I get asked on the regular about how I take such a fearless intentional approach to finding work. Well, it’s been almost a year of covid and I’m going cuckoo ー so here’s an experimental series where I interview myself (I know, what the what) while in between jobs figuring out what I want to do next.
So Steph, why are people so curious about your approach to finding work?
Did you ever watch Nickelodeon’s Super Toy Run, where some frenzied blissed-out kid steering a high speed cart sprints through Toys “R” Us grabbing all the toys their tiny heart desires? That’s essentially the same fervor I have for work. I’ve spent my entire career dreaming about the coolest things I could possibly do, then jungle gym-ing across different industries to take jobs I’m bananas for like:
🎬 Movie production at DreamWorks Animation (landed a teeny voice credit on a Halloween special, if you spot my voice I’ll send you a huge fried chicken sandwich)
🎮 Starting my own game company Kooapps, where we built a global team across 3 countries (our puzzle game hit the App Store Top 20!)
👩🍳 Pricing strategy at Ferran Adrià’s food research institute in Spain (really, mostly cooked and feasted with Michelin chefs)
🧑🎨 Product strategy for Netflix’s fledging animation studio (worked alongside award-winning directors building tools to bring their creative vision to life)
🎲 Designing an educational board game to facilitate problem solving in France (went on to debut at the Cannes Game Festival)
🗳️ Working on both Biden and Hillary’s presidential campaigns, where we created digital products to engage our supporters (and helped elect our current president!)
Wow, you’ve really been all over the place! That is both a very unconventional career and prolonged period of time to experience that kind of career bliss. This type of fulfillment in work is something you’ve seen others struggle with?
Yeah! Don’t get me wrong, I have difficult and stressful days, but what I do with my time is entirely led by what I want to do and get out of life. It is deeply and fundamentally satisfying. And when I look around at my friends, I realize this is not that common. I was talking to my dear friend Johnny who is super smart, incredible at what he does and has the kind of beefed-up LinkedIn profile people just drool over ー great companies, great titles, great pay. But he doesn’t feel whole. His childhood was spent on achievement autopilot, where he was so busy living out the life others expected of him that there was no time to figure out what he wanted to do, much less spend time doing it. So even though now he’s absurdly successful by so many measures, he feels this existential fatigue that something’s missing ー 💭 is what I’m doing meaningful? Am I happy? Is this my passion?
We talked about him trying a new role or taking some time off, but he’s understandably nervous. He doesn’t know what else he would do, he’s afraid of explaining a surprising pivot to a recruiter or losing relevancy in his current field, he’s worried what his family and friends might think. He just feels totally stuck. “Honestly, it’s not like my job is that bad,” he said. “But I feel like I got on this train a long time ago without really thinking about where it was going. Now I’m starting to think that I want to get off, but I literally have no clue how or what other train to get on.”
Hmm yeah, and I think those feelings are compounded by this overarching sense that it’s too late, like we should have figured this out a long time ago. Ideally before we started working! So what does Johnny do now? How does he get unstuck?
I really feel for Johnny! If you dig into his mindset, it’s all around fear ー fear of messing up, fear that it’s too late to start a meaningful change, fear of losing the good stuff he does have going on, fear of doing things that others will perceive as failure, fear of hurting his future career opportunities 😱. It’s almost like he’s wrapped himself in this rigid permission-based structure that dictates what he’s allowed to do next. And it can be really hard to let go of that line of thinking, especially when some of it probably helped him get to where he is now (dripping with that LinkedIn beefiness!).
But I think this kind of fear-oriented mentality around reducing risk or optimizing for the right move only helps you get from point 🅰️ to point 🅱️ when you already know where you’re going. When you don’t know where you want to go (like when you don’t know what your purpose is) and are actively searching for it, you need to throw out thinking that reinforces paralysis and replace it with questions you can actually answer to get you excited and help you find what you love.
Finding and answering those questions is something I’ve built my entire life around! Talking to Johnny really got me thinking about the differences in our approach and how no one ever teaches us how to do this 🤦♀️. We don’t learn it in school. Career books are often dry, detached, written by lifelong academics or people looking back at the tail-end of their careers. They’ve all been out of the game so long (read: out of touch!) that it’s really hard to translate their words into tangible next steps that someone can take. So I started thinking, “If I’m constantly hustling for meaningful work and have figured something out that reliably works, how do I share what I’ve learned to help Johnny and anyone else going through the same struggle?”
Spill the tea then! Where should Johnny start? What are you doing differently??
So I’ve been obsessed with this since I was 12, desperately unhappy and trying to figure out how to make life worth it on my own terms. What started as something that was, quite frankly, in the interest of survival has become a deep belief that purpose isn’t out there waiting to be found, it’s an ongoing relationship you learn to cultivate and nourish. You’re always changing, the world is constantly changing; the only way to not be susceptible to the immense pressures of what others expect of us is to build up our own ability to prioritize the laser focus of intentionality over the busy allure of productivity.
Based on my own experiences over the last decade, I’d developed a practical step-by-step process to figure out what you’re meant to do. The bones of it are quite straightforward ー it really boils down to finding answers in three main areas:
Where are you now?
Based on all of your yesterdays, what do you know to be true about yourself right now and what you find meaningful?
Where do you want to go?
What are the most sublime versions of yourself that make you want to leap out of bed or fist pump the air in excitement? What are things you want to do in life that would make your life worth celebrating?
How do you close the gap?
How do you turn your findings into concrete next steps to get you a little closer from where you are to where you want to go?
The only real secret is that you have to do this work yourself. Hoping that purpose will someday strike and emerge fully formed like Athena bursting forth from Zeus’s head is not only improbable, it’s a surefire path to feel like you’re always living in someone else’s show. This work is challenging only in the sense that it can be solitary, so I’ll be showing all of this live 🚨 to demystify the journey and make it feel more collaborative.
Wait, you’re going to make yourself into a live example of your process?
I’m gonna try! I’m currently winding down after the Biden campaign with a busy recovery rotation of snacking and sleeping, but I’m also thinking about what’s coming up next. Do I go learn modern dance, don Harry Potter robes and teach at Oxford, go on an archeology dig for Egyptian tombs, build a theme park ride using game mechanics, try to squirrel my way to front-row at fashion week, start a web comic about making friends as an adult, learn how to manufacture a line of travel storage... the list is never ending!
As I’m actively evaluating what fulfilling work looks like for me, I’ll share my thinking and how I apply it to dream up the dreamiest version of myself ー someone I haven’t turned into yet! ー then figure out how to get just a tiny bit closer to that dream in reality. Each week I’ll go through the questions I ask myself, the exercises I do, and include a healthy dose of other stories and interviews with my friends going through the same journey of finding joy and meaning in their work.
Ok, so it’ll be kind of like a remote life coach / mentor / live blogging series. Intriguing! Are you ok with folks reaching out to you?
Hah, yes, more like a friend going through the same thing but has come out on the other side before. If you want to do this alongside me, I’d be thrilled! I looove people and I’m dying for some two-way dialogue brimming with hilarious back-and-forth and a personal connection 🤗. So if you’re reading along and something sparks an insight or you share something particularly juicy with a friend, please drop me a note and ask me any questions, let me know what’s working or not, or anything else you’d like to hear about!
I can’t wait to help you get to your “what’s next” list, and while it doesn’t have to look anything like mine (it could, in fact, look very much like what you already do now), it should feel similarly ー get you excited, sit right with you and your values. I’ll be learning and adjusting along the way, and I truly hope you can leave each week with a nugget that resonates with you whether it’s in the form of inspiration, motivation, comfort, or clarity for yourself.
Making my life my own has been my all-encompassing life’s pursuit and in my heart of hearts, I want this for everyone. I want you to have a life that’s intentional, that you chose and crafted with your eyes wide open. A life with texture, with nuance. One that is worth explaining and worth getting out of bed for, one that feels like yours, and only yours. We only pass this way once. We need to make it count.
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