Stories of times I tried too hard, wanted to prove myself, wished I could get to the next level — and failed in some cringe-y way.
Because it's a gift to see others' failures and secretly think "me too."
Noah Kagan agreed to a phone call interview with me a couple years ago. Scheduling options were "wait a couple months" or "I'll try to call sometime sooner." I picked the latter and put his number in my Favorites, so his call would come through even in sleep mode.
Later that week, I tried to turn down my phone's volume while driving. Repeatedly mashed the button and nothing happened. Suddenly I got a call from 911 — I'd been hitting the power button, activating the emergency response. All of my emergency contacts were immediately sent my location, including — CRINGE — Noah. Because I'd also set him as an emergency contact, to make sure I REALLY didn't miss his call.
He was incredibly nice about it and made sure I was okay. We did not do that interview. Sorry again, Noah!
I cold emailed a famous VC partner to be the guest speaker at my dinner party. I'd seen her at a Duke event, so I said there'd be several alumni there. She said yes. I was ecstatic. I invited every SF Dukie I knew, plus a ton of other people. The menu: make-your-own pizza, with gluten-free crusts I made from scratch.
Event day arrived. Every single Duke person from my guest list bailed. I frantically invited more people, moved my mattress into my closet so we could sit on my bed platform. Eight people showed out of the ~75 I invited. The VC sat on my bed-less bed in her Duke swag while we all ate pizza. She was nothing but kind about the whole thing.
I desperately, desperately wanted to work at Copia a few years ago, so I had a plant delivered to their office with my resume. They never responded, but they all stalked my LinkedIn profile.
I once cancelled my own dinner party the day of because I was exhausted and felt guilty asking for help.
The day had started at 3am when a tenant texted that another tenant had punched him. (I was a building manager on the side.) The problem tenant then pulled the fire alarm at 4am. The building evacuated, and the police showed up. I taught two fitness classes, then got called back to the building — the tenant had turned on all of the faucets in his apartment and left. Water was dripping down the walls two floors below. The police had to break through the wooden door because the deadlock was bolted. I called repairmen, building owners, cleaning crews.
The event was in a few hours. I hadn't started cooking or cleaning. In tears, I texted each guest. The event speaker had bailed earlier that week, and I couldn't take more disappointment. I never shared the details of what had happened that day.
I was turned down for a job because I tried too hard to seem competent.
I made it to the final round interview with the founder, competing against one other candidate. I thought everything had gone well — there wasn't a question I couldn't answer. They rejected me. The thoughtful feedback that came later: my abilities weren't the issue. My attitude was. My desperate need to prove myself came off as too aloof.
The then-seed stage company raised its Series E this year.
I paid $150 to talk to Penelope Trunk. She offered discounted coaching sessions one year and I broke my budget to buy the call.
She had me in tears in the first 10 minutes. She said I needed to focus on finding a partner, that the long hours at work weren't worth it, that I'd already have become successful if I was ever going to amount to anything. The worst part was how clearly she could see me. I couldn't create an excuse that lessened the pain she uncovered.
Five years have passed and we are close friends. She's controversial, blunt, and calls me out. Sometimes I have to take breaks from that feedback. She told me recently that trying so hard makes me worse at my job — but that I'm going to have to support my partner, because I'm too good at working to give it up.
I was in charge of Alexis Ohanian for an hour and accidentally made him late to his next meeting.
Alexis was an early investor in my previous company and kindly agreed to do a Q&A session at one of our weekly lunches. I greeted him at the door, showed him the way, gathered the company. Wanting to be fully present for his words, I left my phone at his desk. There were lots of questions. Alexis graciously answered them all.
As he was leaving, he pulled the Reddit sticker off his computer to replace it with our company logo. I secretly kept the sticker instead of throwing it away. (It's still on my personal laptop.)
When I got back to my phone, there were multiple texts and calls from his Chief of Staff. We'd run over time and he wouldn't make his next meeting. I'd failed my one job.
I blew off concert tickets for a Launch House event to prove to myself I was good enough for an invite.
An a16z person told me about it and said they'd get me in. Their schedule changed and they redacted the invite. But I'd been sold on the coolness of going — the event was in Paris Hilton's old mansion, and I'd never been to Beverly Hills. I saw they were taking applications for spots, so I applied. Heard back an hour before the event that I was in.
I took a pricey Uber into the hills, tried to hang with all the web3 speak, dutifully listened to the a16z partners, exchanged contact info with people I never spoke to again. The concert had ended by the time I got back, and I was disappointed in myself for picking status games over something I actually enjoyed.
My worst cringes are probably yet to come, but all I can do is keep trying.
Behind every person who seems like they've figured it out, there are a pile of painful moments that make them who they are.