The Unexpected Secret to Good Leadership

My son, who turned 16 this year, spent the last six months learning to drive. Watching him, and recalling my own experience, I remember how uncomfortable it is to drive the first time. There is so much you don’t know, and the stakes are high. Fortunately, teenagers are good at self leadership. The practice every day in school as they stretch themselves, attempt, fail, and adjust. 

As an adult, your ability to eliminate mistakes is often a critical component of your professional success. You likely spend time anticipating pitfalls and mitigating them. As you get increasingly adept at this, you make fewer and fewer mistakes, and you get increasingly uncomfortable with the idea of failure.

Learning is risky. 

When you are new at something, you are more likely to make mistakes. For a high achiever, that means that learning is uncomfortable — especially when you are learning in public, like learning to drive. Yet you’ll never achieve your career ambitions (not to mention your ambitions in life) unless you keep learning. So you need to learn to tolerate discomfort.

Your ability to tolerate discomfort is arguably the most important leadership quality you can possess. No matter how strong your leadership skills are (decision-making, communication, strategy, motivation, goal-setting, etc.), there is always room to grow. Growth is learning, and learning is uncomfortable, so your continued growth is contingent on your ability to tolerate discomfort. That is why it’s the most important leadership trait you can possess. Without it, you’ll never rise to the level you are capable of.

Leadership is Uncomfortable.

Discomfort arises everywhere in work. Here is just a short list of examples I have coached my clients through:

  • Managing a boss who assigns a torrent of urgent work then criticizes you for being tactical
  • Increasing workload, an overwhelmed team, and boss unwilling to prioritize
  • A peer who undermines you in front of your boss
  • A founder in a struggling business trying to decide if he’s spending his time in the right place
  • Slowing down projects in your core area of responsibility to build cross-functional consensus on strategy
  • A newly promoted VP deciding whether to get involved in bumpy client relationships himself or let his team work through it
  • A new manager learning how to hold others to high standards vs. doing it himself
  • A real estate owner deciding to evict a family member who refused to pay rent
  • Pushing back on the CEO when you’ve made your career by being deferential
  • Fully disconnecting for a real vacation for the first time in 5 years

In each one of these cases, either the situation or the resolution was uncomfortable. But your ability to navigate these challenging situations is what differentiates you as a leader. Look at the difficulties in your work as opportunities to learn, grow, and become a stronger leader. Lean into the discomfort, and it will propel you forward so you become a stronger, more confident, and effective leader — both at work and in the rest of your life.

Not your normal discomfort.

Ambitious high achievers are familiar with discomfort, but it’s the wrong kind of discomfort. They know how to push themselves, work hard, set high standards, and stretch to achieve them. That translates to long hours, missed family time, responding to work issues while on vacation, multitasking, and cutting back on sleep. 

You don’t need to get better at self sacrifice. Exactly the opposite. You need to get better at tolerating the discomfort of not doing everything. You need to get better at the discomfort of setting limits, saying no, not responding to every message, and clearly articulating what can and cannot get done. These skills enable you to focus on the actions that propel the business forward. 

Do not wait until the conditions are perfect to begin.
Beginning makes the conditions perfect.

Alan Cohen

Improve your ability to tolerate discomfort so you can focus on the most important work. That is what’s required for you to rise to the next level. Even if you’re already good at this, there is always more to learn, and learning brings discomfort, especially when you’re unsure of the outcome. But if you don’t face that uncertainty, you’ll never reach your goals.

Build your tolerance for discomfort to improve your leadership.

Use these tools in combination or separately to build your tolerance of discomfort, and watch the impact it has on your leadership results.

1. Increase awareness

Have you ever been working on a project, then suddenly realized you are checking email or in the kitchen looking for a snack? That is discomfort at work. It runs behind the scenes, distracting you before you even realize you were uncomfortable. Pay attention to the behaviors you use when you want to distract yourself (email, snack, etc) and to the feeling of discomfort that triggers those behaviors. Awareness is the first step of change.

2. Remember your why

Once you recognize you’re uncomfortable, remember why you’re taking this action. If your goal is important enough, it’s worth a little discomfort to accomplish it. 

He who has a why to live can bear with almost any how.


3. Focus on progress over comfort

Discomfort is temporary, but progress makes you sleep well at night. Picture yourself at the end of the day, and ask yourself what will feel better to you as you’re going to sleep: tolerating the discomfort and taking the action anyway, or distracting yourself with something more comfortable.

4. Reward yourself

Small rewards can help you get through something challenging. If you like chocolate, spending time outside, scrolling LinkedIn… give yourself a small reward time after you accomplish the uncomfortable, so you have something to look forward to.

5. Increase your tolerance

You can build your tolerance of discomfort. Two of my favorite ways to do this are 30 seconds of cold shower at the end of your shower in the morning, and sitting in a chair for 10 minutes and doing nothing (no meditation, planning, reading, journaling, etc). These are uncomfortable for most high achievers. But when you practice with these tools, you are expanding your tolerance of discomfort, so when it comes to work discomfort, you know how to handle it.

Get Started.

As a leader, you are called on to navigate uncertainty, set direction when others are unclear, and make decisions with imperfect information. These skills are essential for good leadership — and they all require the most important leadership quality: your ability to tolerate discomfort. 

Spend five minutes right now thinking about a work goal and what actions you can take to accelerate your progress. Most people I talk to have a list of ideas that they would love to do, but there is a reason why they can’t. Challenge those reasons. Tolerate the discomfort of going beyond what you think is allowed, and do the work that really moves the needle. That is true leadership.

Photo credits: Markus Spiske, Jackson David,  Christina, Adolfo Félix on Unsplash