How did you start working remotely? Was it something you sought out or stumbled into?

I started in college, when I was a freshman at UNL and we’d escape campus to hole up and study at The Mill and Village Inn. In what would have been my Senior year, I dropped out to work for a startup in Portland. I convinced them to let me work from Lincoln for a few months and I got hooked on working from wherever I wanted to be. In the 15 years since, I’ve only had a “normal, on location, 9-5 job” for 3 years. The rest of the time I ran my own virtual agency or worked as a remote employee for companies in Silicon Valley and NYC.

How did you find places to work from before Workfrom?

I love discovery in person. Coming from a small town in the Midwest, I explored Portland like it was a collection of small towns (which it is in so many ways). I’d simply leave my house and walk to, bike to or drive to a new town/neighborhood and wander into the first place that’d catch my eye. Then I’d ask a stranger for their recommendations and soon I’d be somewhere.

After shared writing spaces started popping up in NYC in the early oughts, I teamed up with a friend to start a local coworking space out of an old fire station. We did a ton of research at that time — on local coffee shops, cafes and rumors of other coworking spaces in the works (as none had existed yet). Sadly, we folded the business before we opened our doors (and lost a good chunk of change on the lease we’d already signed) but I walked away with a great wealth of knowledge of the local cafe & coworking landscape. Subsequently, over the years managing remote teams, I worked from various coworking spaces and met other remote workers who loved to swap favorite code caves and writing dens.

Why Workfrom?

Community without commitment.

I love hosting dinner parties and inviting folks who don’t know each other as I love the resulting conversations and the seemingly random yet meaningful connections that are made. I love road tripping and the freedom of not having to maintain relationships and being afforded the opportunity to be whoever I want to be for a town or a day. If today’s a particularly hard day, tomorrow needn’t know about it. I also love having a home base, having roots, passing down traditions, nostalgia and shared experiences. Workfrom goes beyond being another listing site and juxtaposes these opposing loves in a way that gets me out of bed every morning — whether it’s to connect with other awesome people, be inspired or find a good place to hide.

A way to connect people with rural and dying cities that no longer have their old industries.

When I think of ourselves looking back in 50 years, we’ll comment on the “rural migration” in a way we did when people flocked to the cities for jobs. If we can take our jobs with us and instead choose to travel or live wherever we want … well, that means more people may get to see the Milky Way before they fall asleep than ever before. There are qualities of life and connections with nature that we simply can’t get in the cities. Sorry if that’s off topic and a bit ethereal. I dream big.

How did you meet Darren?

At a coffee shop, of course!

What would you like to see above all else come from Workfrom next year?

All the things!!

Any tips you’d like to share for others wanting to or already working remotely?

Take breaks and assume the best. It’s easy to zone out and then suddenly realize the place you’re in is packed and your bag no longer needs its own seat. I think a lot of what folks see as “rude” is unintentional, so if you see someone else being “rude” assume they simply zoned out into their work and lost track of time and place. Don’t be afraid to ask others to share a table, move a bag, etc. They may even thank you for it and you never know who you’ll meet.

Any tips for those wanting to visit and work from Portland?

Workfrom.co/portland is a great place to start — to find people & places near where you’re staying or to pick a good neighborhood to stay in. If you like to get off the beaten path, check out Old River Road (down South), N River St, Skyline Tavern (and all of the Blvd), River View Cemetery, Lafayette St pedestrian bridge, the bar deck at Salty’s on the Columbia and take the scenic highway to all the waterfalls. Sunrise at Larch Mountain is worth the early rise.