Feeling trapped while being enviably successful in public-facing entrepreneurship is an entire vibe. It feels like a wide-eyed brain freeze, a charley horse in a swimming pool, or worse, like a sightless underground bunker with no windows and all doors barricaded with moldy timbers and Lord of the Rings castle-sized rusty locks.
But I never truly felt the need to muster up the energy to get a sledgehammer and break down the doors—until now. Up until four years ago, my storybook entrepreneur’s life featured my three multiple growing and profitable startup businesses, a W2 husband, and three kids. I was crowned like the queen in the center of it all and was rolling along on autopilot with the Talking Heads song Once In A Lifetime as the soundtrack.
Back then, I didn’t know how aimless, purposeless, and toxic my entrepreneurial endeavors had become. But one evening, I was lying on my back in bed, ridged, staring at the ceiling, arms stock still beside me, panicked, sweating, and trying to sleep. I visualized my quietly desperate rat race with a new despair, and asked myself:
“What if I just bought a plane ticket, packed up my agency work, and landed with my laptop and mobile phone, somewhere totally new, breathtaking, and mysterious?”
Right around this fevered time, as I was Ubering home from yet another performative DEI-focused business networking event in some bland hotel ballroom, I’d find myself looking in other people’s windows. I wished I lived there, seeing white flickering screens, dramatic lighting, large plants, and maybe even a glimpse of some fantastic artwork on the walls. The people who lived in these high-end homes never had curtains—you could see everything you’d coveted.
I would arrive at my own basic home demoralized, and everyone was asleep. But, I’d breathlessly search for my new glossy copy of Departures, ready to devour it believing that one day I might risk it all, and lift off to remote work, get some international customers, and run my company from one of these luxury destinations like the ones they showcase in all the James Bond movies.
Have you ever heard the saying that most people think about sex every seven seconds? Well, I think about my remote work spontaneous exit plan every seven seconds. The Kayak app is my what-if-I-just-go ticket. I use it to fly vicariously and virtually through its robust search engine to see how much it would cost to buy a roundtrip ticket, by myself, business class of course, on a transatlantic journey to Italy.
My daydreaming worked. I was recently invited to speak at an event in London to teach people in the climate change space how to create, establish, and promote their professional brand on LinkedIn to educate and commit new audiences to the green narrative. Without hesitation, I said yes, and booked my roundtrip flight—business class—without any research on London hotels or locations.
At that moment, I had a revelation that the path to the luxury of international travel was through entrepreneurship. Then, I immediately visualized myself in my hotel room, on a balcony, overlooking the streets of London—alone with my laptop, a travel journal, and mobile phone. My body ached at the notion of being alone with my thoughts, in my own space by myself, speaking, networking, seeing landmarks, taking selfies, and above all, strategizing about new business concepts and ideas so I could do it all over again.
I also pictured myself, in an Instagramable restaurant, looking around at the other diners, wondering, who owned the silver Bugatti that I saw at the parking valet, and then, when I found them, I would invite them to be a guest on my show The Honest Field Guide, to learn about their business journey to success.
To keep this vision thriving, I obsessively buy brand new luxury blank journals, that I carry with me, not to make to-do lists, but instead “to-do ideas.” These are my random stream-of-consciousness thoughts that fill dozens of pages with seemingly unactionable ideas. In the harsh day-to-day reality of my rock-bottom entrepreneurial work, my to-do ideas journal motivates me to keep hope alive so I can plan my exit and work in paradise.
My rigorous independent work has rendered me spiritually depleted. But refocusing on the benefits (not in the context of the freedom of working from my kitchen) through working while traveling by train, plane, boat, or automobile, was a game changer for me.
What would happen if instead of meditating, or taking that yoga class this week, you created a mantra like this:
“I’m just going to leave on an airplane next week to get to a new city I’ve never been to. I’ll set up my laptop in an independent coffee shop and write. I’m not going to listen to music, or podcasts or play video games because I want to hear myself think. I will love traveling alone, for the first time, in relative silence to bring my thoughts to the forefront. I will sit up proudly and dine or sit at a bar alone with my book or journal. I will insist on not trying to manifest the Eat, Pray, Love type of trip for myself. I will be safe and unbothered. This is my professional journey to plan in my head, to vision board a new experience for myself through my entrepreneurial aspirations.”
I’ve got some ideas that might help you create that glorious mental escape hatch, to reset your weary working spirit, recalibrate your brain and body, and free your mind to see a refreshed world of work.
And even if you can’t get out just yet, start this visualization process now. Before you know it, your dreams of escape will come to life and you will find yourself on the next flight out to your dream destination.
Visualize leaving. Picture yourself packing your suitcase, stepping out the door, boarding a train, or catching an Uber to the airport. Arriving at the airport, going through TSA, stopping for a cocktail at the airport bar, or better yet, getting a day pass to the lounge on your favorite airline. Imagine walking to boarding, getting to your seat, and buckling up. I did this. I was so inspired by my courage, I designed and created a blank travel journal to help you kick-start the process of believing you can leave.
Pick a destination you’ve always wanted to visit. Do an Instagram hashtag search of the country or city you want to work from. Find influencers who have written or vlogged posts about their beautiful travel. Use Instagram or Pinterest to create a private visual bookmark of your photo and video research. Determine which locations have monuments you want to visit. Prioritize them and arrange your accommodations around these places. Also, nothing requires you to stay in the same hotel the entire trip. Switch it up for fresh experiences. These days, your office can be small and portable like mine.
Go to kayak.com and use filters that fit the way you like to travel. Do you like flying nonstop? Do you want United Airlines? Do you prefer flying at night? I do all of this on Kayak. It will pull all the options for you, and then link to the actual airline websites to book. You may want to use private browsing when you do it, although that doesn’t truly protect tracking of your intent.
Book a refundable plane ticket. A refundable plane ticket means if you can’t go on your spontaneous trip, you can use it for another flight. You’ll pay more, but it takes the stress out of your trip if something comes up or you chicken out.
Try ChatGPT as your personal travel agent. Have a conversation with it to discuss your desires, goals, what you want from your trip, the kind of food you like to eat, the vibes you want to feel, and more. Let AI create your itineraries, and provide you with walking paths, restaurants, monuments, hotels, and more. This is actually pretty fun. I used ChatGPT (combined with Google Maps to help plan my driving route and find motels) when I planned a recent mom-son-work trip to the Redwood National Park in California. ChatGPT helped me plan my entire trip, and most of the recommendations, including B&Bs, hotels, and restaurants, were simply outstanding.
Buy a new suitcase. Before I traveled to the ancient forest to work, I purchased a bright pink and purple suitcase and shot a YouTube short video to get me even more pumped and excited about my new adventure. My colorful suitcase sat in my closet as a daily reminder that “Yes, I am leaving.”
Plan for safety, especially when you are a woman. If you are a woman thinking about traveling alone for a luxury work trip, booking your accommodations at a full-service and fully-staffed hotel might be safer than an Airbnb or private apartment. If you are not renting a car, you may also need to verify that public transportation runs late, that Uber is available 24/7 at the destination, or that you can walk around the city streets and still feel rejuvenated, curious, and inspired. Your safety is always an imperative when traveling alone. Here are some strategies for safety from travel.gov.
Pack smart clothes. Other considerations to ensure your safety include having clothes with inner pockets to carry cash in the local currency and to keep your passport on your person. Stay alert (or maintain a swivel neck when you are a woman of color) to your surroundings. Here are additional considerations and ideas to help you plan for safety.
Start small, with short trips. Booking a stay at an upscale hotel with perks for business travelers in your hometown for a night alone is a good first step toward your great escape. Or go to a destination aligned with your own culture to feel more at home. Avoid booking remote wilderness experiences on your first solo journey.
Buy the most expensive trip you can afford. The memories of your travel experience and the lucrative business results created by your new will to work will outlast any anxiety around the expenses of your trip.
If you are a schedule-C entrepreneur or own a business, check with your CPA to see if you can write off your travel as a business expense. Seeking business opportunities at your destinations is, after all, the cost of doing business.
Ultimately, if you’re not ready to travel solo, especially abroad, and you are still looking for a way out of your dreaded routine, book a week at an experience resort like Miraval in Arizona, The Ranch in Hudson Valley, or One and Only to do your client work. No matter what, finding a way to change can do a weary working person some good.
A Spontaneous Exit is JinJa Birkenbeuel’s curated playlist on YouTube Music.