Dream Job Alert: What It's Really Like to Be a Travel Writer

In our 9–5 series, we ask our favourite boss babes what a day in the office entails. This week, we spoke with travel writer Jennifer Weatherhead Harrington, creator of Travel & Style magazine, about her globetrotting daily grind


Travel Writer Jennifer Weatherhead Harrington

Jennifer at a Christmas market in Cologne, Germany (Courtesy of Jennifer Weatherhead Harrington)

Age: 34

Education: Bachelor of arts in journalism and history from University of King’s College

Length of time as a professional travel writer: three years

What prompted you to start Travel & Styleyour own online travel site?
When I was working at a fashion magazine, I had the opportunity to do a lot of travel, going to fashion shows, doing beauty junkets and that kind of thing. I really enjoyed it but when you’re working for a bigger publication, you can’t always write in a voice that you want to write in, or cover all the travel stories you’re interested in. That’s why I started the blog.

There are so many travel sites and blogs now, how did you set yourself apart?
My intention with the blog was to deliver good-quality writing, because I could see that the trend was going towards the photo side and there were so many photo bloggers and Instagrammers. It’s great to be posing in pretty outfits in different locations, but I also think people want to know a bit of the history behind that too. I wanted to make sure my copy made sense, had no spelling mistakes and was factually correct. That’s a way that I differentiate myself a bit, knowing I have a solid background in writing and storytelling. 

You also geared Travel & Style specifically towards chic female travellers—was that part of the process of getting your site to stand out in this market?
Yes, when I was thinking of starting this blog with a friend of mine, we were travelling a lot and looking at places to go, but there weren’t really any stylish travel sites for women. There were tons of girlfriend getaway sites, but there wasn’t anything geared towards women who want to experience luxury, without always paying luxury prices. Since I noticed a gap, that was the angle that I took.

How did you go from a blog to a profitable, professional website?
It’s been a process. At the beginning, it was more of a creative outlet that I was doing for free. Slowly the site started to gain traction and people were interested, so we started to get advertising on the site. Sometimes we did guests posts for other publications and they would pay you like a freelance writer. Those are the initial ways that I started getting paid. But even in the past few years in digital; you can’t rely on those flat online ads anymore. About a year ago, I put more into sponsored content both on the site and on the social media channels. I think brands are starting to realize that content creators know their readers the best and can sell their products just by being themselves. So it’s gone from that standard advertising model to really integrated content and doing those sponsored posts. The tricky part is maintaining your authenticity—like what you want to do and would actually tell your readers—instead of just doing content for money.

Is it hard to stay objective when hotels and travel companies are hosting you?
It’s always tricky because if a hotel or tourism board is hosting you, they have their own agenda. They’re spending money on you to get there so they have things that they want you to do, but then there are the things that you want to do. For instance, I would never go to a children’s museum. If someone told me to go, I would say that it wasn’t beneficial to me or them because none of my readers are going to be interested, so it’s a waste of everyone’s time. There’s a lot of negotiating back and forth in terms of what you want to do and see. The key is making sure you’re firm, but polite, about what your values are. If it’s a hotel or destination that doesn’t work for you, you shouldn’t go just for the free trip. In fact, that’s also something that can set you apart in such a saturated market: really staying true.

How do you decide on your next destination?
When I started out, it was a lot of me reaching out to hotels or a tourism board, trying to make connections. Now I’m fortunate and I get offered a few things, but they don’t always fit. Even now, there’s still a lot of me reaching out to places that I think would be really relevant to our readers. The biggest tip I give people is that you need to be able to provide stats about your social following and your site views. Having examples ready for them makes you look a lot more professional.

Jennifer in El Tunco, El Salvador

Jennifer in El Tunco, El Salvador (Courtesy of Jennifer Weatherhead Harrington)

How does travelling for work differ from a vacation?
When you’re on vacation, you’re usually away for a week to 10 days. If you’re on a press trip, it’s going to be two to four days and they’re going to cram as much stuff in as possible. You’re going to be getting on that crazy early morning flight then expected to go-go-go as soon as you land. You have to be “on” and professional with all the PR people you’re working with and the people you’re meeting, while also taking notes and pictures and doing social media posts. It’s kind of like a vacation because you get to see these amazing places and have experiences you might not get if you were travelling on your own, but there’s a lot of work that goes into it.

That almost sounds like the exact opposite of a vacation because you’re basically working the whole time you’re there.
Yeah. One of the biggest mistakes I see new travel bloggers making on these group press trips is treating it like a vacation. It’s a job, so I don’t skip out on dinners at night because I’m exhausted and jet-lagged. If I had a 9-5 job and I had an important meeting, I wouldn’t miss it because I’m tired. You have really treat this like a legitimate job, because it is one and you don’t want to waste anyone’s time, including your own.

It sounds like every trip and workday is different, but can you give us a sense of what a workday entails for you?
If I’m home, I wake up around 6 a.m. I like to write and do a lot of my work in the morning, catch up on emails, have a few meetings, do a lot of brainstorming, that kind of thing. If I’m travelling, it could be getting up at 4 a.m. to catch a flight to New York so I can make a PR meeting. If I’m on a press trip, it’s usually getting up really early so I can get that sunrise shot for Instagram, which is always popular, and then doing all the planned activities. It’s very different day-to-day, so it’s hard to keep a normal schedule. If I do a big chunk of travel time, I try and do a month or so where I’m just at home and can catch up on work, get my body back to a normal schedule and see friends.

To date, How many countries have you been to? 62.

In the past, you’ve said your most memorable spots have been Kenya, Bali, Iceland and Peru. Is that still accurate?
I would probably add in Suzhou, China, a town outside of Shanghai. I went there about eight months ago and it blew my mind. It was way more romantic than I ever thought China could be. I always think of China as so full of people and this small town had 10 million people in it, but it had all these waterways and canals that made it like the Venice of China. They had beautiful gardens and temples, and you can go on a boat ride on the canal under these old, old bridges. It was amazing, and it really surprised me.

Elephants in Kenya

Elephants in Kenya (Courtesy of Jennifer Weatherhead Harrington)

What has been your fave experience during a work trip?
My favourite experience was probably on safari in Kenya, that was my first time seeing a big herd of elephants. It was pretty magical. I was also recently in El Salvador, in this little town called Suchitoto and it was so charming, with tons of murals and great spots for coffee if you’re a coffee lover. I just remember sitting there, in a small hole-in-the-wall café, sipping a coffee and being like, “Wow, this is an amazing experience.”

On the flip side, there are a lot of things that can go wrong when you travel. What is the worst thing that’s happened while on a work trip?
I had very serious case of food poisoning one time when I was in Peru, and it didn’t hit me until I was getting on my 8-hour overnight flight back home. I remember the flight attendants asking if I was OK and thinking that I could sleep it off, but by the time the seat belt sign went off, I was panicking. That was probably the roughest travel journey I’ve  ever had. I had a 6-hour layover at JFK and I was just lying on my friend’s coat on the floor outside the bathroom, which is so gross, but I was just so, so sick. Then Chase Crawford walked right in front of me—and this was when Gossip Girl was at its peak—and he looked at me with such disgust. [Note: this experience has not deterred Weatherhead Harrington from going to Peru and she has since been back.]

Jennifer Weatherhead Harrington in Alberta

Jennifer overlooking Peyto Lake in Alberta (Courtesy of Jennifer Weatherhead Harrington)

According to MoneySense, more people are booking trips within Canada than internationally—have you noticed that with your readers?
This is definitely true in part because of our dollar dropping over the past few years—it makes people stop and think about how they’re spending their travel money. Another reason is (sadly) the new president in the United States. I’ve heard a lot of people, even some journalists, say they don’t want to support travel in the U.S. while Donald Trump is president because they don’t agree with his policies. I don’t know how many people will actually avoid it because of that reason alone, but it has made Canadians stop and think about it. Finally, and I hope this is the more common reason, I think Canadians are really taking pride in our amazing country right now, especially with the 150th celebrations. There’s so much going on this year for it across the country, and a lot of other travel bloggers/Instagrammers/YouTubers are sharing great content that I think is inspiring us to see as much of our country as possible.

When you’re packing for a big trip, what are your travel essentials?
My Rimowa carry-on, because no one ever questions you about the sizing of it and it limits my shopping.

Do you speak any other languages, and is that important for a job like this?
I’m not fluent in any other languages but I definitely try and learn the basics like “please,” “thank you,” and “how do I get to” before I go to a country. I find that if you at least try and know a little bit, people are much nicer to you because you tried.

Where is somewhere you’ve been wanting to go but haven’t booked yet?
Tokyo, Japan and Norway.

After a long trip, in which you may or may not have been in a completely different time zone, how do you unwind?
I read (right now, I’m rereading Watership Down), especially if I’m travelling, I find reading will help me fall asleep. I usually try and do some stretching and yoga everywhere I go. I find as long as I do some activity, it tends to help me with my jet lag.

What is your advice to other women struggling to make it in this industry?
Find a niche if you can, something that makes you unique. Make sure that you’re on every digital platform that you can be on. Also make sure you’re very professional and polite on work trips. Even if it’s a part-time thing, if you treat it like a real job, you’ll get a lot more respect. Being professional will win you so many connections, and those connections will ultimately help you grow.

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