by Hope
I turn 50 tomorrow. Yikes! I can’t believe I’m admitting that out loud. Ever! But I am and I do.
These last several months have been filled with self-reflection, difficult conversations, and more than a tear filled moments full of regrets. So many.
I thought making a list I wish my 20-something self had learned and embraced was an appropriate way to close out my last day in my 40s.
If I could sit down with my 20-something self over coffee, I’d pour out years of mistakes, lessons, and hard-earned wisdom in the hope that I could spare her from some of the financial stress I’ve carried over the years.
Here’s the advice I wish I’d followed when I was younger—simple, practical tips that would have saved me heartache, sleepless nights, and so many dollars.
1. Start Saving, Even If It’s $5
I know, saving feels impossible when you’re barely covering rent or student loans, but even $5 a week adds up. It’s not about the amount—it’s about building the habit. By the time you hit 30, you’ll thank yourself for having a cushion for emergencies. Life happens: flat tires, broken phones, sick pets. Having savings can turn a crisis into just an inconvenience.
2. Credit Cards Are NOT “Free Money”
No one handed me a financial guide when I got my first credit card. I treated it like magic—swipe, get stuff. Except “stuff” turned into debt, and magic turned into misery. Use credit cards only for things you can already afford and pay them off every month. Avoiding credit card debt in your 20s will make life so much easier in your 30s and beyond.
3. An Emergency Fund Will Save You (Literally)
If you’re 20-something, life feels pretty invincible. But spoiler alert: emergencies happen. If I’d saved 3-6 months of living expenses in my 20s, I could’ve avoided debt spirals during job losses, medical bills, or surprise car repairs. Start small, but start now.
4. Limit Spending on Kids’ Activities
As a mom, I spent way too much money trying to give my kids “every opportunity.” Gymnastics, soccer, dance—you name it, we tried it. But here’s the truth I wish I’d realized sooner: exposing kids to nature, art, and other free or low-cost experiences is far more valuable than all the paid activities in the world.
Kids don’t need packed schedules to thrive. Exploring a trail, playing at the park, baking together, or getting creative with sidewalk chalk can give them skills, memories, and joy that money can’t buy. And let’s clear up this myth: starting a sport or activity later in life will not prevent their success. I promise, no six-year-old soccer star (or gymnast) is guaranteed a pro career.
What kids really need is your time, creativity, and freedom to explore. You’ll save money, they’ll build resilience and imagination, and everyone will be less stressed. Plus, you can breathe a little easier knowing you’re not stretching your budget to “keep up.”
5. Learn to Budget—It’s Not a Dirty Word
Budgeting sounds boring, I know. But when you tell your money where to go, it doesn’t just disappear on you. I wish I’d started tracking every dollar sooner. Apps, spreadsheets, or a notebook—whatever works for you—just do it. A budget doesn’t restrict you; it gives you freedom. Yes, I know mine is a forecast versus a traditional budget. However, you would be proud of my recent work on this front and evaluation. Maybe more on that in the new year.
6. Don’t Ignore Retirement Just Because It Feels Far Away
Retirement feels like something only “old people” think about, right? That’s what I thought at 25. But here’s the deal: saving even small amounts in your 20s lets compound interest work magic over decades. Future you will thank you a million times over for starting early.
7. Be Smart With Windfalls—Don’t Blow It All
Whether it’s a tax refund, a bonus at work, or an unexpected gift, getting a windfall feels amazing. My younger self treated those moments like free passes to spend wildly—new clothes, trips, or splurges I couldn’t otherwise justify. It felt great… until the money was gone, and I had nothing to show for it.
Here’s the smarter way to handle windfalls:
- Pause and make a plan before spending a single dollar. Give yourself 24-48 hours to think it through.
- Split it up with a simple rule, like 50/30/20: 50% toward debt, 30% to savings, and 20% for something fun. This lets you enjoy a bit of the money without derailing your progress.
- Use the opportunity to tackle a big financial goal, like paying off a lingering credit card or building your emergency fund.
Windfalls are rare, and when handled wisely, they can change your financial future. Trust me: the thrill of knowing you’re more secure lasts far longer than the glow of a shopping spree.
8. Build a Rainy Day “Fun Fund”
This one sounds small, but it’s huge for your mental health. Life isn’t just bills and budgets. Set aside a little “fun money” each month to do something for yourself: dinner with friends, a short trip, or a new hobby. If you don’t plan for joy, you’ll end up splurging impulsively and feeling guilty.
This was always crucial to me. I always had a trip planned, even if it was just (and it mostly was) a road trip to visit family in Georgia. Having those experiences to look forward to, saved me on so many levels. I did this one well…and 100% support it.
9. Date on a Budget (and Pay Attention to Financial Values)
Dating can feel expensive, but it doesn’t have to be. Some of the best dates don’t cost a dime—think long walks, picnics in the park, visiting a free art exhibit, or cooking a meal together at home. Focus on getting to know someone, not impressing them with fancy dinners or expensive outings. And don’t expect it from your partner. The best relationships are built on connection, not credit card debt.
And while we’re on the topic—pay attention to their financial values. It’s easy to get swept up in romance, but money habits matter. Look for someone who shares your outlook: someone who values budgeting, saving, and living within their means. If they think swiping a credit card is “no big deal” or constantly prioritize appearances over security, consider it a red flag.
Building a life with someone who aligns with your financial goals will save you heartache (and money) down the road. A good relationship should make you feel secure, not stressed out about what’s in your wallet.
10. Mistakes Happen—But Don’t Ignore Them
I’ve made more mistakes than I can count. I’ve blown budgets, racked up debt, and ignored overdue bills. What I’ve learned is this: the longer you ignore a money problem, the worse it gets. Face it, fix it, and forgive yourself. Financial mistakes don’t define you. How you recover does.
A Final Note to My 20-Something Self (and Maybe to You)
I’ve screwed up a lot over the years, but I’ve also learned how to pick up the pieces and move forward. If you’re in your 20s—or even your 30s or 40s—start where you are. It’s never too late to change your financial story. I’m in the midst of exactly that right now. But I so wish I had started so much sooner.234
One day, you’ll look back and be so glad you did.
Now go save that $5.
Here’s to making my 50s the best decade yet!
~hope
