The Trouble With Optionality

4 minute read

Optionality’s one of those things you don’t really think about. People don’t generally wake up one morning thinking “Why, it appears I’ve spent the past several decades of my life optimizing for optionality. Perhaps I should figure out why?”.

Most don’t even recognize the term – until it’s already explained to us. If you’re one of those people, this could well be the most important posts you read this year.

What Is Optionality?

Optionality has been drilled into our heads ever since we were young. No one calls it that, but every one of us has heard the advice to follow opportunities that “open up doors” or “unlock opportunities” down the road.

Now that’s all fine and dandy when you’re 12, but our generation is increasingly becoming crippled by the abundance of choices – making it damn near impossible to decide on anything of significance anymore.

That’s tragic because optionality is also a privilege. And this disease has a tendency to afflict the most privileged among us – rendering them hollow.

In this post, we’ll run through how optionality has pervaded our entire livelihood, why it can unconsciously derail entire careers, and what you can do about it. Let’s dive in!

The Obsession With More (Options)

We’ve been taught to seek out options that open up horizons, unlock doors and unleash possibilities. This expansive approach to life works great early on, enabling us to have more choices about what we’d like to ultimately do.

The trouble is that last bit “(what we’d like) to ultimately do” – opening doors is a means to an end, not the end itself. By the time we’re young adults, we’ve had this idea of optionality engrained into our heads – and we don’t stop to reconsider what we’d actually like to ultimately do.

We keep opening doors like it’s nobody’s business – resulting in so many unlocked doors that it’s crippling to pick just one.

This phenomenon seems to have existed for a while, but has become increasingly prevalent in recent years. You see it in students choosing varied majors/minors, to people choosing to rent instead of buy. We crave choice, and are horrified of its opposite: commitment.

Why this deep seated aversion to risk?

I believe it originates from two human afflictions:

  • Fear of missing out (FOMO): What if the choice I make is the “wrong” one, and the other choices somehow diminish in value.

  • Fear of failure: There’s something scary about committing to an idea; that decision can bring about the possibility of real failure. It’s easy to see the allure of deferring the decision, in favor of collecting more and more safety nets to soften a (potential) fall down the road.

Unlike their financial brethren, amassing a portfolio of choices is actually pointless beyond a point. An individual option is useless unless nurtured through the dedication of time and effort – and there’s only so much we can do in one life.

But there’s more to it than that. Let’s take a deeper look at the downsides of optionality, and what we can do about it.

Why Optionality Is Bad

1. The Opportunity Cost

Our net output is the result of focused effort; and optionality is the exact opposite of focus. Rather than exploit any single option, we defer it for some undefined later – a later that often never materializes.

This is akin to someone, in the early 90s having the ideas for Facebook, Google and Amazon all at once – and pursuing none of them in favor of unlocking more doors as a business consultant.

Over 1,000 octogenarians (those aged 80 and above) were asked about their single biggest regret in life. The most common answer by a landslide was this: they regret the risks not taken. You can bet that’s what our fictional character from the previous paragraph would say too. “Oh, I had that idea years ago” means nothing if you chose not to do anything about it.

2. The Paradox of Choice

More options make it harder to choose later, not easier. That’s unintuitive; you’d think more is better, but it’s leads to all sorts of strange side-effects. In his book “The Paradox of Choice” (find an example of the paradox of choice – jam, watches, etc) ….

The trouble with accumulating options is that, like money, you can never have enough. You postpone your dreams, stuck in a continuous loop of preparation that’ll never end. And if you do ultimately stand to pick between the options, you’re less satisfied overall – the sheer number of choices makes you second guess your decision, and ultimately leads to a less fulfilling life.

3. It Changes How You Think

Finally, and worst of all, the pursuit of optionality changes you. It turns you into a dreamer, always amassing options but never executing on any of them. It shares plenty in common with wantrepeneurs, the variety of entrepreneurs that never get started – always waiting for the perfect circumstances to unfold (which, they never do).

The Cure To Optionality Addiction

Now that we realize the grave downsides to optionality, we’re ready to talk solutions.

The first one should be clear: commit. That means picking a single course of action that you would like to pursue – picking one option of the portfolio that you’ve amassed.

You should take your time to study the options, deliberate, and find the one that makes the most sense for you. But once you’ve decided, there should be no looking back.

To assist you in making sure that you don’t turn back halfway, consider publishing this commitment publicly. Tell your friends, write a blog post, publish it to LinkedIn. Sharing this commitment with others can provide the social pressure necessary to continue, despite the internal urge to resist.

Also, as you exercise your option, ignore all the others. Focus solely on the task at hand.