Back to Blog

How You Feel About Yourself Shows Up In Your Leadership

“If we truly loved ourselves, we’d never harm another. That is a truly revolutionary, celebratory mode of self-care.” – Sharon Salzberg

In her latest book, Real Life: The Journey from Isolation to Openness and Freedom, Sharon Salzberg walks us through the ways to move from fear to love, from constriction to openness. Sharon’s conversation with Jerry on this week’s podcast made me think of the ripple effect of our self-evaluations in our lives and leadership.

Our behavior, feelings, motivation, and thoughts are directly influenced by our self-evaluation. If in your own internal experience thoughts of diminished self-worth or a raging inner critic voice with the volume up loud are more common than not, the psychic weight of that inner reflection will impact how you show up in your leadership. A non-generative sense of self makes you see the world, and your colleagues and fellow humans in it, differently.  

If you are being a jerk to yourself, you’re likely to be a jerk to others. In his TED talk, The Benefits of Not Being a Jerk to Yourself, Dan Harris speaks to this impeccably well. He talks about his own experience discovering his negative self-talk and how it affected how he showed up in every relationship in his life. Ultimately, changing your relationship with yourself (which affects how you speak to yourself which further affects your interpersonal interactions) is key to shifting out of what Dan dubbed “the Toilet Vortex,” that space of negative self-talk and negative self-perception. Healthy self-love is not selfish, he asserts. 

“Of all the judgments we pass in life, none is more important than the judgment we pass on ourselves, for that judgment touches the very center of our existence.” writes Nathaniel Braden in his book Honoring the Self. 

Untended to, self-judgments spin out and can potentially hurt the many others in our life: the ones we lead, the ones we live with, the ones we collaborate with. Think about it: If you’re having a bad day, and you feel really crummy about yourself, how do you show up with others? An example: some folks who have a really harsh and demanding inner critic about their own leadership performance, have that same demanding critique of their colleagues and direct reports (which those people then feel). 

Another place this can show up is in your motivation. For some folks whose self-evaluation goes on a downward spiral, they can shrink themselves and their efforts in light of the things needed to be executed upon. In the downward spin of negative self-thoughts and subsequent feelings, it may be easier for one to lay low, do busy work-type tasks, or ‘coast’. Being in such a state makes it hard to manage oneself as well as manage others.

Here’s an exercise: Write free-form and in stream of consciousness about this question: How do I feel about myself? Include things you like about yourself and things you don’t. When you feel complete in your response, reread what you have written. 

  • What did you discover in your responses to the prompt above? 
  • What do you notice about your self-evaluation and how you lead in work and other areas of your life? 
  • What feedback might have you received in the past about this? 
  • What comes up for you when you consider your inner dialogue? 
  • If you were to be your own support system, best parent, or safe friend, how would your inner dialogue shift? 
  • Can you recall a time when your self-perception was positive? How were your interactions with others at that time?

When things get tough in life, some people’s thinking tendencies fall into the camp of touting that “the world sucks” and some go into the camp of touting “I suck.” For the folks that fall into the “I suck” camp, we trod an increasingly lonely path of waning self-worth. Often, this points to a deeply held belief we may have or a story that we tell ourselves (and believe to be true!). 

A challenge for those of us who fall into the latter camp, via poet Lindsay Rush (@maryoliversdrunkcousin) is to practice BYOBF (Be Your Own Biggest Fan). She offers us a model in her poem below as an alternative to our internal critics (our internal ‘shitty committee’) and other well-worn, heard-it-before negative self-talk tapes we have in our brains. Repeat after me: 

Two Very Enthusiastic Thumbs Up – by Lindsay Rush

Today I will be my own best critic / I will give myself 5 stars just for showing up / I will notice every nuanced effort and fine touch / I will applaud the debut performances of new talents / or habits / I will rave about the pacing, the blocking, the lighting, the writing / I will exclaim that this is the best life I’ve ever tasted / I will close my eyes and chew slowly / I’ll give compliments to the chef / and the director / and the artist / and the muse / (me, me, me, and also me) / I will dub myself the voice of a generation / ahead of my time / reinventing the genre / blazing a new trail / a savant / “who knows what she’ll think of next!” / I will insist that everyone see the show / at least once / if not twice / there’s not a bad seat in the house / I will write up the review nicely / unlimited word count / no edits / post it in the Sunday Times / 10 out of 10 would be me again.


Embracing Leadership as a Reluctant CEO This essay is written by one of our first alums from our CEO Bootcamp, Sooinn Lee, CEO of LocoMotive Labs. Last fall, Sooinn also spoke at TEDxBayArea Women in a…
Still Standing Still Years ago, I wrote that founding, running, and working in a startup can often feel as if you’re often feel as if you’re standing still while your hair’s on fire.…
How I met Jerry & Why I do this work “I want to learn how to become a better entrepreneur,” I told him, sitting on the plush couch in his office. My mind wandered over and found momentary stillness in…



The Reboot Podcast with Jerry Colonna, Team Reboot, and Startup Leaders

Check out the episodes

Social Media

Follow us on:


Follow our Medium publication for reflections on leadership and resiliency.

Subscribe to Medium