Winging it

And why it's a perfectly good way to proceed

Good morning!

How the devil are you? I hope really well, despite everything.

I’ve just started a new job in what could be called a leadership position. And what that means, to me, is that I’m helping a team of people do what they do, brilliantly, whilst knowing no more about it than they do.

In fact, I know a lot less about it than they do. I don’t yet know who any of the people in the organisation are, I don’t know how they do things, and I don’t understand what we’re trying to achieve.

As we go on, I’ll learn all of this stuff, but I still won’t know much more than they do. Each of them has specialist skills that I don’t have. I couldn’t do their jobs for them. I’m there to support, to learn with them, and to construct better ways of working.

And that doesn’t mean I’m going to do what our politicians do and make strong, ‘robust’ statements never under any circumstances letting on that I don’t know whether it’s the best way forward or not.

In his brilliant column, Oliver Burkeman argues that we don’t want them to let on that they don’t know what they’re doing either, as much as we might say that we do.

We need them to appear ultra-competent, too, because we derive much psychological security from the belief that somewhere, in the highest echelons of society, there are some near-infallible adults in charge.

It is good to think that someone, somewhere, knows what they’re doing.

Scott Belsky spoke on the Tim Ferriss podcast a while ago about leadership. He compared leading teams to taking your friends on a car journey in which none of you can see where you’re going:

“I use the analogy of driving your team in a car with the windows blacked out, so no one knows where they are and how far they are in the journey. And that is sort of what a startup experience is like, by the way. You don’t know where those milestones actually are. You don’t necessarily even know where you’re going and how far along you are.

The only thing that makes that more comforting or tolerable is a great narrative during the journey. Okay, we just crossed the state line. There’s this on the right. There’s this on the left. Even if it’s not necessarily answering the question of how far are we and where exactly are we going, there’s something about being talked through it. And I think that’s one of the jobs of someone at the helm is to build that narrative.”

- Scott Belsky

It’s reassuring that he could be honest about this. And if we look carefully, we find that the people who do have a good grasp of the world, how it works and how to be a person in it, will admit that they are feeling their way, tentatively.

They will confess that they make mistakes. They will be honest about their failings, the things they don’t know, and what they find hard. Without shame.

Shame prevents us from looking at things that have gone wrong. Shame encourages us to push feelings down, turn away from painful memories, don’t look. Don’t look at what happened.

But this prevents us from working out what we could do better next time.

People who can look their shame squarely in the face, admit the things they got horribly and shambolically wrong, remind themselves that they are just a person who tries, and that’s good enough, can do anything.

And the people who will admit that THEY DON’T REALLY KNOW EITHER are worth sticking with through thick and thin.

Here’s Rainer Maria Rilke, writing to a young poet at the turn of the 20th century:

“Do not assume that he who seeks to comfort you now, lives untroubled among the simple and quiet words that sometimes do you good.

His life may also have much sadness and difficulty, that remains far beyond yours. Were it otherwise, he would never have been able to find these words.”

- Rainer Maria Rilke

The advice columnist Heather Havrilesky writes under the moniker Polly Esther. She says the same thing, in fruitier language:

“When I talk about my husband and my kids and my choices, I am offering one small, narrow, muddled, sometimes even impulsive or bewildered or inherently faulty perspective on life.

Yes, I have the bad habit of dragging these things out into the light of day with an arrogant EVERYONE SHOULD DO THIS tone to my braggy voice! Dude. THAT’S JUST HOW I FUCKING SOUND. But dude. Dude. Dude. Dude. I don’t know what the fuck I’m doing and I never have. 

I am just a person who writes down words to solve PEOPLE PROBLEMS as best she can.”

-Polly Esther

This admission that we’re all just working it out as we go along is A Very Good Thing.

If no one knows what they’re doing, if everyone is grappling with uncertainty, then we have as much chance as anybody of finding happiness and making the things we want to happen, happen.

We don’t have to know how to get where we’re going. We just have to want to get there enough.

And we may not get where we’re trying to go either. We may end up somewhere better:

“I may not have gone where I intended to go, but I think I have ended up where I needed to be.” - Douglas Adams

As we lead ourselves or other people, the best thing we can do is to pay attention to what’s directly in front of us.

Talk about what’s happening now. Build that narrative. And be honest. If the last 12-18 months have taught us anything, it’s that we can’t possibly know what’s coming.

Take care of yourselves, and if you’ve got this far, you may enjoy more regular mini-essays from me. I write posts on my Walk the Pod Patreon page every few days.

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Lots of love, thank you for reading, and please remember to speak kindly to yourself today :)

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Rach xx