Anyone here traveling longterm (while running a biz)?

My family and I are planning on hitting the road longterm (1-2-? years) spending a couple months in various locations around the US and abroad.

Anyone here doing / has done this?

For this forum, my question is mainly about business. What changed for you / your work when you hit the road?

Anything you’d do differently if starting over, or tips you picked up along the way?

Favorite locations?

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Hello! I’ve done this off and on for years. I’m currently in the final month of a seven-month trip.

I’d say it is close to impossible to do this effectively. You’ll be compromising all the time. Never having a good, productive work environment. Trying to fit work in between flights, sightseeing, booking further flights. Frequently getting frustrated at poor Internet and being powerless to do much about it, other than getting the first plane out of the island/city/country you are in.

Much better to work hard at home for some months, then switch to “just-keeping-the-business-barely-going” mode while travelling.

Despite this I still keep doing it. Year after year. Sigh.

Have you interviewed Brecht Palombo about his trip on your podcast?

ETA: He discussed working while on the road on the latest BWK episode.

What @SteveMcLeod said.

I recently spent a month in New Zealand travelling with my family and was able to keep everything ticking over working about an hour a day. It was wonderful. But I couldn’t see myself being able to manage anything more than maintenance and support activities while travelling. The limitations of wifi and working on a laptop, the distractions of travelling and having to share a hotel room with my loved ones make any sort of development or creative work really painful.

As already has been said that is not easy to do. But I happy to share what I did prior to going on a 6 month trip with my wife:

  • I hired someone to handle all support requests and removed myself from the day to day operations
  • You need a recovery plan for any outages that does not involve you doing anything. Luckily I sell a desktop software so server outages are not that painful.
  • I planned out all marketing efforts for the hole time in advance (newsletter, blogposts, …)
  • Don’t plan to work much as it will be hard and frustrating (bad wifi mainly)

As for time planning we did travel for 3 weeks and rest for 1 afterwards. Coworking spaces come in handy at times and are quite good especially in Asia.

Habe fun on the trip!

P.S.: I’ve setup SMS alerts for some positive events (like new sale) which will be a nice plus on the road. Just don’t add negative events (server outage) because you will be stuck in a shittly location without wifi and a nerve wracking stream of “oh god the server is down” SMS without any possibility to fix it. This can ruin your day in no time…

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Hey Steve - that awesome, huh?

I should say though, we plan to live in each spot for a few months, so I expect the Internet situation to be relatively stable, except maybe during the periods we move from place to place.

But part of the reason I want to travel more is to work less–and force myself to work less. At the end of the day, I do what I do for a living in order to have the freedom to do fun things with my family.

Yup, I’m a fan of BWK and following along with Brecht’s journey. Definitely an inspiration along others who’ve done things like this (especially folks with young kids, I have a 1.5 year old).

Thanks Daniel - Great tips. I have a great team in place and systems to run the business (always making them better though). I like the positive alerts (I already have one for Stripe payments). Need to turn off the Slack notifications though!

I really like the idea of having POSITIVE notifications along with the negative.

I’m definitely a Cassandra when it comes to working while travelling!

A practical tip: do a small test trip of, say two weeks, well before you hit the road. You’ll learn a lot during that time as to what systems and processes you need that you don’t have yet. You’ll likely be surprised how often you find yourself thinking, “hmmm, that’s impractical to do here and now - I’ll have to take care of that when I get back home.”


[quote=“danielherken, post:5, topic:3247”]
Just don’t add negative events (server outage) because you will be stuck in a shittly location without wifi and a nerve wracking stream of “oh god the server is down” SMS without any possibility to fix it. This can ruin your day in no time…
[/quote]The only SMS alert we use is “server is down” kind, so that things could be fixed ASAP. Customers get pretty mad when services they are paying for are not working.

The idea of having positive notification sounds really interesting, though :slight_smile:

I use ‘Control’ iOS app to make a “cha ching” sound when a payment hits :slight_smile:

I understand that this is a different matter for Saas applications vs. desktop applications. For me the server is only running the marketing site so it is not that bad if it stays down for a few hours.

Nothing can ruin your trip faster than the ‘Server is Down’ SMS every 10 minutes while you are hours away from any decent internet connection to fix it.

Been lurking here for a few days and still owe an intro. I’m living a nomadic life since 5 years or so. Currently roaming around in Asia.

I’ve been doing SEO for E-commerce businesses, some Fortune 500s and recently more startups from the bay area for the better part of a decade. I started KeywordBrain (a tool that I’ve been using internally for clients for a very long time) with two other guys a few weeks ago and we’re about to launch a few weeks from now.

For me personally, not a lot of things changed work- or productivity-wise. If anything, it fuels my creativity. I travel very slowly, staying for several months in one place I like or want to explore thoroughly. It usually takes 1-2 days to find the best places (to eat, work, work out, relax) and adjust to the environment. Communities like the dynamite circle, hashtag nomads, /r/digitalnomad, facebook groups and the people i met and meet along the way are a huge help, but i have a reputation for just flaneuring around instead of planning everything through when it comes to travels. I take taxis to the airport at 4 AM when I feel like it and just book the next flight to wherever. After a long time on the road, you develop this deep confidence that everything’s gonna be alright.

There are minor annoyances with Wi-Fi in some places, but a backup SIM card or two always saves the day. I use hacks like dispatch-proxy to tie up to 3 connections into one if it gets really hairy. Internal SIM & WiFi card + Alfa AWUS036H. I use mosh when SSH is next to impossible.

When Skype or Hangouts are very flaky, I have talky, & webrtc handy in my bookmarks so I can communicate with clients, team and freelancers I’m working with. I use Slack and Kato for team communication and with clients. Trello for my to-do stuff. Nothing fancy all together. If you have any specific questions, I’m more than happy to answer them.


We’ve also been kicking something like this around. Though with 3 kids (9,4,2) there’s a boat load of logistical considerations :slight_smile: Might do something like a year where we’re traveling in general but not straight. A few months away, a month back to deal with things like braces, etc, month away.

Definitely looking forward to hear how it goes @CasJam. When you trying to start?

Ya we’ve been talking about doing it for years. Now seems like a good time. Wife just stopped working, my biz is in a good place, and our daughter (1.5 years) is still a few years away from school.

We’re aiming to leave by end of September (less than 3 months from now). Toughest part is getting everything in order between now and then.

If you haven’t checked out tropical MBA podcast and their private forum this is exactly the thing they focus on. Butt tons of people slow traveling / perma-traveling.

Probably most of them don’t have kids but I think a good chunk of them do.

o yea… TMBA is a top listen for me. I haven’t joined the DC yet but plan to soon. We plan to spend time in Asia after a few stops around US.

Ya I popped into the DC for a few months. Great group of people. And especially if you’re planning to do some heavy traveling I’d definitely recommend checking it out.

I’m still working on the business, but I’ve been freelancing for the last couple of years while I’ll been travelling extensively. Other than minor annoyances like calls ending at 1am I haven’t really had any issues. If you want to get a better work-life balance it’s definitely a good way to hack it. It’s also a great way to make your Facebook friends hate you :smiley:

In most places you can find free wifi, but whether it’s useable is another question. I get a local prepay SIM card in whatever country I go in - in Europe and Asia you can easily pick them up with a few GB of data for <$30. As long as you have 3G email, ssh and even Skype voice calls are usually doable - if you have LTE even better! Also check with your carrier to ensure your phone is unlocked before you go.

I have a SIP number that I forward to my local SIM so I can always be reached on a single number. You could do the same with Skype-in or Google Voice in the U.S.