Surprise: we’re moving!

Why we’re ditching the Bay Area and heading to Bend

Samantha Weald
The Wealderness
5 min readDec 13, 2018


The countdown is on for our final days in Oakland…

2018 is almost over.
A living reminder that the things we think we know can change…

In summer, trees are green, lush. They offer shade from a warm sun.
And then fall comes, and our trees are slowly emptied, and orange.
Surrounded by leaves that crunch beneath your feet.
And finally, winter, with its cold wind and snowcapped peaks.
leaving our favorite trees brown and bare.

Our knowledge — “the trees are green” — transformed…

It all started in the mountains…

When Ryan’s parents bought their Tahoe house in the winter of 2016, our old routine went out the window. It’s funny, because now that I look back on it, I can hardly remember what we did on weekends before the Tahoe house… but I think it included a lot of camping and climbing.

Over the years, we’ve each grown to love the mountains in our own way — for the peace, exercise, and beautiful photo opportunities to name a few. But we’ve also felt like it’s been our escape: from Oakland, from city life, from traffic. That’s why during countless drives to and from Tahoe when we’ve played the where would you go if you could go anywhere? game, it’s seemed obvious that most places we named included access to the wilderness.

How about Santa Fe, New Mexico? Boise, Idaho? Boulder, Colorado? Salt Lake City, Utah? In a van? On the road?

… then Lantern closed their doors

Then Ryan’s last company, Lantern, closed their doors. We immediately knew that life over the next 12 months would look very different from life during the last 12: Ryan would most likely have new coworkers, a new routine, new availability, and new work responsibilities. Knowing so much change was ahead, we found ourselves intensifying those dreams about leaving the Bay Area. For a minute there, it looked like Ryan might have the chance to live in Pittsburgh for work for six months. Let’s do it! We thought.

In all the hustle, we started focusing in on all the great things we were getting out of living in the Bay Area but also took the chance to ask ourselves what we were missing. It’s a hard question to answer when from the outside it might seem like we have everything we need in California… family and friends close by, a beautiful house, and job opportunities that allow us to succeed. But Lantern failing created it’s own set of opportunities: for Ryan and his friends to co-found a non-profit; for a test phase of what it would be like for him to work remote; for the chance to dream a little bigger than the Bay Area (where I’ve lived since high school)… if only for a few years.

Bend…. where?

Our September trip to Bend.

Each year, Ryan and I pick a new national park like Arches or Joshua Tree to visit for our anniversary. And in 2017 after our amazing trip to the desert, we started dreaming about our 2018 adventure… where else could we drive from the Bay Area in a reasonable amount of time?

In 2016, Forbes featured Bend as a boom-town in the outdoor industry and Outside Magazine included two companies from Bend in their annual “Best Places to Work” list. In 2017 Outside Magazine named Bend, Oregon the Best Multi-Sport Town. In 2018, we noticed that some of the runners and other athletes Ryan follows live in Bend, and through the grapevine, heard about a few friends of friends who had lived there or moved there recently. So when the time came in September to hit the road for our annual trip, we said why not and headed to Oregon for our anniversary, and along the way, spent a few days in Bend.

When we were planning the trip, we had this feeling that Bend was the kind of place that could convince us to leave the Bay Area. A mountain town with good coffee, tons of trails, and high desert weather? Yes please. But even though we planned to like Bend, I don’t think either of us had prepared for just how at home we felt when we got there.

We liked it so much that we came back a few weeks later to meet with a realtor.

We liked it so much that last month, we put our Oakland loft up for sale.

We liked it so much that we put in a contingent offer on a beautiful brand new home in Bend!

Our new house!

See you in Oregon!

Once the loft went up for sale in early November, we were equal parts afraid that it would sell and equal parts terrified that it wouldn’t. Then a week went by, then two… then three and four weeks with no interest. But at the end of November after almost a full month on the market… we got an offer!

That means the countdown is officially on:

  1. we are moving out of our Oakland place this weekend!
  2. escrow should close on both properties by December 21st!
  3. (we will spend Christmas in the Bay Area with family)
  4. then off we go!
Bishop’s new backyard =)

We are looking forward to extra bedrooms (where we hope to house lots of visitors, please come see us!), a yard for Bishop, working from home full time, a different pace of life, and so much more.

We are also both grateful to work with colleagues who support our dreams (looking at you All Mental Health & Wiki Education) and to have families who hear our crazy ideas and allow us to see them through (remember that time we got engaged after knowing each other for less than a year?)

newly engaged babies ❤

Hope to see you each in Oregon soon!