The Old Prom Photo in my Wallet: Overcoming the Plague of Self-Doubt
I periodically clean out my wallet, like any grown woman who’s childhood idol was pre-prison Martha Stewart.
Once, I was doing so in front of my husband, probably during a wait for a flight or for food to arrive at a restaurant. I clacked a variety of debit, credit, and membership cards onto the table like a poker dealer as I got deeper into the pockets that tend to hold the most random items, making a pile of old receipts, loyalty cards, and other junk to throw away as I went.
“Wait…hold up. What is this?” he asks, picking up a photo.
“That? That’s me and my high school boyfriend at prom.”
He laughs and shakes his head. “I’m sorry…what? Should I be concerned that you have a picture of your high school boyfriend in your wallet?”
I playfully snatch the photo back from him and gaze at it. As I stare at myself in the picture, I think of how many times I’ve taken it out of my wallet and done just this. I assure my husband this has nothing to do with an unresolved love from when I was 16 (though, shoutout to Jim! I hope you’re well). The picture sits in my wallet as a reminder, and one I’ve frequently needed.
I’ve kept it as a symbol of a time when I was convinced I was something I wasn’t, and even with evidence to the contrary, I couldn’t see the truth. When that photo was taken, and for at least ten years after, I would’ve told anyone who asked that I went through high school overweight, ugly, and physically unattractive to the highest degree. It wasn’t until I was 30, and home reminiscing through a box of old photos in my childhood bedroom, that I saw the picture again. I was speechless. I had been beautiful, yet I had never been able to see myself or the picture as they actually were, in my twisted teenage and then twenty-something brain. I cupped it like a treasure in my hands, feeling like I was seeing it for the first time, and carried it downstairs. I slid it into a side pocket of my wallet, and I’ve kept it there since.
I’m no stranger to my brain lying to me in a particularly toxic manner, nor am I a stranger to the hard work it takes to overcome this specific brand of toxicity. Growing up, I over-achieved and garnered external praise to manage the voice. Accolades like high school valedictorian, varsity volleyball, first chair in band, lead in the play, and student council president kept it at a manageable, quiet volume. But the floor dropped out from under me when, at 18, I went from my small town environment of 1,500 people to a college of 40,000. Where I had once been consistently recognized for my achievements, I was anonymous. Where I had once heard constant praise, I was met with silence.
I turned to a new method of toxic voice management — anorexia and bulimia. My brain told me that, while I almost certainly wouldn’t be the valedictorian of my 10,000 person graduating class, I could make myself thinner and thus better. Most people who know me today probably have never heard me talk about this brief, but dark, chapter in my life. The summer between my sophomore and junior year of college, the voice and I found ourselves in in-patient and then intensive out-patient treatment for an eating disorder that had gotten to a dangerous point. I have almost no photos from this timeframe, but rather clear memories. I was embarrassed. I was depressed. I was exhausted. And I desperately needed help.
I realized at the age of 20 that these voices, which can seem such an integrated part of our idea of ourselves, can actually kill us if left unattended.
What followed were many years (and ups and downs) of discovering myself and how to challenge what my brain had convinced me was true. It turned out the voice found my professional life as fertile a playground as the personal and academic terrain it fed upon in high school and university. After my parents had helped me find an incredible psychologist for my last two years of college, I connected with another great one upon moving to Boston and starting my career.
Over time, I quietly fought back. I learned, starting with a Cognitive Behavioral Therapy workbook thicker than a college textbook, to consciously recognize when the voice was talking and separate it from my healthy thinking. I learned that when it whispered “you’re the dumbest person in the room,” or “if you f*ck this up, you are absolutely worthless,” I could counteract it by documenting the usually abundant evidence I had to the contrary. Soon, this process happened more organically, and more quickly whenever the voice reared its ugly head. And eventually, the voice shifted from the loudest thing I could hear to that one distant relative who never had anything positive to say, and was easily ignored when they made a rare appearance at the family’s holiday gatherings.
From about 35 to 38 years old, I think I actually sometimes even had an accurate sense of all that I was capable of. I embraced and leaned into my talents — simplifying complex things and leading people through them, inspiring people around a shared goal and helping them reach it, and having the courage to have tough convos with kindness. I looked at my faults with more grace and self-forgiveness than I had ever previously managed, and compared myself less to others. I could even handle criticism and stressful situations better.
(I also deleted Instagram from my phone. It’s crack cocaine for the voice. Highly, highly recommend.)
But you’ll note I have an end bracket on this magical time frame above. A bit more than three months ago, I resigned from my job in order to take a break and spend some time being thoughtful about what I want next in my career. Simultaneously, I found out I was pregnant with our second child. What I had initially envisioned as a timeline of “take three months to relax and explore, then find a job three months later” became “it’s highly unlikely you’ll be back in a full time role until Spring 2025.”
While having this much time is a huge blessing and I know I am beyond lucky to be able to manage it without financial concerns, it’s a shift. And while I’m light years away from where I used to be, I’m still a creature who derives a lot of her worth from overcoming challenges, finding useful solutions, and making the people around her feel good. With busy days full of concrete achievements and fast decision-making replaced with more relaxed days of small to-do lists, long walks, and afternoon naps, I hear eerie echoes of the voice returning.
Whereas I hoped maybe I was cured, it seems I was only in remission.
I recently went to a FemTech conference in London. It was my first time in a professional networking setting without a title and company affiliation behind my name, where I knew no one. There were three levels of reality occurring simultaneously — the actual content, panels, and keynotes of the conference (which were great), the voice’s analysis of how I compared to each person on stage and attendee I met (which was not great), and lastly, my meta observations of the voice and what I should or should not be thinking during the conference (which was just tiring). There were two main stages at the conference, and another two in my brain. What I had hoped would be an inspiring experience to help clarify my future opportunities felt more like two days of muddying my sense of self and my confidence that I could build a future around exciting new opportunities.
I’ve learned that when I feel like this, I need a trusted sparring partner to talk it through with and I’m lucky to have found one in my executive coach, Steve Vinter. From my audience chair at the conference, I scheduled my coaching next session. When I met with Steve, he listened as I ranted about what was going on inside my head and how frustrated I was to find myself even thinking these thoughts again. As good coaches do, he absorbed what I was saying and parlayed it back into a question, asking, “What would bring you joy right now?”
“To be useful, to be challenged, to be doing something that’s actually feeling like it’s building my future,” I said. We sat on that for a bit.
My response led to another thought. “I have this image,” I told Steve, “of lying on my deathbed. I have zero fears that I will have any regrets related to my family or about how much love I gave and received,” I thought of the photo in my wallet. “But I very much think I’ll lie there regretting that I never fully believed in my own potential, and because of that, I never got to achieve and enjoy all I would’ve been capable of.”
“Well then,” Steve said, “I think figuring out how to not end up there is one of the big questions you want to use this time to answer.”
I nodded. As usual, Steve was right.
I’m not sure what comes next, though I think it looks a lot like continuing what I have been doing. I believe that with enough intent, thoughtfulness, and dedication, I will one day find myself more naturally assessing opportunity from a place of “of course I can do this,” instead of “I hope I don’t f*ck this up.” The fear of failure, the idea of people watching me stretch for something far beyond my reach and fumble, sits on my chest. Yet I know the ultimate failure will be letting it stay there, and giving it even more weight.
So, I look at the picture in my wallet. The voice was wrong then, and the voice is wrong now. I just have to keep reminding myself. I will use this time to uncover, to fight back, and while I’m quite certain the voice will never entirely go away, 40 years from now, I’ll be able to say I lived a full life with its volume turned down.
