The Itinerant Geek

This spring I spent almost a month on the road, and last year I delivered 26 presentations in eight different countries, spending almost four months traveling. While doing all of this I am also running a business. I work every day that I am on the road, most days putting in at least six hours in addition to my commitments for whichever event I am at. I can only keep up this pace because travel is not a huge stressor in my life. Here are some things I have learned about making that possible, in the hope they are useful to anyone setting off on their first long trip. Add your own travel tips in the comments.

Before you go

During the run-up to going away, I stay as organized as possible. Otherwise I would lose a lot of time just preparing for the trips. I have a Trello board set up with packing list templates. I copy a list and remove or add anything specific to that trip. Then I can just grab things without thinking about it and check them off. I also use Trello to log the status of plans for each trip; for example, do I have a hotel room and flights booked? Is the slide deck ready? Do I know how I am getting from the airport to the hotel? This way I have instant access to the state of my plans and can also share this information if needed.

It is easy to think you will always have access to your information in its original form. However, it is worth printing a copy of your itinerary to keep with you just in case you can’t get online or your phone battery runs out. For times when you don’t have physical access to something at the moment, take photos of your passport and car insurance (if it covers rentals), and upload them somewhere secure.

Your travel may require a visa. If your passport is expiring within six months of your trip, you may want to get a new one — some countries won’t issue a visa on a passport that is due to expire soon. You can in some cases obtain pre-authorization, such as through the American ESTA form for participating in its Visa Waiver Program. This might have changed since your last trip. For example, Canada has introduced an eTA system as of March 2016. I’ve traveled to Canada for ConFoo for the last four years – if I attend next year, I’ll need to remember to apply for this beforehand.

Tell your bank and credit card company that you are traveling to try and avoid their blocking your card as soon as you make a purchase in your destination.

Make sure you have travel insurance that covers not only your possessions but yourself as well. Be aware that travel insurance will not pay out if you become sick or injured due to an existing condition that you didn’t tell them about first. You will have to pay an increased premium for cover of an existing issue, but finding yourself with no cover and far from home is something you want to avoid.

Make sure that you have sufficient of any medicine that you need. Include some extra in case of an unscheduled delay in returning home. I also usually pack a few supplies of common remedies – especially if I am going somewhere that is not English speaking. I have a vivid memory of acting out an allergic reaction to a Polish pharmacist to remind me of this!

I also prepare for the work I’ll be doing on the road. In addition to preparing for the talks or workshops I might be giving, I prepare for work on Perch or for the business. I organize my to-do list to prioritize tasks that are difficult to do on the road, and make sure they are done before I go. I push tasks into the travel period that I find easier on the small screen of my laptop, or that I can complete even in a distracting environment.

When booking travel, give yourself plenty of time. If you are short of time then every delay becomes stressful, and stress is tiring. Get to the airport early. Plan longer layovers than the 70 minutes your airline believes it will take you to deplane from the first flight and make it round a labyrinthine nightmare from the 1980s to find the next one. On the way home from Nashville, my first plane was delayed due to the inbound flight having to change equipment. The three-hour layover I had chosen meant that even with almost two hours of delay I still made my transatlantic leg home in time. Travel is a lot less stressful if you allow enough time for things to go wrong.

Air travel tips

Try to fly with the same airline or group in order to build up your frequent flyer status. Even a little bit of “status” in an airline miles program will give you some perks, and often priority for upgrades and standby tickets.

If you want to take anything of significant size onto the aircraft as hand luggage, the large roller bags are often picked out to be gate-checked on busy flights. I travel with a Tom Bihn Aeronaut bag, which I can carry as a backpack. It is huge, but the gate staff never spot it and due to being soft-sided, it can squash into the overhead compartments on the smaller planes that are used for internal U.S. flights.

Have in your carry-on an overnight kit in case your checked luggage does not make it to your destination at the same time as you do. Most of the time you’ll find your bag comes in on the next flight and will be sent to your hotel, but if you need to get straight to an event it adds stress to be unable to change or brush your teeth.

If you plan to work on the flight, charge your laptop and devices whenever you can. More and more planes come with power these days – even in economy – but it can’t be relied on. I have a BatteryBox, a large external battery. It’s a bit heavy but means I can work throughout a 10-hour flight without needing to plug in.

On the subject of batteries, airlines are becoming increasingly and understandably concerned about the fire risk posed by lithium ion batteries. Make sure you keep any spare batteries in your hand luggage and remove them if your bag is gate-checked. Here is the guide issued by British Airways on the subject.

A small flat cool bag, even without an icepack, works for a good amount of time to cool food you are bringing from airside as an alternative to the strange offerings onboard. I usually pop a cold water bottle in with it. London Heathrow T5 has a Gordon Ramsay “Plane Food” restaurant that will make you a packed lunch in a small cool bag to take on the plane!

Get lounging

Airport lounges are an oasis. Something I didn’t realize when I started traveling is that many airport lounges are pay on entry rather than being reserved for people with higher class tickets or airline status. If you have a long layover then the free drinks, wifi, power, and snacks will be worth the price – and if it means you can get work done you can be making money. The LoungeBuddy app can help you locate lounges that you can access whether you have airline status or not.

There is another secret to airline lounges: they often have a hotline to the airline and can sort out your travel issues if your flight is delayed or canceled. With the delayed flight in my last trip I checked myself into the American Airlines lounge, mentioning my delay and concern for the ongoing leg of the flight. The member of staff on the desk had the flight status checked and put me on standby for another flight “just in case.” She then came to let me know – while I happily sat working in the lounge – that it all looked as if it would resolve in time for me to make my flight. Once again, far less stressful than trying to work this out myself or standing in a long line at the desk in the airport.

Looking after yourself

If you do one or two trips a year then you should just relax and enjoy them – eat all the food, drink the drinks, go to the parties and forget about your regular exercise routine. If you go to more than 20, you won’t be able to do that and also do anything else. I quickly learned how to pace myself and create routines wherever I am that help to bring a sense of normal life to hotel living.

I try as much as possible to eat the same sort of food I usually eat for the majority of the time – even if it does mean I’m eating alone rather than going out for another dinner. Hotel restaurants are used to the fussiest of international travelers and will usually be able to accommodate reasonable requests. I do a quick recce of possible food options when I arrive in a location, including places I can cobble together a healthy packed lunch if the conference food is not my thing. I’ll grab a sparkling water from the free bar rather than another beer, and I’ll make use of the hotel gym or go for a run to try and keep as much as possible to the training routine I have at home. I do enjoy some great meals and drinks with friends – I just try not to make that something that happens every night, then I really enjoy those I do get to.

I’m fortunate to not need a lot of sleep, however I try to get the same amount I would at home. I’ve also learned not to stress the time differences. If I am doing trips that involve the East and West Coast of America I will often just remain on East Coast time, getting up at 4am rather than trying to keep time-shifting back and forth. If you are time-shifting, eating at the right time for where you are and getting outside into the light can really help. The second point is not always easy given the hotel-basement nature of many conference venues. I tend to run in the morning to remind myself it is daytime, but just getting out for a short walk in the daylight before heading into the event can make a huge difference.

I take care to wash my hands after greeting all those conference-goers and spending time in airports and other places, and am a liberal user of wet wipes to clean everything from my plane tray table to the hotel remote control. Yes, I look like a germaphobe, however I would hate to have to cancel a talk because I got sick. Taking a bit of care with these things does seem to make a huge difference in terms of the number of minor illnesses I pick up.

Many of us in this industry are introverts and find constant expectation to socialize and be available tiring. I’m no exception and have learned to build alone time into my day, which helps me to be more fully present when I am spending time with other speakers and attendees. Even as a speaker at an event, when I believe it is very important for me to be available to chat to attendees and not to just vanish, this is possible. Being at a large number of events I often have seen the talks given by other speakers, or know I can catch them at the next event. So I will take some time to work or relax during a few sessions in order to make myself available to chat during the breaks.

If you are taking extended trips of two weeks or more these can be hugely disruptive to elements of your life that are important to your wellbeing. That might be in terms of being unable to attend your place of worship, meet with a therapist, or attend a support group meeting. With some thought and planning you may be able to avoid this becoming an additional source of stress – can you find a congregation in your location, use Skype to meet with your therapist, or touch base with someone from your group?

Working on the road

Once at your destination, getting set up to work comfortably makes a huge difference to how much you can get done. Being hunched over a laptop for days will leave you tired and in pain. My last trip was my first with the new and improved Roost Stand, along with an external Apple keyboard and trackpad. The Roost is amazing; it is incredibly light and allowed me to get the laptop to a really great position to work properly.

Plan your work periods in advance and be aware of what you can do with no, or limited internet connectivity. In OmniFocus I have a Context to flag up good candidates for offline work, and I also note what I need to have in order to do that work. I might need to ensure I have a copy of some documentation, or to have done a git pull on a repository before I head into the land of no wifi. I use Dash for technical documentation data sets when offline. On a ten-hour flight with no wifi you soon realize just how much stuff you look up every day!

If traveling to somewhere that is going to be horribly expensive for phone data, do some research in advance and find out how to get a local pay-as-you-go sim card. If you want to switch that in your phone, you need to have an unlocked phone (and also the tools to open your phone). My preferred method is to put the card into a mobile broadband modem, then connect my phone to that with the wifi. This means I can still receive calls on my usual number.

The possibility of breaking, losing, or having your laptop stolen increases when it isn’t safely on your desk in the office. Have good insurance, but also good backups. During conferences, we often switch off things like Dropbox or our backup service in order to preserve the wifi for everyone – don’t forget you have done this! As soon as you are able, make sure your backups run. My aim is always to be in a position where if I lost my laptop, I could walk into a store, buy a new one and be up and running within a few hours without losing my work, and especially the things I need to present.

Enjoy the world!

Don’t forget to also plan a little sightseeing in the places you go. I would hate to feel that all I ever saw of these places was the airport, hotel, and conference room. I love to book myself on a walking tour. You can discover a lot about a city in a few hours the morning before your flight out, and there are always other lone business travelers on these tours. I check Trip Advisor for reviews to find a good tour. Lonely Planet have “Top things to do in…” guides for many cities: here is the guide for Paris. I’ll pick off one item that fits into the time I have available and head out for some rapid tourism. As a runner I’m also able to see many of the sights by planning my runs around them!

Those of us to get to travel, who have the privilege of doing a job that can truly be done from anywhere, are very lucky. With a bit of planning you can enjoy travel, be part of events, and still get work done and remain healthy. By reducing stressful events you do have control over, you can be in better shape to deal with the inevitable times you do not.

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