Men Buy Random Stocks. Women Wait.
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Ready for some gender-based observations?!
Now, don't @ me quite yet. I don’t like reductive generalizations and stereotypes either. And obviously what I’m about to say isn’t universally true.
But after years of analyzing different people’s investment portfolios, I have noticed a pattern between men and women that I think is worth shedding some light on.
I don't think these differences are innate, by the way. If anything, I think they're evidence of what we've been taught about who gets to take risks, make mistakes, and trust themselves with money.
Men seem to be more likely to invest in random stocks when they’re younger because they want to try it out. They put a bit of money in the market, try to pick some stocks based on varying levels of research and forethought, and then they come to me years later for one of two reasons:
A. Their “strategy” worked out okay and they’ve made a bunch of money. But now they don’t know what to do with it, whether what they own still makes sense for them, or how to manage it now that there’s actually some money there. What started out as fun is suddenly feeling unwieldy and scary.
Or:
B. It didn’t work. They can’t seem to build wealth despite watching the S&P 500 hit new highs over the last 10–15 years, and they’re finally ready to admit they need some help.
Women, on the other hand, often come to me never having started.
Correction: they come to me with shame and self-blame because they know they should be investing, but they have no idea where to start. It intimidates the fuck out of them, and they’re paralyzed by the perfectionist fear of doing it wrong and losing all their money.
But they’re also worried about falling behind—and the tipping point of that fear is usually what finally drives them to reach out.
Neither approach is “correct.”
But on paper, the men can end up “ahead” because at least they tried something and got started—rather than waiting and waiting and waiting for confidence to magically appear. Or waiting for the time, energy and motivation to learn how to invest and build their own portfolio.
So how did we get here?
It’s worth remembering that the financial system was not built with women in mind.
Until the Equal Credit Opportunity Act was passed in 1974, women had no federal protection against discrimination in lending based on their sex or marital status. AKA, lenders could legally discriminate against women applying for things like credit cards and mortgages.
And it wasn’t until 1988 that the Women’s Business Ownership Act eliminated state laws that could require a male relative to co-sign a woman’s business loan.
1974. 1988.
That is far from ancient history. In fact, I was already alive for the latter law’s passing.
I’m not suggesting those laws single-handedly explain the differences I see in my practice today. But I do think context matters.
We’re only a couple of generations removed from a financial system that explicitly privileged men as financial decision-makers and often required women to rely on them for access.
So is it really that surprising that men and women might still arrive at investing with different levels of assumed authority?
Because here's the thing about the men with the random stocks:
They weren't necessarily more knowledgeable.
They weren't necessarily better investors.
They were just more willing to act while knowing they didn't know what the fuck they were doing.
Now, this isn’t necessarily the path I’d advise.
While I applaud the willingness to get started before feeling completely competent, that approach can absolutely backfire. It can result in concentrated positions that are costly to unwind, meme stocks, performance chasing, taking on more risk than you realize, and sometimes just plain old bad choices.
I'm not suggesting women should start throwing money at random stocks. Please don't take that away from this. 😂
But I do think there's something worth borrowing here:
The willingness to start before you feel completely ready.
Because perfectionism gets particularly expensive when we're talking about investing. The longer you wait to get started, the less time your money has to work for you.
Where do we go from here?
I think women have been sold this idea that we need to feel fully confident before we start investing.
And while the availability of financial knowledge these days is truly amazing, it can also create this quiet pressure to learn everything—and teach ourselves, at that—before we're allowed to begin.
But think about the last time you did something that scared you.
Did you wait until you felt 100% confident and fully ready?
Probably not.
Because most of the time, confidence comes from actually doing the thing.
And regardless of your gender, if you wait for the mirage of becoming a “fully confident investor” before putting your money to work, how long are you willing to wait?
Five years?
Ten?
Twenty??
Women often think we need to muscle our way through everything ourselves.
But we don't.
When it comes to investing, you have other resources available to you.
And time is one of the most valuable.
Starting earlier gives your investments more time to potentially benefit from market growth and compounding—which can reduce how much of the heavy lifting has to come from your own future contributions.
You can also ask for help.
You are allowed to begin before you understand everything.
Starting matters more than getting it perfect on the first shot.
You don't need to build your own portfolio.
You don't need to become someone who reads earnings reports.
You don't need to understand every acronym.
You don't even necessarily need to like investing—or money!
You just need a reasonable way to begin—whether that's learning enough to DIY something simple or asking someone else to help you.
I would much rather help you course-correct something imperfect than meet you ten years from now still sitting on the sidelines because you were waiting to feel ready.
Because there probably won't be a magical day when you wake up and suddenly feel like A Person Who Understands Investing.
You learn by starting. You build confidence by participating. You get better by asking questions, making decisions, and adjusting as you go.
So if you've been waiting until you know enough, have enough money, or finally feel confident enough:
Maybe you don't need to feel ready yet. Maybe you just need to start exactly where you are.
