I first realized that my relationship with self-esteem required repair during a recreational conversation with a female friend 11 months ago. We were talking about my work, the future of it and my role in it, and she was taken so far aback by how unsure of it all I sounded. She asked if I trusted myself; I said absolutely not. She asked if I believed that I had what it takes to earn box office success. I said no — that until this point, I had been really lucky but that I felt the fruits of my labor slowly slipping from my grip. I thought about how frequently I said things like that, how common it was for my mom or my husband to have to try to quell my interminable fear of being exposed as average but how infrequently it worked. 

I first articulated that my relationship with self-esteem required repair during a podcast interview on Sophia Amoruso’s Girlboss Radio. We were talking about fashion and she was touting my willingness to experiment with style as truly courageous. I told her my style had nothing to do with courage, that I used it as a protective shield to defend me from myself — to distract an inevitable confrontation that would ultimately make the truth known: I have no respect for myself. 

Last fall, when I was conducting research for an episode of my own podcast, Monocycle, which would feature an interview with Uber’s chief brand officer, Bozoma Saint John, I was so taken back by the confidence I heard pouring out of her prose. Here was a woman who has said in interviews, when prodded about whether she thought race played a factor in her hiring, that it didn’t matter because no one else was as qualified to do this job — that even if she had been hired because she was black, it was only a matter of time before her employer realized that no one was more qualified to do her job. Or any job she held.

How refreshing it was to hear a woman speak so highly of herself! How novel. How empowering. Though the cycle is slowly but surely coming apart, we have historically been trained to believe that it is arrogant, catty or unladylike to speak so highly of yourself as a woman. It is the antithesis of self-deprecation, which can sometimes run so deeply through us that we forget we are using this storyline the same way I use clothes: as a protective shield. At worst, we begin to believe the lukewarm things we say about ourselves.

I believe this is how it happened for me. I had always known myself to be indecisive but thought it was simply a function of liking to keep my options open. The fewer decisions I make, the more detours I can take. My dad used to call this “flexible thinking,” but as the decisions on my plate have become more important (and higher-stakes), I’ve learned that my noncommittal attitude toward decisiveness is a function of my lack of self-trust and the feeling that whatever decision I make is going to be the wrong one. I’ve always struggled with understanding and recognizing my worth. At times, it has been masked by various accolades or milestones that have validated me, but that external validation always disappears, and like any good drug, it leaves you coming back for more. You crave it, you need it, you do whatever you have to do to get it — become a martyr, a victim, an ostentatious dresser!

That’s when I realized that the past seven years have been a sprint in the pursuit of validation from anyone who will give it to me. It has allowed me to cast aside a much more systemic problem: that I never learned self-esteem, which is arguably because I never had to.

My parents were always so supportive. Of course, this is a privilege, but before I could ever really get knocked down, they jumped to my aid, showering me with superficial compliments and the sort of kindness that serves just enough purpose to delude me into thinking self-esteem is informed by what others say to and about me.

My life has been, for the most part, easy. I have suffered heartbreak in its manifold permutations and one loss that took me to the edge of sanity (this is probably when I learned that my old tricks — seeking external validation, leaning on support from anyone who is not me — don’t work). After hearing Saint John’s story, it occurred to me that her self-esteem is a genuine product of the life she has not just lived but has had to weather, the loss she’s endured and the strength she has been forced to squeeze out of it. 

I’m not sure why I am now feeling the brunt of a lack of self-esteem. Maybe it’s because I recently outed myself as risk-averse. Because I am finally willing to take a leap of faith professionally and launch something new. Because the stakes are different — there is progeny at play and I am only now beginning to understand what love feels like on a cellular level because until now, I’ve shut it out. My lack of self-esteem, for all the defense it has offered, hasn’t really let me feel it. 

But I’m ready — to trust myself, believe in myself, understand my worth for no one but myself. 

For as many times as I have attempted to articulate all of this under the various guises of self-love, self-care, self-respect, compassion and empathy, I see it now for what it is: self-esteem. And with self-esteem will come stronger self-assurance, the termination of insufferable indecisiveness, the wherewithal to just do. To make a difference. To love. To prove, like Saint John did, that I am the most qualified person to do anything — everything! — that is put on my course.

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