This is a story about moving to the Bay Area twice. It’s also a story about unthinkable loss.
At 27, I moved my life to San Francisco from Atlanta. Up until that point, the South was my bubble: metro Atlanta suburbia followed by journalism school at the University of Georgia, followed by a safe career in advertising.
I had spent years dreaming of change while not actually doing anything about it. Luckily, my free-spirited and persuasive cousin, Alan, helped reel me in. He had settled in Nob Hill after moving all over the place in his twenties, from Washington state to New York City to Santa Cruz. I envied his choices and his way of life.
My life felt uninspired compared to Alan’s, and I began scouring job listings in NYC and SF, looking for a clear sign that would make the decision easy. But I soon realized that what I needed most was a strong dose of excitement and unpredictability. Having things be messy for a bit was part of the appeal.
So I quit my job, ended my lease, packed everything in my Jeep, and headed west. I convinced Whitney, my girlfriend (and future wife), whom I’d met only eight weeks prior, to come along. She was weeks away from joining the Peace Corps in Guyana but eagerly accompanied me, adding to the excitement. We made the trek in just four days.
We arrived on a Saturday just before sunset, quickly unloaded, and joined up with my cousin for a low-key house party in Hayes Valley. A diverse, personable group of characters was gathered: Bohemian musicians, professors, waiters, CPAs — San Francisco had everyone.
In Georgia, I often felt like an outsider, an observer. I didn’t find much comfort in college football, church, the historical legacy, or the conservative lean toward uniformity. Atlanta had a more eclectic vibe, but you had to seek it out. This first house party helped me realize that in the Bay Area, nobody is excluded from the scene.
I was hooked. Even at my age, this move was an opportunity for rebirth.
Within a few months, I landed a job, got an apartment, and sold my Jeep. Whitney and I were lovesick and wrote to each other regularly. Eventually, she decided to leave her post and give life with me and the Bay Area a shot instead.
People at the restaurants and stores we frequented would innocently ask us when the baby was due and how excited we were. And nobody knew the truth.
The next several years flew by. The memories are a patchwork of uniquely Californian experiences. Camping in Big Sur, pretending I knew how to ski at Tahoe, driving up to Mendocino, and spending most of our free time eating amazing food and traversing the city by foot. We got married at City Hall and moved to Berkeley. I joined a promising startup, and we became very fond of life in the East Bay.
But eventually, like many transients, I began to question how sustainable our Northern California life would be. Rushing to and from SF each day in a packed, sweaty BART car; a cost of living that was outpacing our ability to travel or save a dollar; and the philosophical wormhole of being at the center of gravity for tech would at times get the best of me.
Concerns about the grind of life faded away when—after nearly a year of trying—Whitney became pregnant, and we felt grounded in a new burst of energy and a sense of purpose.
Whether or not my commute was a picnic or if staying here meant being lifelong renters quickly felt insignificant. Raising our child in a geographical dreamscape full of wonder (day trips to the ocean or the redwoods, for example), along with the exposure to diverse cultures, food, and ideologies, were things we could look forward to.
These romantic visions superseded the drawbacks we anticipated — the primary one being isolation from regular support, as well as free babysitting, which is available to new parents who choose to live near family.
We were ready to embrace that and other challenges and spent the first two trimesters readying for a brand-new life. Baby clothes, practical supplies, cute artifacts, and the lot were acquired slowly and deliberately, and with joyful anticipation. Whitney and I read several books together many evenings before bed on parenting styles and philosophies we respected and even proactively sought advice about the relationship challenges that would likely come from it all.
But during the third trimester, we became aware that our baby had a rare condition that was incompatible with life outside the womb.
He would survive for minutes or hours at best. Cutting-edge medical care was no match for this diagnosis. Simply put, our son’s life was already in its final stages.
Everything froze. The world was stacked against us. We suddenly felt out of orbit, scared, and less secure. We missed our parents and siblings, whose trembling support in those first phone calls helped us realize just how real and tragic this event would be for us. At the same time, we were grateful for the vast distance between us (literally the entire country) and told them not to come visit. We could sense their grief and fear for our psyches through the phone, and it only added to the weight of it all.
Whitney and I clung to each other and stayed quite private during this period, but it wasn’t easy to shield ourselves completely.
People at the restaurants and stores we frequented would innocently ask us when the baby was due and how excited we were. Nobody knew the truth. It was painful to maneuver these questions in public, especially from strangers.
We decided that it would be best to move back east after the birth. While we didn’t want our family to share our burden (or add to it) in the moment, we anticipated that we would eventually need their support to help us become whole again.
The final weeks were spent doing our best to soak up the time we had left. Then my amazing wife gave birth to our full-term son, Charlie, with more grace than I could possibly describe.
We were parents now. But as expected, Charlie never took a breath.
In short, we couldn’t have designed it any better than this. So why the hell did we move back?
We chose not to see ourselves or our son as victims. Who were we to say that he didn’t have a full and beautiful life in the womb?
But regardless of how strong we’d been, it was hard to fathom us snapping back to our prior existence and putting on the rose-colored glasses that are sometimes needed to grind it out in the Bay Area. Besides, everything outside of the afterglow of this event felt inconsequential.
We spent a few months tying up loose ends and researching our next destination. We decided to give Asheville, North Carolina, a chance. By choosing Asheville — a liberal locale that’s as Berkeley as the south gets — we saw an opportunity to fold our two past identities together.
So we left Berkeley and began the drive back east. This time, it took us six days. We weren’t particularly sure of ourselves.
I kept my SF marketing job and worked remotely from a home office, flying back west once a quarter. Whitney got pregnant again very quickly (a mutual decision, believe it or not) with a healthy girl, and we bought our first home, a three-bedroom Craftsman-style house with a modest yard.
Our respective parents all lived about four hours away by car. Not too close, not too far. And we were beginning to make up for lost time with all the family relationships. We even loved our neighbors.
Whitney stopped working altogether to focus on our daughter. And I was always around and able to dedicate my free energy to our family.
In other words, our quality of life in Asheville included many of the material and situational elements that felt out of reach in the Bay Area without a huge windfall from a tech IPO. We couldn’t have designed it any better than this.
But our new haven had its limits. Asheville may be a mountain town, but it at times felt more like a tiny island that could be discovered in a day. In crude terms, it’s a weekend tourist destination and a mecca for outdoor enthusiasts.
Zealous to establish myself as a worthy new resident, I tried my hand at rock climbing. I even bought a pair of rock-climbing shoes. But it never took, and they were quickly discarded into a large box in our crawlspace alongside other relics.
Our routine in Asheville centered on evening strolls in the semi-walkable area of our neighborhood, short drives to the Saturday farmers market, and frequent visits to a handful of restaurants.
So behind the facade, an existential question beckoned: “We moved to California to take ownership of our lives, but it was seemingly too much to handle in a time of crisis. Are we actually happier now that we solved for all those woes?
The aha moment for us came when Whitney and our daughter, Ada, joined me on a business trip back to the Bay Area.
We stayed in an Airbnb for a week on the edge of Rockridge and Temescal, a favorite section of Oakland that we used to flock to regularly. I commuted to work each day, and the two of them settled into the life we would have had with Charlie.
There was an extra skip in everyone’s step, especially Whitney’s. She could easily lose half a day zigzagging to grab a cup of tea, visiting a toddler park, and then perhaps catching up with an old friend for lunch. The opportunity for a new daily routine felt limitless. And the weather, for as much crap as people give it for lacking four seasons, is immensely pleasant most of the time.
They were both far happier by the extra stimulation this larger and more walkable sandbox presented. And it was easier for me to compartmentalize my focus and be fully present with them each evening.
In other words, even though being here meant commuting to the office all week and leaving Whitney and Ada to fend for themselves, it felt like a healthier balance for everyone.
We immediately started planning for them to come on the next trip. This time, we would make it two weeks.
It turns out that we are not haunted by the experience of loss that we suffered while living in Berkeley.
Six months later, a choice presented itself: spin out of my current job and reinvent myself as a consultant, or come back to the Bay Area and take a leadership role at the same startup that allowed me so much flexibility during our hardship. The former would create even more freedom for us to be location-agnostic and spend time as a family. The latter would mean a return to our past life in the Bay Area, including the daily commute and testing whether the happy balance we had created during the recent trips was actually sustainable.
These are privileged choices — that’s for sure. But for Whitney and me, this one felt more loaded and consequential than anything we’d ever considered.
If we had not taken those trips together as a family unit, we probably would have remained in Asheville, pretending that the Blue Ridge lifestyle resonated more than it did and clinging to the coattails of a few dear friends. But the business trips became a North Star for how we could reach an elevated baseline of happiness, and it was only fair that trade-offs would exist.
Our deliberation didn’t last long. We asked our real estate agent to list our house—now no longer our home—in Asheville.