If you follow me on Twitter, you might have spotted where I am right now: Wellington, New Zealand.
Wellington's been putting on a show for us - the entire trip has been sunny (yes!), not too windy (double yes!), and we've had a fantastic time exploring all the cafes, restaurants, and hidden places around town. It hasn't been all play, though - my wife and I have both been continuing to run our businesses while we're out here.
Working for ourselves gives us the freedom to work from anywhere we want, whenever we want, provided we can find an internet connection. Even though we're certainly not what most people consider to be "digital nomads," we spend a lot of time traveling as a family. Most years, we'll take between six and ten 2-3 day trips - sometimes close by, sometimes to cities further afield - and one or two longer international trips, usually 10-20 days.
I'm not going to try and convince you to quit your job to start freelancing while you flit from country to country - there are plenty of other people to do that. What I can help with, though, is some advice and lessons we've learned from traveling that will help you run your online business while you're on the move, without turning into a big ball of stress, or going completely broke.
It's fun to imagine - sitting on the beach, or maybe in a busy café. Enjoying the view, while busily sending emails to clients and generally Getting Things Done. Unfortunately, though, the reality is that trying to work and enjoy where you are at the same time is damn near impossible.
The problem is this: you can't be in work mode and holiday mode at the same time. They're completely opposite mindsets. Working - and finding the intention and the concentration to actually make progress - takes a great deal of mental energy. Traveling, wrangling kids around a new place, and actually enjoying your beach or café also takes a lot of energy and attention. Try to do both at the same time, and you'll find that you'll return from your trip feeling like you were never truly there, and you'll be feeling guilty for completing only a tiny fraction of the work you set out to do.
Staying productive while traveling is possible, though, and I want to share a few experiences and things we've learned over the years. Some of this advice will be specific to traveling as a family, since we've found that to be one of the more difficult adjustments to make, but most of it will still be applicable if you're traveling on your own.
Instead of hopping around and visiting somewhere new every day, make sure you plan to stay put in each location for at least 3 days at a time, or even longer if you're traveling as a family.
When you're constantly moving around, it's impossible to get into a good routine, and without a good routine it's much more difficult to get into the flow of Getting Things Done. Every time you move, you need time to adjust to things you're probably not even thinking about - new accommodations, uncomfortable beds, strange noises at night, finding your way to the local store, finding somewhere to eat.
When you stay in the same place for a while, these things become much easier to deal with, since you have more time to adjust to each change. You also get the benefit of enjoying where you are when you're not working, instead of feeling like you missed out on the experience because you had to catch up on emails.
This tip goes double for families - think more like a week in each place. Even simple things like getting out the door or getting to bed require much more time and effort with kids - it adds a whole boatload of extra things to steal your focus. By slowing down, you'll be less tempted to rush around and experience everything as quickly as possible, because your time becomes much more flexible.
It's tempting to think that vacation is a chance to take a break from client work and make some progress on improving your business, but this isn't as easy as it sounds. Creative work like blog posts (or this newsletter - yep, breaking my own rules here) suck up precious attention and focus you could be spending on your trip.
Stick with tasks that are well-defined and comfortable as much as possible. Avoid hard deadlines or urgent work like the plague. Fixed deadlines limit your flexibility and give you no room for error - if your internet goes out, your flight is delayed, or your laptop gets stolen, you're out of luck. Give yourself a break from the deadlines and the stress while you're traveling.
Break your work up into chunks of an hour or two, max. Chunking out your work like this lets you can stay focused intently while you're working, and then switch off completely for a while before coming back to it later. Make sure you always plan out your next bit of work in advance, before you take a break, so you don't have to spend extra time deciding what to work on when you come back, and will help you make the most of your working time.
Freelancing has the wonderful benefit of giving you the flexibility to choose when you want to work. Take advantage of the freedom you have in your schedule, and work when it works for you.
If you're in a tourist-heavy area, try working more on the weekends, and give yourself more time during the week to visit places when they aren't as crowded. If your business is in a good place, take a few days off - you'll enjoy yourself so much more, and you'll feel refreshed when you come back.
I like to get in a few hours of work in the morning, then grab lunch somewhere new before going out exploring. Sometimes, I'll get in a couple more hours work in the afternoon or evening. Breaking up your work, like I mentioned above, and planning out what you're going to work on next in advance makes it much easier to jump back into your work quickly.
The point is, instead of structuring my holiday around a normal 9-5 schedule, I adapt my working hours based on other things I want to do. Don't constrain yourself to a normal schedule!
Make sure there's a boundary between the times when you're working and the times you're not. If you can't set up a physical boundary - like working in a quiet room or a café outside the house - then set up a time boundary, where you can focus on only your work for a couple hours before putting the laptop away for a while.
Try not to get sucked into working every single day. Especially when you're traveling with kids, it's easy to try working a little every single day, in order to give yourself enough time to get things done. Working every day, though, doesn't ever give you enough time to completely switch off. You need the time to give your brain a rest - so spend a few days working, then make sure you take a break entirely for a day or two.
As soon as you arrive in a new place, before going out on any adventures, spend the first day getting settled and finding all the necessities you need.
Make sure you have access to solid internet. If you're staying in an AirBnB, it helps to request that the owner send you a speed test in advance before finalizing your booking. Don't rely on internet cafes or the local McDonalds for decent wifi, especially if it's mission-critical to your work. Pay for a cellular hotspot if you need to, or tether with your phone - even if it's more expensive. Trust me, when you need it, it's worth it.
Look for local necessities, like grocery stores and cafes to work from, early. If you're staying somewhere with a kitchen, try to stick to cooking at home at least half the time - it's way healthier, and easier on the wallet.
It sounds simple, but it's so easy to become a giant ball of stress on a working trip. Things go wrong, tempers flare up and all of a sudden tiny problems get blown way out of proportion.
Things will go wrong no matter where you are. You'll lose luggage, your rental car will break down, your kids will get sick, you'll get sick, your bags will get stolen, the list goes on. These things happen even when you're at home - it's just that we tend to notice them less, since they're easier to deal with.
Don't let life get you down. Things will go wrong, and yes, they're often harder to deal with when you're traveling, but you're the one who decides how to deal with them.
Rent a car with a carseat, if you need one - the time saved wrangling kids onto buses and trains is well worth the additional cost for a rental car.
Make sure you keep things accessible if you're on a long drive or flight. Always bring a smallish bag of books, travel toys, and things to keep the kids distracted, one that fits under the seat in front of you. We have a Kindle tablet for our daughter, and on long flights like the one to New Zealand, we don't enforce any limits on screen time - the extra distraction helps keep all of us sane.
So there you have it - my best advice for making the most of working while on the move. I know it doesn't sound like the stereotypical perfect vacation - staying in one place, eating at home, routine work, driving a car. But it's simply what's worked for us over many overseas trips, both with and without kids.
The ideal case, of course, is to not work at all on a trip. But, for a lot of business owners - especially service businesses like us - it's frequently not an option. If you have to work, though, my advice should help you make the most of your trip, without that feeling like you were never truly there, or having your business fall apart because you couldn't get any work done.
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