In the last blog post, I gave you some amazing news: The best way to invest is actually the easiest way to invest. It’s all very “set it and forget it,” which couldn’t be better for those of us that prefer to live our sacred lives and not spend our waking hours by the temple-throbbing blue light of the Excel spreadsheet.

There’s a big problem here, though. People fucking suck at the “set it and forget it” method. Like, regularly fuck it up so hard you can barely let ’em near it. But I trust you, dear reader, so DO NOT BE LIKE THEM, DO NOT FUCK THIS UP. To be fair, while some peeps’ investing stylez make me “smh” (as the kids say), I can’t exactly blame ‘em: our caveman brains simply aren’t built for long-term investing.

We’ll dig deep into the mechanics of our (amazing but) limited caveperson thinkin’-machines soon enough, but first, let’s dive right into our ~*Investing Dating Game*~!

Investing Dating Game

In this edition of the ~*Investing Dating Game*~, you have to decide which of the two options you’d rather model your investing style after, using ONLY their dating profiles.

First, for y’all seeking men. Whom do you choose to model your investing style after, Option 1 or Option 2?

Option 1:

index funds, how to invest

Option 2:


Now, for those of y’all seeking women: Whom doth ye choose to model your investing style after, Option 1 or Option 2?

Option 1:

index funds, how to invest

Option 2:

Before taking your ***final answers***, I’d like to brush up on a few items. Let’s talk about:

Why Humans Suck Ass at Investing

Honestly, there’s kind of a lot of reasons, but for the sake of brevity, I’m only going to tackle a few.

First, humans just ain’t constructed for long-term thinking. Do you feel any sort of deep connection to saving for the long term? If the thought of saving for fifty years doesn’t honk your horn, don’t go blamin’ yourself. It ain’t you. Human brains were designed to stay alive each day, to protect their cavebabies and their cavebaby-mamas from mountain lions—not to think about long-term outcomes. Because we aren’t naturally equipped to long-term plan, it requires additional, above-and-beyond brain training.

Second, humans are hardwired and chemically-driven to do something—anything!—in the face of danger. With investing, this creates quite the pickle, because bad times will come—that’s a hard fact. Just like the economy, and my mood, and life in general for that matter, the stock market moves in cycles; a tug-of-war between good times and bad.

Many of you won’t remember 2008, but holy fuck I do, it’s a movie that plays over and over again in my brain, projected against the side of my skull in the way a fresh breakup does. At the time, I was working with old people that had millions of dollars invested in the stock market. Over the course of 8 months, the stock market “crashed” and their investments lost 50% of their value. Think about what that means: If you retired in 2007 with $10 million, you had $5 million by 2009. It’s a horrifying experience that, unfortunately, every stock investor will have to go through at one point or another.

But here’s the thing about big downturns: NO ONE LOSES ANYTHING UNTIL THEY SELL. You have the same number of shares you did before; they’ve just lost some of their value temporarily. (Why? Why does the stock market crash? Because WE cause it to crash. A crash is caused by people like us freaking out and selling our stocks. It is not because any of the companies for which you OWN a small piece of are inherently broken.) As an Investment Counselor, I spent years begging clients not to sell when their stocks were at lows, but many of them couldn’t resist, telling us that they had to “save what they had left.” Hardwired and chemically-driven to do something in the face of danger. 

And guess what happens? The stock market comes back up. It always does. And those people that bailed out at the bottom have no chance to enjoy the bounce-back that happens, EVERY.FUCKING.TIME. They locked in those losses, when they coulda just chilled the fuck out and it all woulda been fine. (The stock market has recovered all losses and grown a ton beyond all previous losses since then.)

To be clear, this same “herd” behavior happens in the reverse, as well. When times are good, everyone’s jumping on the God-damned bandwagon, just like a Golden State Warrior fan. Herd behavior helps keep the world orderly (we don’t have to argue daily about the color of grass, we just agree to it), but humans can get so banded together in either panic or exuberance it becomes irrational and even self-destructive. Said another way, if everyone around you is really jazzed on something, you might (blindly) be jazzed on it too. If everyone is freaking the fuck out, you are probably going to freak the fuck out too.

The very construction of our brains also happens to be the reason the easy method—“set it and forget it”—is so damn hard for us.

Okay, do you got it? Would you like to change your final answers to the ~*Investing Dating Game*~ above? Below are the correct answers!

The Correct Answers

In series one, the correct answer is Option 1. Here’s why:

-He doesn’t think he is better than anyone else. Being overly confident in your investing abilities is a surefire way to dick yourself over. Thinking you know more than the entire investing public and that you can “beat” the stock market is some of the most narcissistic, recipe-for-failure shit EVER.

-He is lazy, and investors who are chilled out and simply stay the predetermined course are far more successful than investors that try to “game” the market and switch shit around. (Stop trying to be cute.)

-He doesn’t buy into the hype when shit’s overblown and also doesn’t mind when everyone else is freakin’ out, and always stays even-keeled through the ups and downs. This mindset is too boring for lots of people—people secretly love the drama—but it is the only path to investing success.

In series two, the correct answer is Option 2. Here’s why:

-She goes with the flow. Wanting to control stock market outcomes will destroy your soul and your pocketbook. (Who the hell has a pocketbook these days? You know what I mean.) The stock market has returned 10% annually over time (we should downgrade expectations and expect 7% returns), but this is an average. Some years are up a lot (+30%) and some years are down a lot (-30%), but these numbers smooth out over time. But you have no control over what it will do—EVER. The only way to be successful is to play the long game, going along for the ride. Hang loose, brah.

-She understands that the world moves in cycles. Just like the moon and her moods, the stock market will always, ALWAYS move in cycles. It is an inevitable fact of this world that we live in. Just like you are not “broken” when you are going through a “phase,” the stock market is not “broken” when it goes through a downturn. Trust me, I’d slap her on the mouth if I had a terrible month and she told me that “within this darkness lies opportunity” or some shit, but that’s actually how good investors think.

-She is chill to the point of apathy. This is actually a good quality in investing, so long as you’re doing the initial work—both the saving and investing. But after that, don’t be checkin’ your account balances every five minutes like an overprotective mom, because what happens to your investments on a monthly or even yearly basis DOES NOT MATTER.

Hope you enjoyed this round of the ~*Investing Dating Game*~! I seriously encourage you to make up your mind about what kind of investor you’re going to be when the next big downturn hits, because it could come at any time. Might be tomorrow, might be in five years, but it will come and you can’t wait to decide when we’re in the midst of it all; you’ll be too busy shitting yourself.

Want to learn EVEN MORE about investing? Sick of trying to cobble together a complete education using blog posts and online resources? Take my live, online, four-part Invested Development course. It’s Investing 101, but fun and actionable, and geared towards young women. Finally, feel confident in your investing plan and knowledge! Read more about it here