In my 20s, I thought I was doing fine with money. I didn’t carry much debt, kept my checking account out of the red, and felt vaguely proud every time I contributed more than the company minimum to my 401(k). I figured “investing” was something I’d worry about later—maybe when I earned more, or when I stopped renting, or when I stopped Googling what “compound interest” actually meant.
Fast-forward a decade: later came fast.
Now, firmly planted in my 30s, I can look back with more clarity (and fewer excuses). There are five investing moves I wish I’d made earlier—not because I missed the boat entirely, but because the power of starting sooner is real. And also? These moves are still very much available now. No shame, no time machine needed.
So, whether you're navigating your late 20s or rethinking things in your 30s, this isn’t about regret. It’s about re-engagement. Real, practical, momentum-building moves that still matter—and could change the way your money works for you.
1. Automating Investments Early—Not Waiting Until I “Knew More”
If I could go back, I wouldn’t try to time the market or learn to analyze stock charts. I’d just automate small, regular contributions into a diversified investment account and let them ride.
The mistake I made in my 20s wasn’t not investing. It was thinking I had to be an expert before I was allowed to start. That hesitation cost me valuable compounding years.
Automating doesn’t have to mean big bucks. Even $50 or $100 a month, if consistent and thoughtfully placed in a Roth IRA or a low-fee brokerage account, can build meaningful traction.
This isn’t about “set it and forget it” blind optimism—it’s about acknowledging that consistency beats complexity. And it’s about making investing part of your routine, not your resolutions.
Still possible in your 30s? Absolutely. In fact, automation might matter even more now, because your time is more limited, your obligations more layered, and your decision fatigue very, very real.
2. Treating My Roth IRA Like a Priority, Not an Afterthought
In my 20s, I thought 401(k)s were the retirement plan. I contributed enough to get the employer match and called it a day. I didn’t know how powerful a Roth IRA could be, or how much flexibility it actually offered.
For example, I had no idea you can*withdraw your contributions from a Roth IRA at any time, tax- and penalty-free. That would’ve made it less scary to start one back then. I also didn’t realize how crucial it is to get your dollars into a Roth while your income is likely lower (and therefore taxed less).
And unlike employer plans, you control how your Roth IRA is invested. That means more freedom, more access to low-cost index funds, and no being stuck with whatever 10 mutual funds your company picked.
Still possible in your 30s? Yes, and arguably smarter now—especially if you’re in a stable earning phase. You’ve got until the tax deadline each year to fund the previous year’s contribution (up to $7,000 in 2024 if you’re under 50). And yes, you can open one even if you already have a 401(k).
3. Investing in Skills That Compound as Powerfully as Portfolios
Not all investing happens in the market. Some of the best returns I could have had in my 20s were skills-based: learning how to negotiate, write persuasively, build something online, or understand how to sell an idea or product. Skills compound, just like money does—only faster in many cases.
I spent too long trying to be “good enough” at what I already knew instead of deliberately investing in what I didn’t. I now realize that building income-generating skills is one of the most under-discussed forms of investing—and one of the most powerful, especially in an uncertain economy.
This might look like:
- Taking a course in digital marketing or coding
- Building a personal brand or online portfolio
- Learning how to create digital products or run a freelance service
- Developing public speaking, storytelling, or consulting skills
The ROI on these moves isn’t always immediate. But they widen your career path and increase your earning power—giving you more to save, invest, and spend with intention.
Still possible in your 30s? Not just possible—ideal. You likely have more context now to know which skills matter to you, and how they might expand your financial options down the line.
4. Understanding Risk Before Fear Made the Choices for Me
In my 20s, I equated investing with gambling—mostly because I didn’t understand risk tolerance, timelines, or asset allocation. So I either avoided it entirely or kept everything in “safe” (read: low-interest) savings accounts.
But playing it too safe with long-term money is its own kind of risk: the risk of erosion from inflation, of missed growth, and of staying stagnant when your money could be doing more.
What I wish I’d done instead: sat down with a basic risk tolerance calculator, learned the difference between volatility and loss, and understood that my 25-year time horizon could afford a bit more growth-focused investing.
I also wish I’d known that investing isn’t a personality trait—it’s a skill you can learn. And you don’t have to love volatility to respect what long-term investing can do.
Still possible in your 30s? For sure. You may even be better equipped now to understand what kind of investor you are. There’s power in being actively engaged, not just cautious.
5. Diversifying Sooner (Beyond Just Stocks and Retirement Accounts)
Most of my 20s investing energy went into the stock market and employer-sponsored retirement accounts. That’s not bad—but it wasn’t the full picture.
Looking back, I wish I’d explored broader forms of investment earlier. That might’ve included:
- REITs (real estate investment trusts), which offer exposure to real estate without buying property
- Fractional shares of companies I admired, through platforms that didn’t require $1,000+ upfront
- Passive income experiments, like investing in digital assets, peer-to-peer lending, or low-capital business ideas
- Diversified index ETFs, which balance exposure across industries and markets
I also wish I’d set up systems to learn from these investments—tracking progress, reflecting on what worked, and evolving my strategy based on actual experience.
Still possible in your 30s? Completely. In fact, your 30s might be the sweet spot for diversifying, since your goals are likely becoming clearer and your risk tolerance more informed.
According to a 2023 Vanguard study, the median account balance for investors in their 30s is just over $28,000. That might not sound like much, but the earlier and more consistently that balance is diversified, the more powerful it becomes.
Wealth Wisdom
- Time matters, but intention matters more. Starting in your 30s with a strategy can outperform aimless investing from your 20s.
- Small, consistent moves > one-time big wins. Momentum is built quietly—often $100 at a time.
- You’re allowed to be a beginner, even with money. Curiosity builds better portfolios than ego.
- Investing in yourself doesn’t expire. The earlier, the better—but later is still powerful.
- Fear is a terrible investment advisor. Learn enough to quiet the panic and make decisions you trust.
No Timeline? No Problem.
There’s no “right” age to get investing right. There’s only right now—and what you do with it.
Looking back, I can name the investing moves I wish I’d made earlier. But here’s the truth: I can still make them now. And so can you.
You don’t have to have it all figured out to get started. You just need to start in a way that feels manageable, meaningful, and real. Maybe that’s opening a Roth IRA. Maybe it’s automating $100 a month into a total market ETF. Maybe it’s finally reading that investing book that’s been in your cart for six months.
Wherever you begin, begin. Let your 40s and 50s thank you—not for being perfect, but for being in motion.
