To Step Into Leadership, Get Comfortable With Discomfort

Peter Chapman
3 min readFeb 12, 2021
Prince Siddhattha is shown travelling to a park in a palanquin drawn by courtiers and soldiers.

Let’s get real: If you want to be doing substantial work as a leader, you’re going to be uncomfortable all the time. Not mildly-spicy, challenging-in-a-fun-way uncomfortable, either. I’m talking deep, existential, I’m-in-the-deep-end-and-I-don’t-know-how-to-swim uncomfortable.

Why is this the case? As a leader, it’s your job to solve problems that other people in your organization are not well equipped to solve. These problems tend to be thorny, ambiguous, and ill-defined. They often span multiple functional domains and don’t have clear owners. They might involve areas of deep controversy, political obstacles, or historic tensions that no one wants to dig up.

Unfortunately for us, our natural inclination is to avoid these problems. Stepping into them — steering towards ambiguity — feels inherently unpleasant. When you do wade into these problems, you may feel anxious, avoidant, and distressed.

You’re on the right path! Without conscious mechanisms to keep pointing ourselves towards the scary and uncertain, we will dawdle endlessly in work that is comfortable and insignificant. The difficult and crucial practice here is to take these internal signals that scream out to us to turn back and use them as a reminder that we are heading into highly fertile territory.

You know what I’m talking about: it’s the thing that makes you squirm a little bit when you think about addressing it. Maybe you’ve been snoozing your calendar reminders about it for weeks. Maybe you keep deciding to tackle it in some indefinite future “once things calm down.” Tackle it now.

Here are some tips to help steer you through and towards ambiguity and discomfort:

Recruit an avoidance buddy

An avoidance buddy is a partner that can help you orient yourself towards difficult, messy problems. Go for a long walk with your avoidance buddy once every two weeks and take turns asking each other, “What are you avoiding?”

Notice when you’re talking about someone who isn’t there

We all gossip. In fact, it can be healthy and productive to use your peers as a means to sanity-check your own reactions and get feedback on potential resolutions. There’s a difference between this sort of productive gossip and unhelpful perseverating. Complaining about someone who’s not in the room can be a strong signal that you’re avoiding having a potentially uncomfortable but transformative conversation. Very often, the sort of powerful, uncomfortable work we’re called to do involves other people. When we call out tensions explicitly and address them directly with our colleagues, we open the door to forging new, transparent, and collaborative relationships.

Label your comfort tasks

A comfort task is something that is familiar to you and makes you feel competent. For a head of marketing, it might mean copy editing. Most technical leaders’ comfort task is writing code.

The trap of comfort tasks is that they feel productive. And they are! They’re just not the most significant thing you can be doing.

I’m not suggesting you spend your entire workday staring at huge, ambiguous problems. It’s totally ok to engage in some comforting, easy tasks now and again, as long as you make that choice consciously. Rather than using comfort tasks as a way to avoid tackling thorny problems, use them to recharge so you’re ready to face the big, scary stuff.

Take care of your body

When we are physically stressed out and undernourished, our capacity for handling emotionally taxing work is severely diminished. To show up as a powerful leader in your organization, allow yourself plenty of sleep, eat in a way that nourishes you, and move your body. If you’re going to get emotionally uncomfortable, give yourself the physical resources required to meet that challenge head-on.

Consume uncomfortable content

In the Buddhist practice of Maranasati, a meditation on death, Buddhist monks spend time observing a corpse going through the gradual stages of decay, noting that this same process will one day consume their dead bodies.

If you want to get more comfortable being uncomfortable, consume content that induces distress. You may choose to read books that remind you of your own death or our impending environmental collapse. Consider it an emotional workout: by consuming content that is inherently uncomfortable, you will increase your tolerance for staying still in the midst of uncertainty and distress.