Finding Home 1: Decisions, Decisions

Dispatches from our search for the right place to spend the rest of our lives

Bruce Overby
The Shadow
Published in
6 min readAug 11, 2021

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In America in the wake of the COVID-19 pandemic, lots of people are seizing the chance to dramatically change their lives. In my case, the pandemic accelerated changes my wife Caroline and I had been planning for years: we both retired early from our Silicon Valley careers, and we sold our house, using California’s red hot housing market to secure the nest egg bump we needed for the long haul. Just as thousands of Californians do every year, we will now retreat to a less-costly place for retirement. The challenge now: Which less-costly place?

Exploring our options

A few years ago, one of our trusted advisors suggested two critical steps toward answering this question: 1. Determine exactly what you need, and articulate it clearly, and 2. Explore your options as thoroughly as you can — i.e., go and actually live in the places you’re considering, for as long as you can afford to, and during what would typically be the most difficult time to live there (in a desert, during the summertime; in a beach town, during tourist season, etc.) We’ve landed on a reasonable set of criteria — I describe them below — and now, we’ve begun our explorations, which I’ll share in this series of dispatches. But first, a little about the transition we’ve just made.

The decision to move

I had been planning to retire from my high-tech career for several years. Despite the last few years being happier than any time in the preceding 30+ years of my work life, I still found myself drawn to my fiction writing, and often regretted the hours I would spend in meetings and head-down on spreadsheets and PowerPoints. My plan, year after year, was to wait for the annual round of layoffs that would happen every autumn, fully expecting I would be impacted, and therefore might get a severance package. Year after year, my number never came up, and instead I found myself looking at a job I enjoyed, making more in salary than I ever had, and most importantly, working at a great company with terrific people. So year after year, I stayed on and relegated my fiction writing to a few early morning hours on weekdays.

The pandemic changed all that. My company, like so many others, needed to dramatically cut staff and so offered generous early retirement packages to employees who fit certain criteria. As a sixtysomething long-term employee, I qualified, and so finally landed on the decision I had been pondering for years. What’s more, the company had shown tremendous compassion throughout the early months of the pandemic, and in October 2020, when the staff reductions started, that compassion continued, and the severance packages were surprisingly generous. Not only did I realize the dream of early retirement, but I also did so with some unexpected financial breathing room.

After a few months of watching me spend my weekdays at the gym or off on long bike rides, Caroline decided to join me in retirement, and we turned the page on our new chapter. The catch, of course, was that we weren’t quite able to retire without selling the house we owned in what can only be described as a highly desirable Silicon Valley neighborhood. We needed to inject massively into our nest egg, and this was the only way to do it. We had been in the house for fifteen years, had remodeled it five years into our exact specifications, and had enjoyed it, and the neighborhood, for a truly wonderful decade. The decision to give up our neighbors and our nearly ideal home was a tough one, but we decided it would be worth it. The house took six days to sell at 20% over our asking price.

The House We Sold (Photo by author)

What we need

Caroline and I are two different people, of course, but we’ve been married almost 30 years, and so we're able to agree on a basic set of requirements for our new home:

Proximity: We both grew up in Silicon Valley — I in San Jose and Caroline in Palo Alto — and our aging parents and some of our siblings and their families still live here. As such, our plan is to buy a permanent house away from here, but not too far away, and to secure a modest condo we can use for frequent return visits. We’re also frequent travelers, and plan to travel even more once we’re clear of the pandemic, so we’ve set a limit of living no more than two hours from a major airport. Given housing costs, none of this will be easy, and that’s certainly our biggest challenge, which leads us to…

Affordability: Our three-bedroom, two-bath ranch house fetched a tidy sum when we sold it, but there is still a limit to what we can spend on a new house. Again, a good portion of the proceeds from our house has now gone into our retirement fund. If we were free to fly anywhere, we could decamp to any of a number of places outside California and live like royalty, but (see “Proximity”).

Community: We’re quite attached to the idea of being able to “walk downtown.” From three of the four houses we’ve owned, we were able to walk to revitalized downtown streets in Silicon Valley’s most vibrant cities: Mountain View, Sunnyvale, and Palo Alto. We sacrificed that when we bought our last house, opting for a large lot and a quiet neighborhood well clear of downtown, and, for the last fifteen years, that’s been the source of some regret.

West Cliff Drive, Santa Cruz, CA (Photo by author)

Amenities: Like many of our generation, Caroline and I are both very active. She is an avid runner, and I’m an avid cyclist. We also swim for fitness, play tennis, hike, and, as though we needed something else, Caroline is now taking up golf. We want to continue with all of this, so we need a place that is bike-friendly, with facilities for active adults and seniors, and golf courses and some reasonably high mountains nearby. Good mass transit is also important, since, very soon, we’re planning to ditch one of our two cars.

Weather: One would think that, in Northern California, the weather would never be an issue. But there are places that get too hot for many of our outdoor activities, particularly for Caroline, who is fair-skinned and has more difficulty in the heat than I do. We expect that climate change will continue to raise the temperatures, so we’re drawn to the nearly magical microclimates of Monterey Bay and the San Francisco Peninsula coast, where the fog and coastal breezes cool the air, even in the midst of a hot California summer. Still, we’re native Californians, so if trade-offs dictate that we’ll need to deal with the heat, we’re certainly up to the challenge.

First stop: Santa Cruz

Santa Cruz Beach Boardwalk (Photo by author)

Silicon Valley natives know the north Monterey Bay beach town of Santa Cruz as the place we’d get away to for weekend days on the beach. Going “over the hill” from San Jose to Santa Cruz involved a 40-minute drive over the Santa Cruz Mountains on California Highway 17, which includes eight miles of winding road that is occasionally treacherous. That difficult drive is the one downside to a town that, on paper, meets all of our needs. With a population of 64,000, Santa Cruz is a progressive, youthful college town with a range of cultural activities and a vibrant economy. As a bonus, it’s also home to the Santa Cruz Warriors, the NBA G-League affiliate of the Golden State Warriors. We’ve just settled into temporary lodgings here where, for the next three-plus weeks, we’ll experience the height of the tourist season and some of that windy, overcast coastal weather the Monterey Bay is known for. Look for my first dispatch from Santa Cruz in the coming weeks.

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Bruce Overby
The Shadow

Silicon Valley native, retired tech industry professional, long ago social media researcher, and writer.