The Jump
The Unceiled Alice Series — Part 2: Taking Risks & Oh Shit Moments
In my last post I talked about curiosity. About the White Rabbit. About what it means to feel that pull toward something more. But curiosity alone doesn’t change your life. The jump does.
After Alice sees the White Rabbit cross her path — one of the most influential moments in the book for me — she follows him to the entrance of a rabbit hole. She watches him jump. Her curiosity is completely piqued. She wants to know where he went, what he is rushing to and how there is even a talking rabbit in the first place.
And then she hesitates.
She peers down into the darkness and she knows — this is completely irrational. In the 1951 Disney film she even says it out loud —
“Curiosity often leads to trouble.”
And then she follows him anyway.
What happens next is one of the most vivid scenes in the story. She falls — slowly, surreally — for what feels like minutes. Clocks, books, food, lessons, mirrors flying past her. Time loses all meaning. She is no longer where she was. Not yet where she is going. Just falling. The full weight of her decision hitting her on the way down.
And then she says something that has stayed with me my whole life:
“Well! After this I should think nothing of falling down stairs.”
In other words — I survived that. I can survive anything.
When I read that as a kid it gave me a framework for something I didn’t yet have words for. That feeling you get when you do something brave. When you take a risk because you’re curious about what’s on the other side. Sometimes it’s exhilarating. Sometimes it feels exactly like falling — disorienting, scary, all the you can’ts and you shouldn’ts rushing past you on the way down.
But I loved the feeling when I came out the other side. Stronger. More myself.
One of the most pivotal jumps of my life was the decision to go to college.
I didn’t consider myself particularly smart. I had no burning desire to attend the best school or collect acceptances. What I did know — deeply and urgently — was that I had to leave my hometown. That I desperately wanted a world bigger than the one I had grown up in.
I was 17 when I started. And in what I can only describe as a spectacular coincidence — I was placed in senior apartment housing on campus with the only other Indian girl enrolled. So there I was. Seventeen years old. Living with juniors and seniors. Some of them over 21.
As you can probably imagine — without a burning desire to be top of the class and surrounded by basically adults — I did not exactly thrive my first semester. I earned a 1.9 GPA. And if that wasn’t enough — I also got kicked out of campus housing for being too noisy and having boyfriends spend the night.
At the end of that semester my mom gave me a choice. Get your act together. Or come home, go to junior college, get a job and pay rent.
I sat with that for a long time.
It would have been easy to go home. Easy to convince myself I didn’t deserve to forge my own path. Easy to let that first semester be the whole story.
But I didn’t go home.
That ultimatum from my mom was my first major Oh Shit Moment.
I didn’t have a name for it then. I didn’t name it for myself until about five years ago. But looking back — it was the moment that taught me everything I know about how to move through the hardest parts of life.
Here’s what I’ve learned about Oh Shit Moments.
They are inevitable. Every jump has one. Sometimes it hits on the way down — that sinking realization of what you’ve just done. Sometimes it hits after you land — when the gap between where you thought you’d be and where you actually are becomes very clear. And sometimes — if you’re lucky — it’s a good Oh Shit. The kind where you can’t quite believe how far you’ve come.
But the real power is in the uncomfortable ones. The Ohhhhhh….Shiiiittt kind. The ones that sit in your chest and won’t let you sleep.
Because if you can pause in that moment — really pause — something extraordinary happens.
When my mom gave me that ultimatum I was angry. Disappointed in myself. Scared of the future. I let myself feel all of it. The anger at her. The grief over a wasted semester and the money she had worked so hard for. The fear that maybe I really wasn’t cut out for this.
I didn’t rush past any of it. I let each emotion move through me until it was done.
And when it was — I felt peace.
That process taught me something I have used every single day since. When you are in the middle of an Oh Shit Moment — don’t perform your way through it. Don’t skip to the lesson before you’ve felt the feeling. Sit in it. Breathe through it. Let it move.
And then — when you’re ready — ask yourself one question:
What am I meant to take from this?
The biggest thing that Oh Shit Moment taught me was this.
When everything feels uncertain — go back to your why. It’s like putting your bare feet on the ground. It brings you back to yourself faster than anything else.
Once I had let the emotions have their space I asked myself the question that changed everything.
Why was college so important to me?
Everyone has their own relationship with education and I hold no judgment for any path. But for me — from a very young age — education meant freedom. Financial independence. The ability to stand on my own two feet and never need anyone to take care of me.
I had watched my mother be controlled — physically, mentally and financially — by a man who should have protected her. I had made a quiet vow to myself somewhere in those mountains where I grew up that I would never allow that to be my story. That I would never rely on anyone other than myself. For anything.
College was never just school. It was the first concrete step toward that promise I had made to myself.
And when I remembered that — really remembered it — giving up was not an option.
What happened next still surprises me when I think about it. I found a full time job thirty minutes from campus. I sat down with a counselor and intentionally mapped out every class I needed to take. I went to school fall, winter and summer every year. I moved into my own apartment. I worked my way to a 3.9 overall GPA — yes including that 1.9 first semester.
But more than the grades — I fell in love with learning. I would go to the library at night and spend hours researching and writing papers and just following one idea to the next. I found joy in it. Real joy. The kind I hadn’t felt since I was a little girl hiding with her books waiting for her mom to come through the door.
The White Rabbit had found me again. This time in a library at Sonoma State.
I want to leave you with something you can actually use. Because Oh Shit Moments don’t stop coming. Not when you get more experienced. Not when you get more senior. Not when you think you’ve finally figured it out. They just change shape.
What changes is how you move through them.
Here is how I actively and intentionally work with Oh Shit Moments — in my life and in my leadership:
Name it. Write it down. Sometimes I walk away from it for a specific amount of time — 24 hours, a week, whatever it needs. Distance is not avoidance. It’s perspective.
Feel it fully. Don’t perform your way through the emotion. Don’t skip to the lesson before you’ve lived the feeling. Let the anger be anger. Let the disappointment be disappointment. Let it move through you until it’s done.
Go back to your why. Ask yourself why you made the decision in the first place. Is that still true? If yes — that’s your ground. Stand on it.
Ask the one question. What am I meant to take from this? Not what went wrong. Not who is to blame. What is this moment trying to teach me?
Find one next step. Not the whole plan. Not the full recovery. Just one next step. That’s enough.
The Oh Shit Moment is not the end of your story. It is the part of the story that makes everything else possible.
When Alice lands at the bottom of the rabbit hole — it is not the end. It is the beginning.
Wonderland is waiting.
We have talked on Unceiled about curiosity — finding your White Rabbit and following it. We have talked about the jump — what it takes to leap before you feel ready. And we have talked about the fall — and how to use the Oh Shit Moment to ground yourself and move forward.
Now we are ready for the adventure.
In the next posts I am going to take you into my Wonderland. The stories from inside the rabbit hole. Crazy fun experiences. Deeply life altering moments that fundamentally changed who I am. The fear that almost cost me someone I love more than the world. The Oh Shit Moments that finally made their way into my leadership frameworks and the lives of the people I lead.
If you are ready — let’s go.
— Monisha