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On leadership, self-esteem, and confidence

August 2019

Joe and I have a bit of a reputation. We’re known to have a high level of self-esteem — so much so that we’ve been asked “how do we do it?” quite a few times.

In this essay, I’ll try to answer how I think about it:

A. Your goal is to convince yourself that you are a confident leader with high self-esteem

Your inner critic knows you best, and they’re the hardest to convince. Yet they are the most important person that we need to convince: all our behaviors and beliefs stem from there.

Now, you could try to convince your critic by describing yourself as a confident leader with high self esteem: “Oh I’m confident, oh I’m a leader”

But your critic is too smart for that. If you try this the words will seem hollow. After all your inner critic knows what you really think.

To truly convince our inner critic we’ll have to get more concrete: what do these words actually mean?

To convince your critic, first

B. Identify the behaviors behind self-esteem, confidence, and leadership

Take a step back and ask yourself: what do these words mean to you?

Self-esteem: To me, self-esteem means you have strong core values, which you won’t change to appease other people. You are okay with who you are. You are capable of being vulnerable and risking rejection, because you value your self-opinion higher than those of the crowd.

Confidence: To me, confidence means, you go after ambitious goals because you believe you are capable of achieving them.

Leadership: To me, leadership comes from taking care of other people, empowering other people, thinking of others before yourself, doing the hard work, inspiring others.

Now you can start to describe yourself with these behaviors

Instead of I have high self esteem, you can say

  • I have strong core values

  • I stand up for what’s right.

Instead of I’m a leader, you can say:

  • I am a person who looks out and takes care of people.

  • I am a person who coaches and empowers people.

At this point your inner critic will start to listen…but we’ll need to do more before it catches on. To truly cement those beliefs:

C. Prove out behaviors with your actions

As life goes on, you’ll come across many opportunities to help others, to stand up for what’s right, to dig the ditches and do the hard work.

To illustrate how frequent these opportunities are, let’s think about something very simple. Say you want to meet your friends

  • Instead of waiting for people to invite you, take initiative and invite others
  • When you’re choosing where to eat, instead of asking yourself where you specifically want to eat, ask yourself, where your friends would enjoy eating the most
  • When you’re about to order, instead of thinking about what you want to eat first, think, would the group like some appetizers or drinks?
  • Now say you arrive, and you notice one of your friends drops a fork: take the initiative and pick it up, ask the waiter to help
  • Say you’ve been at this restaurant a few times, introduce yourself to the staff, and thank them for taking care
  • Say at the dinner there’s a pretty person you’re interested in, but they say something you disagree with. Stay strong and say what you think (I still struggle with this one :P)

These opportunities are everywhere. Notice them, pick them up, and all of a sudden, your description of yourself gains strength. With that you can begin to make the jump and tell yourself “I’m confident”. This time the words have depth.

The best part of all of this is that your internal critic will change roles: from critic to advocate. Initially, all they did was hold you back. But, as you train them to describe you with positive and worthwhile behaviors, the tone will shift: when something bad happens, they’ll start giving you reasons why everything will be okay, why you have the strength to deal with this, why you will behave with class.

This will reverberate throughout your life.

End Notes

1) One thing that helps: role models for these behaviors.

Personally, adventure novels (Scaramouche, Captain Blood) and anime (Naruto, One Piece) left an imprint on me. I often think about what some of my favorite characters would do in certain situations 😄.

2) One thing to watch out for: ego

It’s easy to take this thinking too far and begin to think you are special, an exception. You don’t have actually pay the price, you’re born this way. This is a recipe for disaster and it is very easy to fall into, especially when you receive praise from others.

What helps me:

  • Remember that we are all one, a part of a community. It’s weird to say this, but in case you don’t already believe it: All human life is worth the same, no matter what we do.
  • Tie your self belief to your actions: it’s easy to stop being a leader: all you have to do is let it get to your head and stop caring for other people.

3) This may generalize

Thinking about it, this generalizes to a whole bunch of other characteristics. How do you become a great communicator, or how do you become a great writer, an exceptional engineer? The steps seem the same. Something to think about!

Prior Art

  • James Clear talks a lot about the effect describing yourself can have in his book Atomic Habits. Highly recommend reading

  • My previous co-founder Sebastian Marshall would always tell me: judge yourself by your actions. This definitely played a part in my philosophy

And with that, we have a rough roadmap for leadership, self-confidence, and self-esteem 🙂

Thanks to Alex Reichert, Giff Huang, Joe Averbukh, Luba Yudasina for the review

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