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The 4 People You’ll Want to Meet When You Plan To Work While Traveling the World

12. Nov. 2021


This time four years ago, I packed my life into a suitcase, sold everything else I owned, closed the door of my office cubicle, and headed to New Zealand on a one way ticket. My goal: to chase down a dream, to stay connected and “in the loop” with my professional life while traveling the world.

It’s everywhere: saturated across our news feeds are filtered photo scrolls and LinkedIn updates of wonderful, glamorous tales of leaving the office and successfully taking work on the road. You’ve seen it - the laptops at the counter of an artisan bakery in Bali, or the ease at which we can grab WiFi at the patio of a farm to table cafe in East London.

As someone who took the jump, I can tell you that these tales are true - working and living on the road is life-changing. But, as I’m now on the other side of completing a work and travel experience, I’ve learned a few key things that I wish I knew before I left.

What I’ve learned came from other “jumpers” I met while on the road - people who took a risk to do things like work and live remotely. These people and their stories are what formed the beginnings of what is now When to Jump, a global community I founded that brings together the stories, people, and ideas relating to leaving something comfortable to pursue a passion. (Our story is told in 150 seconds here.)

Today, When to Jump has reached millions through our email newsletter and weekly podcast, recent international book release, and annual member festival called Jump Club. And from all the stories I’ve been lucky enough to collect and curate as I build WTJ, I keep coming back to what I wish I knew: the four types of people that any soon-to-be-jumper should meet before he or she goes to work remotely.

So wherever you are in your preparations to work remotely, add these four people to your list of who to meet before you jump:

  1. The Legend: the person who has done exactly what you want to go do - who has jumped to working and living remotely and has lived to tell the tale on the other side. The Legend could look like you, or not, but The Legend inspires you because The Legend has done it. And The Legend wants you to do it, too. From step one to when you return home, The Legend is there for your highs and lows - the wins and victories, but also the inevitable bad days and headaches - that you’ll encounter as you go on your way.

  2. The Kindred Spirit: the person who is looking to jump, too - but shares the same concerns, fears, hopes, dreams, and roadblocks  you do. The Kindred Spirit (or KS as you call him/her, because you two are such good pals you do things like talk in acronyms) bond at once, become each others’ sounding board, and source of accountability. You bond like childhood buddies, or co-pilots preparing for the same flight ahead, together. Heading off to travel remotely can feel like a daunting, if not lonely, experience. With a KS by your side, you will never be alone in your travels, and in your work.

  3. The Rolodex: the person who knows the people you need to be talking to/meeting with/writing love letters to as you plan to work remotely. I can’t stand the word “networking” because it sounds too forced. Instead, think about doing things to create “collisions” with a Rolodex: if you read a blog and like the post, message the author (you can message me if you want!). If your old boss’ mother once worked and lived overseas, reach out to her. Take people to coffee. No one will refuse coffee. And through these collisions, you’ll meet The Rolodex, the person who has just the book to lend you to read, who knows a friends’-dog-walkers’-sister you should definitely grab coffee with, who went to dinner just last week with an old friend who did what you’re trying to do. The Rolodex is not only helpful before you leave town, but also when you’re flying through countries and need help tracking down that one type of person that you don’t yet know. The Rolodex will help you, because he or she was once you.

  4. The Little Sibling: Taking a risk to pack up and work abroad for a year requires sacrifice - and not just from you. Mentors, advisors, bosses, colleagues, and countless others are going to help make this jump possible. As much as this makes you the center of the mission, it’s important to find someone who hope to follow your lead, and stay in touch throughout your travels. When you’re off on your way, stay in touch. You’ll serve as the role model, The Legend, to the next generation of jumpers to work remotely. Just like in our When to Jump community, your experience will shape theirs - your guidance and friendly check-ins and updates and lessons learned will impact their life and likely yours as well.

No jump is ever made alone - and these four folks will help you make your move to working remotely more than if you were to try to go at it alone. Meet them on your own, or with me and jumpers from around the world, at Jump Club this fall. If I can be helpful, reach out. But no matter what you do, be sure these core four types of people are in your corner before you make the jump.

Mike is the founder of When to Jump. A bit about their upcoming event: Jump Club is one part farmers market, music festival, and ideas festival, bringing together entertainers, keynotes, chefs, makers, creatives, and people aiming to make a jump in one place, for one weekend. This year Jump Club Boston takes place Sept 7-8th, and friends of Remote Year e-mail list can use RYVIP as a code for 10% off tickets our All-Access regular admission passes before they sell out.