How I Stumbled into My Dream Job

Last week, I quit my day job. After working at Twitter Inc. for five and half years, I left to pursue my dream job… to help other people find theirs. I’m a Life and Leadership Coach. I’ve been doing this work as a side hustle for a number of years now but I didn’t even know it existed as a profession until a short time before that. Becoming a Coach and an entrepreneur was not the dream I had envisioned for myself. On the contrary, I discovered this dream over time. When I started learning about coaching, there was no clear end-game in mind, just a nagging sense that I longed to do more, reach deeper. By leading with my longing, I stumbled into my dream.

Once upon a time I got to be what I wanted to be when I grew up — an actress. When I was in kindergarten, I used to steal my mom’s makeup, put on my favorite floor-length nightgown, stand on a step-stool in front of the bathroom mirror, and recite Oscars acceptance speeches while practicing crying on command. I took my dream very seriously. I was devoted, disciplined, and determined, even at age 5.

Knowing exactly what I wanted to do with my life was a luxury. Getting there was, primarily, the result of privilege. I was born into a middle-class family in the heart of San Francisco where arts and arts education were accessible. I was afforded singing lessons, dance lessons, acting lessons, and a college-preparatory education. I was accepted into a highly competitive arts college and graduated with a fancy degree that my parents paid for. When I arrived in New York City to start my career, my fancy degree landed me a fancy agent who got me access to fancy auditions (IE: Broadway auditions). I did it. I had “made it” as an actress in NY.

And then something surprising happened. I found myself…. Unhappy. WTF? I was living my dream. I thought, “Who the hell am I to be unhappy in the life I had envisioned for myself since kindergarten… the life that my family worked so hard for me to have.” I was well aware of how fortunate I was and I felt like a complete asshole for being miserable.

Having a clear dream, a “True North,” for your life at any age is a rare gift. But what do you do when you get there and you find out that your True North doesn’t feel as great in reality as you had imagined? Look, I followed my True North with eyes wide open. I did not have romanticized notions that achieving this dream would be easy. I was well aware that this profession would be brutal and full of criticism and rejection. I worked my butt off to get where I was and I was practiced at having a stiff upper lip when I was shamed for my body, my talent, my lack of talent, my not being “pretty enough,” not being “white enough,” not being “ethnic enough,” or whatever the reason du-jour was for not being hired (yes, those are direct quotes from casting directors). Believe it or not, that wasn’t the hard part. The hard part was this: even when I got the jobs I wanted, I was inexplicably…unsatisfied.

Maybe this has happened to you. You convince yourself that you’ll be satisfied when you have that job, or that promotion, or that extra $20K a year, or that house, or that marriage, or when you finally shed those 10 lbs; only to realize that the satisfaction is either fleeting or non-existent. When you get to the thing you thought would bring satisfaction and it doesn’t deliver, you grasp at the next shiny thing that you think will make you happy and the cycle continues. We spend a lot of time looking outside of ourselves for happiness. We trick ourselves into believing that it’s something out there that we’ll have one day in the future. The truth is, happiness is available to us at every moment. The real trick is to look inwards, not outwards for it.

Seven years into my career as an actress, I left it and returned to San Francisco. I had no idea what I was going to do with my life, how I’d make a living, let alone, what would make me happy. I was lost. The only thing I knew for certain, is that my current life wasn’t cutting it. So I walked away.

From there, I meandered through a series of random jobs. I didn’t have a clear destination in mind which was unfamiliar and uncomfortable. Without the distraction of a future-facing dream, however, I was forced to start listening to my present longing. What I longed for at that moment was not a state of doing, it was a state of being. I wanted to be fulfilled.

I had a habit of looking to my career as the primary means for personal value. Now that I had no idea what to do professionally for the first time, I started focusing on all the other areas of my life and looked to them as a source of fulfillment. I invested time in meaningful friendships. I did stuff that challenged me like hang-gliding, singing in a hip-hop band, and… crossfit :/ I developed a soulful and playful romantic partnership. I got a job at Twitter, Inc. a company whose work I admired. As an assistant to various members of the executive leadership team, I started to get curious about what it takes to be a great leader — to have a positive impact on others. I took on leadership roles of my own, curating professional development events for women at the company. I found that work fulfilling. So, I followed that clue to the field of coaching, a craft that I ultimately fell in love with and pursued professionally with delight and vigor. It took time, risk, and deep listening but eventually I found myself living a new dream.

Maybe you’re lucky enough to know what your dream is. If you do, by all means, go for it! Having and achieving our dreams is one of the great thrills of being human. And if you don’t know what your dream is, or maybe you outgrew your dream, or you achieved your dream and it didn’t pan out how you thought it would. IT’S OK! As a Life Coach, 95% of the clients I work with do not have a clear destination in mind for their lives. I’d be out of a job if they did. I can tell you that a place of not-knowing is fertile territory for discovering your ideal life. Feeling lost is not a life-sentence for unhappiness. It’s a clue. Follow it, like breadcrumbs, to your own longing. That’s what dreams are made of.

A few good ideas for falling towards your dream:

1. You don’t have to know the destination ahead of time

If you do, great. If you don’t, join the club. Trust me, I’ve tried both ways. One way is not easier or more reliable than the other.

2. Listen to your intuition

Notice when you heart and/or body says “yes” and “hell, no.” You know what I mean.

3. Take Action

Act on your intuition. Doing this will always move you forward.

4. Fail and stretch

The classic “do shit that scares you.” Because if you’re not stretching, your not growing. You’ll make the same decisions, and you’ll exist in a homeostasis hell where fulfillment is 100% not possible. The remedy: exit the safe zone.

5. Trust the unfolding

Trust that wherever your internal compass is pointing you is exactly where you need to be.

If you are interested in learning to point your compass towards your true north, join me for a two-day event for women June 2nd-3rd in San Francisco; brought to you by Inside Out, an organization dedicated to championing women in leadership.