What I’ve Learned While Working on the Road

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I’ve been road tripping across the U.S. while working for the past few months and even though it’s only been a little while working from the road I’ve learned a lot. From the places we’ve stayed to the advice I’d give other business owners thinking about doing the same, I’m here to spill all the glamorous and not-so-glamorous things I’ve learned and experienced. 

On the days you’re traveling, don’t plan anything 

When we first started out, I told myself, when we get to the hotel by 4 pm I’ll have some time to do work. But then you hit a flash flood or you drink too much water and have to pee a million times or you need to stop and stretch your legs. And soon enough 4 pm turns into 7 pm and by the time you get to the damn hotel the LAST thing you want to do is work. 

(I don’t know why, but there’s something seriously exhausting about just sitting in the car.) 

Even on the days when we’re only driving ONE HOUR, the most ridiculous things come up that we never could have planned for. 

Like getting the wrong address for a Rover sit which leads to trying to break into a random person’s house who turns out to live over an hour from the place where you’re supposed to be dogsitting. 

Or someone tries to reset the wifi password so you have access to it and then the whole server goes out for the next TWO days leaving you 30 minutes from the nearest wifi location, a brewery. 

So yeah, on travel days – I assume I’m going to get absolutely nothing done because when you do, you stress yourself out when all the unexpected things come up which they will. 

Don’t plan on getting anything done that way whatever you do accomplish is a bonus. 

Prepare to be flexible as f*ck

Personally, I’m a routine girl. I LIVE for routines and the lack of routine has been the biggest challenge I’ve encountered while traveling. Given that we’re staying with friends, applying to housesits across the country (thank you, Trusted Housesitters), and filling in the gaps with Airbnbs, I have very little say over my schedule. 

And that’s just part of traveling. 

Don’t try to stick to a rigid routine. Know that things are going to come up that disrupt your plans. And try to be as flexible as you possibly can. 

Everything costs more than you think 

You probably could have guessed that, but it’s worth blatantly stating. Even if you’re not spending a lot of money on rent, the one-night hotels as you’re driving to your next location, the Airbnbs to catch up on work, the coffee shops, the buying prepared food because someone’s stove doesn’t work, the gas, the eating out, and all the sight-seeing expenses add up. 

While it’s totally doable, it’s not as cheap as you think. Plus, it’s hard to not want to spend money exploring cool places!

Give yourself a cushion that way if/when extra expenses arise, you don’t feel freaked out. 

Expect to feel torn between work and play 

I love what I do and I can be a bit of a workaholic, but I also value making time for new experiences, especially when I’m traveling. 

The tension between those two has been hard. Often, when I’m working on my biz I feel guilty that I’m not taking advantage of the cool place I’m staying in. And when I’m out exploring somewhere new and cool when I could be working, it can feel a little stressful.

The way we’ve been combatting this is by switching between cool and not-so-cool places. 

In the places you know you’re going to want to take time off work to explore, factor that into your workload, and then book somewhere the week after that’s not so exciting where you can hole up and get a lot of work done. 

(Right now, I’m holed up in Poughkeepsie, a location we weren’t terribly excited about, putting in some long hours to get “ahead” on work before heading to New York City, where I’m sure my productivity will fly out the window.)

Explore the random places around you 

My favorite part of getting random housesits in odd locations has been exploring places I never would have traveled to otherwise. If you find yourself in a random area over the weekend and you have time to take off work, do some research. 

Find out what towns and cities are near you, pick something you enjoy, like coffee shops, bookstores museums, cool restaurants, and go check them out. Exploring what’s nearby the places we’ve stayed has by far been the coolest part of traveling.

(And I love choosing certain things to do in every town we visit. No matter where we’ve gone, I’ve almost always checked out a bookstore or a coffee shop. It’s fun to compare the differences.)

A few smaller lessons I’ve learned:

  • Meal plan diligently 

So you’re not throwing away extra food that you didn’t eat in time and can’t take with you. 

  • Do your laundry whenever you can

AND, if you need to do laundry make sure you look for that amenity in the places you’re staying. 

(Don’t assume it’s a given, we learned that one the hard way many times.)

  • Document everything you can

You think you’ll remember, but as you hop from place to place, time passes a lot quicker than you’d think. Keep a little journal of things you do in each place that you don’t want to forget and take photos too! 

  • You don’t need all the clothes you think you do 

You’re gonna end up wearing the same things a million times so just take what you thought you wanted to bring and halve it (and expect to hate everything you do bring because you’re wearing so much). 

  • Be honest about what you’re comfortable with 

If you know you don’t enjoy staying in rural areas, don’t do it. Be honest with yourself about what you want and try your best to prioritize where you stay accordingly.

  • And always, ALWAYS check for bed bugs

Preferably, before you go to sleep in your hotel…YUCK. 

There are going to be some awesome moments like visiting places you’ve always wanted to and there are going to be some s*itty times like staying in less-than-ideal places that are the most affordable.  The good and the bad tend to ebb and flow, or at least, that’s what I’ve learned. 

Any gems of wisdom to add? I’m all ears!

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