It’s arguably the sexiest selling point of independence: if you have a phone, a laptop, and a good Internet connection, you really can work from anywhere. (Sure there are some limits—but far fewer than if you were a “regular employee!”) check your mindset, do some research, and set realistic goals before you hit the road.
Check your mindset. While you don’t need to plan your schedule down to the hour, you should know whether you plan to spend the majority of your time working or playing. Are you a disciplined, productive worker when sitting in your boring apartment or familiar coffee shop every day? If not, be realistic about how much you’ll be able to focus on work when ocean waves are lapping the shore or street music is coming through your window. Practice building good habits before you go. Challenge yourself to 90-minute work sprints of intense productivity, or experiment with apps like Toggl and Todoist to get your productivity muscles into shape before you go. Remember, you’re going on location, not on vacation – and that’s a big difference!
Prepare your business. It’s fun to fantasize about spontaneous travel, but you should do a quick health check of your business before you hit the road. Are you in the midst of pitching a big proposal, or half-way through a project that could make or break your year? If you’re in a high-touch business, would it make sense to engage a backup or temporarily hire a virtual assistant to answer emails, handle phone calls in your time zone, and keep things humming while you’re away? Do you have a reliable income stream so you don’t run out of funds part-way through the trip? Consider setting a goal to get at least one client on retainer so you have some guaranteed income on the road. Start reaching out to trusted colleagues who could handle fires on the home front if anything goes awry in your absence. The preparation you do pre-trip can benefit your business even after you’re back home.
Do your homework. Aside from all the usual traveling advice for vacationers – get your passport in order, know whether your health insurance follows you, pack more underwear than you’ll ever humanly need – freelancers should also add a few more to-do’s.
Set a realistic budget. Crunch the numbers for accommodations, food, and transportation before you go – and be sure to include access to any meeting space or office equipment you might need. Break the total down into your hourly earnings rate so you can see the real cost. If you have to work 90 hours a week while you’re on the trip, you probably can’t afford it in the first place! Save until you’re financially ready. Set yourself up to be able to enjoy the experience and have some spontaneous fun without a financial hangover later.
Great internet speed is non-negotiable. A mountaintop retreat or a remote beach might sound like the ultimate freelancer’s escape…but if you can’t connect with your clients or access reliable WiFi, you’ll spend more time driving back and forth to civilization (or the nearest WeWork) than enjoying your travel. Your business reputation is on the line while you’re on the road. Don’t trust the reservation desk or a random Expedia review; do your homework and find other travelers who have stayed where you’re going to get the real scoop on internet strength and speed.
If you’re leaving the U.S., be crystal clear about your travel visa and educate yourself about any risks. InterNations is a great place to start planning your globe-trotting. It includes tips to make the most of your time, access to other ex-pats, and a way to ease into a new culture if this is your first attempt at international travel.
Should you tell your clients you’ve traded your kitchen table for a coffee shop in Madrid? There’s no right or wrong answer—it’s your business, so it’s up to you. But unless the client is accustomed to meeting with you face-to-face and will notice your absence, you can choose to share your location on a need-to-know basis. The beauty of technology and freelancing is that you can create a seamless experience for clients, deliver awesome work, and reap the rewards of traveling on your own terms. And that’s the epitome of what freedom and flexibility are all about.