Are options actually good?

Is keeping your options open always a good idea? I used to think so, but starting to think that holding on to 'having options' leaves me floating, and can result in not doing anything (of note). Can cover any area - career, dating, exercise, ice-cream flavours.

What is optionality?

This definition from Mihir Desai makes a bit more intuitive sense than the dictionary one:

Optionality is the state of enjoying possibilities without being on the hook to do anything

He further provides two examples of optionality in action

• Going to graduate school "creates optionality by enabling more opportunities than a narrow professional trajectory"
• Working at prestigious firms and building networks there can lead to more options

While I think he stops short of critiquing optionality as a whole, he cautions against taking on too much optionality:

Instead of enabling young people to take on risks and make choices, acquiring options becomes habitual. You can never create enough option value—and the longer you spend acquiring options, the harder it is to stop.

This can result in an unfortunate situation. Options are supposed to give you the platform to eventually move towards the direction of your 'true calling', whatever that is.

But the pursuit of optionality somehow takes precedence. It becomes challenging to discard that prestigious job, good money and of course, the collection of even more options. He paints this outcome well:

"These safety nets don’t end up enabling big risk-taking—individuals just become habitual acquirers of safety nets. The comfort of a high-paying job at a prestigious firm surrounded by smart people is simply too much to give up. When that happens, the dreams that those options were meant to enable slowly recede into the background. For a few, those destinations are in fact their dreams come true—but for every one of those, there are ten entrepreneurs, artists, and restaurateurs that get trapped in those institutions.

Check out the full article here.

David Perell touches on a similar concern, but labels it as a "struggle with commitment". He notes a tradeoff between novel experiences (which I relate to the concept of optionality - where you could enjoy numerous possibilities by not picking and sticking to one) and commitment (which by definition should eliminate/reduce optionality).

Examples he gives:

• Digital nomadism
• Listening to books at 3x speed
• Frequent job hopping

Referring to his students, he observes a reluctance to make the effort to commit to an area of expertise, sensing that

they’re scared of trapping themselves in an intellectual box that’ll constrict their identity

He shares three possible causes for our fear of commitment

1. Cultural - liberal values detach the individual from constraints such as family, culture, location, tradition. As these become less constricting, people gravitate towards a low-commitment mindset.
2. Technological - this ties to the paradox of choice. Looking at dating, he sees people 'holding out' for a better prospect through the next swipe. With more options, there is less certainty over whether you are making the 'best' choice, leading to a reluctance to commit.
3. Sociological - A bit less intuitive than the first two reasons. This is to do with people being more short-termist. People with a short term horizon tend to be more frenzied because every detail seems to matter, whereas someone with a longer-term outlook tends to be calmer, recognising that daily volatility is just part of the ebbs and flows of life.* By default, sticking to something meaningful comes with having a long term horizon, because good things rarely happen right away. I like his tie-in to game theory, where people tend to have better interactions with one another if they play 'repeated games'.

*Reading a book "4 thousand weeks" now, related to this concept of time horizons.

According to him, total optionality is

a recipe for emptiness... the greatest rewards generally go to people who are tied down in certain ways. A real lifelong marriage is the deepest relationship you’ll ever have because you’ve committed to a lifetime of faithfulness. Likewise, you only get to raise money for a startup when investors are confident you’re committed for the long haul

Too many options can result in no commitment, leading to less meaningful living. Recognising that commitment comes with opportunity cost, he nevertheless urges experimenting rather than collecting options.

With the former, while you are scratching the surface on a variety of paths, you do it with a view to picking something to stick to. This contrasts with collecting options, which leaves us anchorless, going nowhere in particular.

What to do about it?

David Perell advises that if you are (and I certainly am guilty) reluctant to commit, try to raise the bar a little.

If today you’re comfortable committing to something for two hours, try committing for a weekend. If you’re comfortable committing for two weeks, then raise it to two months; once you’re comfortable with two months, raise it to two years; and once you’re comfortable with two years, raise it to two decades. It’s okay to start small. All big things do. But they have to start somehow and with commitment comes momentum.

I am not doing the full article justice, read it here.