The Decision

A meandering account of how we ended up living—and loving—life on the road.

Sutro Tower

I’m a person who wants to have their cake and eat it too. I'm a fun-seeker. I want to see new things, new places, play in the sun. 

So maybe my logic is terribly self-indulgent, or maybe it’s just the right amount of whack—I’m still not sure. But the thought was this: maximize my favorite things, minimize my least favorite things, and build in a neutral safe zone for me to try things I’d been meaning to try. (Cue Ella Fitzgerald, “You’ve got to… ac-cen-tuate the positive…”)

The most important piece was to lose the soul-wrenching, fury-inducing, albeit money-making job. That was non-negotiable. I could apply for other jobs, or switch roles within my company. But you could say I was afflicted with the famed and oppressive Millennial burnout that it seems we all feel—I needed a break.


With no job and the steep cost of living in San Francisco, I could maintain a cheaper version of my city slicker lifestyle for a few months, have probably nothing to show for those months, and then have an incredibly stressful and desperate job hunt afterward and cross my fingers and hope to hell that I land a good gig, or else be sent to the streets like… we won’t go there. I know I’ve got a wild streak, but I’m still reasonably risk-averse, and this option was really pushing it for me.

Another enticing option was to buy a house somewhere more affordable than the Bay Area. We could pack up the apartment, move into a beautiful historic home in an up and coming city, and I could spend several months of unemployment renovating it into the perfect dream home. Dreamy. But where? I’ve travelled a bit around the country, to a handful of major cities, some of which I’ve loved. So I’d been sending Kyle Zillow home listings all across the country for the past few months. But the truth was, I’d only ever spent a few days in any of those places. And I’d have to get a new job shortly after closing. And I’d have to find that house and close before I quit my job. And I’ve never done any sort of renovating before. So at the end of the day, if I really wanted a break, I couldn’t afford a house.

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Then there’s this other dream of mine to have a farm… with chickens, an orchard, a veg patch, and fields of flowers that I’d sell at farmer’s markets and to wholesalers. That dream can be summed up by watching the awesome recent film, Big Little Farm, which a friend recommended to me after I’d shared this dream and expected to hear how absurd an idea that is. (He also told me that my running a farm is “an inevitability”—which I love.) But I don’t know how to do any of that. And that costs a lot of money to get started. And land. And maybe more than just one person…

Truck and travel trailer of So Tiny So Big.

So that brings us to the plan we ended up choosing. Buy a travel trailer, buy a truck to tow it, travel. Kyle continues working remotely—just now he does it from somewhere new every couple days. Oskee stays in the trailer when I go on hikes in doggy-free zones. I still own a home, just not a conventional one. And this plan was surprisingly way more affordable than every other option. I can do this without desperately searching for a job right away. I can take the break I need. I can read, paint, draw, learn to cook, bake, write, all from this tiny home on wheels. I can spend some time to see this beautiful country, hiking in our public lands. I can have my cake and eat it too—and share it with my boys.

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The DecisionPersonal