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The Uncomfortable Part of Leadership

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So you want to be in leadership, huh?

Get ready to be uncomfortable… all the time.

Here is why putting yourself in uncomfortable situations is so important and how you can turn those uncomfortable moments into growth.

Ss much as the word uncomfortable has kind of become the new “Hustle,” it is a very important aspect of leadership, of business and in particular of driving your own personal performance forward.

And the idea of getting uncomfortable with being uncomfortable is something that I’m coming across more and more. I’m reading a tremendous book from Robert Green called Mastery.

It’s a very thick, very dense read. Lots of examples, lots of case studies, well worth the investment in your time.

In that book, Robert Greene highlights Stoics, Renaissance painters, Suffragists, Civil Rights Activists, Inventors… some of the most brilliant people in the history of the world who’ve mastered the craft in which they work in.

A subtle theme that weaves through every one of these individuals’ lives is their willingness to be uncomfortable.

If these individuals are willing to be uncomfortable, you can be uncomfortable.

I can be uncomfortable.

I think we all should be uncomfortable every day.

Now, frankly, most of us just simply don’t want to be uncomfortable or don’t understand why this might be something that we’d actually have to work into our lives.

If you’re interested in growth, you have to stress the muscle, whether that muscle is your brain, your actual muscles, your skills, your ability, whatever that is, your situational awareness.

These things have to be stressed and there’s all different ways to do that. But the idea of being uncomfortable is not going to come naturally to most of us.

For some of you as I know, because I’m different times in my own life, this has absolutely been the case, creating situations in which you actually are uncomfortable is almost difficult because your job may be very mundane, very routine, and it may not actually in any way create, create stress or, or a situation that challenges you to be better than you currently are.

3 Tips for Being Uncomfortable

1) Growth Mindset

The first is that you have to have a growth mindset. There’s no reason to put yourself in uncomfortable situations. There’s no reason to embrace the idea that you need to be uncomfortable if you don’t have a growth mindset.

Like if you’re not trying to advance your career or your life or your own just wellbeing or, or just your own happiness, being uncomfortable sucks.

There’s no doubt about that. But what you’re hoping is that that that really crappy part that the uncomfortableness puts pressure on you. It forces you to grow, it forces your mind to expand your, your body to expand your, your, your skills, your experience, all that stuff.

It is that pressure that, that, that feeling, that roughness, that that creates true growth.

If you’re not interested in that growth, then there’s no reason to be uncomfortable in the first place.

2) Accept Failure

Number two, you have to accept failure.

If you’re going to put yourself in uncomfortable situations, then really what you’re most likely doing is putting yourself in situations in which you may not succeed.

And you have to be willing to accept that one potential outcome is that you don’t actually succeed and then learn from that failure.

If you’re not willing to accept failure, if you don’t have it in you to fail, then this might not be the right path for you.

3) Let Go of Your Ego

The third and final is that you have to let go of your ego.

You have to let go of that part of you that thinks everyone is attacking you, that you’re always right, that everyone’s out to get you.

If you can’t accept that others may have better ideas than you, that you may have to learn from other people.

If you always have to be right, then you’re in big, big trouble putting yourself in uncomfortable situations.

It is simply not gonna work.

The Rub

How do we make being uncomfortable part of our lives since we don’t just wake up every day and have uncomfortable situations shoved in our faces?

Something I do is I take cold showers.

I’ve talked about cold showers on the show before. They’re very in style right now. I use them partially for the physical and mental benefits that you get. It’s essentially a negative toxin flush out of your body, of sorts.

The other part is I just don’t like doing it. I don’t like taking cold showers. I don’t enjoy going from a very warm, comfortable shower to be very, very uncomfortable freezing cold shower.

By turning that dial every day I’m essentially telling myself you can do things you don’t want to do every single day.

“Do one thing every day that scares you. Those small things that make us uncomfortable, help us build courage to do the work we do.

Eleanor Roosevelt

One Benefit of Being Uncomfortable

Being uncomfortable isn’t just a “You” thing, it actually helps improve the lives of everyone around you because instead of waiting to have a big blow-up with your spouse or your partner.

You would dress that small microaggression that they came at you with when they questioned the fact that you leave too many pairs of shoes by the door immediately either by just doing the thing they wanted to do or explaining why I bothered you that they said that, but what you didn’t do, what you didn’t do is take the comfortable route and just avoid it and let any resentment or negativity or hostility towards that person build up.

And not just with your spouse or your partner, but also at work with your friends, with your peers, with vendors, partners, clients, customers, whoever it is.

By practicing being uncomfortable, you’re willing to intervene in situations that normally you would have avoided so that you could have remained comfortable and taken that small little bit of uncomfortable-ness dealt with the problem and ultimately had a more successful in meaningful communication with whoever that individual was.

It has been my great pleasure to talk to you about the idea of being uncomfortable. It’s something that I haven’t always been good at.

I have been classically an excuse maker, and I’ve had to work very hard at just dealing with things upfront and dealing with that little bit of uncomfortableness in order to ultimately have more successful and happy relationships.

It’s something I struggle with, and if you struggle with it too, I hope this video helped.

If it did, please subscribe, comment and share this video so more awesome people like yourself can find it.

I love you for watching this video.

Thank you,


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