Last autumn, I had one of those pee-your-pants-is-this-my-life moments as I swung open a pair of massive doors in an ancient Sicilian monastery, welcoming sixteen strangers to a thoughtful seven course meal surrounded by the booming acoustics of 30 foot ceilings and the ghosts of monks past. We wore white and drank too much wine and let our tipsy laughter bounce off the ancient stone walls. The year before, that dinner was in a 200 year old hacienda in the jungles of the Yucatan. Before that, it was in a candlelit wing of a 12th century French castle. These are the kinds of dinner parties I thought only happened in movies. I get to do this for work?!
My cute husband, Tim (whom I only know because he used to translate this very site in its early days. Thanks for the hubbie, G!), and I run a retreat business and a photo studio, and acquaintances often tell us: “you’re so lucky to run these businesses! I wish I could trade jobs!” Whenever some sweet soul says this, I want to cup their earnest little face in my hands, get a little too close, and stage whisper so the lady eavesdropping in the coffee shop can hear it too:
“You don’t want to trade. You want to create something entirely your own — that singular thing with your unique gifts and passions and soul written all over it. You’re doing this earth a huge disservice if you don’t hustle it into being. DO. IT. Don’t let your 95 year-old self look back and shake her damn head at you!”
Just beyond the breezy social media pictures of us hosting retreats in castles or flight-hopping for photoshoots, you’d find the severely uncomfortable and insecure season of changing careers entirely that it took to get us here. Tears on the living room floor. The unsexy stuff. The shitty and vital season I would do again and again and recommend to everyone I know. Changing careers is scary as hell, but you can do it intelligently!
1. Know Thyself, Babe
Several years before the Sicilian dinner party, I was mere months away from finishing my Master’s degree in social work. I remember the air in my professor’s office, still and dusty, as I presented my thesis proposals. In retrospect, maybe I couuuuuld have narrowed down my overflowing lists of topics before meeting with her, but why deprive her of the joy of hearing all my cool ideas? But, I very clearly remember her chilly gaze as she stared down her nose at me, nonplussed.
“You really have some pointy butt bones, Laura.”
Shots fired! But, I knew what she meant: that my attention was too scattered to make anything real and deep happen out of this thesis. That my brain was too flighty to settle into a niche, and my pointy butt bones would probably prevent me from sitting in a chair long enough to get on her level.
In short, she wasn’t impressed.
I shrank under her gaze, eventually turned in a thesis, and quit social work a month later. Did leaving my job right after graduating prove my snobby professor’s point? PROBABLY. But by that point, I didn’t care: I was stagnating in my career and didn’t know how to escape. And the sting of that professor’s comment was sharp because at my core, I knew it was true. But holy shit is it uncomfortable to think about the things you’re bad at! I became totally convinced I’d never find a job that fit me.
It was at this place– humbled, tired, and scared– that I began the deep work of transitioning out of the only career I had ever known and creating a new one from scratch. Hello terror my old friiiiennnd… but a deep understanding of the areas in which I was most embarrassed to talk about in a job interview (“yes I have 100 ideas in a week and only want to act on like two of them!” “of course organization isn’t my strong suit!”) was the first step in creating a new career that was truly based on my real self, not some idealized person I hoped to be. I had to stare at myself in the mirror, wink at my flaws and turn them into co-conspirators, and armed with a full sense of who I was, start fresh.
Now, Tim and I co-own two businesses (Moveable Feast Retreats, a luxury travel company focusing on dreamy high/low travel experiences all over the world, and Sullivan & Sullivan Studios, a boutique photography and branding company) that take us around the world and the country regularly, let us choose work that speaks to us and our strengths, and has allowed us to create a life that we only dreamed about a half decade ago. If you would have told me that day in my professor’s office that everything that I thought sucked most about myself would be the foundation for my dream life, I would have been like “please just leave me here to fester in my own insecurities, random stranger!” But several years into self-employment, I look back and see what I now affectionately think of as The Four Horsemen of Transitioning Careers Intelligently (maybe I’ll workshop that clunky name at some point):
Learning how to know yourself, how to quit things boldly, how to build new things intelligently, and how to grow fruitfully.
2. Quit Things Wisely
So I left social work behind. It sounds casual now, but if you’re a recovering people pleaser like I am, quitting any job is stressful to the max. I had spent my entire adult life in the same field, and it was the only thing I “knew how to do.” Leaving was terrifying. I was working with refugees for like $15 an hour, barely enough to pay my share of our rent, and it still terrified me to tell my sexist boss I was out of there. Perhaps your situation is the opposite: golden handcuffs are keeping you somewhere that saps your soul, or you have too many bills to even consider quitting your day job. I get this! Quitting your job tomorrow isn’t always the right choice, and there are so many other things that I think women should learn how to quit. Things like saying yes to every project, feeling insecure about our skill-sets, or letting other people dictate our value. Quitting gets a bad rap in our culture, but quitting intelligently should be a skill we all teach ourselves incrementally throughout life.
Quitting things when they no longer serve you is the first, and possibly hardest, step in creating a life and career that you love. Being brave enough to say “no, thank you” to jobs, relationships, habits and patterns that you feel deep down aren’t right for you is the deep, difficult work that preps the soil for new growth. Quitting is hard, but it’s so crucial.
People often ask my husband and I how we “became brave” and quit our jobs to create these businesses, and my answer (after “work”) is always the same: no one wakes up one morning doing big brave things out of the blue. They started by doing small brave things, like quitting one thing that no longer serves them. One small act of courage opens the door to the next. And the next. And the stakes keep getting higher, but your bravery muscle keeps getting stronger. Don’t worry too much about the huge bold decisions you may have to make one day. Just focus on the small ones that scare you a little bit right this moment.
Stretch your courage bit by bit, and you’ll be able to look back in delight at the compounding interest that bravery creates.
3. Ok, so You Quit! Now, to Build.
After leaving my job, I found myself writhing around on the living room floor in our downtown apartment (so pathetic!) wondering what I could even do next. I was paralyzed by fear and insecure about my flaws, which felt endless. My husband tiptoed over to me and asked gently, “Well, what do you WANT to do next?”
I peeked one eye up at him and said “I want to be a photographer.” Well, actually I whispered it, because not only did I have no idea how to actually use my camera, I was unendingly daunted by the logistics of it all. I had a grandiose vision of the life I wanted to live, and my dream world was built on creativity, service, travel, and weeks where no two days were the same. The rough part about dreaming like this, though, is that I quickly realized my ideal job didn’t exist. I’d have to build it.
Fear speaks as loudly as you let it, and it particularly loves grabbing a megaphone during life’s transition periods. How do you prance out of the house and do the things you want to do, even when you’re scared and feel unqualified?
First things first:
Someone who knows you and your pointy butt bones, your flaws and your strengths and who thinks you’re the shit no matter what. And you put that angelic gem on hype duty indefinitely. I was lucky enough to find this person in my husband, but no matter who it is, they’re vital. This is a person who never sugar coats, and someone who really truly believes that you can kill it when you switch tracks in life. You need real talk and real love; one without the other isn’t enough.
And then, even with grandiose dreams in your head of the life you want to create, you start with one, tiny thing.
And do it as beautifully as you possibly can. Don’t look too far ahead to the tenth or hundredth thing; just do the one. It will inevitably lead to the next thing, and the next and the next, and the hundredth thing will work itself out in due time.
We said yes to every project that came our way, spent all day at work and came home to build our business until the wee hours of the morning (I should note that at this point, I got a day job while we built. Creating a career is fun, but you gotta keep the lights on). I skipped sleep to learn how to edit photos and write contracts. I learned daily that if you really want to transition careers, you must know the grind on an intimate basis.
As a non-trust fund baby, work had to spill into the small corners of our lives on both ends of the day. But because I already knew myself, I knew that semi-frenetic energy was my resting state. Instead of a weakness, it became my greatest strength. Thank you, pointy butt bones! The same traits that made choosing a Master’s thesis so difficult became the exact qualities that starting a business required: a flood of ideas on an hourly basis, a thrill about almost all of them, and the unwillingness to become stuck in old patterns. They might not have helped me nail a job interview, but as we built our OWN game, we could shape it all around the things we were good at. Which is why you don’t want to trade careers with anyone. Boom, full circle.
The “build your own thing” strategy popped up again during our honeymoon in Asia. We had promised ourselves a six month honeymoon early on in our relationship. It took us three years, but we finally left with one-way tickets to Chiang Mai, Thailand. We took about three hours of R&R before getting back to work. It was during this dreamy time, while we motorcycled around the lush jungles of Northern Thailand, rode slow boats down the Mekong, ate street food in Malaysia and skinny dipped in Bali, that we developed our second business plan: launching the gorgeous travel company we dreamed of existing in the world.
We had spent so much of our twenties traveling, to the detriment of my career (or so I thought). I’d get a job, work for a while, and save for plane tickets to leave again, never quite gaining traction in any single spot. On our honeymoon, we became obsessed with traveling well and curating the right balance of high/low epic travel experiences. We noticed that many of our wealthier friends would travel with no clue how to curate an experience beyond spending top dollar: they’d go to the fanciest hotel in any given city and eat at the most expensive restaurants, whether or not these places were even very good. Conversely, our budget travel friends would brag about spending a dollar a day somewhere, eating hardly anything and completely miss out on the diverse richness of the country they were traveling through. Enjoying street food and luxe accommodations shouldn’t be mutually exclusive.
So Moveable Feast Retreats, our second business, was born out of our years-long obsession with traveling well. Yet another career weakness became a strength: all those years spent wandering the world, the same years I thought I was regressing in my career prospects, became the foundation for creating a business of my own. We’ve taken groups to our favorite countries, immersing ourselves in other cultures’ ideas on how to live well, diving deeply into a place and bringing a little of it home so your daily life is improved by travel. Moveable Feast is the opposite of mindless consumption, and it’s one of the things we’re most excited to build.
You might be doing something right this moment that makes you feel a little guilty, like it’s not helping you advance your career. Consider that there is a reason you’re still doing that thing– and that it might be a building block for you to grow something new from.
4. You built It, Now Grow.
We’ve spent several years now in constant growth mode, but there is one thing I wish a fairy godmother would have sat me down and told me all those sleepless nights ago:
For so long, I felt like I had “wasted” too much time by leaving social work behind, like all the skill-sets I had developed were now going to be boxed up in the attic, never to be used again. What I hadn’t yet learned was that every single skill, experience, and connection I had made during my former life would only expand. Nothing ever goes to waste. How liberating! How amazing to know that every little tangent, conversation, career sidetrack and weekend hobby will all speak to the life and career you want to create. Maybe not all at once, maybe not immediately, but no one else has shaped their life in quite the same way you have. That’s not a weakness. It’s your greatest strength.
Everything builds, everything shifts, and the same can happen for you. I traded a career that no longer fed me for one that I wouldn’t even have known how to dream of five years ago: in different cities, states, or countries every month, hopping from project to project at a pace that never allows for boredom or stagnation. No day is ever calm and no week is ever like the one before. Oh, and we added a real cute baby to the mix this year.
My little pointy-butt boned self is in heaven.