On the Tyranny of Optionality

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Our obsession with “keeping doors open” ends up hurting us. Sometimes you have to make hard choices — and you are better set to make these decisions yourself than for life to make them for you.


There’s a temptation in modern American culture — especially among high-performing young people and their parents — to constantly keep options open and do things that “open doors.” Camps are signed up for, tests taken, colleges applied to, jobs worked, and lives written entirely under the justification that they may open up doors down the road. This temptation is particularly strong when you’re young and you feel like your teenage and early adult years are essentially the training ground for living a life you want later on — but they easily extend into later adulthood as people hold out in jobs they don’t like or living in cities they despise out of the justification that these may open up doors for them down the road.

Rarely is the question asked, though, “why do we want these doors to be open?” Rarely do young students or their parents ask what they want and whether or not pursuing those things that increase optionality will actually get them closer to their goals. In the pursuit of optionality and opening up doors, they lose sight of what optionality and open doors are actually for — getting to places, goals, and achievements.

The justification that one may give for opening up as many doors as possible early in life is that we rarely know what we want when we are young. But this is simply begging the question. What if the listlessness and inability to know what one wants that we see in teenagers (and, disturbingly, increasing numbers of young adults) isn’t a natural fact of life but is actually an extension of focusing so much on optionality?


I was one of these young people, myself. I pursued classes, extracurriculars, and even college on the basis that I wanted to get to that which closed the fewest number of doors (while still allowing me to do things I wanted to do — optionality doesn’t make you non-human). I turned out to be an excellent student and got into my top choice college on a scholarship. Once I got there, I met other young people just like me who were also top notch students looking to maximize their optionality.

The perverse outcome of being around so many other high caliber, top notch people is that nobody ends up really being great at things. People turn out good at things and just a few weirdo, niche outliers turn out great at their interests.

The particularly perverse outcome of this is that once you get to this level of the game, to progress to an even higher level, you have to become great at something. You can keep plodding along in optionality land with a good job in DC or New York, but you aren’t going to build something truly impressive in that process.

All Rhodes Scholars had a great future in their past.  — Peter Thiel/Blake Masters

So, people who were looking to keep doors open to access resources to do impressive things end up limiting their ability to actually access these resources. (To speak nothing of whether or not one can be fulfilled by seeking optionality.)

These elite students climb confidently to a level of the game where optionality is no longer a bonus but a detriment and end up having to play catch up to those who specialized earlier on.

Or worse, they get to this level of the game and realize that they didn’t even want to be there in the first place and are now stuck looking for meaning. In its most pointed form, this is the quarter-life crisis that a young person hits once they land their first job, maybe get a promotion, and get caught asking themselves, “what is this all for?”


I’ve also been fortunate enough to see evidence to the converse through the high caliber young people I meet who are not obsessed with optionality. They tend to have a much better idea of what they are good at (even if it is just learning things very quickly and competently) and know how to filter through the noise of life. They have fewer problems with fulfillment and with rising to a level of competency that makes them truly invaluable to the teams with whom they work.

Unfortunately, these are often the people who are not given the spotlight and the attention for being successful and rising through the ranks. Rather, they are usually stuck at home or at work, doing what they do well so much and for so long that they don’t have time to go hop into the limelight at media events and conferences.

They don’t let the tyranny of optionality dictate how they ought to live their lives. They just go ahead and live them and do so very, very well.


From where does this optionality-obsession come? It isn’t just inherent in human nature — as it is easy to find cultures across the planet who view the importance of mastering certain things or at least specializing early on. In fact, we learn best through play — which requires specialization and picking up skills at the cost of other experiences — not through credential-seeking.

The first cause is cultural. It is what Peter Thiel calls “indefinite optimism” and, like all culture, is designed by no one person but reinforced by the actions of many. It is a belief that we don’t need to make choices now and build paths now, but that we can make these choices down the line or that others will make them for us. It’s a general cultural belief in the United States since the mid-late 20th Century that is closely associated with the collapse of the USSR. We are born into comfort, the wars of the past are won, and the future is getting brighter. Let’s take that momentum and keep it going.

High-optionality, low-expertise students and professionals are rewarded with impressive credentials and lucrative jobs in careers like government and finance while low-optionality, high-expertise students find themselves in less-prestigious careers like trades or IT. If you are a young person with the drive and capacities to build your own path, you have more obvious incentive to opt for the former path.

The other element is parenting. Baby Boomers and Gen X’ers are too afraid of the idea of closing doors for their children that they keep everything open for them and don’t ask them to make hard choices while young. They coddle their children through a culture of “everybody is a winner” until everybody isn’t. Many of them were burnt in the Dot-Com crash or the Great Recession and want their children to avoid that burn — but out of their good heartedness, they simply delay and amplify the difficult choices their children will have to make in the future.


bhorowitz writes in his book The Hard Thing About Hard Things of a time when he was a young father who was working at a startup while having several kids, a wife, and not enough money to afford air conditioning.

His visiting-father asks him if he knows what is cheap. No, he replies.

“Flowers. Flowers are really cheap. But do you know what is expensive?”

Again, no.

“Divorce.”

Horowitz nearly learned the hard way that optionality is a tyrannical master and made hard choices before they were made for him.

Unfortunately, too few young people learn this lesson early on. Driven by a culture that rewards high-optionality outcomes and parents who are too scared of closing off doors for their children, they go through life until life makes those hard choices for them — and usually with a suboptimal outcome.

This work originally appeared at The Mission. Email me at zak@slayback.xyz to discuss.

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I'm Zak. School should have taught you how to succeed at work and build a great career. Instead, it taught you that mitochondria is the powerhouse of the cell. Thankfully, I teach what school never taught.

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