Imagine with me, for a moment, that the year is 1953. The Great Depression and most of the horrors of World War II are behind us, and you’re ready to build wealth. Your home cost $7,000, and you’re diligently paying off your $50/month mortgage and, I don’t know, attending sock hops regularly?

The 401(k) won’t be invented for 25 more years (44 more for the Roth IRA). You might have a pension (25% of workers did), but if you want to get money in the stock market, you have to jump through a carnival of hoops. And you likely don’t want to get money in the stock market—because it’ll still be another year before the Dow Jones surpasses its pre-Depression 1929 peak. The era of poodle skirts and saddle shoes has not been kind to compounding.

But let’s say you are able to get some skin in the stock market game. You’re almost certainly going to pay high, fixed commissions to a broker in a rather time-consuming process—and that’s assuming you know what you want to buy! The “mutual fund boom” hasn’t yet happened, so you’ll probably spend a lot of time poring over the finance section of physical newspapers (gasp) or getting your stockbroker on the line, via the clunky plastic phone adhered to your kitchen cabinet.

Americans love to romanticize the 1950s, but it was an unmistakably unromantic era for the individual investor—so let’s hop in our time machines and head somewhere a little friendlier, shall we?

The year is 2023.

You have a supercomputer in your pocket that has 100,000x more computing power than the Apollo 11, and access to more information than former presidents. This magical device can do just about anything: find you a date in minutes, take you turn-by-turn to the nearest Taco Bell and warn you of the cop stationed in the speed trap between you and your Crunchwrap Supreme, and yes, even create wealth with a few clicks.

You might not have a pension, own a home, or regularly attend drive-in movie theaters, but you have access to something no previous generation did (at least, not this early in their lives, which—as we know about compounding—is a unique advantage): the ability to invest in a professionally diversified portfolio, for free, with just a few bucks and five minutes.

I spend a lot of time reflecting on all the things that are wrong with our world today, and there’s no shortage of things for me to write about—our country’s collective f***-ups keep my production schedule jam-packed. But sometimes, it’s refreshing to focus on the things we do have going for us, and as far as I can tell, this is our edge. 

It’d be a shame to squander that, don’t you think? (Please read that last sentence in that weird, semi-Transatlantic accent everyone seemed to have in the mid-20th century.)

Defining your own investment strategy—and making moves

Investing’s barrier to entry went from a free solo up the sheer granite cliff face of El Capitan to an airport moving walkway toward a flashing neon line on the ground that says “STEP HERE.” And sure, we’ve had our missteps: Robinhood’s casino-adjacent user experience turned investing into a playground for teenage boys, bequeathing us with limitlessly memeable content like this margin-called king. Hang it in the Louvre.

But for the most part, the fintech space has (so far!) been a boon for regular-schmegular investors like you and me. So in the spirit of celebrating that progress, I want to highlight the way I think about our options (and no, not the same kind of options that got our aforementioned day-trading connoisseur in hot water with the Feds). 

Level 1: The BuzzFeed Quiz

Which Taylor Swift album best matches your personality? Which Mean Girls character are you? (Speak Now and Regina, for what it’s worth.)

If you want an experience that feels like the investing equivalent of a ~fun~ BuzzFeed quiz, you can use a robo-advisor. Think Betterment, Wealthfront, Ellevest, Fidelity Go, Vanguard Digital Advisor…you basically can’t throw a rock at “investing” Google search results without hitting a robo-advisor, but with good reason: They’re an excellent way for the Average Jane (and even, I’d say, the Above-Average Jane!) to invest in the stock market safely and wisely.*

*My lawyer wants me to remind you this is just my opinion and is not investing advice, and while some of the platforms we’ve mentioned here have been previous sponsors, this post is not sponsored.

Level 1 is where investing in 2023 really shines. Your grandmother, who might have slogged through the limited wealth-building options of the 1950s (like mine, who bought Toro stock on a whim in the 1980s in what would become the trade of her life—we joke that she now has “Big Lawnmower” money as a result), couldn’t even begin to fathom the ease with which we can get diversified exposure to public markets today. 

These robo-advisors will determine your up-front allocation on your behalf, and then ensure any additional cash that’s added is invested accordingly. 

Level 2: Writing an essay with Grammarly

You know how when you use sites like Grammarly or Hemingway, artificial intelligence will steer you in the right direction? You’re the one generating the sentences, but color-coded warnings appear every time you swap “your” with “you’re” or when you meander too far with a run-on sentence (my favorite). It’s like training wheels for your ideas: You know enough to get something down on paper, but you weren’t an English major, and sometimes a little assistance goes a long way in making you sound smarter more intelligent. 

M1 Finance is the Grammarly/Hemingway of investing. If you know enough to have a sense of what you’re looking for (a 60 stocks/40 bonds portfolio for this goal, a 90/10 for another, moderate exposure to the S&P 500 with some Small Cap Value), M1 is a great place for a unique mix of guidance and customizability. It also automatically distributes new cash you invest based on which positions are over- or underweight based on the target you’ve set, so there’s essentially no ongoing maintenance on your part once you’ve selected your asset allocation. 

Level 3: Hard-coding your own MySpace profile

Remember when MySpace first came out and we discovered the wonders of <b>bold typeface</b>? I felt like a tiny Mark Zuckerberg in my friend Nathan’s computer room (yes, back when every house had a “computer room”) rifling through T-Pain EPs for my profile song and dropping angsty status updates (busy, don’t txt). 

It’s fun if you’re into it, but if you just want the most beautiful profile, it’s probably not in your best interest to mess around with the HTML on the backend. Investing with a traditional brokerage firm (Fidelity, Vanguard, Charles Schwab, etc.) is a little like that: It’s fun…if you’re into it. 

I’ve long said that using these platforms feels like I’m one erroneous click away from bankrupting my family, so I rarely venture to Level 3 unless I absolutely need to (Vanguard, for example, is the only platform I use regularly that offers a Solo 401(k), so I use it). But it’d be a stretch to say I enjoy it, and the added friction makes frequent investing, rebalancing, or tax loss harvesting a little more challenging than necessary for my taste.

But no matter, right? I just mosey back down the ladder to Level 2, where the soft safety net of investing’s “Grammarly” equivalent gently nudges me in the right direction. And to these platforms’ credit, the user experience for certain actions has improved markedly—plus, their 21st century mobile apps (a truly miraculous development) are generally pretty user-friendly.

No matter which level you pick, commit to it

The message I try to reiterate to friends (as well as strangers who have the misfortune of being in my general proximity for longer than a couple of moments) is that ignorance is no longer a valid barrier to investing. 

You don’t need to have memorized Taylor Swift’s entire discography (guilty) in order to take a BuzzFeed quiz that can tell you you’re a folklore girly—you just need to have the patience to click through the questions.

And once you start, staying consistent is the difference between having a couple grand in a few years that you’ll probably liquidate for your upcoming trip to Positano, and sitting on tens upon tens of thousands of dollars that’ll make the difference between buying the home you actually want and the one across town with the weird floor plan. Too many investors open an account with the best of intentions, fund it with a little bit of money, and then sit back and poke it with a stick occasionally. 

When I helped my close friend with a great income but poor money management skills set up her Betterment account in 2019, she was understandably skeptical—but allowed me to set up an auto-transfer anyway. Just a few short years later, I received a text: “Holy shit,” her text bubble announced with a bloop, “I have $30,000 in my Betterment account.” 

Commit to (and automate) a monthly contribution from your checking account of at least $X come rain or shine, leave the account alone for a couple of years, and then check back in. You’ll be shocked at the number staring back at you. 

(Just remember to elect what you want your automated contribution to actually invest in if you’re playing the game on Level 3—otherwise, it’ll sit there anticlimactically in cash or get swept into a money market fund—not the worst thing in the world, but definitely suboptimal.)

Grandma Jean may have made her fortune off of a once-in-a-lifetime rarity of a stock pick against all odds in the late 20th century (I come from a long line of strong-willed women, as you can tell), but you don’t have to. Building real wealth today via one of these levels is more accessible than ever before—especially if you’re an American woman (who, until 50 years ago, couldn’t even open a bank account without your husband’s permission).