My New WFH (wine, farming, hikes): How I Packed Up My Life and Moved Across the Country

Chi Thorsen-McCarthy
Life @ Thumbtack
Published in
4 min readSep 28, 2021

Earlier this year, my partner, Ian, and I moved from the Bay Area across the country to the Finger Lakes region of New York in the village of Watkins Glen — known for its incredible waterfalls, world-famous race track, and the Seneca Lake Wine Trail. The only reason this was possible was because of Thumbtack’s decision to challenge the status quo and fully embrace a new way of working as a virtual-first company. We bought a farm (it’s still wild to say that) on 15 acres of land, complete with an old farmhouse, sheep, chickens and a quintessential big red barn.

Making that dream a reality

While I’m originally from the midwest, I’d been in the Bay Area for all 4 years of my time at Thumbtack. My partner — whom I met at Thumbtack’s San Francisco headquarters — and I had collectively spent the last 15 years renting outrageously expensive apartments in the Bay Area, in what we jokingly referred to as “setting our money on fire.” For years we had dreamt about what it would be like to own our own home but buying a place in Northern California wasn’t realistic for us — especially for what we wanted. Ian is a winemaker and dreamed of eventually owning land, growing his own grapes and starting a winery. We both had dreams to start a sustainable, organic family farm. And I’d always desperately wanted to raise chickens (now I have 10!).

But again — before the pandemic, these goals just didn’t feel realistic in the Bay Area. So we started to think about places where it could be possible, like the Pacific Northwest or Upstate New York. Even still, it just wasn’t in the cards because I didn’t want to leave my job leading our Creative Team at Thumbtack, a role I’d worked really hard to grow into. So we put the idea on ice, thinking we could put pen to paper in about 10 years.

Then Thumbtack announced it’s launch of a virtual-first working model and everything clicked. Anything felt possible all of a sudden and from there, it just sort of fell into place. We made an offer on an awesome plot of land in the Finger Lakes and within 2 months we were ready to go. We said goodbye to the friends we’d made over the years in California, packed up our van, and drove 2,750 miles to our new home across the country.

We’ll be planting our vineyard in Spring 2022. But for now, it’s not a bad view.

My New WFH (wine, farming, hikes)

Since moving, we’ve begun renovations of our farmhouse, built in 1850, and are building a small starter winery space. We plan to plant at least 7 acres of organic hybrid grape varieties in the spring and have already started to grow our own food. As we slowly build our infrastructure, we have plenty to keep us busy — chickens for egg production, 6 Katahdin sheep to keep the pasture healthy, a couple cats who roam the property, and the latest addition to our pack, Pepper, a border collie pup who’s learning to herd the sheep.

Working remotely while on a farm has been surprisingly calm. I get up at dawn for farm chores or puppy training, and then I get plenty of quiet time to do Thumbtack work before my meetings start at 12pm EST. I feel balanced for the first time in a long time. No commutes. No rushing to get home. No having to change out of my farm clothes to join zoom calls. And I can check on the sheep during lunch, I love it.

After hours, we hike with our pup in the Finger Lakes National Forest (basically in our backyard) or go foraging for apples and pears to make cider with. And when I need to satisfy my intense desire for Chipotle, Ithaca is only 30 minutes away.

Our puppy, Pepper, hanging out with our sheep and chickens.

Having it all

These days, most of my challenges have to do with herding sheep and keeping chickens alive, and less with working remotely with co-workers. It can sometimes be challenging to connect with people or have quick water-cooler conversations but it just makes me even more excited for our upcoming in-person events in the months ahead. By far, the benefits of this hybrid working model outweigh the challenges. Like me, employees have the freedom to customize their lives outside of work with more flexibility than ever before. And as a team leader, it’s great to see that my team is doing really well too, with folks now in four U.S. time zones, living their best lives. It’s like everybody got to come up for air and take a look at what their lives could be and prioritize their personal lives without the expense of compromising their professional lives with this new working model.

So, clichés be damned — I get to have it all. It’s been really rewarding to make these life-changing moves while still having the stability and peace of mind from Thumbtack. Okay, time to go feed the chickens.

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