My 100-Rejections Challenge

Two days ago, I had what I thought was a brilliant and original idea: I would seek rejection 100 times and document everything about it.

Where did this idea come from?

I’m a cliche, you see. Have you ever heard of a mid-life crisis? I turned 40 a couple of months ago and immediately started to hyper-focus on the things I haven’t done. All that introspection led to one glaringly obvious conclusion:

I HAVEN’T BEEN DARING ENOUGH.

Sure, I’ve done things that would require gumption. After all, I willingly quit a cushy corporate job to become a YouTuber and entrepreneur. I got divorced. I went on international trips by myself. I became a public speaker. I even (briefly) entered the treachours world of online dating (I’ve got the stories if you’ve got the time). But each of those was preceded by careful thought and deliberation. For the most part, I’ve never been the type to shoot from the hip.

Then something occurred to me. The missing piece in all this is a Yiddish word that’s become part of our vernacular: Chutzpah. Everything I’ve done thus far is good and fine and relatively brave, but it’s still not 'ballsy'. I’m still not flying by the seat of my pants when that’s what I need to do.

Truth is, I fear rejection. It’s why I never played full-out when it came to sales, business development, personal branding, or networking. In my mind, it’s why I didn’t achieve the Oprah-level success I’d previously envisioned. I couldn’t silence that inner asshole that said, “Why would anyone want to listen to you? What do you have to offer?”.

Enter the 100-Rejections challenge. Call it a cop-out if you want, but I figure if I deliberately seek it, getting rejected won’t feel so much like a failure. And through the process, I’ll gain insight into crafting more intentional asks.

Welp, turns out, this is already a thing …

It’s a movement called ‘Rejection Therapy’, invented by Jason Comely and popularized by Jia Jiang. Did I go down a Rejection Therapy rabbit hole the very day I learned bout it? Does a bear poop in the woods?

So maybe my idea wasn’t groundbreakingly original. Who cares? As a result, I’ve decided to do things a little differently. In their versions, Jason Comely and Jia Jiang took on challenges ranging from fairly innocuous to delightfully whimsical. Some even went viral.

But I’m going to stick to my original vision. I want to take on challenges that are directly connected to my work - things that have historically caused me to tremble in my boots. I can travel solo and befriend a stranger in a restaurant, no problem. I’ll wear a rainbow tutu and dance around to ‘Thriller’ in a park. Been there, done that. But ask me to send a cold sales email or ask an influential person to appear on my podcast and I’d rather confront a literal bear mid-poop in the woods. So that’s what I’m going to do. No, not confronting the bear. The cold outreach.

My 100-Rejections challenge may not be as entertaining and sensational as the ones that garnered national attention. But, I believe it’ll be worth it. And not just for me...

There are many people in my life, South Asian women in particular, who, like me, have never put themselves out there. They weren’t encouraged to be the misfit, the troublemaker, the one who lets their freak flag fly. I want to show them (and myself) what happens when you’re unabashedly daring, when you chip away at your ‘daakshan’ (hesitation) every day, and little by little you finally get to your fiery core and unleash the badass within.

By the way, if you want to keep up with my 100-Rejections challenge, head on over to my substack where I will eventually chronicle Day 1.

Am I nervous? Does a bear … ok, you get the idea.