I Tried to Get Rejected. It Backfired Beautifully.
Somewhere between the No’s, silence, and spirals… I might have found my future self.
What if the only thing standing between you and the life you want… is 10 uncomfortable questions?
This month, I’ve been running an experiment: Ask for 10 No’s. Not to get rejected (though, yes), but to practice becoming the version of myself who asks boldly and often.
Some asks were small. Some were terrifying. Some never even got a reply.
But one did. And sometimes that all it takes: one yes.
That’s what I’ve been learning this month, as part of the “Rejection Resilience” challenge I started with my AI coach (still quiet, still sandal-wearing, still all Zen mode).
Welcome to week 8, day 57, of this wild experiment.
March Recap
This month wasn’t about subscribers count or any sort of vanity metrics. It was about building the bridge (the one that leads out of corporate life) and making sure it was sturdy enough to hold me - if this sounds too cookoo, check this post to understand what I mean.
We focused on three experiments:
Deep Learning: exploring the history and future of work through writing, on the first half of the month
Rejection Resilience: asking for 10 No’s to neutralize fear, currently in progress
Offline Living: this one has been happening, in the background, for the whole month. I’ll tell you more about it next week.
The way to measure progress we defined as experiences and hours invested in developing these key skills.
The Rejection Tally: 7 Down, 3 to Go
Let’s recap the list so far:
🛫 Airline upgrade: Denied.
🎤 TedX last-minute ticket: No.
🧑💻 A big “No” at work (took effort to earn it).
🏋️♀️ Discounted gym membership: No, but got a flexible package of classes instead.
And then I decided it was time to up the game: to ask for the really scary No’s. The kind that inch me closer to the life I hope to live one day: a life built mostly around writing. These weren’t just asks; they were glimpses into dreams I’d been too hesitant to say out loud.
But I promised you I’d raise the stakes. So I did. Here’s what happened next on the road to the magical 10:
🧑💼 Guest post request to a larger Substack: No reply.
📰 Pitch to a newspaper back home: No reply.
🧠 Pitch to Forbes: No reply.
I am finding that the silence is the toughest form of the rejection. Because silence doesn’t give you feedback. It doesn’t teach you much.
So here’s what helped me keep going:
Having a clear goal (10 rejections) reframes every unanswered pitch as progress
Sharing the process here gives me a reason to try bolder things
The challenge became a permission slip to act like the version of me I want to grow into
Why I Didn’t Reach The 8th Rejection
I pitched a guest post to a substacker I’ve admired for a long time: someone who left corporate, being very transparent about his financials goals and progress, by document his journey shared tips on everything from how to position yourself to how to negotiate, and helped me believe I could do the same.
I expected silence or a polite decline. Instead… he said yes!
This person was the reason I started my newsletter in the first place. So getting a green light to collaborate? It felt like crossing a threshold into a new version of myself, someone who doesn’t just consume stories like his, but contributes to them. This can look like a small step, but to me means one step closer to the life I hope to live one day: write, reflect , collaborate with other like minded people.
Now I just have to write the piece. (Not me spiraling with mild anxiety and excitement about this. Not at all. 😅)
My Own “No”
Last week, I also promised myself I’d practice boundaries, saying No to others, too.
I started simple: I said no to early-morning weekend plans. I love slow mornings, and I wanted to protect them. And guess what? It was fine. We just moved the plans to later. Peace preserved. Energy protected.
March’s Final Week
Here’s what I’ll focus on for the last stretch of the month:
🧘♀️ Keep spending more time offline and in presence
📨 Collect the last 3 rejections and make them bold, scary, close to the life I want
💌 If you have ideas for rejection challenges or April experiments, hit reply and tell me! I’d love to hear from you.
I said no to someone recently that was pretty hard. One of my friends, coincidentally they also have a substack and that's how we met, is writing a book. He asked if I could hop on a call and also read a beta copy of his book. I really wanted to help but I'm just too overloaded right now. I politely said no because I wouldn't be able to give it the focus it deserved but man it was hard.
This was very brave. I salute you. Rejection is really hard. I agree that silence is the absolute worse form of rejection. It is brutal. And the more vulnerable you are in what you have offered, the more more brutal silence feels when you are met with it. Thanks for sharing this with us.