Dwelling in Possibility

Epistemic Status: Intuitive, Casual

One of the things I’ve noticed in people who are farther along in business or management than I am, usually men with a “leaderly” mien, is a certain comfort with uncertainty or imperfection.

They can act relaxed even when their personal understanding of a situation is vague, when the future is uncertain, when the optimal outcome is unlikely.  This doesn’t mean they’re not motivated to get things done.  But they’re cool with a world in which a lot of things remain nebulous and unresolved at any given moment.

They’re able to produce low-detail, high-level, positive patter for a general audience.  They’re able to remain skeptical, expecting that most new ideas won’t work, without seeming sad about that.

Talking to someone like that, it feels like a smooth layer of butter has been spread over the world, where everything is pretty much normal and fine most of the time — not a crisis, not a victory, just normalcy.

This isn’t me.  If something I care about is unclear to me, it’ll bother me. Either consciously (in which case I’ll try to learn more until I understand) or unconsciously (in which it’ll be an unpleasant blank spot on my map, that’ll nag at me uncomfortably.)

It also bothers me, as a radical, when I don’t see a path to my long-term goals being possible.  “Business as usual” feels not okay to me, much of the time.  I don’t like having a “forget about it, it’s Chinatown” attitude.  I don’t want to be a naive idiot, but I don’t want to be complacent either.


Being okay with vagueness seems to be a prerequisite to managing other people — after all, you can’t know every detail of everyone else’s job.  When I managed people, I struggled with that a lot. I couldn’t be sure a thing was done right unless I checked it for myself.  I’m pretty good at holding large systems in my head, but eventually organizations defeat even the most heroic attempt to micromanage them.

Being okay with uncertainty also seems to be a prerequisite for managing a portfolio of anything high-risk and high-reward — investments, sales leads, technologies to adopt, etc.  If you are elated every time an opportunity appears, and dejected every time it doesn’t work out, you’ll have a very hard time emotionally when dealing with a large volume of such opportunities. (My husband is a salesman and he’s long since stopped telling me about leads because I’ll get over-excited about every one of them.)

This reminds me of some of the stuff leadership coach Bryan Franklin says about paradox.  I don’t know if I can represent his ideas accurately, since he comes from a very different paradigm than mine, but I think he’s alluding to “both/and” thinking, the ability to simultaneously hold, for instance, the frame “this business is bound for incredible success” and “this business will fail unless we solve this problem.”

Consider the common example of a leader who needs to convince her followers that, while the team is experiencing significant challenges and there is a very real risk of failure, ultimately the team will prevail. There are two ways a lesser leader could falter in this moment. The first is to simply pander to neg activism: agreeing with everyone’s feeling that the current situation is rough or hopeless, without offering any vision, possibility, or credible plan. This would be a good display of empathy, but it won’t lead anyone to change. The second mistake would be to hold the opposite view, that the future is bright and the current setbacks are illusory or insignificant. This could be seen superficially as inspiring, but more likely it will backfire because it will be dismissed as being noncredible and unrelatable to the lived reality of the employees.

A superior leader learns how to hold paradox: to believe, at the same time, that the situation is dire and hopeful, meeting employees where they’re at, but also convincing them of the actions they can take that will lead to a brighter future. The evidence is that things are bad (anyone denying this will be seen as a Pollyanna); and also, the evidence is that things are good (anyone denying this would be seen as a weak leader, lacking creativity to produce a positive way forward). Followers need to feel met in the reality that they are scared, yet they also need to be given a realistic expectation of future success.

When you’re confronted with a paradox, you are presented with a choice. You can either ignore it and take a side (believe one side of the statement is true while the other is false), or you can do what we call hold paradox, which is to believe both contradictory statements or implications simultaneously. It’s an expression of faith in a greater truth that is currently invisible to you, but resolves the paradox and allows for the truth of both sides to harmoniously coexist. This is what great leaders do.

Holding paradox is the ability to literally hold in your mind the truth and acknowledge, for example, your utter insignificance on a cosmic scale, and then without allowing that experience to dissipate, add to it the unmistakable truth of your profound significance to those you love.

Believing a literal paradox is believing something that is logically impossible, and so, obviously, I don’t want to do it.  But believing in lots of different possibilities at the same time, believing that a thing can be viewed from lots of different points of view — there might be some purchase in that.

The real world is parti-colored. It doesn’t have a single theme or mood or color scheme.  But to really know in your bones that lots of different things are possible is a deeply scary option to me. It feels like letting go of things that are important to me, like commitment or ambition or rigor or even personal identity. If I care about something, how can I allow myself to chill out about it? How can I allow myself to fully enter into the worldview of someone with the opposite belief?  Wouldn’t that be a betrayal? Wouldn’t that mean losing myself?

There’s a common thread between this notion, and people like Jonathan Haidt who believe in worldview diversity and people at the Integral Center who believe that higher human developmental stages involve the ability to move fluidly between frames, and who sometimes connect this to business through books like Tribal Leadership.

All of them share a view that the principled or systematic person — the person who believes in one truth according to one set of principles — is weaker or less spiritually advanced than the person who sees things through multiple points of view.

In particular, one idea I picked up from Tribal Leadership is that if you believe a particular thing as an individual, you’ll be a weaker leader, because you’re just saying what you personally believe (which is selfish, in a sense, or at least private, and thus taken less seriously by others).  The leader has to be not just John Smith but the voice of Acme Corp.  Expressing your own thoughts (speaking as John Smith) has value coming from an individual contributor, but there’s a different, more facilitator-like, skill where you try to encourage dialogue or distill a common thread between different people’s views, and encourage teamwork and unity — and that’s leadership.

What I worry about, in all these kinds of philosophies, is that if I gain this balance, this ability to stay cool in the face of uncertainty and ignorance, this ability to engage with multiple perspectives, then I’ll no longer be able to be an individual with a particular point of view and set of goals and detailed knowledge of my areas of expertise.

Is it possible to love something, or pursue something, without freaking out about it?  Doesn’t equanimity trade off against passion?  Wouldn’t a person who kept their cool all the time be boring?  Wouldn’t a person who tried to “diversify worldviews” be inherently an unprincipled pragmatist?  Doesn’t the chillness of leaders sometimes look uncomfortably like privilege or elitism?  Isn’t there a lot of potential for manipulativeness when people try to “facilitate” for others?

And yet, pretty much every book about business success counsels equanimity — to a very high standard, from what I can see.  Seriously, flip through something like Emotional Intelligence 2.0 the next time you’re in an airport bookstore. Apparently ordinary middle managers have to be unbelievably good at handling emotional stress just to scrape by.

I have definitely seen chillness coexist with strong technical skill; quite a few people with that relaxed, leaderly affect are also top-notch at engineering or data science.  Accepting that some information “lives” in the “collective mind” of a group clearly doesn’t preclude knowing some things very well in your own mind and being able to execute well individually.

I’ve even seen a certain kind of chillness coexist with radical commitment. Rick Doblin, the founder of MAPS, has been steadily working for forty years on trying to promote research into the therapeutic use of psychedelics.  He’s a pleasant, mild-mannered family man; despite his controversial mission, he seems to bear no ill will to anyone, including the regulators he’s been trying to persuade to ease up drug restrictions.  He’s willing to collaborate with anyone, from any perspective or background, if it’ll help psychedelic research.  He’s my role model for how someone can be profoundly committed to a cause without being an angry or rigid person.  His way is like water wearing down a stone.

But I definitely have heard people tell me that equanimity cost them something — that they lost the chance to have a personal perspective and to want things for themselves when they learned to see things from all possible angles and be a facilitator for others.  I’ve seen people who are very good at sparking “interesting” conversations complain that they have a hard time connecting personally rather than remaining a third-party observer.

I’ve had occasions myself when I deliberately “took myself out of the picture” in order to hold space for others — and it worked pretty well, and was fun in its own way, and people responded well to it, but I had a strong intuition that this wasn’t what I wanted to spend the majority of my life doing.  I have a self, and it’s not going to like being cooped up forever.

So I’m genuinely uncertain.  Maybe leadership is fundamentally incompatible with stuff I want to keep? Maybe I just have hangups about harmless stuff, or resistance against working on things I’m naturally not good at? I wonder what older and more accomplished people would think about this issue.


20 thoughts on “Dwelling in Possibility

  1. Surely if one learns to hold paradoxes, it is also possible to hold the paradox that one can hold multiple frames while also still having a personal, favoured frame? You set this up as an either/or when the whole point of the skill is to transcend either/or thinking.

      • Either-or thinking implies that there are exactly two outcomes to a situation, you know what both of them are, and one outcome is desirable while the other is not. Like if you are coding something, someone can click on the “yes, I like your product” button or the “no, I hate it” button to answer a survey and you never have an opportunity to ask why. But real life is more messy and complicated. You could fail, but learn something, and these could be some of the most special and victorious moments of your life. You could have a whirlwind 24 hour romance that doesn’t last in any traditional sense except that it stays with you your whole life and is your template for every romantic relationship you have after you’ve experienced it. If you always think wistfully about what a failure that botched romance was, you will never see how much it has given you and it will be very difficult to value it as the positive experience that it was.

    • Yes. This. You want to hold *all of the frames* in your head, because they might be held by someone else and also might be useful, without thinking that *all of the frames are equal* which would destroy your identity and is also nonsense. Understanding is almost always good, even if the thing you understand is kind of wrong and/or dumb and/or something alien to you.

  2. Loved this post. It is a tricky negotiation that I face all the time in my field, which is nutrition. The paradox here is that we would like to encourage everybody to eat a healthy diet (a point that basically goes without saying) and–we don’t know what that really means for any given individual. (I won’t get into the painful details of the science & politics of the situation, but let’s just say that a topic that has been this controversial for this long is certainly not “settled”). What most folks end up doing is promoting the way that they, personally, eat as the “healthiest” way to eat. While this is typically rationalized by the science that suits the situation (there’s plenty to choose from, everyone can find their favorite notions supported by some research), it more honestly justified by personal belief, preference, or what “works” for that person. It makes sense on one level–why would you tell others to eat a way that you don’t “believe” in?–but with regard to “holding paradox”–and for that matter actually helping individuals find what dietary pattern does work best for them–it makes no sense at all. Context, complexity, and constant change are key features that help me remember that my way of seeing the issue is not all ways.

  3. (The following reply is pure speculation on my part. I can’t properly back it up with science, it’s mostly based on the personal experience and observations of a relatively young person)

    It makes sense that older people would be less invested in specific outcomes, and have a more “wait and see” attitude. If you live long enough (how long is long enough depends on what kind of life you live), you will fail at, and be proven wrong about, things you were invested in. And that hurts. Not just emotionally, but socially. So the rational thing to do is to reduce your level of investment, or at least reduce your signaling of how invested you are. It keeps people from screaming “IN YO FACE!” every time you’re wrong. It is, at minimum, a better way to deal with the possibility of failure than never doing anything productive again.

    As for the price of equanimity, my personal experience is that it does have, at minimum, a social cost. I had to develop some measure of equanimity relatively early in life, for reasons that are not relevant. One thing I noticed, as an outside observer, is that people react to power. And power can manifest in unexpected ways. Making people laugh, or feel any specific feeling, is having power over people. And feelings a very tied to identity, and to how things relate to you. So, for example, if you can make people laugh at your tribal enemy, or make people feel proud of their ingroup, they will react positively to you. You are reinforcing their worldview, and that feels good. If you instead question stuff, you activate deep instincts of protecting the ingroup, and protecting one’s place in the ingroup (because in the wild, being alone is death). So, equanimity at the wrong time will cost you opportunities to secure status in the tribe. It’s a luxury for high status people, who have enough social capital to afford such idiosyncrasies. If you have not already secured your position in the tribe, you are expected to sacrifice pragmatism and rationality, as a costly signal of allegiance.

    From that paragraph, I think it’s easy extrapolate to how the superficial charm of narcissists and sociopaths works, why leadership is usually given to the worst people to hold such power, and why political movements consisting of mainly young people tend to get so crazy so fast. For a soundbitey generalization, genuinely good leaders are mostly either the first ones, who had to be competent enough to create the thing they lead, and the post-catastrophe ones, who have to be competent enough to survive the bad but charismatic leaders until they are the only ones left to clean up the mess.

      • Sorry, that was vague. I was aiming at the idea that the ideas that high systematizing people often use as their grounding is much less stable than they believe. The shoddy version of this is scientism where people simply treat scientists like priests who deliver the truth from on high. The slightly more upmarket version overlaps with LW style stuff, where 99% of people don’t ever check any of those cites (and if you do it will start raising your eyebrows). Chapman has noted that the thing that often leads to the transition discussed in this post is when STEM people get deep enough into their field (PhD level work typically) to realize that they were standing on sand and assuming it was bedrock the whole time.
        It’s proxies all the way down refers to the fact that any legible level of abstraction on which to axiomatically base construction of things is not real.

  4. I don’t think there is a contradiction between being okay with uncertainty and being a person with a healthy self and a strong point-of-view. The tricky thing is to keep convicted while at the same time realizing that – as a result of complexity and ambiguity – there might be other aspects which you didn’t consider. It’s basically a form of self-awareness where you acknowledge the limitations of your own knowledge. And to some extend of what can’t be known with certainty.

    There are domains where you can achieve a high degree of certainty, e.g. math, physics, biology. And there are other domains. Everything social sciences. A fair chunk of economics. They are called soft sciences for a reason. Many challenges that occur in managing companies are in the latter domain. There simply might not be an absolute, correct answer. And even if there were, it would often not be feasible to discover it. It would take ages and cost tons of money; alas companies have to operate with limited resources. Thus, you need to make decisions with incomplete information. It is well researched that under such conditions, singular viewpoints perform worse than groups – given that you have a smart system in place. If you are interested look at prediction markets and stuff like that.

    And once you work with incomplete information, it is super useful to be aware of that fact. In doing so you recognize that you might be on the wrong track. It allows self-doubt. Which is very useful because, unlike strong conviction in such a situation, it helps you to say: “we made a mistake; let’s right the ship”.

    Also, the paradox you mention often isn’t a real paradox. Take the example you give at the beginning: Acknowledging a significant problem while also being convinced that you are working on a thing with incredible potential. These aren’t two contradictory beliefs. Instead, it’s thinking in two different time frames. It’s a dilemma particularly prominent among startups. The core idea you are working on might be directionally right and come with a lot of upside. Say the future of mobility-as-a-service provided by self-driving cars. Yet, there a short-term realities that stand between your current position and the future in which you could potentially be very successful. Think Uber and its ongoing crisis.

    I could go into more detail but will spare you that. I have written a fair deal about these issues elsewhere. For instance in that piece. You might also want to read Nassim Taleb’s The Black Swan and Antifragile (in that order). While those aren’t management books (I’d say: luckily so), his work gives a lot of statistical, logical and philosophical backdrop to the form of management thinking you reference above.


  5. Is the ability to be comfortable with uncertainty the same thing as the ability to maintain multiple perspectives? You seem to treat them as the same but they seem distinct to me.

    I can see some cases where they are equal (when you maintain genuinely conflicting perspectives, as in your example), but in general I tend to think that different views tend to mostly describe different aspects/ways of conceptualizing reality rather than actually make conflicting claims.

    I’m here influenced by the book _Cognitive Pluralism_, which I’m currently reading, and which argues that humans do not have a single consistent worldview in the first place, but rather a variety of domain-specific mental models that describe entirely different aspects of reality and which they flexibly switch between. E.g. our intuitive mental models for modeling physical objects and for modeling social agents have entirely different use criteria and their own specialized inference rules.

  6. Haven’t many of these themes appeared in MacIntyre’s “manager” archetype from After Virtue? Could what you name “equanimity” be alternatively described as indifference to the ends of the activity?

    As the other commenter notes, “equanimity” also has a social cost. It is reserved for the middle manager, while the highest social position belongs to the “aesthete” who selects ends (e.g. a Jobs, or a Trump).

  7. To this discussion I’ll just add that I think you’re seeing a key part of the pattern of reality when you notice the convergence of what effective management looks like. Enlightenment looks the same no matter the path you take to reach it (at least for humans), and that applies to people working in the domain of management as much as anywhere else, although we probably suffer more for less enlightened managers and so think and write more about it.

  8. In my experience as a manager of small-to-medium sized engineering teams, there are at least two not-mutually-exclusive ways to come to terms with the loss of individual strong viewpoint expression that equanimity and being a sounding board seem to demand.

    1. You can surround yourself with people who are thinkers of extraordinary quality, so your sadness at the loss of expression of your own viewpoint is compensated for by the pleasure you take in your ability to understand and amplify their viewpoints. When managers say platitudinous-sounding things like “it’s an honor to lead such an exceptional team,” I think they are sometimes sincere and this is what they are sincerely expressing.

    2. You can gently take the chance to insert your own viewpoint when others are unsure. This happens a lot because people are indecisive a lot, and also because framing works. If you ask whether people have strong opinions, and they don’t, you can offer a well-thought-out “strawman” proposal and often people will just go with it. Also, your means of asking for opinions can often shape the kinds of opinions presented in a direction you want, much as “push polls” can influence people’s expressed political opinions by how they ask their polling questions.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s