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Here’s How We Traveled Across America For A Year Without Telling Our Bosses

Here’s How We Traveled Across America For A Year Without Telling Our Bosses


“Better to beg forgiveness than ask permission.” It’s a popular mantra in corporate America, and if it’s good enough for management, it’s good enough for us.

We’re two people whose full-time jobs became so unsustainable that we decided to swap our city apartments for the vagabond lifestyle of full-time, van-dwelling travelers. We also decided not to tell our employers about it.

As members of the New York City rat race, one of us (Hailey) was fed up with the subway commutes, 12-hour workdays and after-hours fire drills; the other (Mitch) was at a loss over the recent appointment of an incredibly inept executive who was destroying team morale. Both of us were eager to remove ourselves from these elements, but as two people who pride themselves on putting a lot of effort into improving corporate culture, merely resigning in the face of its faults didn’t sit well with us.

We wanted to prove to employers ― our own and others ― that giving people more freedom is an investment, not a risk. We also sought to inspire America’s workforce to remember that mental health and personal time are rights, not requests. To that end, we nicknamed our little experiment “Rogue Trip.”

And what better way to prove our case than to take the trip without permission? Within a few days, we’d drawn up an itinerary with the intention of visiting a handful of national parks, dozens of distant loved ones and hundreds of ice cream parlors. Mitch can’t go too long without ice cream ― he claims it’s a medical condition.


Via Hailey Herdlinger and Mitch Turck

A map of Hailey and Mitch’s route

Of course, the big step was convincing our jobs to allow us to work remotely (admittedly easier for folks like us who work in the tech sector). Mitch was already working remotely from when he first negotiated his product marketing job. Hailey held the title chief of staff, which is about as far from being remote-friendly as jobs get. But with a bit of negotiation, her company agreed to alter her role and allow her to telecommute.

In November 2016, we told our respective companies that we were moving to Florida to be closer to friends and family, some of whom had health issues at the time. That part was true. What we omitted was the fact that after we stopped in Florida, we planned to venture through 45 more states.

Hailey sitting in the school bus graveyard in Alto, Georgia.


via Hailey Herdlinger and Mitch Turck

Hailey sitting in the school bus graveyard in Alto, Georgia.

Here are some of the most notable tidbits from our experiment:

Hailey’s daily commute in NYC was roughly two hours (an hour each way) of unusable time. In doing some simple math, it was pretty startling to realize that driving 75 miles per day together through the U.S. would actually provide better availability to her employer than commuting into the office. In other words, many of you commuters are already traveling enough in a year to circumnavigate America; you’re just doing it back and forth hundreds of times over the same tiny part of the country.

We were mostly worried about missing meetings due to spotty service, but it turns out the internet Wild West is more forgiving than you’d think. With an unlimited data plan turning our phones into hot spots and an app that maps signal strength, we were golden. When we needed the help of Wi-Fi, our options included libraries, parks, malls and cafes. Neither of us drinks coffee but we managed to patronize over 150 cafes, ordering the stale muffin as our signature move.

Hailey crossing the Quince Street Bridge in San Diego.


via Hailey Herdlinger and Mitch Turck

Hailey crossing the Quince Street Bridge in San Diego.

Also helpful was the fact that modern conference calls are already atrocious, with people dialing in from airports or hopping on 10 minutes late or struggling to share their screen or muting themselves so they can take a nap. By comparison, we were often the most attentive attendees in the virtual room.

The biggest threats to our conference calls were actually local background noises. “So, transitioning to Q2, we want to be ― I’m sorry, does anyone else hear parrots?” Luckily, our cover as Florida residents made for a great excuse. You’d be surprised how often “Florida” will suffice as the reason for a strange sound leaking through your phone. Even bears.

Mitch at the Out of Africa Wildlife Park near Sedona, Arizona.


via Hailey Herdlinger and Mitch Turck

Mitch at the Out of Africa Wildlife Park near Sedona, Arizona.

Perhaps the only constant downside to our experiment was the need to deceive co-workers in otherwise harmless situations, like responding to “How’s the weather down there?” by Googling it and blankly reporting it back like a meteorologist. On the other hand, distancing ourselves from certain employees was magical: Mitch actually received documented praise from his problematic supervisor for “much improved behavior” while out on the road. Several months later, that supervisor was demoted. A lot can happen while you’re writing video scripts from the comforts of an inner tube.

Mitch tubing down the Deschutes River in Bend, Oregon.


via Hailey Herdlinger and Mitch Turck

Mitch tubing down the Deschutes River in Bend, Oregon.

So, how did our jobs fare over the course of the experiment?

A few months into our trip, Hailey’s role fell victim to a mass layoff (unrelated to her clandestine remoteness), at which point she informed her co-workers that she was traveling. But as proof positive of what we set out to do, her company responded several months later by bringing her back on as a consultant, thereby showing they fully supported her nomadic lifestyle and did not see it as a hindrance to doing excellent work.

Mitch actually survived the entire year, though he recently caught the layoff bug in February 2018 … a fairly frequent fate in the tech world, after all. So, like you, his former employer and colleagues are hearing all this for the first time.

That’s one of the biggest takeaways for us: Had we toed the company line and stayed at our desks like obedient dogs instead of gallivanting around the U.S., we probably would have been pink-slipped anyway. This isn’t 1968. Nobody gets a gold watch for their subservience. Fear will not save your job.

Another crucial lesson we cemented is that there’s no written rule stating work should suck, or that it’s performed better when it sucks. At no point during the journey did either of our employers question our performance; having emerged with that proof, we want you to use it as ammunition. If the only thing stopping you from working remotely is the perception that you will be less productive, we’re here to say that perception is wrong.

Hailey getting a little work done on Route 12 in Boulder, Utah.


via Hailey Herdlinger and Mitch Turck

Hailey getting a little work done on Route 12 in Boulder, Utah.

Living out of a van may not be your shtick ― what with the minimalism and sporadic showering and whatnot ― but whatever you choose to do with the freedom of remote work is surely better than polluting the city with your commute and polluting your mind with busywork.

We learned a ton about our country and its people. We saw more distant friends and relatives in a year than some will see in a lifetime. We went to nine Mardi Gras parades in three states, and still have the beads to prove it.

Ultimately, our journey also taught us a lot about ourselves. We learned how much our creativity is affected by our surroundings. We reaffirmed that we’re far more productive on our own schedules, even when working fewer hours. Above all, we learned that partnerships ― both professional and personal ― thrive on freedom.

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