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What I’ve Learned While Working on the Road
Business, Life
For the past few months, I’ve been road-tripping across Karnataka while working remotely. Even though it’s only been a short while, 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. Here, I’m sharing both the glamorous and not-so-glamorous aspects of my experience.
1. On Travel Days, Assume You’ll Get Nothing Done
When we first started out, I thought, “When we get to the hotel by 4 pm, I’ll have some time to work.” But then life happened: flash floods, nature calls, or just needing to stretch your legs. Before you know it, 4 pm turns into 7 pm, and by the time you arrive at your destination, 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 days when we’re only driving for an hour, the most ridiculous things come up that you could never plan for. Like getting the wrong address for a housesit, leading to a wild goose chase to break into a random person’s house (who lives over an hour from where you’re supposed to be dogsitting). Or someone resets the Wi-Fi password, leaving you without internet for two days, stranded 30 minutes from the nearest Wi-Fi location (a brewery).
So, on travel days, assume you’ll get absolutely nothing done. When you do manage to accomplish something, it’s a bonus. Don’t plan on getting anything done that way—whatever you do accomplish is a win.
2. Prepare to Be Flexible as F*ck
Personally, I’m a routine girl. I thrive on routines, but 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 control over my schedule.
And that’s just part of traveling.
Don’t try to stick to a rigid routine. Know that things will come up that disrupt your plans. Try to be as flexible as you possibly can. Embrace the chaos and go with the flow.
3. Everything Costs More Than You Think
You probably could have guessed this, but it’s worth stating: even if you’re not spending a lot on rent, the one-night hotels as you drive to your next location, the Airbnbs to catch up on work, the coffee shops, the prepared food because someone’s stove doesn’t work, the gas, the eating out, and all the sightseeing expenses add up.
While it’s totally doable, it’s not as cheap as you might think. Plus, it’s hard to resist spending money exploring cool places!
Give yourself a financial cushion so that if/when extra expenses arise, you don’t feel stressed.
4. 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 work and play has been challenging. Often, when I’m working on my business, 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, I feel a little guilty that I could be working.
The way we’ve been managing 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.)
5. 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 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 going to 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.
- Always, ALWAYS Check for Bed Bugs: Preferably before you go to sleep in your hotel… YUCK.
The Good and the Bad
There are going to be some awesome moments—like visiting places you’ve always wanted to see—and there are going to be some not-so-great 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.
Blog by user – Aks***19