Resist Optionality, Eventually

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Let me take you back to the first day of my career. I was 21 years old, two weeks removed from my college graduation (shoutout summer birthdays). Dressed in my best shirt, I marched through the lobby doors of my big bank job and took the elevator up to orientation.

At some point in the day, an HR representative began discussing our benefits package. She said, “You all receive three weeks of vacation per year, and those of you who stay with us for ten years will earn an additional week.”

“Ten years?” I thought to myself, “I’ll be long gone by then.”

I hadn’t even met my boss or started the job yet. I already knew I wasn’t sticking around that long. Why? This job was supposed to be a stepping stone, a means to something better. I’d work there for a couple of years and then upgrade.

Gone were the days of growing at the same company for 40 years and riding off into the sunset of retirement. LinkedIn profiles today look more like CVS receipts. Two years here, two years there. Each stint leading to higher pay, a fancier title, and a wider network.

Acquiring options has become habitual. It’s a tempting course of action, and it’s no wonder this mindset has spread to other areas of life.

In the world of dating, there’s never been such an abundance of options when it comes to choosing a partner. Dating apps give us the sense that something better is just a few more swipes away. So we keep our options open and never commit to one person because we’re afraid of missing out on someone better.

Remote work and lack of home ownership mean that bouncing around to different places is as easy as booking a ticket. In the past three years alone I’ve lived in Boston, Ann Arbor, and NYC. I wanted the classic options that a college town offers students, but also couldn’t miss any of the potential options that come with living in a big city.

I went to grad school a couple of years into my career because I knew it would unlock a world of options better than anything else at the time. It’s the same way that working at a big bank or consulting firm creates optionality because of the broad work you’re exposed to.

As someone who spent his early twenties accumulating optionality for optionality's sake, I can vouch for the appeal. You can enjoy many possibilities without being on the hook to make big decisions. It’s arguably what young people should do. Very few of us have any idea where we want to live, who we want to date, or how we want to spend our time.

In the world of finance, there are these things called options. They are financial instruments that give the holder the right, but not the obligation, to buy or sell an underlying asset at a predetermined price within a specific time frame.

The catch? An option gradually loses value as its expiration date approaches because there is less time for the underlying asset's price to move in the anticipated direction, reducing the chance that it will pay off. This is known as time decay.

And that’s where the dangers of optionality start to set in. Options aren’t valuable forever. Time passes while you indulge yourself in the idea that you’re one partner, one job, one city away from securing your dreams. Before you know it, ten years pass and all you’ve become is the sum of your choices: the serial dater, the job hopper, the nomad.

We find ourselves in a paradox of wanting to remain non-committal to maximize alternatives. But we also want to build a stable life and make something of ourselves. Over the years it becomes clear that you can’t develop something meaningful while living in the hypothetical.

When options are wide open, each one is in a constant state of comparison. You’re always deciding what you should do and what the next thing is and don’t have the mental bandwidth to fully devote yourself to what you’re actually doing.

As James Clear said, “If you commit to nothing, you’ll be distracted by everything.”

Avoiding commitment doesn’t actually let you do a bunch of things, it just gives you the potential to do a bunch of things while not really immersing yourself in anything at all. Our depth is limited when we are constantly reallocating life to higher potential outcomes.

Keeping your options open is great. But eventually, it leads to things that demand commitment. Things that don't make you say “I need to do X to get to Y”. If you don’t double down on them, you miss the chance to fully experience life.

Fear of failure is a real thing. Maybe a job or relationship isn’t what you thought it was, so you want to minimize those risks by avoiding commitment altogether. But if you never risk committing to a bad thing, you probably won’t know enough to commit to a good thing when you see it.

Through optionality you discover things worth committing to.

Imagine Thanksgiving. You throw all sorts of foods on your plate until it’s overflowing. But when you go up for seconds, you aren’t getting more of the green bean casserole. You get more of what you liked; the stuffing, the potatoes, and yes, the cranberry sauce.

In trying a little bit of everything in the first round, you find something you can latch onto and commit to in the second round. Maybe it will take more than seconds when it comes to life, but once you do find those things, you have to be willing to dig in.

Our minds have an uncanny ability to restructure thoughts to make us feel good about our decisions. Once we commit to a course of action, to some extent, the mind stops thinking about alternatives. Of course there will be downsides to any decision, but by committing, we dwell less on those downsides.

If you don’t like something about your life, you can readily change it. You can move to a new city, swipe for a new partner, or apply for a new job. Our modern society offers abundant opportunities with infinite choices. So go ahead and enjoy the possibilities while you're young. But keeping your options open only works for so long.

Truly great rewards from anything — your work, your family, your hobbies — require care after the initial investment. Only then can you compound the gains. And maybe, just maybe you’ll earn that extra week of vacation.

-Sam

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