Investing in Your 40s: A Midlife Crisis Disguised as a Financial Plan

Yes, I’m investing in my 40s. Yes, I started young. Yes, I’m a millionaire. And yes, I still have to psych myself up to open a Fidelity statement like it’s a paternity test.

He doesn’t check his portfolio—his portfolio checks on him.

Why Your 40s Are the Sweet Spot for Investing

I began investing every two weeks when I was 23 years old. I wasn’t “good with money”—I just feared being broke more than I feared commitment. Twenty-four years later, I’m a millionaire, which feels incredible, until you remember milk is $7 and healthcare is a casino.

It takes consistency like a man who’s worn the same pants since the Bush administration and dedication like a cat returning to the same patch of carpet to puke for eight years straight. But when the day is done, you’ll be happy like a dad who found an outlet mall on vacation. That is to say: inexplicably smug.

You’re Not Too Late—You’re Just Not Rich Yet

If you’re in your 40s and haven’t started investing, don’t panic. But maybe…panic a little. Just enough to stop buying “anti-aging” moisturizer and start buying compound interest. You’re not behind, you’re just early to your future regret—so make it count.

The beauty of investing now is you still have time. Not a lot of time, but time. Time to recover from mistakes. Time to pretend to understand ETFs. Time to open a Roth IRA while Googling “what is Roth short for?”

What I Actually Did (and You Probably Should Too)

Here’s what worked:

• I used Vanguard index funds. Not sexy. Not flashy. But neither am I.

• I contributed automatically every two weeks, rain or shine, job or no job, break-up or emotional spiral.

• When I left a job, I rolled everything into an IRA and set it and forgot it—like a crockpot of generational wealth.

• My dad was an actuary. His entire financial advice to me? “Use Vanguard. Low expense ratios.” The man calculated death probabilities for a living. I trust him.

• I avoided actively managed funds like I avoid people who say “crypto is dead.”

Do I look at my portfolio? Yes. Do I understand it? Not entirely. But I know what expense ratios are, and I know the difference between .04% and “someone’s yacht.”

Don’t Be Afraid of a Little Bitcoin on the Side

Look, I’m not telling you to sell your house and go all in on Bitcoin. I’m just saying: wet your beak. A little nibble. A little digital spice.

Bitcoin is the future of money… probably. Or maybe it’s a very expensive punchline. Either way, I keep just enough to make Thanksgiving dinner uncomfortable when I bring it up.

When Should You Hire a Financial Advisor (or Just Panic Quietly)?

I never used one. Not because I’m some wizard with spreadsheets, but because the idea of paying someone more money to touch my money felt like getting charged a cover to enter my own living room.

Hiring a financial advisor can make sense if you:

• Just got divorced and your ex was the “money one”

• Made a ton of money fast (and now you’re terrified)

• Want to avoid emotional investing decisions (like buying Dogecoin at 2am)

But beware: their fees can eat your returns faster than you eat Girl Scout cookies when no one’s watching. Vanguard’s low expense ratio (about 0.04%) versus a 1% advisor fee over 30 years? That’s hundreds of thousands of dollars you won’t have.

So instead, I used target date funds when I had a job, and index funds when I rolled it into an IRA. That’s it. No spreadsheets. No suits. No condescending brunch meetings. Just boring, glorious wealth.

Midlife Crisis or Strategic Diversification?

Some people buy sports cars. Others buy weird hats and start DJing. I bought index funds and solar stocks and whispered, “Daddy’s feeling frisky.”

Your 40s are when you start to ask life’s big financial questions:

• Should I finally buy life insurance?

• Can I afford a second home, or should I just live inside my own head more often?

• If I die tomorrow, will anyone know my Coinbase password?

Investing at this age is no longer about Lambos—it’s about not dying in a recliner next to a stack of medical bills.

What Nobody Tells You About Risk Tolerance

Risk tolerance is code for: How chill are you when the market drops 30% and you still have to pretend everything’s fine at work?

In my 20s, I was aggressive. In my 30s, I got cautious. In my 40s, I’ve gone full Buddhist—I accept volatility the way I accept my hairline: with detached amusement and sunscreen.

Keep your core in index funds. Sprinkle in a few gambles (crypto, solar, your friend’s terrible startup). But don’t let “optimism” become your whole portfolio. That’s how you end up explaining NFTs to your spouse mid-eviction.

The Emotional Return on Investment

Nobody talks about the emotional ROI. You sleep better. You feel like a functioning adult. You get to say smug things like, “I maxed my Roth this year,” at dinner parties while someone refills your wine out of shame.

There’s power in knowing you did something smart—even if you’re still a hot mess emotionally. Investing doesn’t fix your soul. But it does let you spiral in nicer pajamas.

If You Take Nothing Else from This Article…

• Start now. Just open the account. I don’t care if it’s $50. It’s a start.

• Use index funds. Because you don’t know better. And neither do I.

• Keep going. It’s boring. That’s the point.

• Add a little Bitcoin. Just to feel alive.

• Never take advice from someone wearing loafers with no socks.