Life as Digital Nomads

Working from our hotel room in San Fran

From Gracie: Some of you have asked us how it’s been working from the road. Others have asked if we won the Illinois lottery.

Here’s the short answer: We didn’t win the lottery and it’s been challenging. In a good way.

Here’s the long answer: After working in relatively traditional, 9 to 5 office environments for several years, it’s been a pretty big adjustment to work for a couple hours here, a couple hours there, from various cafés and wifi hotspots around the country. We don’t have established working hours; we don’t have “off hours” either. We’ve carved out time for client project work, phone calls, and emails — on Sunday mornings, on Friday nights, during long stretches of driving — whenever we can and want to.

Therein lies the biggest difference we’ve found between full time freelance consulting and our past office gigs: it’s on our schedule.

If we want to take a day or two to crank out emails, catch up on blog posts, and follow up with clients, we do it. Even if that day is a Sunday and the World Series is on and everyone we know is likely at a bar. If we’re feelin’ work mode, we get into work mode. And if we want to take the following three days to explore, hike, and order another beer flight, we do it.

It’s liberating but also challenging since we’re allowing ourselves to work on our own schedules while also redefining what “being productive” truly means. To us, being productive nowadays means working when we feel most creative, inspired, and attentive. Being productive is no longer punching an invisible timecard while diligently sitting at our desks trying to convince ourselves to “do work.”

Over the past year, I’ve gotten more accustomed to a flexible work schedule than Andrew. Any given work week in Chicago meant writing and editing on a Monday, working at the wine shop from 3-11pm on Tuesday, volunteering Wednesday, back at the wine shop Thursday afternoon and evening, then more freelance work Friday. This not-so-scheduled schedule helped me accept that everyday might not look the same but I was still accomplishing a great deal while working toward various professional goals.

Even though he was working in an intense office environment and would oftentimes clock 70 hour weeks because the expectation was simply that, it was Andrew’s longtime goal to start a small business coupled with reading various books such as The Four Hour Work Week and Good to Great, and following The Holstee Manifesto that eventually helped him escape the office cube as well. (And by the pics of him I’ve been able to snap over the past few weeks, I think he’s taking to his new work environment quite well.)

You know this part: we leapt. And we didn’t think about it too long and hard because if we had, we probably wouldn’t have leapt the way we did. It’s absolutely reassuring to have job security, known expectations, and a predictable routine. And it’s kind of scary not to.

Yes, it’s a bit scary and challenging–at times we find ourselves missing daily chats with co-workers or missing cutting out of the office on a Friday night to meet friends for a post-work happy hour–but we just do it our way now.

We’ve made a routine of not having a routine.

We may stay up late writing emails one night but we take plenty of time to enjoy coffee the next morning. Well, it also just takes a lot longer to make coffee on the road with a small cookstove, a stubborn old French press, and often limited counter space.

We may choose to work in an office setting again someday or we may not, but for now we’re enjoying our new challenge. We’re trying to live more mindfully and everyday we push ourselves to personify our mantra, YOLO!

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