Isn't That Rich Podcast

Let’s be real: adulting is hard, especially when it comes to managing money. We've all had those moments where we look back and think, "What on earth was I doing with my finances?" In this blog post, we’re spilling the beans on some of our biggest financial faceplants, all in the hope that you can dodge these mistakes and maybe even have a good laugh along the way.

1. Jill’s Abercrombie Obsession: A Wardrobe of Regret

Picture this: 13-year-old Jill, armed with a broom and a fierce determination to have the best wardrobe in town, hustling as a housekeeper at her grandparents' resort. Fast forward a few years, and she’s raking in the dough as a cart kid at a fancy Golf and Yacht Club. With tips flowing like a broken ATM, Jill did what any teenager would do—she spent it all. Who needs savings when you can have a closet full of Abercrombie & Fitch, right?

In hindsight, maybe dumping some of that cash into, oh, I don’t know, a retirement account, would’ve been a better idea. But nope, Jill was too busy making sure she had the latest distressed jeans and logo tees. Lesson learned? You can’t wear your retirement fund, but it sure can wear you out if you don’t have one!

2. Jared’s Miss Me Jeans: A Lesson in Poverty Mentality

Jared grew up believing that financial literacy was as mythical as unicorns. Schools didn’t teach it, and society seemed to think that paycheck-to-paycheck living was a rite of passage. Naturally, Jared fell into the trap of spending every dime on things he thought would boost his status—hello, Miss Me jeans with the bedazzled back pockets!

But here’s the kicker: Jared didn’t start saving for retirement until his 30s. That’s right—while others were riding the compound interest wave, Jared was dog-paddling in a sea of missed opportunities. He’s now playing catch-up like he’s in the finals of a financial Olympics, and let’s just say, it’s not a race he’s thrilled to be in.

3. Credit Cards: The Double-Edged Sword

Ah, credit cards—the siren song of easy money. Jill's freshman year of college was marked by the allure of a $100 sign-up bonus at a career fair. And thus began her love affair with plastic. Soon enough, she had not one, but two credit cards.

Jill quickly found herself in $2,400 of debt, which might as well have been $24,000 to a broke college student. The lessons here are simple: Just because you can get approved for a credit card doesn’t mean you should, and if you’re carrying a balance every month, you’re not winning at life—you’re losing at interest rates.

Meanwhile, Ashley learned the hard way that not building credit early can come back to bite you—like when she needed her dad to co-sign for her first car loan because she had zero credit history. Jared, on the other hand, was raised to believe that credit cards were the devil’s work. It wasn’t until his 30s that he realized they could actually be a good thing—when used wisely. Now he’s raking in rewards like a seasoned pro, but he’ll forever mourn the plane tickets and hotel stays he could have earned in his 20s.

4. The Curse of Not Paying Yourself: Jared’s Business Blunder

Jared’s dream of owning a coffee company came with a side of financial naivety. “Don’t take any money from the business for the first five years,” they said. So, Jared did exactly that. He worked tirelessly, poured his savings into the business, and lived off fumes—literally.

Five years later, Jared had built a successful business but was financially drained. The moral of the story? Even if you’re passionate about your business, make sure you’re paying yourself, even if it’s just a small percentage. Otherwise, you might find yourself resenting the very thing you once loved—and that’s a recipe for burnout, not success.

5. Skipping Job Benefits: Jill’s Early Career Oversight

Graduating college in 2009 during the Great Recession was like entering a marathon with your shoelaces tied together. Jill was in commercial real estate, which was about as promising as a snowman in July. She scraped by on commissions, often questioning if she’d need to apply for food stamps. But instead of jumping ship and finding a job with actual benefits, she stuck it out, living on a prayer and some expired ramen noodles.

It wasn’t until later that Jill realized how important things like health insurance and a 401(k) actually were. So, if you’re in a job that doesn’t offer these, consider making a change—because no one wants to be 30 and still calling their mom to ask if they’re covered under her health plan.

6. Ashley’s Skincare Regret: The Esthetician That Never Was

If Ashley had a time machine, she wouldn’t go back to prevent any major historical catastrophe—she’d go back and get her esthetician license. After high school, Ashley did what everyone else did: she went straight to college. But her true passion was always skincare, and she now wishes she’d taken a year off to get licensed and work her way through college as a part-time esthetician.

Imagine the glow she could’ve had—not just on her skin but in her bank account, too. Instead, she’s left wondering what could have been, stuck with a job she loves but without the side hustle of her dreams. So, her advice? Don’t rush into college if you’re not sure—explore your interests, get a trade, and you might just find a way to blend passion with practicality.

7. Invest Early, Invest Often: Compounding Interest Is Your Friend

Ashley might love skincare, but she’s also a big fan of compounding interest. If there’s one thing she could shout from the rooftops, it’s this: Time is money. Literally. Every dollar you invest in your 20s is like planting a money tree, and by the time you’re 50, you could be living in a forest.

Jared, unfortunately, missed out on his compounding years, and Ashley never lets him forget it. But she’s right—investing early and consistently is the key to financial freedom. So, even if it’s just $20 a month, start now, because future you will be eternally grateful.

8. The Dangers of Not Budgeting: Jared’s "Hope and Pray" Strategy

Jared’s financial planning strategy used to be simple: get a paycheck, hope it covers everything, and pray for a miracle if it doesn’t. Spoiler alert: This isn’t a great plan. Over time, Jared learned the hard way that budgeting isn’t just for Type-A personalities—it’s essential for anyone who wants to avoid financial panic attacks.

Whether it’s setting aside money for big expenses like a family vacation or just making sure you can afford Christmas presents without resorting to IOUs, budgeting gives you control over your money. And let’s be honest, it feels a lot better to be in control than to be at the mercy of your bank account balance.

Don’t Be Us—Be Smarter With Your Money!

We’ve made the mistakes, so you don’t have to. From excessive spending to credit card catastrophes, from business blunders to missed investment opportunities, we’ve learned some hard lessons along the way. The good news? You can skip all that heartache and start making smarter financial decisions today.

Remember, financial literacy isn’t something that just happens—it’s something you have to work at. So, take our advice, laugh at our mistakes, and start building a future you can be proud of. And who knows? Maybe one day you’ll look back and thank us for saving you from the financial faceplants that once tripped us up.