It was the third day in a row that the guy with the giant backpack chose to sit next to me on the bus ride to work. He set the monstrous bag on his lap and I winced as the jagged edges of its contents dug into my leg. He must have been transporting granite slabs in there, which were now spilling through the canvas of his Jansport and onto my thigh.
It’s a testament to humans’ capacity for adaptation that the inhumanity of a daily commute can become commonplace. We can learn to tolerate otherwise intolerable things, like people eating egg salad at 7am in the winter when the bus is heated to 200 degrees.
The bus was better than driving on the rush-hour choked freeways, which I had done for a while for the sake of convenience, but quit when I realized it made me a quantifiably worse person. On one evening’s particularly congested slog, someone rear-ended my car. Too jaded and singularly focused on getting home, I made eye contact with the driver, gestured to ask if they were fine. When they confirmed they were, I drove away. A bit of insurance money to fix a bumper wasn’t worth adding yet another hour to the ordeal.
The bus helped me avoid that kind of situation, and it saved me hundreds of dollars in vehicle maintenance and parking tickets.
Of course, a bus commute is not without its own challenges. Catching the right bus at the right time is a special gauntlet. The cabin temperature is usually set to either Steamy Broil or Ice Wind, depending on the season. Plus there are the people, including some who seem unaware of the protocols of sharing a space, like Backpack Guy with his slabs and whoever made the whole bus smell like sulfur with their breakfast that just couldn’t wait.
When my team at Oracle began offering partial, and then fully-remote work options, I embraced the change. The perks were immediate and obvious. I loved staying home with my dog all day. I saved serious money thanks to Mr. Coffee and at-home lunches, but the biggest savings came in the form of time. Without the primping, dressing, hair-drying, breakfast-making, and bus-catching, I could suddenly have a real morning. The kind of morning you dream about. I could put on a cozy sweater and sip my coffee from a steaming mug, cupping it in two hands on my patio like someone in an L.L. Bean catalog. And even with that mellow morning routine of romantic coffee sipping and dog walking, I still managed to start work earlier. It often went later, too.
When you’ve got a penchant for productivity, and your laptop is your office, the urge to “just finish one more thing” becomes a roaring inevitability. Noticing that workday creep, I started taking long lunches to reclaim some time in the middle of the day. I enjoyed another leisurely dog walk, a pop to the grocery store (which was delightfully not jammed with the after-work rush), or a yoga class. I left the stress at home and traversed my midday, carefree.
This schedule, with its two distinct blocks of work time organized around a respectable midday reprieve, continues to serve me well. It helps me feel fulfilled and maximizes productivity, so it works for work, too.
Remote work is not for everyone. Being a successful remote worker requires strong autonomy, intrinsic rather than extrinsic motivation, and a gentle harmony between focus and flexibility. The lifestyle plays to my strengths, it naturally fits with my tendency toward self-mastery as well as my low tolerance for rules that feel arbitrary. It never made sense that I was required to sit in my desk until 5pm if I’d gotten my work done by 3. You can call this a sense of entitlement, I call it self-awareness. It reflects a desire to co-create great things – from content projects to work/life balance – with my employer.
How I Went From Working at Home to Intentionally Homeless
The benefits of working remotely began extending beyond the day-to-day, and into how I approached the structure of my whole life. When my best friend got married that first year of working from home, I was able to attend both her bachelorette weekend in San Luis Obispo and her wedding in Oakland without missing a beat at work. I even rolled one of those trips in with a work event to optimize my travel time.
Work travel became a welcome break from the quasi-isolation of the work-at-home life. I jumped at opportunities to attend customer events and team meetups, and that year I got to attend SXSW in Austin, a digital transformation conference in Chicago, and Oracle’s ModernCX in Las Vegas. ModernCX was particularly special. My role was to manage the schedules of global executives and entrepreneurs as they jumped from speaking slots to media briefings to happy hours. As we navigated Vegas together, we developed a kind of wartime rapport that blossomed into amazing professional and personal relationships.
The Trip That Lit The Spark
Soon after that exhilarating week in Las Vegas, one of my new connections reached out over email. Ruth’s sharp intellect and passion for her work had locked us into increasingly spirited conversations at the conference. That energy also came through as a deep pride for her home town. Ruth is originally from Mexico City and invited me to come visit her next time she was there.
A few weeks later, I touched down at CDMX. Unsurprisingly, Ruth was an incredible tour guide. We spent a long weekend climbing the pyramids at Teotihuacan, getting lost in the anthropology museum, and exploring the markets near the Zócalo. She made me be brave and use my rudimentary Spanish to order cajeta churros for us both and ranted enthusiastically about her feelings about how Frida Kahlo is a problematic feminist icon.
After the trip, I floated happily all the way back to Denver, where I found a stack of letter piled up in the mailbox. A credit card bill and lease renewal offer brought me crashing back to earth. The impromptu flight, the dog sitter, Airbnb, and adventure money; it had all stacked up, and rent was coming due. If I renewed at my current place, rent would rise, although they assured me my rate was still very competitive and under market in the fast-growing city. I looked around the one-bedroom apartment that was both my home and my office. It was nice enough, and I had worked hard to make it cozy, spending money on furniture, cookware, and high-speed Internet. I could have spent that money on adventures. Suddenly, my place felt like a beautiful, beige prison.
I couldn’t afford to pay rent and travel.
I chose to travel.
Over Memorial Day weekend, I packed my things into a truck and drove to my parents’ place outside Milwaukee. Their unfinished basement became a storage unit for the contents of my life. They held a ‘Welcome Home’ party, during which I obnoxiously reminded everyone that I was not home, just stashing my stuff and establishing a base of operations.
The next week, I interviewed for a new job working with Oracle’s startup program. Despite working remotely, my career had not stagnated. By nurturing relationships, staying curious, and leaning into challenges, I continued to encounter opportunities for growth within the company. I joined the new team comprising fiftyish mostly-remote workers around the globe. If my new teammates asked where I was based, I’d smile and tell them ‘nowhere in particular, at least for now.’
An Underlying Quest
For the next three years, I traveled. It was fun and exciting and gave me a sense of purpose. The motivation that drove me across the country, and in some cases the world, was to find a place that felt like home.
Growing up, I moved around a lot, so I didn’t feel particularly connected to one place over another. Answering the question “where are you from?” never comes easy. But I wanted a home badly, and each new city that I visited was unwittingly auditioning for the role.
I pored over lists with names like “Best Cities for Millennials” to plan my adventures. I went to Los Angeles, Atlanta, Chicago, Portland, Austin, and Nashville. I felt, almost everywhere, the same sense of frantic expansion that had expelled me from Denver. I heard the same story of a city that was growing too quickly for infrastructure to keep up and experiencing crazy new traffic and skyrocketing rents that expunged the locals. I had taken it personally when Denver got too cool for me, so I wasn’t interested in being an invasive species in someone else’s city. I wanted to slide into an established community and adapt, make myself a part of it.
So I kept going, tried smaller cities and resort towns like St. Augustine, Savannah, and Charleston. I tested the waters in parts of Wisconsin that would keep me close to family.
I was looking for a place with great coffee, ample nature, and a connection to history. My future home needed to be high-end but down-to-earth, welcoming to outsiders but not completely comprised of us.
I was searching for a paradox and I knew it. I followed my whims and, in each new place, found a unique Airbnb, settled in, met the locals, explored the trailheads, sipped the coffee, toured the museums. I tried on homes like a bride trying on dresses.
If I ever ran out of money, I’d cruise back to the midwestern homestead and let my savings refill. My full-time job was the engine that powered my adventurous life, and I never took that for granted. Meeting deadlines and maintaining contact with work remained my number one priority because work was the primary enabler that let me live a life that felt like vacation.
By 2019, two years after I’d left my bachelorette pad in Denver, I had remote life down to a science. Each year, I stayed with family over the holidays, and as the polar vortexes descended upon the upper Midwest and the snowbirds took flight for Florida, I packed my car and headed out. That year, I drove west.
An Artsy-Fartsy Tour of the Southwest
For the first month on the road, I reconnected with friends in Colorado. My relationship with the state was an on-again-off-again love affair. I always wondered if Colorado and I could make it work, maybe under different circumstances, that one day I would finally fall in love with the place that I had tried to make my home for almost a decade. This time, I rented a mountain cabin outside Boulder to test the hypothesis that I needed to live properly in the mountains to achieve my own Rocky Mountain high. The time I spent there was lovely. I made pot roast and watched a “snowicane” dump two feet of snow on the canyon in one day.
On weekends, I hiked with old friends and frequented longtime favorite coffee shops. It was nice, but it wasn’t home, as hard as I tried to make it so.
Opening Airbnb, I searched the map and quickly found a pristine casita six hours south in Santa Fe. I rolled out of Colorado on a sunny Sunday morning in April, sad and satisfied that it wasn’t meant to be.
As the backbone of my experience, I held my Airbnb accommodations to high standards. They needed to be well-rated by previous guests, and be in a location with relatively convenient access to things I wanted to see. I booked places with kitchens and fell into a routine of cooking most of my meals to save money and prevent digestive weirdness (this mostly worked). Most of all, I did my best to try different ways of living. I mixed up the location and the vibe with each transition, sliding from mountains to beaches, cities to countryside, apartments to yurts. The idea was to maintain my core routine (work, exercise, cooking, writing) while switching up everything else.
The Santa Fe casita had stunning sunset views and excellent WiFi. I had adjusted to working East Coast hours to stay connected with my team, I woke before dawn and wrapped by early afternoon to go wander around Meow Wolf or peruse the rabbit wool hats and Zuni fetishes at the downtown market.
After a few days in New Mexico, I got a serendipitous call from family, who told me they would be in Sedona and wondered if I could meet up. It was another breezy six-hour poke through the Navajo Nation. Connecting with familiar, friendly faces during the adventure recharged my batteries and reminded me how to feel grounded even as I skittered across the continent.
The time in Sedona included sunrise hikes and tamales and taking meetings from a fresh juice bar where the locals hung out barefoot. When I had time, I made day trips to Jerome, Flagstaff, and the Grand Canyon. I looked at the map of wherever I was and made plans to see as much as I could without getting road-weary or burned out, making sure to spend enough time in one place to actually experience it.
I turned my sights from Sedona to my original home state of California, which was suddenly within a day’s drive. Back to Airbnb’s map view and I found a cottage on a farm in Julian, tucked in the mountains between the desert and the beach. Onward!
A Wild Welcome to California
I pulled into the gate of the sprawling farm property just after dusk and saw my cottage tucked under old-growth oak trees and illuminated from within by golden lamplight. It was a welcome sight after another six hours on the road through farmland, dunes, and desert.
I got out of my car and stretched, looking up to see a night sky drenched in stars. My senses tingled in the darkness and I realized I wasn’t alone. Squinting into the inky blackness, I saw a monstrous form emerging from the meadow, making its way deliberately toward me. One set of long legs and swinging hair and then another and another loped out of the gloom. I considered bailing back to my car and finding the nearest Marriott as my heart pounded out of my chest, but I stood my ground and soon discovered I was just getting acquainted with the farm-stay’s resident horses. The enormous creatures approached me fearlessly, sniffing my suitcase and nuzzling my outstretched hand before settling in to chew on grass while I unpacked. Their gentle sighs and munching blended with the rhythm of the tree frogs that floated into the cottage on the breeze, keeping me company as I fell asleep.
I woke to the sound of scratching on the wooden porch and rose from bed to peek out the window. I was ready to see a horse, but wholly unprepared for the five-foot-tall emu I found pecking at the shrubs. This was a truly immersive Airbnb experience!
I made some coffee and set up my laptop on a wooden beam on the porch. I took my calls while emus chased each other in the meadow.
From Julian, I spent a few weeks at the beach and then in a yurt in Topanga Canyon before heading back to the town where I went to high school in Northern California. I stayed in wine country, and took morning walks through the grapevines as fog poured over the foothills.
Nights and weekends, I spent time with my best friend from high school, eating In-N-Out burgers on the floor while her baby toppled towers of blocks. I was so relaxed that one morning I slept right through my first call which was scheduled for six a.m. My boss understood, saying “Your body was telling you something!” I appreciated her graciousness, but didn’t make a snoozing through meetings a habit.
A Fork in the Road
It was midsummer and I had a choice to make. I could keep going north, into the Pacific Northwest – connect with some people I knew in Hood River, work my way up to Spokane before dropping over to see friends who had moved to Missoula. But then I received an email from an acquaintance, inviting me to work the US Open at Pebble Beach. The job would pay, but I needed to find my own lodging, which would be expensive. It came down to a once-in-a-lifetime experience versus the endless possibility of the open road. Ultimately, I went with novelty.
This was the first time in the journey I actually took time off work, and ironically it was also the most taxing. For ten days, I reported to my post at four in the morning to open a security gate in the chilly predawn darkness.
I witnessed the golf course wake up each day as armies of lawnmowers and sprinkler systems came roaring to life and the sky went from black to lilac to grey to blue. For the duration of the tournament, I triaged with a team of facilities managers, security guards, and California Highway Patrol officers to manage the crowds that surged through the gate to mob the first tee when big names like Tiger and Phil teed off, but mostly I just handed out will-call tickets, gave people directions, and bantered with cops. The best part happened after my shift when I could wander around freely, follow the golfers and watch the otters play in the Pacific, before jumping on the shuttle bus back to my Airbnb to try to fall asleep by eight.
That week, simultaneously exhausting and soul-rejuvenating, reconnected me with my love of helping people and solving complex problems. Unfortunately, my accommodations, a pristine apartment in a newly constructed neighborhood in Monterey, wiped out the rest of my reserve travel cash.
It was time to point my car east, back through Moab, Denver, Lincoln, Des Moines, and ultimately Milwaukee. It had taken me months to get to California, but I made the return trip in just 3 days. It was good to be, well, not home, but, you know.
When I drive for more than a few hours, my mind tends to slip into road time. Hours drift by like traffic signs as I consume a whole queue of podcasts. I munch on beef jerky and pumpkin seeds and other handheld delights that deliver quick, sustainable energy. When I arrive where I’m going, I am usually a little strung-out, wild-eyed from scanning the road for hours.
I had barely recovered from that jittery feeling when I started putting out feelers for the next adventure. That’s one very unzen thing about my brand of travel; it’s easy to always have one eye on what’s next. With intense future focus though, you become attuned to every opportunity, scanning the horizon for something to chase. Things mentioned in a passing comment in a conversation over coffee leap out, like when a friend mentioned a skill-building retreat for remote working professionals that was coming up in the fall in Portugal. Why the HECK not? I wondered, still buzzing from the road.
I spent two weeks at a sunny coworking space in Lisbon, averaging 15,000 steps a day as a traversed the hills of the old city. I watched the sunsets over the basilica from the panoramic windows in my Airbnb, a sixth-floor birdhouse at the top of a narrow, winding staircase. The views were more than worth the climb.
From Lisbon, I flew to London for meetings with coworkers, in a rare opportunity to connect live with a distributed team, before taking the train to Paris for a quick stopover on the way to ten days in Barcelona. Traveling through Europe was its own brand of magic. I loved walking everywhere and trading my morning coffee for espresso. I loved trying my luck speaking Portuguese and sitting at the furthest western point in continental Europe. But I also missed my car. I missed beef jerky and the freedom of the open road spreading in every direction before me from sea to shining sea.
Back to Reality
Once again, I stayed in Milwaukee for the holidays and made loose plans for the 2020 adventure season. I was in Tucson – delivering presentations in the morning and picking through gemstones in the afternoon – when the world turned upside down.
In the age of COVID, the activities that had come to define my life – traveling, exploring, talking to strangers – were suddenly forbidden, even dangerous. My initial reaction to the pandemic was extreme grouchiness. I felt like a dog whose leash had just been yanked back and tied to a tree. On the other hand, I had a unique advantage. While everyone else scrambled to adjust to working from home, I was years ahead. I shared best practices with friends who were new to remote life, obvious things like “check your background when you’re on video” and “you’ll be more productive if you put on pants everyday.”
As states shut down, a friend in Asheville, North Carolina reached out with an offer. She’d just renovated a lower level bedroom with plans to list it on Airbnb. With a global shutdown, that wasn’t feasible, and the room was mine if I wanted it, for however long.
So, I moved. I drove 12 hours south and moved myself and all my stuff into a semi-permanent living situation to wait out the storm. As I unpacked boxes that had been stowed at my parents’ for years, it felt like Christmas morning, like reconnecting with old friends.
I was happy to be settling in, nesting, and resting. I hiked along the Blue Ridge Parkway and encountered the locals, both human and black bear, both generally friendly. Under the vibrant green canopy of Western North Carolina’s towering trees, I wondered if I was home. A whisper of wind through the leaves reminded me that yes, I was home all along.
I’m a few months in, and that familiar wanderlust is tugging at my mind. I’m getting itchy in the humidity and wondering what else might be out there for me. For now, I’m here.