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How to Travel and Work From Anywhere

July 14, 2022


how to travel and work as a business owner

“To travel and work from anywhere is the dream.” ~every freelancer ever.

As I sit in a hospital waiting room, I can’t help but think back on the conversation I’ve had a million times:
“You work for yourself? So, you can work from anywhere and make your own schedule?”

“Well, kind of, but it’s actually harder than you think to work from a beach, and my clients expect to work on their schedule. So, no not really.”

Maybe you are a business owner hoping to take a vacation, or maybe you’re just trying to keep up with family obligations like kids’ soccer tournaments, or parents undergoing chemotherapy treatments. I’ve been there… yes, I’ve been through all of these scenarios and more.

Here’s how I manage to travel and work from anywhere:

Plan Ahead

If you can, delegate as much of the work as possible. This isn’t always possible, for budgeting reasons or simply because emergencies happen, but wherever possible, take tasks off your list.

Don’t tell clients

Others may disagree, but after 12 years of running a business, I know that when I tell my clients I’ll be unavailable, they will call me, then follow up with an email, a text message, and possibly leave messages on your website’s bot! It’s almost like you planted a seed that grows while you’re away.

Give realistic deadlines

I used to think providing deadlines would be bad, but I have found that my clients love them, and as long as I am realistic and meet them at least 90% of the time, clients will leave me alone to get it done. I know I sound like I work with tough clients, but it’s more about my anxious need to please my clients all the time.

Schedule your downtime.

Most of my clients are on East Coast time, but I have clients on the Pacific Coast time as well. So, I make personal time in the morning and evening. I work during the day and late at night. This week I’m driving to the hospital one hour from the house every day, so I leave early morning, check-in with the doctors and my father, then work from literally any surface possible until it’s time to leave, then I drive back to the house, work for a while, spend time FaceTiming my kids, and then work in the evening. It sucks, but my Dad’s getting treatment, my clients will stay my clients, and we will all get through this ????

Make a packing list for every day

A packing list for a pool bag seems like a nutty Marie Kondo thing to do, but trust me, you’ll wish you had listened the first time your computer battery runs out.

  • Computer or iPad (are you working with any files that can’t be accessed on the iPad? That’s how you’ll choose. Going on a trip? Take both! Going to the pool? Take the iPad)
  • The charging cables for ALL the things. Computer, iPad, phone, ALL the things
  • Back up battery
  • Headphones with a mic. Not one of those customer service ones, but Beats, EarPods, or some similar knock-off. When you’re doing a Zoom call from your niece’s bedroom and your client has the mouth of a saucy sailor, you’ll be glad you did.
  • Notepad and pen. Sometimes you just need to take a note.
  • Water, snacks, lip balm, sunglasses, moisturizer, sunscreen, cash, and a spare pair of underwear. Trust me, when you have to make an emergency landing in Bermuda and stay there for 18 hours, you’ll thank me.

Working for yourself is not always easy, but it is possible to be there when your father goes through chemo, when your kid scores her first goal, or when your son earns an African safari! Sometimes it’s fun, sometimes it sucks, but that’s life and work should be able to go along with it, not stand in your way.

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