Episode 40: Work and Wanderlust

There are so many people telling you to quit your job, sell your belongings, and travel the world on $50 a day.

That’s one way of doing it, but it’s not for everyone.

If you have a 9-to-5 job, you can travel the world and still collect your salary!

Don’t believe me? I’ve been working a full-time job in corporate America for 22 years, and I’ve been travelling to all sorts of places. Since the pandemic started, and my company has allowed us to work remotely, I have been able to work from several vacation destinations.

Here are some tips and tricks to help you make the most out of your work and travel:

[05:42] Plan your work and travel.

If you’re travelling for work, consider adding a few days to your trip – if you have a meeting on a Monday, Thursday, or Friday, you could always request to add the weekend to the trip.

Sometimes you could save your company money by booking flights a few days before or after the meeting.

Having this bleisure (business + leisure) trip allows you to spend some time at the destination outside of the necessary working time.

[07:43] Use holiday weeks maximise travel days.

If you plan your trips just right, you could score an extra day or two. Often, a public holiday falls on a Monday or Friday, and you would be able to take a long weekend trip without using your vacation days.

I have 4 weeks of work vacation days. If I take long weekend trips along with my 4 weeks of vacation days, I could turn it into 5 weeks of vacation.

[09:41] Explore on weekends and nights.

When I was working at vacation destinations, I would keep to my regular work hours, and leave the vacationing time to the evenings and weekends.

[12:01] You must have trust.

My boss and company knew I was travelling while also doing remote work.

If you’re travelling and working remotely, your company needs to be able to trust you – if you can show that your work will be consistent even while living the best life all over the world, they’ll be more comfortable with the idea.

[13:18] Work within your time zone.

If you’re travelling to different time zones, you need to be aware that you may need to adapt your work hours to stay within your usual work schedule.

If the time zone if vastly different, you’re going to have to communicate your schedule with your team.

[15:31] Be mindful of scheduling.

If you’re planning a vacation, be mindful of your company’s schedule – know when the high and low busyness times are in the year and try to plan according to those dates. I know if I book a trip at the beginning of a quarter, I’m going to have to work extra hard to catch up on work. It is not fun.

[17:02] Prep your team.

Your team needs to know ahead of time that you’re planning to take some vacation time.

I do three things:

Send an outlook calendar invite to everyone who will be affected. This puts your vacation time on their calendar, so they won’t forget that you’re not available. Do it two or three weeks ahead of time.

Send out an email. Let your team and customers know that you plan to take time off on certain dates. This allows them to let you know if there is anything you need to take care of prior to your trip. I do this two weeks before my trip.

Put your vacation in your outlook signature. If you add the vacation dates to your outlook signature, you’ll be preparing everyone you contact for the times that you’ll be unavailable. It’s also helpful in case you forget to let specific people know.

[20:20] Understand your manager.

If you have a manager that’s more traditional and prefers people working from an office, you can start to make changes that reassure your boss that your work will not be influenced by you travelling and working remotely.

There are so many digital nomads that tell you to sell all your things and travel the world. If you’re into that sort of thing, then go ahead. But, if you want the security of a full-time job paycheque while travelling, these tips and tricks will help you live that best life.


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