Let’s be real: If you had a dollar for every time someone said “start investing early,” you’d already be retired and sipping mezcal somewhere tropical. But instead of feeling bad about what you didn’t do in your 20s (no shade, but we saw those concert ticket receipts), let’s talk about what you can actually do now—because spoiler: it’s not too late.

This is your no-fluff, slightly sarcastic guide to the three investments your younger self should’ve made—and how grown-up you can still cash in today.

1. Index Funds: The Boring Badass of Investing

What You Missed
In your 20s, even a few hundred bucks tossed into a low-cost S&P 500 (Standard & Poor’s) index fund could’ve grown into tens of thousands while you ignored it completely. Seriously—this is the “lazy genius” move of investing.

Had you started investing $200/month at age 22 in an S&P 500 fund with a 10% return, you'd be sitting on over $400,000 by age 52 (source).

What To Do Now
Start. Like, this week. Not perfect? Doesn’t matter. Perfect is a myth invented by productivity bros and overpriced planners.

• Open a brokerage account (Fidelity, Vanguard, Schwab—whatever gives you low fees).
• Look for index funds like VFIAX, FXAIX, or SWPPX (S&P 500 trackers).
• Automate monthly deposits—even $100/month grows over time.
  

Pro tip: This is a set-it-and-don’t-touch-it situation. You don’t need to “watch the market.” Go live your life.

2. Roth IRAs: Tax-Free Money is the Real Flex

What You Missed
Opening a Roth IRA early means all your investment gains grow tax-free. Let me say that again: TAX. FREE.

When your 20-year-old self was out there buying $9 smoothies and avoiding anything with the word “IRA,” you could’ve been locking in decades of tax-free wealth.

What To Do Now
If you have earned income and make under $153,000/year (as of 2025 IRS limits), you can still contribute up to $7,000/year if you’re under 50—or $8,000 if you’re over 50.

• Open a Roth IRA through your brokerage.
• Choose the same index funds mentioned above, or target-date retirement funds.
• Contribute monthly or in chunks. Just max it out if you can.
  

Bonus: Unlike 401(k)s, Roth IRAs let you withdraw your contributions anytime (penalty-free), which makes it feel slightly less like you’re locking your money away in financial jail.

3. High-Income Skills: The Overlooked Investment That Pays Forever

What You Missed
While you were mastering the fine art of ramen hacks, you could’ve been learning skills that pay serious dividends—like coding, UX design, data analysis, digital marketing, or project management.

A $400 course in your 20s could’ve translated into a $100k+ salary by your 30s. (Ouch.)

What To Do Now
The good news? Upskilling isn’t reserved for Gen Z TikTokers and tech bros. You can still invest in your skills now and make a massive financial leap.

• Platforms like Coursera, edX, and Google Career Certificates offer legit courses for $0–$500.
• Focus on high-demand fields: AI, cybersecurity, digital marketing, cloud computing.
• Already working? Ask if your job offers learning stipends or tuition reimbursement. (A lot of companies do.)
  

ROI check: A $300 course that lands you a $10k raise = better return than most stock portfolios.

TL;DR: You’re Not Late. You’re Just Wiser Now.

Listen: You don’t need to feel bad about what you didn’t do. Regret is a waste of brain space. But action? That’s your power move.

Whether you're 32 or 57, the best time to start investing was yesterday. The second-best time? Today—with more money, better habits, and fewer hangovers.

So here’s what you can do right now:

✅ Open a low-fee brokerage
✅ Start with index funds (automate that ish)
✅ Max out your Roth IRA (even slowly)
✅ Upskill into a higher income bracket
✅ Stop doomscrolling and start compounding

🔥 Want to Really Level Up?

Don’t just stop here—your wallet deserves a full glow-up. Head over to TheRoad.com/money for more real-talk guides on:

• Budgeting without boring spreadsheets
• Credit hacks that don’t require selling your soul
• Investing for people who hate jargon
• Retirement strategies that aren’t just “work until you die”
  

Basically: smarter money moves, minus the shame spiral.

👉 Click here and binge your way to financial clarity, confidence, and the kind of freedom your 20-year-old self wished they planned for.