What If I Invest In All The Wrong Things? Cover

What If I Invest In All The Wrong Things?

I’ve always been a planner. The Joker would call me a schemer:

“You know, I just do things. The mob has plans; the cops have plans. Gordon’s got plans. They’re schemers. Schemers trying to control their little worlds.”

“I’m not a schemer. I try to show the schemers how pathetic their attempts to control things really are.”

While giving that speech in The Dark Knight, the Joker is wearing a nurse outfit. He’s in a hospital, visiting someone he put there in the first place. It might be ironic, but it’s also easiest to doubt my plans on days when I’m sick.

What if they’re really just…pathetic?

Trains Leave Stations All The Time

When I first got into crypto in the summer of 2017, choosing what to invest in was easy. The space was growing, but the good, serious projects were far and few between. One year and thousands of new companies later, selecting among even the top 1% feels like an impossible task. There are 17 good solutions to every major problem and all sources of information have their own, hidden agenda.

Once again, infinite choice has caught up to us. The community even has a word for it: FOMO. The fear of missing out on the next, hot investment keeps individual players forever anxious, circling around a single question:

What if I invest in all the wrong things?

Stuck in bed with a cold recently, thinking about my portfolio and my many other plans, I realized this question is about more than allocating your money.

It’s the defining struggle of a generation.

The Essence of All Philosophy

One of the easiest ways to distract two millennials is to tell them to arrange a meeting. It sometimes takes me as many as five or six attempts to schedule a simple lunch. Don’t even get me started on Friday night. Now I’m not perfect, but more often than not it’s the other party who can’t make up their mind.

That’s why, usually, I feel pretty good about my ‘schemes’. Whenever I’m done setting them up, I’m rewarded with fewer decisions in the moment. Planning allows you to forget the big picture, forget yourself, even, and to focus on the task in front of you. But on days like the past few, days when I’m sick or not working as much, the Joker’s ideas start to visit on me.


What if this project is a complete waste of time? What should I do next? Who should I hang out with, when do I really need to focus on dating, and what if I invest my money into things that go to zero? Is it stupid to keep it all in cash?

What if, what if, what if.

Two little words that ruin a lot more than just Friday night. The bigger the decision to make, the worse it gets. It’s a phenomenon that’s especially pervasive in my generation, but it’s far from new. As the wealthy and famous 19th century philosopher Søren Kierkegaard would remark:

“Marry, and you will regret it; don’t marry, you will also regret it; marry or don’t marry, you will regret it either way. Laugh at the world’s foolishness, you will regret it; weep over it, you will regret that too; laugh at the world’s foolishness or weep over it, you will regret both. […] Hang yourself, you will regret it; do not hang yourself, and you will regret that too; hang yourself or don’t hang yourself, you’ll regret it either way; whether you hang yourself or do not hang yourself, you will regret both. This, gentlemen, is the essence of all philosophy.”

You could call Kierkegaard the prototypical millennial of his time. Equipped with many more possibilities than his peers, he was still haunted by constant anxiety. “The dizziness of freedom,” as he would say. Given our modern-day choice cornucopia, it’s no wonder young peoples’ heads are always spinning.

But that’s not what we choose to see.

Three Rungs on Every Ladder

The most famous millennial meme is that we feel entitled. We’re eager to skip three rungs on every ladder and if we can’t, we don’t start climbing at all. That’s the story and it’s everyone’s go-to explanation for why we refuse to make many of life’s most important decisions.

We’re not marrying, we’re not having kids, we don’t even move out. We don’t make enough, save enough, invest enough. We’re not willing to get our hands dirty, we’re blinded by bean bags and ping pong tables, and we hope for the big payday that never comes.

And yet, having grown up in a world where school shootings are normal, where banks get bailed out for losing our money, a world full of fake news, corrupt systems, and crushing student debt, our expectations aren’t all that high. According to Stephanie Georgopulos, we’re well aware it’s up to us to do something about these things. But that doesn’t make committing any easier.

Maybe it’s not entitlement that’s at the heart of our procrastination at large. Maybe it’s the fact that, with 300 hours of video being uploaded to Youtube every minute, with thousands of potential Tinder matches, with over 200 types of bread in every Walmart and so much pressure to get it all right, it’s become really hard to choose.

This is beyond existentialist philosophy. Something’s happening in our brains.

The Joker of the Millennial Generation

One reason we stay on the edge of our seats when the dismal clown torments Gotham is that the choices he offers always seem so simple. Pay half your fortune or watch the Batman take the mob apart; save the lawyer or save the girl; sacrifice the convicts or the regular citizens — which one is it going to be?

As we listen to the Joker present our options, an answer forms in our gut right away. And yet, because they’re so full of moral dilemma, they quietly drive us insane. Like Kierkegaard, we know we’d regret the decision either way. This is where science kicks in. In The Paradox of Choice, researcher Barry Schwartz explains why the explosion of individual freedom in the past century continues to make us miserable today. He talks about five things:

  1. Postdecision regret. It’s now easier to imagine we could have done better in hindsight, even if a more suitable alternative doesn’t exist.
  2. Anticipated regret. The thought of making a choice only to find out you could have made a better one two days later is a paralyzing threat in itself.
  3. Opportunity costs. The more things you can select among, the easier it is to factor in all the attractive features you’re missing.
  4. Escalation of expectations. With such a big selection, it feels natural that perfect should be possible. But it never is and that’s depressing.
  5. Self-blame. Finally, it’s clear who’s at fault for all this disappointment: we are. It was healthy to blame a lack of choice, but that excuse has gone.

These are all bad, especially in conjunction, but it is number two that is the bane of our existence.

“How will it feel to buy this sweater only to find a nicer, cheaper one in the next store? How will it feel if I take this job only to have a better opportunity appear next week?”

The questions millennials ask themselves on a daily basis are all variants of the same theme: What if I invest in all the wrong things?

Anticipated regret is the Joker of the millennial generation.

The sheer number of options we have makes every decision feel like a moral dilemma. So we stand there, frozen, dizzy from all this freedom. Paralyzed by choice, regretting what we have not yet screwed up. That’s why we keep watching superhero movies, rather than living them.

But, as in any good superhero movie, there is a silver lining.


The Purpose of Supporting Actors

For as much as he claims to be an “agent of chaos, a dog chasing cars,” the Joker then turns right around scheming. It’s only on the surface that he’s aimless. From Kevin Lincoln’s piece about the 10-year anniversary of the film:

“The Joker’s plan is to appear as if he has no plan, and by hiding the plan — and, most importantly, disguising the inevitably tedious moment in which the villain reveals his plan, as the Joker does in [the hospital] — [the creators] reinforce the Joker’s purpose.”

There’s a lot to be said for plans if even the self-proclaimed antithesis of schemers has one. I don’t have a perfect list of arguments, but here are three I can take comfort in when doubting myself:

  1. It’s okay to take your time with life’s big decisions. Our grandparents probably wouldn’t have an easier time than we do if they had to make the same, big choices today. It’s easy to belittle the situation from the outside, but in the end, it’s your life, not theirs.
  2. What you choose will probably be good enough. As a corollary, for everything that isn’t all-important, which is most things, you might as well “introduce a little anarchy,” as the Joker would say. Where to get lunch? Which bar to hit on Friday night? Flip a coin, these things don’t matter, and you won’t remember them two weeks from today. Anything will do.
  3. Last, and most importantly: At the very least, I am investing. There is boldness in the act of commitment itself. And no matter how hard any particular decision may squeeze your brain, it is far better to sacrifice your time, your money, your energy, for a cause you think is worthy than to stand on the sidelines waiting.

The Joker’s role in The Dark Knight is so powerful, so all-consuming that it’s hard to focus on any other character. My generation might often feel like supporting actors in their own lives, but, ultimately, it’s always the sidekicks that get the hero to carry on. Like commissioner Gordon, when he gives advice to a newbie, which feels a little like a tip for growing up:

“You’re a detective now, son. You’re not allowed to believe in coincidence anymore.”