These days, working vacations are more feasible with jobs that can be done remotely and an increase in the availability of wifi and working spaces for travelers (i.e. coworking spaces). They are also a great way to enjoy the benefits of travelling while still generating income. Here are some tips for making a working vacation work for you:
Before you leave.
Set up expectations with work. If you work for a company or business, make sure you set up dedicated times of availability with work before you leave. This allows you to enjoy the vacation part of your trip without getting interrupted or having to worry about whether you’ve missed any important emails while you’re trying to sightsee and relax. Let people know upfront if you can the times you will be exclusively working, or give an update each day when you have a better idea of your availability. If you’re a freelancer/solopreneur, this is less of an issue.
Set up expectations with the people you are travelling with. When travelling with others who won’t be working, it’s important to set up expectations as well. Be clear about your set work time(s) so there won’t be any surprises when you have to take off to a working space (more on those in a bit).
Set up expectations with yourself. Finally, make sure you have some guidelines for your upcoming work set up. What projects will you be working on? Are there any deadlines you’ll need to meet while away? In a perfect situation, you have the ability to do plenty of planning and preparing ahead of time to get as much done in advance as possible, but realistically, you may not be able to look ahead. Another thing to keep in mind- if your work is creative in nature, spending a little time away could actually be beneficial.
Where to work.
Some people have an easy time getting work done from anywhere– on the plane, on a bus, or in their hotel room. Others may want a more structured work space. Here are a few options available to travelers:
A lot of coffee shops will offer wifi to paying customers. This is a great option if you want to be somewhat immersed in local life and support another business. However, it’s not a great option if you have a hard time working in loud places, need to make phone calls, or want the ability to get up and move around without worrying about your belongings. Depending on how long you stay, you may end up spending a lot of money (and consuming a lot of sugar/caffeine) by the end of your work session.
Another alternative is a local library, as these often have wifi as well. While libraries tend to be much quieter than coffee shops, they still are not ideal for those who need to make phone calls or participate in webinars. Also, you may not have the same ability to bring food in while working.
Coworking spaces are another great option for working while on vacation. For instance, WeWork has a location in Chicago as well as throughout the globe. If you have a membership, you have access (varying depending on your membership level). Do a bit of research in advance and see if there is a coworking space nearby that you could use intermittently while on vacation. (If you are interested in learning more about coworking options in Chicago, check out this list of spaces from 42 floors).
And finally, keep in mind that working vacations are meant to be enjoyed! Try to maintain that work-fun balance while you’re away to gain as much of the “vacation” benefits as possible.