurgery was so expensive ($10,000) that we had to borrow money from my in-laws, which was embarrassing. A few years later she developed an autoimmune disorder that now requires steroid treatment.
Charlie is 5, and her medical expenses have cost more than $15,000 out of pocket.
Pet insurance is so cheap for a puppy that we can’t quit kicking ourselves for not investing in Charlie’s health. Now that she has so many medical conditions, the cost is too prohibitive or she’s not eligible.”
“I’d Be Better (Financially) Prepared to Pop the Question”
Justin Vesci, 32, commercial building manager, Los Angeles
“I’ve had credit card debt forever. Whenever I’d get close to being under $10,000, something would happen to push that number back up.
Well, something—or someone.
I met a girl, and after dating for over two years, I dropped $3,500 on an engagement ring and flew us to Kauai last Christmas. We hiked from Shipwreck Beach in Poipu to a semi-secluded beach, where I proposed.
The good news? She said yes! The bad news? The engagement pushed our wedding planning—and spending—into full force.
Our wedding is in October, even though I’d hoped to have a longer engagement to get out of debt.
Since the savings I had left went to the ring, I’m now $8,000 in debt. After the wedding I’ll be over $10,000 again.
While my fiancée does know about the debt, I regret not having even more open communication with her.”
“I’d Avoid the Costly Mistakes of a Newbie Home Buyer”
Alfred Meuller, 44, university dean, Media, Pa.
“When my wife and I began house-hunting in our 20s, a broker showed us seven homes, with no luck.
The eighth was on a quiet street five minutes from my work. My wife was concerned about the small kitchen and lack of a master bedroom, but the agent reassured us that buying was all about location.
I didn’t realize the only way to address those shortcomings would be to expand the home outward, which was too expensive for our then-entry-level salaries. We also used the agent’s recommended inspector, who didn’t catch some serious (and pricey) problems with water seepage into the basement.
All of these issues came back to bite us when we remodeled the home and put it up for sale.
I’m actually buying a new home now—and doing things very differently.
I’ve interviewed several brokers. I’m researching everything about homes in the area, such as whether a two-car garage is standard and expected. And I plan to source my own inspector.”
“I’d Resist Getting Carried Away by My Kid’s Birthday”
Jane Dizon, 24, wedding photographer, Adelaide, Australia
“My husband and I planned to celebrate our daughter’s birthday with a small dinner.
But as the big day approached, I felt this impulse to throw a huge bash. C’mon, she’s our baby girl!
And, admittedly, I watched so many wedding reality-TV shows that I was drawn into planning something fancy myself.
We found a reception hall, booked photography and videography services, and ordered a three-tiered Hello Kitty cake, plus custom Hello Kitty invitations and decorations. I even bought a sparkly gown for my little one.
The 120 invitations indicated a pink-themed dress code, but only 60 guests came and only seven in pink. The venue ran behind schedule, and my daughter was in tears.
If I could redo it, I would’ve stuck to our initial idea: a few of us bonding over homemade food. It would have cost a fraction of that disastrous party.”
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