Isn't That Rich Podcast

If you’ve ever hit a new year feeling motivated… and then immediately felt this weird heaviness settle in, you’re not alone.

It happens to so many people. You start thinking about goals, routines, the year ahead. Maybe you want to save more, get organized, pay off debt, buy a house, finally feel like you’re “caught up.” But then your brain starts layering on something that doesn’t even feel like it came from you.

It’s the “shoulds.”

The quiet little pressures that show up when you’re trying to build a life. The invisible checklist that feels like it came with adulthood. The voice that says, “If you were really doing well, you would be doing this by now.”

You should own a home.
You should have more saved.
You should already know how this works.
You should go to college.
You should be further in your career.
You should have kids.

And here’s the thing we want you to hear loud and clear: most of these “shoulds” are not actually yours. They’re tied to a version of success that used to be called “the American dream,” and a lot of it was built for a world that looks nothing like the one we live in now.

The problem isn’t that those goals are bad. The problem is when we try to force them into our own timeline, our own budget, and our own season of life. That’s when they create stress. And honestly, that’s when they can lead to financial decisions that don’t match what you truly want.

A lot of the pressure comes from good intentions, too. Most parents and older generations genuinely want better for their kids than they had. They want stability. They want security. They want you to have a life that feels easier than what they grew up with. So they repeat the milestones they were taught were the “right” steps: graduate, get a job, buy a house, settle down, start a family, save for retirement.

But the world has shifted. The cost of living has shifted. Career paths have shifted. Home prices have shifted. And the “one right path” idea is not only outdated, it’s exhausting.

Should #1: “I Should Own a Home”

One of the biggest “shoulds” we hear all the time is homeownership. Owning a home is treated like the ultimate sign that you made it. Like you’ve arrived. Like you’re doing adulthood correctly. People say renting is throwing money away. People talk about building equity. People act like you’re not stable until you have a mortgage.

And yes, homeownership can be an amazing decision. It can also be one of the most stressful decisions if you do it because you feel like you’re supposed to.

Because a home is not just a home. It is a mortgage payment, closing costs, property taxes, insurance, appliances that break, repairs that show up out of nowhere, lawn care, maintenance, and responsibilities that don’t stop when life gets busy. When home prices are high, interest rates feel heavy, and everything costs more, it makes sense that some people look at the monthly payment and think, “This isn’t even realistic.”

Renting gets a bad reputation, but the truth is: renting can be smart. Renting can be peaceful. Renting can be exactly what makes sense when you’re young, moving around, building a career, not sure where you want to settle, or simply not interested in maintaining a house right now. You are not failing because you rent. You are not behind because you didn’t buy in your twenties. You are not less successful because you chose the option that fits your current life.

A much better question than “Should I own a home?” is “Does owning a home make sense for me right now?” That question feels calmer, doesn’t it? Because it puts you back in control.

Should #2: “I Should Have Saved More by Now”

Another “should” that hits people hard is savings. “I should have saved more by now” is one of those thoughts that can spiral fast. And the hardest part is that it usually comes with comparison. Comparison to a number you saw online. Comparison to a friend. Comparison to an assumption about what people “your age” should have. But saved more compared to what? Compared to who?

Everyone is living a different life with different costs, different debt, different responsibilities, and different starting points. And life is expensive. If you’re paying off student loans, trying to get stable, raising kids, dealing with health expenses, or just trying to keep up with rising costs, it makes sense that savings might feel slower than you want. Shame doesn’t build savings. Consistency does.

We love the idea of progress over perfection here. Saving $25 a week consistently is better than saving nothing while you beat yourself up for not being able to save $500. A small, steady habit builds momentum, and momentum changes everything. Also, it helps to ask yourself what you’re even saving for. Is it an emergency fund? A future home? A trip you’ve always wanted to take? A buffer so you can breathe? When your savings has purpose, it stops feeling like this vague scoreboard and starts feeling like a plan.

Should #3: “I Should Know This Already”

And while we’re here, let’s talk about the “should” that makes people feel secretly embarrassed: “I should know this already.”

This one is so common. You should already understand credit. You should already understand property taxes. You should already know how mortgages work. You should already know how to budget. You should already know what questions to ask.

But the truth is, most of us were not taught these things in school. People don’t know what they don’t know, and then they feel behind the second they step into adulthood because suddenly they’re expected to navigate systems that are complicated, full of fine print, and honestly… not intuitive.

That’s why so many people avoid asking questions. They don’t want to sound dumb. They don’t want to admit they don’t know. And that silence is where mistakes happen. The reality is, you learn this stuff by doing it. Adults are still learning. People in their fifties and sixties are still learning. The most confident people are usually not the ones who know everything, they’re the ones who are willing to ask questions without shame.

If you take nothing else from this post, take this: ask the question anyway. You are not the only one wondering. You’re just the one brave enough to say it out loud.

Should #4: “I Should Go to College”

Another “should” that we could talk about all day is college. “You should go to college” has been treated like the golden ticket for years, but more people are starting to step back and ask, “Is it really the only path?”

We want to say this clearly: college can be wonderful. It can open doors. It can create lifelong friendships and connections. It can be the right choice, especially if the career you want requires it.

But it is not the only path to a good life.

What’s hard is that teenagers are asked to pick a major and make a massive financial decision at 18 years old when they barely know what careers even exist. You know maybe eight jobs in high school, and the rest of the world is a mystery. So a lot of people pick something because it sounds good, because their friends are doing it, or because they’re terrified of falling behind. But there are so many alternatives now: trade school, certificates, apprenticeships, associate degrees, on-the-job training, online programs that actually teach marketable skills. Sometimes the best thing a young person can do is take time, work, explore, and figure out what they’re actually interested in before committing to years of school debt.

Taking a gap year is not falling behind. Changing your mind is not failing. Trying something and pivoting is not a weakness. Life moves on just fine.

Should #5: “I Should Earn More or Be Further in My Career”

Then there’s the career “should,” and honestly, this one is brutal. “I should earn more” or “I should be further in my career by now” can live in your head for years. It’s the pressure that shows up when you see a friend with a big title, when you see people online posting promotions, when your parents suggest a job you didn’t ask for, or when you compare your income to someone else’s and it makes you question everything.

But success doesn’t always mean climbing upward as fast as possible. Sometimes success looks like stability. Sometimes it looks like flexibility. Sometimes it looks like not hating your life when you wake up on Monday morning. People switch careers now. People job-hop to increase income. People build side hustles that become their main thing. People decide peace is worth more than a title. And no one else is thinking about you as much as you think they are. They’re worried about themselves, too.

Should #6: “I Should Have Kids”

And finally, let’s talk about one of the biggest “shoulds” women carry: “You should have kids.”

This pressure shows up everywhere, especially around the holidays. If you’re single, people ask if you’re dating. If you’re dating, they ask when you’re getting married. If you’re married, they ask when you’re having kids. And it’s framed like casual conversation, but it’s actually deeply personal. It’s also deeply tied to finances, because people know kids are expensive. Childcare is expensive. Housing is expensive. Everything feels expensive.

Here’s the honest truth: there is no perfect time to have a child. It doesn’t suddenly become easy. And also, not everyone wants kids, and that is okay too. You should not rush one of the biggest life decisions you’ll ever make just because you feel like you’re on someone else’s timeline.

Why “Shoulds” Lead to Poor Financial Decisions

So why do these “shoulds” matter financially?

Because “shoulds” create urgency. They create shame. They create comparison. And those three things are the perfect recipe for financial decisions that don’t match your real life.

That’s when people swipe the credit card to look like they have money. That’s when people buy a car to impress people who are not even paying attention. That’s when people feel forced into the mortgage, the degree, the lifestyle, the timeline… even when it doesn’t fit.

Trying to look rich will wreck your financial life faster than almost anything else. The real solution is not to reject goals. It’s to update the definition of success. The American Dream isn’t dead. It just needs to be rewritten for modern life.

Maybe success for you looks like peace instead of pressure.
Maybe it looks like flexibility instead of the perfect timeline.
Maybe it looks like stability instead of status.
Maybe it looks like building a life that fits you, not one that looks impressive from the outside.

If you’re trying to sort through your own “shoulds,” here are a few questions we love:

• Do I actually want this, or do I want the approval that comes with it?
• Can I afford this without sacrificing my future peace?
• Am I doing this because I feel motivated, or because I feel ashamed?

Because motivation that comes from your values is healthy. Motivation that comes from comparison gets expensive.

If you feel behind sometimes, that doesn’t make you broken. Sometimes that feeling can point you toward what you truly want. But if the only reason you want something is because “everyone else is doing it,” that’s where trouble starts.

You are not failing because your life doesn’t match the checklist. The goal is not to keep up with the shoulds, the goal is to build a life that fits you.

And if there’s anything you feel like you “should” already know financially, ask anyway. Learn one thing at a time. Give yourself permission to be a beginner.

Progress over perfection. Every time.