I’m Leaving My 6-Figure San Francisco Startup Career to Sell Ice Cream on a Beach

Jeanna Barrett
Jun 21, 2016 · 10 min read

A year ago, I compulsively booked tickets to Belize while already on a vacation in New Orleans. It was the first time I had traveled with one of my friends from San Francisco, and we couldn’t stop talking about how we were the best vacation partners. I was lying on the bed in front of a floor-to-ceiling fireplace in the turquoise and orange shotgun house in New Orleans’ Bywater neighborhood when a Hipmunk push notification popped up on my phone. Tickets to Belize had dropped to $550 round trip. For awhile I’d been tracking flights to the tiny Central American country on the coast of the Caribbean Sea because I was intrigued by a place that boasted the second largest reef in the world and a landscape that included both jungles and beaches—the perfect mix of adventure and relaxation.

“Wouldn’t it be funny to book another vacation every time we’re on vacation together?” she said. I couldn’t think of a better idea, so we bought the tickets. These are the kind of friends you keep around for eternity.

Over this five-minute conversation, I made a split decision that would change the course of my life forever.

Belize was everything I thought it would be. We spent four days on Caye Caulker before taking off on a three-day sailboat tour through Caribbean waters and finishing our trip at a treehouse resort in the jungle where we could hear hundreds of rainforest sounds come through the screens that surrounded our beds in the canopy tops.

On Caye Caulker, we traveled by beach cruiser bikes on the three dirt roads aptly named Front Street, Middle Street and Back Street. We sunbathed by the pool at the AirBnB we rented from an Italian woman who moved to Belize to be a dive instructor and has since opened her own vacation rental complex. Her on-site bartender blended fresh passion fruit margaritas for us before we headed out on the town for dinner at restaurants that didn’t have menus but would instead display their fresh catches of the day on tables outside. Red snapper, lobster, conch and grouper were at our fingertips, and we ate like kings while licking hot sauce off our fingers. We ended our nights with drinks at an open-air bar on the beach that had a tradition of dancing on the tables and served the best jerk chicken wings I’ve ever had. I reluctantly left the island but not before it left a message for me on the bathroom wall of a bar. We can find our calling in the most surprising of places.

I sat crouched in a bathroom smaller than the span of my arms with my sundress around my waist, swaying from four vodkas and groping for toilet paper while reading the bathroom message with squinty eyes. I wasn’t happy where I was personally and professionally. Why would anyone stay stuck in the same place if it wasn’t making them happy? Then I asked myself the same thing.

This bathroom Sharpie oracle came to me during one of the hardest years of my life. I was at the pinnacle of my career in San Francisco, leading inbound marketing at a startup that was a ‘unicorn’ and hadn’t gone public yet. It was a job I had pushed my entire career to get with a salary that afforded me to live in a city that many only dream of moving to and stock options that just might turn out big. I had enough cash and great friends to do, eat and buy whatever I wanted. I thought I’d checked all the boxes of life except for the last one left—I needed love to complete my, “You can have it all.”

I thought this love had finally arrived soon after starting my job, and I gladly fell with my arms and heart wide open. For five short months, I had never been happier. Can you really have your dream career and fall in love? But, just as quickly as he had arrived, he was gone. He wasn’t right for me and that’s okay, but unfortunately he left me with the shattering memory of what it feels like to no longer be alone every day and to have someone to share moments and meals, and stand in my corner. With that gone, I began to realize — no amount of success or money matters if you don’t have someone you love to share it. This realization rang throughout my life, in everything I did and every conversation I had. I started to show up to my job asking myself, “What is the point of all of this?” For a girl who had pushed her entire life to get to the top, to be the best, to excel at everything I did and to be a #ladyboss, this was a life-shattering realization. I felt like all I had was my career, and it wasn’t what I needed anymore to feel fulfilled and happy.

During all this, the loneliness in my apartment could be cut with a knife. It lingered in the air; it sat on my chest when I woke up in the morning and was waiting for me when I got home from work; it brought me to tears over the simplest canceled plans; it made me feel like I didn’t have a support group in San Francisco; it highlighted that I was hundreds of miles away from my tribe in Seattle. I hated who I was because I felt needy, desperate, alone and jealous during the time all of my best friends were getting engaged, married and pregnant. I genuinely celebrated their love and happiness, yet every announcement seemed like a personal reminder of how I had failed and was failing. How all I had was a career I’d killed myself to build, but I had no one to love. I had put all of my eggs in one basket, and I didn’t want to carry the basket anymore. I wanted to break those fucking shells and scramble those eggs until they didn’t even resemble their former state.

This life I had left in San Francisco was on my mind as I laid on a sailboat deck, looking up into the blue clouds of the Caribbean sea through two large sails marked with Rastafarian flags. We had left Caye Caulker to travel as the bird flies on a three-day sailboat tour through remote private islands with 20 other travelers from around the world. For the next three days I camped in a tent on the sand of remote islands, dove off the edge of the boat with Canadians and Germans, drank Rum while dancing to the beat of local drum circles, napped in hammocks with the salty breeze rolling over my tanned skin, jumped off in the middle of the Caribbean sea to snorkel, kissed boys under the stars in a midnight black sky, and ate fresh ceviche and spear-caught lobsters that had been captured by our boat crew. It was the best thing I had ever done with my life, to date.

I felt like I was a different person by the end of my trip to Belize.

For 10 days I wore a bathing suit all day and didn’t feel affected by negative body image that often makes me feel not good enough or pretty enough. I didn’t wear makeup or do my hair. I wasn’t desperate for someone — anyone—to hit on me, tell me I was beautiful or ask me on a date. But, I had never felt more beautiful.

For 10 days I enjoyed meals with friends without a phone as an uninvited guest. I didn’t feel discouraged and overwhelmed by the online conversations around our volatile political landscape, expensive health care, unruly gun laws, subpar education system or terrible food industry. I didn’t check my email or social media all day, and I had no idea about the latest meme or celebrity gossip. But, I didn’t miss anything important.

For 10 days I didn’t fight my way downtown to sit in a windowless office all day. I didn’t desperately grasp for five minutes to eat or pee between back-to-back meetings. No one told me I was too aggressive for stating my educated opinion or snippy for disagreeing, and I didn’t feel stressed out, overwhelmed, misunderstood, not liked and under supported. And, I still felt challenged and educated, just in different ways.

For 10 days I laughed a lot, danced on tables, slept well, read books, ate great meals, didn’t worry about going to a gym, made new friends and experienced a new part of the world with beautiful people and a vibrant culture. My spirit was lifted.

Coming back to reality from the trip of a lifetime is a cold, hard bitch-slap to the face. Suddenly I had a very, visceral “fight or flight” moment with my life. But here’s the thing—you can fight against your life, or you can choose to leave everything you don’t like lying on the floor and take flight to a new place, a new journey, a new you. I started talking about moving—to Atlanta, Denver or New Orleans, even back to Seattle. Anywhere that could get me out of this unruly mess. My friends would ask, “What’s going on?” I would respond with, “I dunno, I just want to leave it all behind and sell ice cream on a beach.” Selling ice cream on a beach became my metaphor for giving up the rat race, the money and the stress in exchange for living a simpler, happier life. I felt like connecting with people and community, unplugging from technology, and focusing on my health and hobbies could be my key to happiness. I wanted to be the person I was in Belize, all the time. But, I didn’t think I could walk away from my career, my salary and my unvested stock. If you could be who you are on vacation and never come back, but had to quit everything you worked toward to trade for that happiness, would you choose it? Would you choose happy?

It was at this time that I sent a message out into the universe. The Twitter universe, that is.

It took nearly a year, but the universe responded — this April my company eliminated my position and disbanded my team. Two years of my life’s blood, sweat and tears came to a grinding halt, and I learned a very important lesson: you are never more than a number on a budget spreadsheet, no matter how much you give of yourself or how much you drink the Kool-Aid. It was a weird, out-of-body experience to have what you thought was your life rug ripped out from underneath you in a moment’s notice. The day it happened, I sat on top of an apartment roof overlooking the city, drank two vodka lemonades with a friend, spent one hour getting everything out that I thought was frustrating and unfair, and then I never looked back. Sometimes it takes awhile for the whispers of your journey to thread together into a new story. And sometimes the new story is packaged up in a box of hurt and tied with a bow of misunderstanding. But all we can do is untie the box; trust that what’s inside will take you where you need to be; embrace the change; let go of what can’t be understood; and move forward into building your new story.

I woke up the next morning and a weight had been lifted. I am free to go and be exactly who I want. I can see clearly. This life of working in technology and living in San Francisco has left me feeling disconnected from myself and my community. In the process of giving everything to my career, I lost who I was. I became too exhausted to go out for dinner or drinks during the week, to cook, to network, to date or even to workout. I complained a lot even though I had endless privileges and reasons to be happy. I also hadn’t written anything personal in four years. All of this left a listless version of myself. Who have I become? I don’t recognize the person I knew used to be a great writer, friend and girlfriend. Who used to be funny, outgoing, vibrant, positive and active. So, I’m answering the call of the universe and going where I know I can be the best version of me—I’ve booked a one-way ticket to Belize on June 30th. I’ll be moving there to bootstrap starting my content strategy and freelance writing business and most importantly, get back to what makes me happy.

We can reinvent ourselves 10 times over in this lifetime. If you could reinvent yourself, what would you choose? I’m choosing someone who values a simpler life and has gratitude for every privilege. I’m choosing to leave a successful career so I can unplug and connect to myself and my community. I’m choosing to “sell ice cream on a beach.” This beach just happens to be in Belize.

Please click Follow on both Medium and my publication, Get Growing, if you’d like to join me on my journey.

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Jeanna Barrett

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Founder & Chief Strategist at FirstPageStrategy.com. Big believer in the power of words + data. Freelance writer! Big Hair! Tea! Books! Vodka!

Get Growing

Writing about personal growth through love, happiness, gratitude, friendship, career, change & adventure.