Although I don’t remember which country I was in, I remember the conversation very well. I was staying at an Airbnb rental with an extremely friendly host. I sat in a funny colored chair in my host’s living room while I worked on the emptying my e-mail inbox. My host walked into the room and smugly ordered me to stop working.

“You are on vacation, stop working!”, said the host with a smile that showed he was not really joking.

“I have to handle this first, then I will go out and about!”, I replied with an appreciative smirk.

“This is what I don’t understand about technology people, they are always working and never having fun!”

My host then picked up his briefcase and headed out the door to work. It was a Sunday morning.

I smiled to myself with a brief sense of enlightenment. Who was the one that really was working too much?

I am currently committing an act that many people have advised me not to attempt. I am traveling full-time while working on a start-up. My co-founder, Sam is essentially doing the same thing. And you know what is weird? Despite the warnings, we are doing quite well!

Below are some of the resources we use to get our work done.

Helpful Resources For Traveling Entrepreneurs:

  1. World Timezone Buddy – Meeting scheduler
  2. Google Voice – Video conferencing and cheap calls
  3. Skype – Video conferencing and cheap calls
  4. Dropbox – File sharing
  5. Gmail – E-mail
  6. Google Calendar – Online calendar
  7. OmniFocus – Todo list manager

Notice that our toolset is essentially the same as most tech entrepreneurs who are not traveling. This wasn’t done on purpose but it does show how the Internet makes it essentially the same experience to work 1 mile apart or 5,000 miles apart.

So What Exactly Are You Doing?

Sam is in Maui right now taking kite surfing lessons while I am in Rome checking off more bucket list items. We are still working 40ish hours a week but now when we burn out after several hours of working hard, we take more exciting breaks. Below is my schedule from today.

Today I woke up, shot off a series of e-mails to my co-founder (who as I mentioned is in Maui, Hawaii), our designer (who is in Calgary, Alberta), our videographer (Seattle, Washington), several clients (Chicago, Illinois and Los Angeles, California) had a phone call with my sister (Nashville, Tennessee) and then sent a Facebook message to a friend I will be meeting in Switzerland.

I then showered, hopped on the metro and went to see the Pope speak in Saint Peter’s Square in Vatican City. I am not sure what he said (I don’t speak Pope) but I did see a Nun do a fist pump so I am assuming his speech was good. :-p

I then did about three hours of work at a cafe before feeling restless and decided to take a jog up the Spanish Steps. I then grabbed some delicious pizza from a restaurant a stranger had recommended and walked back to my room to relax and do some additional work. All of this happened before my co-founder even woke up. He is 12 hours behind me (in timezones and in life ;-p) so without even meaning to we make progress on our company almost 24 hours a day (at least in theory).

The key here is that these are not atypical days. Last week I was in Florence and had a similar schedule. Instead of jogging the Spanish Steps, I biked with a friend around the city. The week before that, I had a similar routine in Stockholm, Sweden. Before that I was in Prague. You get the picture.

The process is I do multiple hour stints of work that require high concentration and then once I inevitably burn out, I go on a fun adventure. I then repeat the process. Work hard, play even harder.

What Are The Hard Parts?

It is not a perfect system and we occasionally run into issues but really it is not any harder than when we worked at the same desk in Seattle years ago. We have the advantage that our individual skillsets complement each other well and we are constantly making an extended effort to make sure we are communicating well.

Counterintuitively, it is not the distance or timezones that are hard, it is the subtleties of language that work against us. Was that a joke? Is he taking on more work than he should? Is that something I should have handled better? All of these questions can result from a simple miscommunication caused by a lack of a punctuation or the inability to see a facial expression.

To correct for these, we do the following.

Workflow Tips:

  1. We host most of our meetings over video chat so that we can see body language
  2. We make a concerted effort to over-communicate
  3. We rely on the experiences we have had working together in person to understand what is happening when we work remotely
  4. We talk as plainly and honestly as we can
  5. We use a lot of bulleted lists in e-mails
  6. We verify we have Internet connectivity 10 minutes before all important meetings

So the next time someone tells you it is impossible to start a company and travel at the same time, tell them they are wrong. It is hard, but with a few simple tweaks to routine and a lot of hard work, working successfully while traveling becomes possible.

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P.S. That image is of me at the top of Duomo in Florence. If you look closely, you will notice the strap of my laptop bag around my shoulder. Yes, I took my computer to the top of Florence :-p I had just finished working at a cafe!