Three years ago this month, I took a major leap of faith. On what seemed like a whim, I quit my job at a software company in San Francisco, sold my car, furniture, and belongings, gave nearly all my clothes away to charity, and flew one-way to New York with one suitcase and a dream.
This all happened in about 48 hours. As I was carefully putting the puzzle pieces together, I told very few people about what I was doing. It wasn't until I was en route to the airport that I called my mom, who I'm incredibly close with, to tell her what was going on.
I knew that this was the right thing for me to do, and I didn't want any other voice to cloud my own better judgment. By the time I got to New York, I had no idea what was next—but I knew that whatever it was had to be better.
This is the day that my journey began. It was the day that I was free to roam, explore, experiment, follow my heart, and make the right things happen for the right reasons. Of course, not everything changed overnight. Three years later, I just now feel like I've arrived at living on my own terms. And now, my vision—for myself and for the world—is clear.
But that's only one side of the story. The other, and perhaps more valuable, side lies in everything that happened leading up to the day that I left San Francisco. I call this the period of pre-journey pain. I was lost, confused, and uncertain about what I wanted from life. I took failure personally, went after guys who were emotionally unavailable, and cared too much about other people's expectations of me. I seemed happy, but deep down, there was so much to figure out and explore. This period taught me about what I didn't want from life.
If you're in a similar place where you know what you don't want and you feel like you're on the wrong path, here's how I found my way.
1. Do What You Can With What You Have
Even though the job in San Francisco wasn’t a perfect fit, I gave what I had to the experience. I traveled around the country to speak at conferences and meet incredible people in the internet and marketing worlds, some of whom I'm still close with today. I learned about the world of enterprise community software (and realized it's not all that interesting to me). But making the best of what I had all along led me toward discovering what I'm meant to be doing.
2. Listen to Your Inner Voice
For most of the time that I was working this job, something felt missing. I found myself lacking the deep passion and drive that had come naturally to me my entire life. I knew, deep down, that the work I was doing wasn't the work I was meant to be doing. Every month or so, especially the last six months I was there, my inner voice kept creeping in to remind me of this. When I tried to explain to people how I felt, they looked at me like I was crazy. In their eyes, I was lucky to have a job in the recession. But I knew better.
3. Redefine Success
I had a great paycheck that afforded me everything I wanted at the time. I had a great wardrobe, lived in a beautiful apartment that overlooked the Golden Gate Bridge, and went out to nice dinners. I drank more wine than I care to remind myself about. People called me lucky.
But I didn't feel lucky. All of the things I had—none of those were the things I actually wanted. I didn't care about the clothes or the apartment. It was all just stuff. The things I owned were starting to own me. That's when I realized that I had the opportunity to redefine success. For me, it wasn't about money or things. It was—and still is—about feeling deep fulfillment and meaning, eliminating unhappiness from my life, and experiencing progress every day. Once I redefined success, it became much clearer what possibilities lay ahead for me.
4. Find Someone Who Believes in You
The icing on the cake for me was when Amit, a friend in the San Francisco startup scene and founder of his own company, showed me he believed in me. When I told him my plan of moving to New York—still then in its nascent stages—the only questions he had for me were "Why not?" and "What's the worst that can happen?"
He was the first person who I felt understood where I was coming from. He was the one who encouraged me to go and make the leap. Within twenty minutes of talking with Amit, the puzzle pieces began forming in my head. Having someone like that, who believes in you that much, is invaluable when you're taking the leap.
5. Pick Something
I had no idea what I wanted when I first arrived in New York. I only knew what I didn't want. So I decided to pick something, anything, that seemed interesting. I figured that picking something was better than picking nothing at all, and the only way we figure out what we really do want from life is when we go out and actually do something.
So I picked startups. New York had a burgeoning scene, I had been playing with computers and the internet since a young kid, and it seemed like a perfect match.
6. Make it Happen
With that goal in mind, I asked Amit Gupta if I could be the East Coast side-kick of his company, Photojojo. I came up with three ideas for the company, and explained to him how they would work and why they'd be good for his business.
And it worked: We agreed to a deal where I’d get a cut of any commissions on sales from partnerships or ad deals I landed. I got introductions to Tumblr, Vimeo, Busted Tee's, and Thrillist, among other startups and people within the community. With Amit's backing, I quickly found myself connecting with people in the New York tech scene. I made a few thousands dollars, and many priceless relationships.
And that was my starting point. Looking back, here’s my advice: If you have an in with a company that aligns with your new definition of success, be assertive and tell them how you want to help. If they say no, keep trying until you find one that says yes.
If you find yourself feeling like you’re on the wrong career path, don’t panic. Follow these first six steps, and I guarantee you'll start heading down a path that’s more aligned with the life you imagine. If you're wondering what happens once you actually take the plunge—how to support yourself, meet the right people, figure out what you're really meant to be doing—that's what we'll get more into next week. Stay tuned!