Working on the Road: How to Work Anywhere (and Actually Get Stuff Done!)

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As you plan your calendar for 2019, it’s likely you’ll need to consider working on the road at some point during the year. Whether it’s for business or pleasure, travel can throw a big wrench in your normal work habits.

People often underestimate how challenging it can be to work on the road, but like with most things, planning ahead and being realistic about your expectations can have a huge impact on your success!

The “Working on the Road” Myth

So many of us started our businesses to gain freedom and flexibility in our lives. We dreamed of working on the road so we could travel, explore, and get work done.  

We struck out on our own to not only do the work we love but also do it in the way we want. And, yet, I talk to so many entrepreneurs each day that feel trapped by the business they’ve created.

There are so many “laptop lifestyle” mantras out there, but working on the road is not always as simple as you’d think.

As a service provider, working on the road can feel like a huge undertaking. You have to figure out all the arrangements for working from a different (or multiple different) locations aaaand how to make sure your clients get the level of service they are used to.

Here are some tips for taking your work on the road AND preserving your sanity.

Plan Your Time Intentionally

There’s a common misconception that you should be able to work exactly the same hours or way while traveling as while you’re at home. While there may be days that that is entirely possible, there are also sure to be days when the logistics of traveling need to be considered.

When you first decide on a trip, spend some time reviewing your travel schedule, and intentionally decide when you’ll be working and when you won’t be. Be realistic about what constraints you’ll have and what you’ll have access to. While it may be possible to take a call at the airport, it isn’t always a good idea.

Also, consider any activities you want to do outside of work while you travel. These are likely to impact your normal availability, so plan ahead! (Need help planning your week for productivity while you’re working on the road? Check out this post!)

Once you’ve established when work will be realistically possible, block off your calendar immediately. Even if you’re talking about a trip three, six, or nine months out, take the time now to block the days out on your schedule.

Far too many times, I’ve forgotten to do it until a week or two before the trip and then looked to see 10,000 things that need to be rebooked. Annoying! There’s enough to be done while you’re getting ready to leave that you definitely don’t want to add to the workload.

I also make sure not to schedule any appointments on travel days. There’s nothing worse than rushing to make a call after 12 hours of traveling, or, worse yet, stressing because you scheduled a call during a layover, and your flight is delayed!

Add Rest After Major Travel Days

Since I live abroad, many of my trips require international travel. So, even when I’m working on the road, I ensure adequate rest time after major travel days. As tempting as it is to schedule calls the day after a 20+ hour trip because I technically can, I’ve learned it’s not a good idea.

I’ve had too many instances of missed connections that delayed my arrival or was suffering from sheer exhaustion due to jet lag that I now avoid any scheduled commitments for the day or two after a long haul trip.

While it may be possible to do client work on these days, I don’t want to be committed to scheduled calls or appointments. I also don’t recommend any time-sensitive tasks that have to be completed. It’s far, far better to have nothing urgent to complete and feel inspired to work than to be exhausted and have 10 critical things on your to-do list that you can’t ignore.

Even if you’re not traveling a huge distance, work some rest into your plan. Traveling is always more exhausting than we anticipate!

Set Expectations Early

When it comes to clients, let them know at least 30 days in advance — and remind them frequently!

Generally, travel will impact calls and sometimes turnaround times, so it’s important to plan ahead. If clients have plenty of notice, you can work together to ensure smooth handling of their tasks.

I also coordinate with my team, so they know I’ll need some extra help. They always have an itinerary, so they know what days I’ll be fully available versus days with restricted availability due to travel or rest.

Take the time to review all the tasks that need to be done during these times, and ensure that your team has everything they need, so they can continue to work without you.

Last, set expectations for yourself with kindness. It’s so easy to hold ourselves to impossible standards that don’t accurately reflect what’s really going on in our lives and our businesses. Don’t let working on the road be one of those times.

Wifi Workarounds

As an online entrepreneur, your business is likely incredibly dependent on Wifi. This makes working on the road heavily dependent on whether or not you have access to the Internet.

Alas, though, reliable Internet is not always possible when traveling.

I learned early on that one reality I have to face in order to work successfully while traveling is that I cannot depend on free Wifi. I invested in a SkyRoam hotspot after a colleague recommended it to me. It’s been remarkably helpful for my productivity while traveling because I can depend on having access to the Internet on my terms.

I may not be able to do really intense tasks online in some instances, but I have a lot more reliable Internet with it! [If you decide to grab one and want $20 off, use my referral link! Full disclosure: I will get two free day passes, too, but I only recommend things I use myself and believe in.]

I also like to keep a list of things I can do without Wifi. There is nothing more frustrating than wanting to work but not having what you need to do it because you’re without Wifi. This generally means a little bit of prep work beforehand but is so useful when you need it.

For instance, before I get on planes, I’ll be sure to download any documents I might need to access and make a list of content topics I could work on. I find it quite difficult to work on my laptop on planes so I also make sure to have a notebook and pen available in case I decide to put the computer away.

Working on the Road Is NOT Vacation

It may go without saying that working on the road is NOT a vacation, but I’m going to say it anyway! Why? Because even if you have lots of trips for work planned, you also need to schedule proper vacation time.

So be sure that you’re scheduling some downtime for yourself throughout the year — whether or not you plan to leave your house in the process!

When you’re planning for actual vacation time, not just taking your work on the road, check this out for more details on preparing your business for it.

Working on the road is possible with a bit of planning and preparation! Before your next trip, be sure to set aside the time to get ready so you can be productive and enjoy yourself.

Getting things done when you’re working on the road can feel tricky, but it doesn’t have to. It all starts with great planning.

What kind of entrepreneur are you?


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