Currently, I’m on a long term travel project (it’s been a little over a year now) going back and forth from my home city to the client site. Over that time, I’ve certainly made a few mistakes in how I do things, how I think about things, and how I approach specific aspects of the opportunities given and I wanted to share what I would do differently if I am put on a long term travel project in the future.


One of the things that I didn’t do very well was network – network with friends, network with coworkers in different cities, and network with leadership (I happen to be in a city where my company has an office) to really understand how I can help. The interesting problem that travelers have at my company is that they are away from their home office and since they aren’t really part of the office that they are traveling to, they aren’t connected anywhere except at the client and on the project. It’s important though to stay connected to help you understand what you may be able to support in, what business development opportunities there may be, what ways you can support recruitment of individuals, etc.

Create checklists

I can count on one hand how many times I’ve forgotten things that I should not have: underwear, dress socks, cables. It’s actually embarrassing writing about what I’ve forgotten. After the first time, you would think that I would have learned my lesson and created a checklist. A checklist, as I learned from Atul Gawande’s excellent book The Checklist Manifesto can help simplify complex tasks (such as a packing list) into something simple, easy and digestible. Of course, the problem is in creating a checklist that is easy enough to do without being onerous and in using the checklist each and every time even though you might feel you have everything packed and you don’t need it (which is what happens to me). The checklists don’t just apply to packing and luggage though, it can also apply to other activities such as review of deliverables, points to give during a presentation, and much more.

Carry fewer books

Before I embark on the trip, I always feel like I can get a lot of reading done. The reality is, I get much less reading done than I think. Part of it is being distracted all the time and a part of it is working on my concentration and focus on a single activity. It’s easy to watch TV on the whole trip home rather than cracking open that book you were planning to read 200 pages of. I also feel like I need options when I want to read but I know that I would end up reading more if I had fewer options – I also am not lugging around numerous books back and forth without opening them up at all.

Be more adventurous with food

When one of my coworkers left the project, we tried to hit up as many restaurants and cafes we could. We realized that over the whole year that we had been there, we kept on going back to the same places and never really exploring all that the city provided. I think there’s certainly merit in going back to the same places, especially if you like the food and get good service but I think you do have to balance that with experimenting with new places, even if sometimes you don’t get the best food or service.

Travel and explore more

My coworkers that traveled and ended up moving to this city explored more of the city than I did even though I had equal and ample opportunity to do so myself. I think that might have been a mistake on my part – anywhere you go to offers something new, interesting and exciting and will make for good stories. I never like coming back from a weekend and getting asked what I did and replying with nothing so go out there and explore (unlike me).

Reconnect with lost friends

On the bus ride over recently, I just happened to sit next to one of my coworkers and friends from university. We got to catching up and I only then just realized that my friend had moved to the city I work in a few years ago (even though I thought he was still in the same city as my university). It was a lot of fun just getting a sense of where he was in his life (with a family and two kids) and I got to share my thoughts about life in my home city and the travel project. I might take the approach that Keith Ferrazi takes in his book Never Eat Alone – basically consult a rolodex of all of my contacts whenever I travel and make sure that I book some time (coffee, meal, etc.) with them whenever I travel. I believe Keith takes a more strategic approach and makes sure that interfaces with the right individuals according to what he’s thinking about or planning but you don’t have to take the same approach.

Learn where the Winners and local pharmacy is

This was so key to having a good travel experience that I wish I had known it earlier. Any time I forgot maybe workout clothing, or dress socks or just didn’t have any flu or couch medicine handy (I usually pack something but sometimes you run out and you forget to re-stock), these places were a lifesaver. It helped me get in my workouts, made me feel less like a doofus for wearing athletic socks with dress shoes and generally helped me feel better and get the rest that I needed for a productive day.

Bring an ipad with a bluetooth keyboard

I ended up bringing three laptops each time I traveled: my company laptop, my client laptop, and then a personal laptop as well. Although I haven’t experienced anything yet, I’m sure that I’ll see some long term effects from having to carry heavy things all the time. I thought for the longest time about purchasing a bluetooth keyboard that I could just bring along with my ipad but never ended up pulling the trigger. I think doing this would have helped me get more stuff done during travel because it’s so much smaller and more convenient than a laptop is.

Stay a weekend

I don’t regret this as much because I do have commitments that I need to get to at home but I would have liked to just stay the weekend, explore new restaurants and places, and not have to stress about traveling and making sure I have everything packed. I think this would have been a nice thing to do and you get to experience more of the city this way without having to spend most of your day working.

Plan out my travel time activities

One thing I learned from Nir Eyal’s new book Indistractable is that in order to be ‘distracted’ from something, you had to have planned something in the first place. A lot of us tend to have very open calendars where things come in and out at will. If your boss comes by with an ask and you had nothing in your calendar but you were working on a task, you might say that you were distracted but the very act of putting it in your calendar means that you are committed to doing that task and then you can truly say that you were distracted from doing whatever you committed to. In the same way, I travel for long periods of time with the aim of reading, writing and generally being productive – but I rarely, if ever, scheduled these activities into my calendar. When I inevitably go to my ipad to watch Netflix or listen to podcasts and then pass out, I can’t actually say that I was distracted because I was never committed to anything in the first place.

What about you? Do you have lessons learned from traveling? Let me know in the comments!