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.