When we’re young, it’s easy to brush off the idea of investing.
After all, there’s “plenty of time” to build wealth or focus on financial security.
Except time has a habit of flying by, and suddenly you’re at the halfway mark—or beyond—looking back at the moves you could’ve made earlier.
It’s a common refrain among men over 50 who find themselves wishing they’d prioritized certain investments back in their 30s or 40s.
Below are 7 investments many older men say they regret not jumping on sooner. Whether you’re 25 or 45, it’s never too late (or too early) to plan.
1. Prioritize your retirement fund
Retirement might sound like a distant speck in your 20s or 30s.
Then one day, you blink and you’re five years out, staring down the reality of fixed income and medical expenses.
The guys who waited too long often say they wish they’d maxed out their 401(k) or IRA contributions from the start. Compound interest is a powerful ally, but it needs time to work its magic.
If you have a workplace plan with matching contributions, put in enough to get that match.
It’s free money.
If you’re self-employed or your employer doesn’t offer a retirement plan, look into IRAs or similar vehicles. Automate the process so you never have to remember to transfer money.
The more hands-off you make it, the easier it is to build a solid nest egg.
Start small if you must, then gradually increase your contributions as your income grows.
2. Invest in your health and fitness
Plenty of men hit their 50s and realize their bodies don’t bounce back the way they used to.
They mention regrets like “I wish I’d dropped that extra 20 pounds earlier” or “I should’ve listened to the doctor’s advice on cholesterol.”
Your health isn’t just about living longer; it’s about having the energy and mobility to enjoy life in your later years.
Consider a gym membership you’ll actually use, or invest in home workout equipment if that’s more your style. Maybe hire a trainer to nail down proper form, preventing injuries that can set you back.
Embrace regular medical checkups to catch issues early.
Don’t forget mental health: therapy sessions, meditation apps, or stress management tools can keep your mind as sharp as your body.
Your body is the vessel that carries you through every adventure, career pivot, or grandkid’s baseball game. Think of taking care of it as an investment that pays dividends in everyday quality of life.
3. Build a diversified portfolio (beyond just stocks)
Many men jump into the stock market, which is fine, but they often overlook other assets.
Real estate, bonds, index funds, or even a small chunk of crypto for the adventurous can spread out risk and provide different growth avenues.
I’ve mentioned this before but it’s key to explore more than one type of investment — because markets fluctuate, and you never want all your eggs in a single basket.
Real estate can be particularly appealing if you’re willing to deal with tenants or property maintenance.
Some opt for REITs (Real Estate Investment Trusts) if they want a more hands-off approach.
Remember, diversification is about smoothing out the bumps. If one sector tanks, others might stay stable or even flourish.
Don’t let “analysis paralysis” hold you back. Do your research or chat with a financial advisor you trust. Even a modest, balanced portfolio can build a serious cushion over a couple of decades.
4. Acquire new skills or get additional certifications
Ask a 50-something about career regrets, and you’ll often hear, “I should’ve sharpened my skills or learned new ones.”
The job market evolves, and the best way to stay relevant is continuous learning.
Whether it’s going back to school part-time, earning an online certification, or mastering a new software tool, investing in education can pay off big time.
You don’t necessarily need a master’s degree if that’s not your style.
Sometimes a simple industry certificate or specialized training can open doors.
The sweet spot is figuring out which skills align with where you want to be in five or ten years. Skills that make you more valuable, either in your current role or a potential pivot, are golden.
And it’s not just about money, either.
Learning keeps your brain sharp and helps you stay connected with younger colleagues who might be up-to-speed on newer tech.
Plus, it’s a confidence boost to know you’re evolving instead of staying stuck in your comfort zone.
5. Cultivate relationships and networks
We often think of “networking” as purely professional—handing out business cards or adding connections on LinkedIn.
But it’s much broader than that.
Strong relationships can lead to job opportunities, business partnerships, or even just personal growth.
Many older men wish they’d dedicated more time to building meaningful connections in their 30s and 40s, not just surface-level acquaintances.
Start by reaching out to colleagues, mentors, or people you admire. Offer genuine help or collaboration without expecting anything immediate in return.
Real networks are built on trust and mutual benefit.
Don’t shy away from local business groups, community events, or online forums where you can engage in conversations about your industry or interests.
Family and friends matter too, obviously.
But from an investment standpoint, a robust professional network can pay off in unexpected ways, like landing you a contract gig during a rough patch or introducing you to a life-changing partnership.
6. Invest in experiences, not just items
Think back on your best memories — chances are, they revolve around experiences rather than material objects.
Men who’ve hit their 50s often look back wishing they traveled more, tried new hobbies, or spent money on personal growth activities rather than accumulating gadgets or fancy cars.
Experiences can range from a backpacking trip through Europe to a weekend cooking class.
The point is stepping outside your usual routine and building memories or skills that enrich your life.
You can even blend experiences with your career, like attending conferences in new cities or volunteering abroad in a field related to your expertise.
This doesn’t mean you should never buy nice things.
But if you’re always choosing the latest tech toy over that dream trip, you might be missing out on stories and personal development that outlast any gadget’s shelf life.
7. Shore up an estate plan or legacy strategy
This one isn’t flashy, but it’s critical.
Whether you have a spouse, or kids, or just want your assets managed responsibly after you’re gone, an estate plan ensures your wishes are carried out.
People over 50 often realize they should’ve set up wills, trusts, or power of attorney documents sooner.
It’s not just about distributing assets, either — advanced healthcare directives, guardianship details, and other legal safeguards can be part of the package.
If you don’t have kids or a family to provide for, you might want to designate charitable causes or specific friends you’d like to leave something to.
Without legal structures in place, your estate could get bogged down in bureaucracy, leaving your loved ones in stressful, time-consuming battles.
This might all sound grim, but think of it as removing uncertainty for the people you care about.
You’re not just investing in your future — you’re also making a statement about how you want your life’s work handled when you’re not around to manage it yourself.
Wrapping up
And to round things off (though it’s no small matter) — the biggest regrets people have looking back are usually tied to missed opportunities.
Whether it’s neglecting your retirement fund, ignoring your health, or failing to diversify your investments, each choice can echo decades later.
The good news is, it’s rarely too late to start.
Even small steps — a bit more into your retirement account, a new course or skill, or some time prioritizing important relationships — can make a huge impact.
So if you’re under 50, consider this a head start. If you’re over 50, it’s never too late to adjust.
Until next time, friends.
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