Musings on Working from the Road

This past month, I’ve been traveling. Gallivanting around. Taking the show on the road. It’s been a trip, both literally and figuratively.


When I started my coaching business all those years ago, I had a notion that I didn’t want to be tied to a desk, or a 9-5 schedule, and so I played around with ways work that felt freer, and more flowy.


Back in the late 90’s/early 2000’s, being a digital nomad wasn’t really a thing yet, and the phrase “location independence” didn’t have the meaning it does today. Yet I knew I wanted to be able to work from anywhere if I felt like it; a girl’s gotta be free, ya know?


So I set about making my business one where I only had to show up in-person if I wanted to; everything could be done either over the phone, or nowadays, via video. Over the years, I’ve taken advantage of the fact that I didn’t have to do my work in a certain place, and have worked from various coffee shops and bookstores (naturally), my parent’s dining room table (cozy), and even my car, or while standing in line to get into the grocery store (a recent pandemic location addition).


Yet, in all this time, I haven’t put my theory of working from anywhere to a rigorous test, not the way I have this past month. And as you’d expect, it’s been revealing.


Before I share what I’ve noticed about working not from home this past month, let me just say that however you want to work is fine. There are a lot of shoulds out in the world about how to arrange your work life, when or how to work, idealized notions of being a digital nomad, and how it’s such a great way to live… The truth is that the best way to work is whatever works best for you, and you’re allowed to arrange your work-life however you please. I’m on this adventure because part of me was curious, and so I went for it. What I’m sharing here are aspects of my business and findings, and I’m curious to hear what they spark in you.


My business model is such that I make a lot of my income by doing one-on-one coaching with clients. I love the connection and being able to dig deeply into their businesses and lives to create the changes they’re looking for. What this means logistically is that I need a quiet and private place to talk, uninterrupted, and a solid phone and internet connection.


Turns out these aren’t as easy to come by as they may seem.


During this trip, which I’m taking with my boyfriend, Erwin, and my dog, Finch, we’ve covered a lot of territory. We’ve driven from San Francisco all the way to Missoula, Montana, spending time in Northern California, Oregon, Washington, Idaho, and Nevada along the way. And if you’re on a dirt road in the middle of Nevada for five hours (true story – we had nooooo idea what we were getting into that day, yet it was such an incredible experience; I’ve never heard silence that was that truly silent), chances are nil that you’ll have internet or cell service, or that you’ll be inclined to talk with a client.


A big consideration has been privacy. Since Erwin and I both work for ourselves, and are sharing hotel rooms, if one of us needs privacy to talk with a client, or have a business meeting, the other person needs to be somewhere else. Hotels have all sorts of nooks and crannies, outdoor spaces, and business centers that seem perfect for working, until you need to use them for a truly private, uninterrupted conversation.


Here’s a sampling of how my client conversations went over the course of several days, as Erwin and I tried to figure all the logistics out… I found a great table in a hallway, only to discover my voice carried and it sounded like I was speaking into a microphone. I sat in the outdoor courtyard, where I froze in the morning and boiled in the afternoon, not being able to see my computer screen from the sun’s glare, and making sure to stand in one tiny spot to keep the internet from going goofy. I snuggled into a comfy sofa in a very cool lobby annex, where I learned 15 minutes into my conversation that they polish the floor with a giant machine there every morning. I took up residence at a picnic table in the park, just as all the middle schoolers arrived to play volleyball for P.E. All enlightening experiences, and frustrating, too, when I wanted to focus solely on my clients. (A big Thank You to my clients who spoke to me from these locations – your generosity is much appreciated!)


You don’t know what you don’t know, until you try it.


Other realizations include:


The pros and cons of batching all my client-facing work into a few days a week. Pro: the ability to concentrate, be effective, and have all my client-facing work completed in a few days a week. Con: Working with clients one-on-one requires a lot of focus, and putting all that focus into a few days is tiring, which means I need more recovery time.


The inevitable distractions which come from working someplace other than my desk at home. Not having all my usual things in the usual places, and having my routines disrupted, is discombobulating.


The old assumptions about how much I can get done, and how long things take, don’t necessarily apply in a new environment. It’s taking me longer to get things done that it would back at home. On the plus side, I’ve gotten better at doing things quickly when I have a few minutes, which is a nice bonus.


The desire to do something other than work when in a beautiful place. It’s hard to concentrate when there’s a tall mountain, flowing river, or crashing sea right outside the window.


The inspiration that the same beautiful places offer, and the freedom of thought that comes from not working in my usual environment.


For all the cons, there is a pro available if I sit with it, something that urges me to take a fresh look, and come up with a more flexible solution. This will serve me and my business well going forward, regardless of whether I’m working from home, or some other location.


Now that I’ve had a month of working not from home, I have a greater appreciation of what my business needs to function as a baseline, as well as ways to add flourish. I’m also learning more about self-care, and having fun as I explore.


My hope is that if you’re reading this, you’re inspired to take a look at how you’ve been working, and how you might arrange your work life to serve you and your clients best. Having a great life, being of service, having freedom and choice, having fun – these are the reasons why you started your business to begin with, right?


As for me, we’ll spend the rest of the week on the coast, then start making our way back to San Francisco. I look forward to being back in my space, and sleeping in my bed… and to doing this again, very soon. The spaciousness, stillness and inspiration, and yes, even the stress, have made this trip worth every minute.




Let’s keep this discussion going ~ add your comments below, or join me over on Twitter @kristinecarey for a real-time conversation, about what it’s like to work and travel – have you tried it?


  1. Eve Siegel on November 13, 2020 at 1:05 am

    Great post, Kris! Great life on the road! Thanks so much for sharing what’s been special for you working and exploring throughout the West. Reminds me a lot of Gloria Steinem’s new book, My Life on the Road. Like you, she says “I can go on the road– because I can come home. I come home– because I’m free to leave.” Congrats to you in “following the seasons”!

    • Kristine Carey on November 13, 2020 at 3:00 pm

      Eve! So great to hear from you, and thank you for your kind words. It’s been a trip (literally), and so very much fun. I hope live is treating you well ~ sending a virtual hug.

  2. Kristine Carey on November 13, 2020 at 6:15 pm

    Eve! Thank you for your well wishes – we’ve had a blast on the road, finally getting to truly test what I thought about all those years ago. Hope you and your hubby are doing well during the pandemic, so grateful to still be connected. xx

  3. Lupe Wood on November 20, 2020 at 1:34 pm

    This is so incredibly inspiring. I would love to do what you’ve been doing someday.
    Yes, one good thing out of the pandemic is the ability to have that location independence! It’s amazing.
    Does the travel to new places spark your creativity? It seems like it would. Perhaps this is an upcoming book?
    Again, I’m just so inspired by the freedom of it all and the sense of contrast…freedom at a time when we are the most restricted ever in our lives.
    Thank you so much for the inspiration!

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