How to combine full-time work with travel

Today I announced I was going interailing at work and, like clockwork , got the same responses I always do:

“But you just got back from a holiday!” and “How many do you even go on?!”. Or, my personal favourite: “You’re hardly ever in the office!”.

Excuse me, Miss Mug-stealer (yes, I know it’s you), I have just as much time off as you do. You see, my job isn’t a travel-centred one. If anything, according to mid-level management, our work-related world could probably fit in one building. If you’re lucky enough to work in an environment that lets you combine work trips with annual leave, please go ahead and do it (you’re living the dream). But for those trapped within the confinements of 25 day leave, here’s how to combine the two without completely giving up the comfort of office air conditioning.

Get into remote working

If you’ve got a laptop and a decent WiFi connection, you may have just struck gold. A lot of companies offer employees the opportunity to work from home to cover a range of work-life arrangements: a plumber coming over to repair something, long commutes or being savvy enough to make arrangements in such a way that allows you to work from home a day or two per week.

I have a colleague who is in a long-term relationship. Thanks to his schedule arrangements, he works slightly more three days a week (an additional hour or two) and takes a train to go and see his girlfriend on Thursday afternoon (working from her place for just a couple of hours on Friday). If you want to book a cheap afternoon flight without digging too much into your annual leave, negotiate with your line manager so you can work a few more hours earlier in the week and leave for the airport straight after lunch on Thursday.

Short breaks are better than long ones


Due to school holidays, a lot of people decide that three weeks in Tenerife work better than a few long weekends throughout the year. However, for my own peace of mind, I nearly always choose short breaks over long ones. It might mean budgeting more and leaving at 3AM in the morning, but smaller breaks let you take frequent rests from work, reenergise and give you something to look forward to every couple of months instead of only once or twice a year.

Additional tip: if you work in the UK, the guys over at The Debrief featured a post on which days you should book off to turn 25 days of annual leave into 55. Not a bad deal at all.

Work a bit every day

Holidays are times to relax and, according to some, completely disengage from work. However, the thought of disengagement may be the very thing putting you off holidays. Many employees get anxious about leaving emails unread for long periods of time, while tasks going unresolved during your time away could bring about even more work upon your return.

Instead, whilst on holiday, take 10 minutes every morning to catch up with your emails. Don’t answer, just check them. This will help you stay in the loop of what’s going on and give you the chance to get rid of the spam emails that usually make up 70% of your inbox.

If you do encounter any urgent emails, make a note and attend to them when you return. Your holiday is meant to be enjoyed, and there’s little you can do about them whilst abroad. Just knowing what’s going on will give you some peace of mind and enough knowledge to directly take action on your first day back,.

Cover yourself in every possible way


My friend Alex once said “The secret to being good at your job is knowing how to cover your sh*t at every turn”. In non-swear terms, you should know how to justify and back up every action you take throughout the day.

The same principle applies when you plan to go on holiday: book in advance and send group emails to project coordinators to let them know your exact leave dates, delegate tasks where possible and make sure your out-of-office email covers all alternative contact details.

People may also need a little reminder before you leave so, a couple of days before you’re due to go, send an email asking people if there is any unfinished business they’d like to discuss beforehand, as you will be unavailable during your time away. Any verbal communication should be reiterated via email, as anyone who complains will then feel the wrath of the large paper trail you bring along to your next meeting.

Late Thursday travel

A lack of sleep may be worth the trouble when it comes to cutting back on the amount of leave you take. If you travel late on a Thursday, you’ll have all of Friday to explore your chosen destination. While I generally chuckle at three-day travel guides (they are famously over scheduled), they do show how much you can see in a city given a short period of time. Fridays should be spent exploring or relaxing,  not waiting in a queue at baggage drop off.

Understanding families

As workers, Christmas is the longest break we get that doesn’t actually involve using annual leave. As a result, the idea of using it to travel is even more alluring. An understanding family that will be supportive (if not completely over the moon – you are missing Christmas after all) of you jetting off to Puerto Rico during the holidays will be one of your strongest weapons for winter escapades. Just make sure you have good connection to call them on Christmas and New Years to share the holiday joy.

Never give up on your career Wikitrip_with_botanist_in_Lodenice_region_in_2012_(8)

If dreams were possible, no one would ever have to work. Why would you, when faced with the prospect of long hours, colleagues who keep all the good biscuits to themselves and going to meetings about meetings (also called ‘pre-meetings)?

Travelling is a fantastic opportunity for personal development and meeting people who can help us see things from perspectives we’ve never considered before. However, years of wandering around without a sense of purpose can be equally damaging and hard to justify to future employers (and yourself). If you are travelling, keep on developing your interests and look for a way of combining the two.

Work and career can be as equally fulfilling as it is painful at times. When placed in the right job, people thrive and gain a sense of self-appreciation for what their personal strengths are. Working friendships and relationships often blossom into lasting ones and, whilst money doesn’t buy happiness, it sure helps you pursue what really can.

What are your thoughts on combining work with travel? Have any tips of your own? Share them in the comments below or tweet me at @sideroutes.

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