The Pain of Choosing.
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Hello friends,
I’ve been reflecting on decision-making and some of the choices that I am making recently: what to do, who to be with, how to spend my day etc… I used to be very into the decision-making self-help literature like Decisive.
While I've learned and applied such advice with objectively better result, one aspect seemed missing. Many of these decisions are computationally hard (i.e need to do a lot of cost-benefit calculation, need a lot of information about the world), but not philosophically and personally hard.
What amazes me is how common the latter one is, yet relatively uneducated we are about it. How can you “follow your heart” if you don’t have any much practice in listening to it?
The consequence of putting off this kind of hard choice is vast though. In my own experience as well as being with my ambitious, high performing peers, I found a common theme of dealing with a nagging sense of emptiness or that elusive "something doesn't feel right" that gnaws at their vitality. Most of the time, we push on, ignoring this nagging feeling because it’s so uncomfortable and unproductive anyway.
Many have come to realize that their real issues originate from inner world, which cannot be dealt effectively with by external solutions of analyzing or achieving more. In our case about decision making, making more objectively optimal decision will not solve the heartache. It requires us to cultivate a different faculty: an inner, almost tactile sensitivity that I've been trying to develop and express through my writing.
I want share that with you in this short post, especially if you are going through the deliberation process. Maybe pick a difficult decision and reflect with me?
Khuyen
You Belong Here
A meditation on belonging, place and the question of purpose.
ahhh, hard choice
At exactly 7am five years ago, my alarm went off and I had a “man in the mirror” moment of insight. Looking at the groggy guy brushing his teeth after a stretch of full day of work and night of social enrichment activities in Saigon, Vietnam, I felt like shit.
I was feeling guilty about not maximizing all the opportunities to develop my fullest potential. Mostly, I was in huge FOMO. Somehow I was in such a terrible state that this insight came.
“When I said No to something, I’m saying Yes to something else.”
A moment before, I was struggling to justify my rest. A moment after, I felt as if something finally clicked into a delicious inner coherence. With that comes an immense release: there is no trade off between rest and work, between inner and outer. Eventually they all are part of a larger, continuous flow of life.
I thought I learned this well, and yet five years after, another painful, practical and seemingly opposite lesson is on its way: “When I say Yes to something, I’m saying No to something else”.
I am learning to close my options, and it’s painful.
Especially if you are one of those super lucky people who are young, talented, ambitious and presented with ways too many options, you know this dilemma too well. (As you can tell from my mediocre existence, I’m not one of those, although I happen to know and really like this group of lovely folks)
Mihir Desaj wrote an excellent article about the trouble of optionality.
Options have a “Heads I win, tails I don’t lose” character — what those in finance lovingly describe as a “nonlinear payoff structure.” When you hold an option and the world moves with you, you enjoy the benefits; when the world moves against you, you are shielded from the bad outcome since you are not obligated to do anything.
Optionality is the state of enjoying possibilities without being on the hook to do anything. […] Of course, the more optionality, the better. In contrast, the closing of doors and possibilities signals the loss of optionality. Even if not explicitly stated, optionality was always the end rather than a means to an end.
Yet, option is only good in the absence of a deep knowledge of what we are truly after, what Mihir calls the pursuit of alpha.
In short, it is very hard to attain in a sustainable way and the only path to alpha is hard work and a disciplined dedication to a core set of beliefs. Given the ambiguity over the correct risk-adjusted benchmark, one never even knows if one has attained alpha. It is the golden ring just beyond your reach — and, one must enjoy the pursuit of alpha, given its fleeting and distant nature. Ultimately, finding a pursuit that can sustain that illusion of alpha is all we can ask for in a life’s work.
But what exactly is the hard work and disciplined dedication? And why choosing seems so hard, from your important career move to your next relationship to where you live and find your tribes?
The hard thing about hard choice, as philosopher Ruth Chang well articulates in this talk, is that they are on a par, meaning that they don’t have clear criteria and metrics of comparison. Yet, its very difficulty is indeed a powerful invitation, a godsend opportunity. Ruth Chang continues:
“When we choose between options that are on a par, we can do something really rather remarkable. We can put our very selves behind an option. Here’s where I stand. Here’s who I am.
Such choosing sounds so wonderful, yet we tend to avoid it simply because the implied burden of self-making is just too much to bear. It takes up a huge amount of seemingly unproductive reflection and psychological capacity to be ok with the discomfort of uncertainty, something we get trained neither in school nor on the job.
Sometimes these are really thorny decision that are understandably prone to procrastination. Who do you rather spend time with? How would you choose to show up today? What kind of life are you willing to live for and die for?
Yet sometimes these decisions don’t necessarily to be big: what type of cereal for breakfast, as first world problem as it could sound, can also be a chance for us to practice mindful choosing. If you do it well and often enough, you will slowly acquire taste and becoming an interesting and unique person. Not a bad result for sweating over the small stuff.
Continue Ruth:
The response in hard choices is a rational response, but it’s not dictated by reasons given to us. Rather, it’s supported by reasons created by us. When we create reasons for ourselves to become this kind of person rather than that, we wholeheartedly become the people that we are.”
As I’ve written, part of the journey to arrive at wholeheartedness involves plenty of pain points along the way. When we become more acutely aware of our moment-to-moment choosing, it often initially feels painful. The more we know the doors we have to close, the more painful it is.
It’s worth noting that it is not overthinking oneself with cost & benefit analysis paralysis. Rather it is learning to notice our spacious capacity for choice in the moment and simultaneously the need to let go of other options.
Why should you care? Here is the kicker.
The celebration is more satisfying if we also honor the pain of it.
So learn all the decision making techniques and framework you can. They do help you make objectively better decision. But remember, when we rush over this deliberation process, we miss out both the pain and the joy of it.
All decisions, all steps forward, involve loss. The root word of “decide”, -cid and -cide, comes from Latin which means ‘cut’ or ‘kill.’ A decision, for instance, is a ‘cutting off’ of all possibilities except for one; if you are decisive you have ‘killed’ all other options.
This killing, as painful as it may seem, also holds the renewed energy of finally making a definite choice, of stepping through one door and effectively closing others. The more we commit to this choosing process instead of shying away to the default script “everyone does that” or a meh “that sounds kinda good”, the more wholehearted we become. With that comes a deeper inner joy of truly living in the world instead of just floating around.
That’s what I’m after, and I hope you do too.
Practice:
My invitation for you is to make space for the pain that you intuitively sense when you deliberate a hard choice. Quiet, lone time without much distraction so that you can sit with the choice.
Make a list not of pros and cons but of different possible versions of yourself that you will stand for. What value am I standing for if I choose this and not that? Every time you sit with that list, you are training your inner faculty of discernment that will complement your objective decision-making capacity. For example, I choose meaningfulness over speed, emergence over conclusion and joy over achievement. (When they are mutually exclusive, of course).
May you keep listening and choosing well.
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Read the full post here on Medium.
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Quotes I'm contemplating this week
This paragraph from the sociologist Jennifer M Silva has been so resonating about the Millennial generation... apparently this use of every pain point they had as a platform for transformation seems specific for us. Would love to hear people's thoughts on this.
Lastly..
Do reach out for the Inner Critic Assessment or general conversations about life. I'd love to be helpful.