8 Money Moves I REGRET Not Making In My 20s

Your twenties matter more than you think. Clinical psychologist Meg Jay said it best: '30 is not the new 20.' According to her, 80% of life’s most defining moments happen before age 35. Now that I’m almost there, I’ve had some time to reflect. And if I could go back and do it all over again, there’s a lot I would change—starting with the people I chose to spend time with.

Show Me Your Friends, I’ll Show You Your Future

I wasn’t intentional enough with my friendships. Jim Rohn said, “You’re the average of the five people you spend the most time with.” Turns out, he was absolutely right.

There’s real science behind this. In a 32-year study, researchers Nicholas Christakis and James Fowler found that if a close friend becomes obese, your chances of gaining weight increase by 45% over the next few years. If your friend smokes, you’re 61% more likely to pick up the habit yourself.

Why? Because your standards shift based on the people around you. If your friends normalize unhealthy habits or reckless financial behavior, chances are, you will too. But the opposite is also true. If your inner circle is made up of financially savvy, driven, health-conscious people, that becomes your new normal—and you’ll rise to meet it.

That’s why, in my late twenties, I created a Meetup group called Wealthy Women to surround myself with the kind of people I wanted to become. We met for brunch and talked about money, business, real estate, and our goals. Fast forward five years—those women are now some of my closest friends, and we’re all debt-free and thriving.

I wish I had met them ten years earlier.

Don’t Just Work for Money—Make Your Money Work for You

In my early twenties, I got a high-paying job on Wall Street. Sounds like a dream, right? But after a few years, I was burned out. I wanted to quit—but I couldn’t. That job was my only source of income. It was then I realized: not all income is equal.

I spent all of my twenties focused on job income—the worst kind. After taxes, even a $100K salary doesn’t go as far as you think. If I had started building business and investment income earlier, I could’ve had freedom a lot sooner.

Business and investment income give you leverage. They're taxed less, and they don’t require you to be present 40 hours a week. That’s a game-changer. If you’re in your twenties, use this time to learn about these other income streams. Don’t wait until you’re trapped in the paycheck hamster wheel.

Spend on Growth, Not Image

I didn’t go to therapy until I was 30. And when I finally did, I uncovered so much baggage I had been carrying—baggage that was showing up in my financial life.

Back then, I spent a ton of money on my appearance. Not because I loved myself, but because I wanted to look like I did. I was chasing validation with expensive clothes, makeup, bags—none of which actually made me feel better. Therapy helped me connect the dots.

Personal development doesn’t just fix your inner world—it transforms your outer world too. Therapy, books, courses—whatever works for you. One course that changed everything for me was The Landmark Forum. I took it at 27, and it shattered the limits I had set for myself.

Invest in yourself. The ROI is exponential.

Set Boundaries—Especially Around Money

One of the most expensive mistakes I made in my twenties was not setting boundaries. Ever split the bill at a restaurant even though you barely ate or didn’t drink? I’ve paid for other people’s alcohol more times than I can count—and I don’t even drink.

It’s not just about dinner. It’s about being afraid to talk about money, to say no, to draw the line. I once lent money to someone I thought was a friend. Never got it back. From now on? If I lend money, it’s in writing, with a repayment plan and interest.

Your money is for you. Not for guilt, not for appearances, not for saving people who won’t save themselves.

Start Investing—Yesterday

We’re taught to work for money, but no one teaches us that money can work for us. If you invest early—even small amounts—you’ll be shocked at what happens.

Let’s say at 20, you invest just $100, and add $100 every month into something like the S&P 500. In 30 years, you’d have over $100,000. But if you start at 30? You’d only have half that.

The earlier you start, the less work your future self has to do. Compounding is magic—but only if you give it time. Start now. Even $100 a month.

Don’t Overpay for Your Degree

I spent over $200,000 on my college education—half in debt—and I spent the rest of my twenties paying it off. Looking back, I never asked the most important question: Is this worth it?

One of my best friends skipped college, did a $15,000 coding bootcamp, and landed a six-figure job at 21. Another friend did two years at community college, then transferred to NYU. We both got the same degree—but they saved six figures.

Before you go into debt for a degree, ask:

Smart choices at 18 can free you up at 28.

Budgeting Isn’t Basic—It’s Freedom

I used to think budgeting was for people who didn’t make enough money. So I ignored it. And every month, I was shocked by my credit card bill.

When I finally started budgeting, everything changed. No more mystery stress. No more surprise overdrafts. No more guilt when I splurged—because it was planned.

I use an app called YNAB—You Need A Budget—and it helped me finally take control. I stopped reacting to money and started directing it.

The Truth About Your Twenties

My twenties were a mess. And also, some of the best years of my life. I made every mistake in the book—but that’s how I learned. And that’s how I became the person I am today.

If you're in your twenties, take this as a nudge, not a lecture. You don’t need to be perfect. Just aware. Small, smart choices now can save you a decade of regret later.

You're not behind. But you are in the pilot seat. And where you go from here? That's up to you.