Lean Into Discomfort

How to apply courage.

When I asked my role models about the most important principles or values of leadership, things like honesty, ethics, loyalty, and quality came up several times. While I absolutely agree, I’ve seen a lot of people that live those values fall desperately short of what I’d call leadership. The downfall to anyone with ambition, especially a leader, especially in an organization is a lack of courage.

A beautiful definition from one of the best people I’ve ever met:

Courageous leadership.  Courage – from the French – often used in English as shorthand for macho (which it is not) or bravery – which it requires, but is not the thing. Courage – is of or from the heart.

I’m going to define heart in the next essay. First, let’s talk more about courage. Courage, to me, is the ability to do what you know is right in the face of backlash, consequence, and pain. Pushing through discomfort to the place you know you should be.

The Flinch

At the moment that we encounter discomfort, as we face that instant where we decide whether to push on or back away, we flinch. It could be the wince before stepping into a cold shower. It’s the deep breath before we knock on the boss’s door to give bad news. It’s the hesitation to start the sentence “we have to let you go.”

It’s these tiny little moments that determine whether we actually live the way that we know we should. Everyone can sit down and write out principles to live by that would make them an amazing person. Not very many can consistently live them.

Pushing through this flinch, and sometimes eliminating it completely, is a trainable skill. If you don’t believe me, consider professional boxers. Over time they’ve trained themselves to not flinch, but to react, when someone is trying to PUNCH THEM IN THE FUCKING HEAD. The most evolutionary instinct of self-preservation is managed through practice. (Julien Smith talks more about this in his book, The Flinch)

Could the discomfort be a sign that I’m about to make a mistake?

Maybe, but that’s usually a different kind of discomfort. Thinking hard about where it’s coming from can give you that answer. When we’re about to do something and we feel discomfort, it usually comes from one of two places:

The first is that sinking feeling that we’re unprepared or haven’t thought this through.

We should absolutely listen to this one. Many times, we know if we’ve half-assed our preparation. It’s feels quite a bit like guilt. Depending on the stakes, and whether we have a tendency to over-prepare or behave like a perfectionist, we might have to push on before we’re comfortable. This feeling is usually a bit weaker than the second one.

The second one is fear. Either that we’ll fail or that we’ll be judged harshly because we’re not going along with what everyone else is doing.

This type of discomfort is pure gold.

We should seek this discomfort as often as possible and when we find it, we should go after it with everything we’ve got. Why? Because this is where growth happens. This is where innovation happens. This is where making real changes to the shitty status quo happens.

“You’ll know you’ve opened the right door when you feel a strong, irresistible impulse to do something else, anything else.” – Julien Smith

When we find things that elicit this strong of an emotional response, we know we’re on to something. The thing that you most want to avoid is probably the one thing that you actually should do. Let’s talk about how to deal with that fear.

Dealing with the fear of failure

When we develop attachment to expectations, we overweight results and spend an inordinate amount of time thinking things like: will I hit the target, will I miss it, will I fail, idk if this is working, shit I missed it, I did my best but fell short, yayy I hit it, yes! it worked. In most settings, we should measure things. Progress, problems, performance, etc… But when the measurement becomes the goal, we’re missing the point. What is much more useful, what will actually help us, is the learning mindset.

Use performance against metrics as feedback to help you learn, not as judge, jury, and executioner. If you ask my 4 year-old daughter what happens when we fall, she’ll say “we learn.” But if we don’t look at our successes in the same way, learning about what works and what to double-down on, we leave a lot on the table.

Taking this learning mindset, as opposed to a hyper-focus on whether or not we’ve met (often) arbitrary targets. Many “goals” set by organizations are either unreasonably high in the name of motivation, or unreasonably low in the name of predictability.

Don’t let them dictate your self-worth.

Dealing with the fear of being judged harshly.

Going against the grain, interfering, is scary for good reason. It used to kill us. Literally.

“Homo sapiens is a communal species that delves in groups. … That fear of ostracism, which is engraved in our DNA, is the reason why social situations can induce anxiety in some people. Public speaking is specially anxiety inducing because the situation itself makes us feel threatened.” – Julia Pardo

In hunter-gatherer days, if you went against what every one else was doing you probably got kicked out of the group and had to fend for yourself. And you probably didn’t last long. Our DNA hasn’t caught up to the modern world. If you screw up socially, you won’t die.

You might be laughed at, or get fired, or you might trend on twitter for a day if you really screw up, but you’ll be fine. The worst case scenario is no longer getting eaten by a lion, and that’s a good thing.

So I should just YOLO against everything that I think is wrong?

It’s not that simple. Meet King Pyrrhus of Epirus.

His army defeated the Romans at both the Battle of Heraclea and the Battle of Asculum, in 280 & 279 BC respectively, during the Pyrrhic war.

In both victories, lots more Romans were killed than Pyrrhus’ soldiers, but the Romans had replacements and Pyrrhus did not. So the report read:

“If we are victorious in one more battle with the Romans, we shall be utterly ruined.” and “Another such victory and I come back to Epirus alone.”

This is the origin of the term Pyrrhic victory, a victory that inflicts such a devastating toll on the winner that it negates any true sense of achievement.

If your purpose is to shift the culture of your current company, you won’t be able to do that if you’re not allowed in the building.

So we come, again, to finding the Middle Way between courage and self-preservation. You can’t be so bold, so rigid, that you give up your position of influence to win a small battle. Focusing on your purpose, i.e. the war, will allow you to know when to push and how hard. And when a tactical retreat is the best move.

That’s why the principle is to lean into discomfort, and not to burst through it like the kool-aid man.

For most, pushing too hard isn’t the problem. It’s having the courage to find that discomfort and lean into it.

Courage is foundational

Without courage, every other leadership principle, every other core value, is softened. Made weak by a lack of fortitude to push past obstacles to do what we know we should.

This is another concept that is misunderstood to be a personality trait, but it’s a practice. The goal is not to eliminate fear. But to understand it, throw it in your backpack, and go on doing what you know you should.