I tend to write about my failures because they make me feel human and flawed, and I think we can all connect to that raw and painful feeling of having missed our ideal target at some point in our lives. But once in a while things go the other direction for me and I feel equal parts of surprise and confusion. I think I struggle with owning my successes because I have a major case of impostor syndrome- I always assume that my failures are entirely my fault, but my successes are accidents- which makes me very nervous to write about my accomplishments. What if everyone finds out I’m a fraud?
That feeling makes this post particularly tough to write. As I write this sentence, I still wonder if I’m allowed to feel proud of this milestone in my life. Do I truly deserve this?
I just finished writing my first book. It will be published by Harper Collins in November this year. I’ll be 33 years old next week.
I never thought I’d write a book this early in my life, especially not a book about my life, my work, and my many failures. I had always pictured myself writing a book when I was sixty-years-old, looking back on my career and threading pearls of wisdom and clever metaphors into a riveting best-seller.
I was offered my book deal by Harper Collins 2 years ago. Since then, I’ve met many aspiring and inspiring authors and creatives, and the one question I get asked over and over is, “How did you get your book deal?”
I remember how embarrassed I was the first time someone asked me that question. We were standing in the corner of the communal kitchen used by the Grub Street writers and I was making coffee to help me stay awake late into the evening of my memoir class. A fellow writer approached me and loudly, almost accusingly asked, “Do you have a book deal already?”
I wanted to keep it a secret in this class that I had sold my book. I felt like all the other students were much stronger writers than me, and they had years of experience and various publications under their belt, but I was only one with a deal on the table and a deadline to work towards.
It felt like I didn’t really deserve it. “Why me?” I’d ask myself over and over. “What did I do to deserve this? Everyone else is so much better than me.” The haunting lore amongst aspiring authors is that it’s easier to get into Stanford than it is to get a book deal if you’re a first time, non-fiction, non-celebrity writer. Most writers end up spending years writing a large portion of their manuscript, sending it around to tons of agents, getting rejected hundreds of times, and finally, maybe, finding one agent who is willing to try pitching their manuscript to a handful of publishers. And then, more rejection from publishers until one day, seemingly magically, a publisher picks up their book for a deal.
That was not my experience and for that I felt guilty. I felt like I jumped the ladder or I got lucky and I should have kept my mouth shut because I was going to offend hard working people who wrote, unpublished, their whole lives, while I sat there with all my book-deal-chutzpah without any real writing abilities whatsoever. But then I thought, maybe that’s how we all feel.
I started writing publicly in 2008. I had quit my job on Wall Street, accepted a job in Cambodia, and was feeling nervous and scared. I thought I would lose touch with my friends and family, but at the same time I couldn’t imagine putting the effort in to write people individually. So, after watching Steve Jobs’ commencement address, I grabbed a free blog URL for “Hungry n’ Foolish” on WordPress, and I started a travelogue.
Cambodia was a lonely time for me; minutes on the internet were expensive back then, Netflix and Hulu hadn’t expanded beyond the US yet, and I didn’t know a soul when I first moved there. I spent a lot of time reading and thinking that year. Slowly, I started writing more and more introspective pieces- pieces about life, my purpose, and meaning. I remember meeting a guy at a party that year who was a journalist. By our third date, he had printed out all of my blogs and brought them with him on our date so he could read highlighted sections of my pieces back to me. That was the first time I realized my words might have the power to move people.
My pieces were often poorly constructed, riddled with grammar mistakes and contained no narrative arc, a bit like this one. I didn’t care, though. I was writing to stay connected and speak my mind, not to win an award or a deal. I wrote because I had an opinion that I thought might be a little bit different from other people’s.
Eventually, I left Cambodia and moved to India to become an entrepreneur in education, but I kept blogging. Facebook, Instagram and Twitter picked up traction and my post cadence diminished, but I wrote whenever I felt compelled to speak up in long form about something that mattered to me.
I gave a few talks on TEDx stages around the world about my theory of change: that failure had become a Grand-Canyon-sized pothole on the road to success that we had learned to avoid at all costs. But instead of taking the long detour around to avoid it, it was time we embraced failure, explored it, and used it to our benefit.
When I built my third startup, a few online publications asked me to write pieces for them- pieces about female entrepreneurship, edtech, failure and India. I didn’t always get approached, sometimes I reached out to pubs to see if they wanted a piece- usually they did not- but since my writing was free, sometimes they said OK.
Then, one day an editor from Harper Collins sent me an email. She said she had seen my talks and read my blogs about startup life, female entrepreneurship and failure and wanted to know if I’d be interested in writing a full book on the idea. That’s how it happened.
We spoke on the phone, met up in person, emailed ideas back and forth, and within 3 months I had a signed contract in my mailbox.
I remember when I was fundraising for my startup around that time, I would read articles in TechCrunch about stupid business ideas with idiot founders who had raised millions of dollars when I could barely close a few hundred thousand. Why not me? I thought to myself.
The hard thing about hard things (c/o Ben Horowitz) is that it’s never 100% clear why certain people succeed and others fail. It’s not necessarily because I’m a worse entrepreneur that I failed and other entrepreneurs succeeded. It’s definitely not because I was a better writer that I had a book deal and other writers didn’t (yet). Sometimes it’s luck or serendipity or timing. Sometimes it’s earned and deserved, and sometimes it’s not.
At the end of the day, what does it really mean to deserve something? Maybe I blogged and spoke and marketed myself so much that a book deal was inevitable. Maybe my editor was searching for someone else and google gave her me on accident.