The Business of Starting a Business: Working From the Road

One of the things that most drew me to freelancing was the freedom of it. Not only can I set my own hours, but I can work from anywhere that has an internet connection. I could be in a Parisian cafe, or holed up in an apartment in Buenos Aires, and I can still run my business exactly like I would at home.

There’s a beautiful and incredible power in being so flexible. Or at least, it appears that way from the outside. Once I hit the road in a few short weeks, I’ll be putting this flexible business to the test. I plan to continue working while on the road. I’ll be meandering my way through seven states over four weeks. If I don’t work, I’ll be one broke lady when I get back to Austin.

What does working on your business from the road look like? What does it take?

I have an idea of how I’m going to do this but I never actually have before. Thankfully, being a digital nomad is very popular today. There’s a plethora of information how to work from the road.

My road trip is designed to take me off the beaten path. There won’t be a Starbucks every seven feet as I drive eight hours through West Texas. Finding places with the internet will be tough over several stretches of this trip.

I also know I’m a procrastinator of the first order. If I can wait until the very last minute, I absolutely will. On top of that, I’ll be seeing some friends and family I haven’t seen in years in some of the cities I’m visiting. I’m not going to want to block off five hours in a coffee shop when I could spend that time with friends.

With all this in mind, I reverse engineered my work-from-the-road plan. It’s simple and straightforward, just the way I like it.

Get Ahead on Work

As I write this, I have several deadlines that I know are coming up in September. I’ll be writing and turning in all those articles before I leave town. I’m going to do everything I can to limit the amount of work I need to do on the road.

Become a City Morning Person 

It’s important to note the city part of this point. When I’m in major cities where they have fabulous things like 24-hour coffee shops and internet coming out the wazoo, I’ll have to take advantage. Anyone who knows me knows I am not a morning person. My alarm goes off at 7:00 am every morning- I almost always sleep until 8:00.

I’ll have to bite the bullet and get up early when I’m in cities. I’ll be able to get ahead on aspects of my business like social media scheduling, emails, and writing before my friends wake up. It will suck, but with the help of coffee, I will prevail.

Set up Email Responses

One thing I hate is an unreturned email. To spare people the pain of that, I’ll be setting up an automatic email response that lets people know my access to email is limited, and I’ll respond when I’m able.

Pitch Only in My Two Week Zone

Sidenote: writing this all out is showing me how deeply dependent I am on the internet. My life is the internet.

Anyway, I do plan to continue pitching when I’m on the road. Freelancers always need to be seeking new work- or at least this freelancer does. Like I said above, though, no one likes an unanswered email. My nightmare scenario would be to pitch a story and have it accepted while I’m in an internet dead zone.

I’ve found most editors get back to me within 1-5 days. I have a stretch of almost two weeks where I’ll have constant access to the internet, bouncing from city to city. I’ll only pitch during those two weeks. That way, I can be (almost) sure that I’ll be able to immediately respond.

Have any of you worked on the road before? Specifically, anyone out there who has worked from their car, or on a road trip before? I’d love to hear some other ideas, or experiences people have had!

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13 Replies to “The Business of Starting a Business: Working From the Road”

  1. Hi Kara! My experiences working remote/from the road have been hit or miss. Sometimes I’m able to stay productive and other times there are waaay to many distractions. Anything that requires me to be “in the zone” creatively is harder on the road. I find “the zone” to be elusive when traveling. Designing without my huge desktop monitor also slows me down. Your strategy to try and get as much as you can done before you leave is a good one.

    Best of luck on your work from the road adventures!!

    1. Thank you! I think I will probably get very distracted out there, so it’s now or never.

  2. Good info. While I don’t think I’ll need to worry about road tripping any time soon, I do have fun trying to stay connected whenever we go to my dad’s lake house and I have to depend on an in and out phone internet connection. I can usually at least respond with “I’ll get back to you soon.”
    Please update us and let us know how it worked for you!

    1. I’ll keep you posted for sure! Also phone internet- throwback!

  3. I’m SO the opposite of a procrastinator. I would be that annoying kid in school who would try to get the homework during the class rather than listen to the lecture so that I would have my afternoon free to goof off on the internet, watch tv, or shoot hoops. haha. I had some disappointed teachers. Also I am totally a morning person, though there was this one winter break during college where I was obsessed with an MMORPG and was essentially nocturnal Kinda trippy.

    Looking forward to see how you handle life on the road with your business. I too will be trying to freelance while on the road….and building that from the ground up, but I hopefully will have enough of a safety net that it’s okay if it doesn’t work out.

    1. Ahhh, I was NEVER that kid! I always resented that kid in school, hahaha. I also can’t believe you’re a morning person. Double luck! We’ll see how this whole digital nomad thing goes. ????

  4. Whenever I’m on the road, I try my best to commit to a few hours to working with my staff remotely. It can be quite daunting at times especially when there’s time difference. Commitment’s the key. 🙂

    1. Thanks Eric! Good tip. Committing to work is 90% of the battle.

  5. Sounds like you have a good plan in place. I consider myself a morning person and personally I like being able to knock my work out early and enjoy the rest of the day so I hope that works out for you too. Can’t wait to here more stories about your experience on the road!

    1. I’m jealous you’re naturally a morning person! It’ll be a struggle for me. And I’d love to meet you at FinCon!

  6. Never worked in a car before, but have worked in trains, airports and other locales. It’s fun, but can be frustrating any time the internet connection is not like at home. Also time differences can be a doozy. Or last-minute requests when you really can’t accommodate them. But it’s all part of the adventure!

    1. I’ve been thinking about the internet connection aspect. Seems like it could be the difference between making this work or not. But you’re right- it’s all in the adventure!

  7. […] People say the first step to success is admitting you have a problem. Allow me to be the first to say it: I have a problem. I’m taking a whole week off this month, and unless I change things up real quick, I’m going to end up working during that week. Luckily, I know exactly what to do, and I’ve done it before when I went on my four-week road trip. […]

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