Illustration by Fanny Luor

Work Culture

Your obsession with optionality is holding you back


Published on March 01, 2021

When does the freedom to choose swing from being a luxury to a liability? If you look hard enough, you’ll realize it happens to you almost every day. It’s the moment where you get an 89% compatibility match on a dating app, but you’re secretly holding out for that elusive 98th-percentile connection. It’s the 20 minutes you spend trying to find a takeout spot with the most five-star reviews—followed by another 15 minutes scrolling through a streaming app (as your food gets cold) to find the right thing to watch while you eat.

It’s the idea that if we keep our options open, good things will happen. But if options are like browser tabs, are we all coming dangerously close to crashing our mental operating systems? We have always been encouraged—or, more recently, pushed via algorithm—to wait for the best-case scenario in all aspects of our lives. The thinking extends to our careers. Entire generations have been told to hold out for something better, sample without committing to a “locked-in” career path, and give ourselves as many exciting choices as possible.

This phenomenon goes by many names: Optionality, the Paradox of Choice, Analysis Paralysis. But they all speak to the same fascinating issue: When you’re surrounded by potential life paths and choices, choosing just one can feel like giving up on all the rest. So let’s talk about how you can choose direction over perfection and stop holding yourself back.

Choose your own adventure

The myth of the American workforce used to go something like this: get a job, stay in it for 30 years, and receive a gold watch on your last day before retirement. But things have changed.

Many of us follow the wisdom of optionality from a young age. College students are advised to major in something broad enough to help them maximize their potential post-graduation career moves. After college, they may keep this up, taking jobs that keep as many doors open as possible. It’s an easy way to keep your options open, yes, and maybe you have a clear end goal in mind. But this type of thinking also makes it harder to act on the more important thing: pursuing what you actually want

This is by no means exclusive to recent grads or even individuals as a whole. Companies go through this, too! As Neil Soni, author of The Startup Gold Mine, explains in a blog post coining the term, startups and corporations can find themselves in the “Optionality Trap” when it comes to pivoting towards new projects and initiatives too frequently or without a vision beyond “chasing something new.” It has never been easier to try something new, work on a new skill, or dip into something new just far enough to get a taste without having to make a capital-C commitment. There’s (potentially) a lot of joy and freedom in that level of self-expression.

And while there’s a lot of freedom in that way of living, the risk is great, too. By not committing to anything, we sacrifice harder won, strategic wins. On a personal level, optionality can prevent us from reaching our highest levels of career satisfaction.

An endless coin flip

On a base level, the idea of keeping your options open is a way to protect ourselves from the pain and frustration of not being able to make our own choices. It gives us the space to plan, consider, and choose a situation that won’t leave us with regrets over the path we could have taken instead.

But there’s another level of happiness and satisfaction that only kicks in once we’ve made a big choice or commitment. A 2011 study found that subjects felt more regret after making an easily-reversible decision than after making a large, irreversible choice. The reason, writes psychologist Heidi Grant Halvorson, is because our brains are built to help us see the silver lining of all our options. After you commit to something, your brain enables you to forget all the other possibilities and focus on the path ahead of you. On a psychological level, happiness comes from dwelling on the downside of any given situation as little as possible—which is impossible if you haven’t made a decision. 

In a world full of options, every upside is always within reach. But so is every downside, and juggling all those potential futures (and potential versions of yourself) in your mind can quickly go from exhilarating to exhausting. It’s a mental exercise without the break that comes from making a choice and putting those alternate futures to rest. Picture a coin toss that never ends, and it’s easy to understand why a world of exponentially spreading options can backfire.

Happiness comes from dwelling on the downside of any given situation as little as possible—which is impossible if you haven’t made a decision. 

But it’s not as simple as removing your options and saying yes to the first choice that comes your way in any situation. Not only does that do a disservice to the self-discovery and diverse skills and interests we can pick up while keeping our options open, but it essentially would leave all of us in the same place previous generations often found themselves. The solution, it seems, would lie in being able to have your options and choose them too. In essence, it’s about following your passions and finding an appreciative audience for them.

The path of passion

The last 100 years of history, when it comes to jobs and careers, are just a blip in the story of humankind. That’s how Adam Davidson, author of The Passion Economy, frames it when discussing our current approach to our working lives. That “blip,” as he calls it, resulted in another phrase of his: The Widget Economy. A new society of dramatically improved living standards in almost every category was driven by this new workforce, focused on iteration and repetition. Jobs were grouped into a few general categories and were remarkably similar to each other. Competitors successfully replicated or improved products until the global market became saturated by a handful of dominant brands. But the individual craftsperson or artisan was lost along the way as the definition of work became repeatable and impersonal.

But anything lost can be found again, which is exactly what the Passion Economy represents. In some ways, it’s a return to an era before the industrialized workforce was the norm, when artisans were able to monetize their crafts. The biggest difference is that now, people actually have the freedom to explore what craft it is they enjoy. In a time where more people than ever have the time and space to consider what makes them truly happy, it’s the type of change we need.

In the Passion Economy, people embrace their individuality and niche interests, regardless of how they fit into a wider corporation’s structure. It’s about knowing that your unique offering might not be something everyone on the planet will want to buy, experience, or participate in, but that there is an audience on your wavelength out there.

It’s the difference between a factory-assembled product and an individual craft. It’s a way of emphasizing the human connection when we could all use a bit more of that in our everyday lives. And for many, it could be the missing link between the open-ended search and finding something worth committing to: themselves.

You are the best option

The tendency to lean towards Optionality is rooted in fear. As Erik Torenberg wrote in his blog, it often comes from a fear of looking foolish or making the wrong choice. But it also comes from many unfounded societal fears: of being locked in a job we hate, of missing out on our true calling, of being viewed as a job-hopper.

The job-hopping label is particularly sticky, tied to a belief that Millennial and Gen Z workers are more prone to leave jobs than their forebears. A quick look at U.S. job tenure stats puts that entire idea to bed: In 1983, the average worker moved careers every 3.5 years, compared to every 4.6 years in 2014. If anything, the current workforce stays at a job for longer than they used to. But even more importantly, it highlights a universal, cross-generational human truth.

We want to be happy, respected, and satisfied with our work. And we’ll leave to pursue that happiness.

The Passion Economy can take many forms, but it’ll always be dictated by each of us as individuals. Those moments of Optionality, under this lens, now become productive moments of incubation, when we’re taking the time to pursue what makes us happy, knowing that it’ll inform what we create and pursue later on. A Passion Economy needs passionate people, after all, and passion comes from experience and knowledge. You need to know what you like to know what you love.

It’s pretty much certain that technology will continue to throw us more choices for where to eat, what to watch, and who to meet. But reducing Optionality when it comes to your career and passions is mostly about forgiveness and trust—forgiving yourself for committing to one choice and trusting yourself to use that new experience to inform your next one.

On the path to finding what passions you have to offer the world, the only wrong choice is not making one at all.