Isn't That Rich Podcast

If you’ve ever looked at your bank account and thought, “Well… that was probably not the most responsible choice,” this one’s for you.

Because not every good financial decision is about cutting back, saying no, or living off rice and regret. Sometimes the best money you spend is the kind that buys you a memory, buys you time, buys you peace, or makes your day-to-day life feel lighter. The key is that it actually does something for you. It matches your values. It improves your life in a real way.

So we started talking about the things we’re genuinely glad we spent money on. Some of them are big. Some are simple. Some might look “bougie” on paper. But if it’s aligned with what matters to you, it can still be a smart move.

1) Experiences You Actually Remember

There’s a reason people say “collect moments, not things,” even though it sounds like something written on a Hobby Lobby sign. It’s true.

Family trips hit different

One of the first things that came to mind was family vacations, especially the kind where you’re all together, doing something memorable, and you can still laugh about it later.

You can’t always remember what someone got you last Christmas. But you can remember the fishing trip with Papa. You can remember the weird restaurant you stumbled into late at night. You can remember the inside jokes that still get brought up months and years later.

And that’s the point. Experiences have a way of sticking.

Friend trips become lifelong stories

Friend trips are basically memory factories.

There are trips you still talk about like they’re agenda items. You know the ones. You’re not even reminiscing casually. You’re reviewing footage, sharing pictures, quoting each other, and bringing up the same taxi ride incident like it’s a quarterly board meeting.

That is money well spent.

Seeing something new changes you

There’s also something about traveling to a place that has what your hometown does not.

Mountains next to you with snow on them. Ocean views when you’ve never lived near water like that. Architecture that feels like a different world. Nature that makes your jaw drop.

It’s not just “a trip.” It reminds you how big the world is, and it pulls you out of your routine brain. That’s why it feels so worth it.

Restaurants can be an experience too

If you’re a foodie, you already know.

A really great meal in a cool place can become a core memory. Not because the steak was scientifically the best steak ever served on planet Earth, but because it was tied to a moment. The atmosphere, the people you were with, what you did before and after.

Sometimes you’re paying for the meal. Sometimes you’re paying for the memory.

2) Weddings: Worth It, But Only If You Keep Your Sanity

Let’s talk weddings, because this is where spending can get… intense.

On one hand, a wedding can be one of the only times in your life when everyone you love is in one room at the same time. That is rare. That is special. That is worth something.

On the other hand, weddings can turn into a high-stress production where nobody is even enjoying it because they’re managing logistics, timelines, emotions, and a very aggressive seating chart.

One of the most interesting observations we kept coming back to was this: low-budget weddings often feel the most joyful.

The couple is present. They’re happy. They’re soaking it in. The vibe is celebratory instead of stressful.

And if you do want the bigger wedding experience, here’s the spending category that tends to be truly worth it.

A wedding planner can save the whole day

If you’re doing a big wedding and you want to enjoy it, paying for someone to handle the details is not frivolous. It’s protective. It protects the experience you’re spending all that money to have in the first place.

3) Convenience Spending That Gives You Your Life Back

This is the category where people feel the most guilt, and also the category that can genuinely improve your quality of life.

Lawn mowing services

If you hate mowing, you hate mowing. There’s no moral prize for sweating in Southern Illinois heat, fighting with a pull-start mower, and wondering if you’re about to step on a snake.

Paying someone to mow your lawn can be money well spent because it saves time, avoids misery, and removes a weekly dread from your life.

Sometimes “worth it” is that simple.

House cleaning

Hiring a cleaner is not just about having a clean house. It’s about not spending your weekend scrubbing toilets and resenting everyone you live with, including yourself.

It also saves arguments. Which, honestly, is priceless.

Delivery and pickup services

Here’s the honest version: DoorDash and grocery delivery can be worth it, but you need boundaries.

If you’re sick, exhausted, overwhelmed, or you live far from town, paying the fee to have food show up at your door can be a lifesaver.

But if you’re DoorDashing every day for lunch when you live two minutes from the restaurant, that’s probably a sign to revisit your routine, your budget, or both.

A good rule is to use convenience spending as a tool, not a habit.

Buying back time is a real strategy

This came up in a big way. Wealthy people often “buy their time.” If you value your time highly, then spending money to get hours back can be logical.

That doesn’t mean everyone should outsource everything. It just means you should be honest about what costs you the most energy and what frees you up to do what matters.

4) Paying for Peace of Mind

This is the kind of spending that doesn’t feel exciting until the moment you desperately need it.

Professionals like accountants and advisors

Paying an accountant to handle taxes and give advice during the year can be one of those “I sleep better at night” expenses.

It’s not just the work they do. It’s the reduction in stress. It’s the confidence that you’re not missing something major. It’s not having to spiral in April.

Same idea for financial advice, when it’s the right fit. Peace of mind is a value, not a weakness.

Extended service plans for used cars

This one surprised people, because extended warranties get a bad reputation.

But if you buy used vehicles, and you’ve had repairs that cost thousands, that plan can pay for itself fast. If you’ve ever stared at a transmission quote and felt your soul leave your body, you understand why that coverage can feel like a gift.

The point is not that everyone needs it. The point is that some “extra” costs are actually protection against a bigger financial hit.

Safe rooms, storm shelters, and generators

If you live where tornadoes, ice storms, and power outages are real possibilities, spending money on safety and backup power is not dramatic. It is practical.

A storm shelter is the definition of peace of mind. You hope you never need it. But when you do, nothing else matters.

A generator can also save you from losing food, losing heat, or dealing with major damage when outages happen. In some homes, it’s not a luxury. It’s a plan.

Home choices that prevent future pain

Paying more upfront for insulation, building systems, or preventative measures can feel annoying in the moment, but it can pay you back in comfort and lower bills later.

It’s not always exciting spending, but it can be deeply satisfying spending. Especially when you compare your bills to someone else’s and realize you made a smart choice.

5) Security Spending You Forget About Until You’re Grateful

Things like camera doorbells, security systems, and monitoring subscriptions are easy to roll your eyes at, until you’re on vacation, a package gets delivered, or someone knocks on your door late at night.

Being able to see what’s happening, record it, and check in from anywhere is one of those modern conveniences that actually provides value.

It’s also a good example of how “small monthly spending” can be worth it when it prevents bigger problems, or even just gives you peace.

6) Investing in Yourself Counts Too

This is where the conversation got fun, because we started naming things that people love to judge.

Classes, workshops, and learning new things

A candle-making class. A pottery class. A cooking class. A mahjong class that we’re still trying to convince people to take.

It’s not just about the activity. It’s the learning. It’s the joy. It’s the fact that you did something different on purpose.

Sometimes the best money you spend is on skills, curiosity, and experiences that make your life feel more interesting.

Beauty and confidence

Yes, we said it. Beauty spending can be money well spent.

Not because you “need” it, but because confidence changes how you show up in the world. When you feel put together, you act different. You speak different. You carry yourself different.

And for a lot of people, that creates a real return, whether it’s social, personal, or even professional.

You do not have to spend a fortune. But you also do not have to feel guilty for investing in yourself in ways that genuinely improve your confidence.

Health and fitness

Gym memberships are not cheap, especially good ones. But if you actually go and use it, it can be one of the best investments you make.

It’s hard to regret spending money on something that helps you feel stronger, healthier, and more energized in your everyday life.

How to Know If Something Is “Money Well Spent”

Here’s the simplest test we kept coming back to. If it aligns with your values and it noticeably improves your life, it’s probably worth it.

If it creates stress, debt, or regret every time you think about it, it’s probably not. If you want a quick gut check, ask yourself:

Do I still feel good about this purchase a month later?
Did it save me time, stress, or conflict?
Did it create a memory I’ll actually keep?
Would I buy it again, or do I want to hide it from my own budget?

You can be responsible with money and still enjoy your life. You can save for the future and still live in the present. You can spend on things that look “extra” to someone else and still be making a smart decision for you.

Because “good with money” is not only about cutting back. It’s about spending with intention. And if it’s intentional, aligned, and it genuinely adds value to your life, then enjoy it. That’s the whole point.