What’s Her Secret? Travel & Style Co-Founder Jennifer Weatherhead Harrington

Most of us dream of living a life where we get to travel the world, but so few actually get to do it, especially for a living. We spoke with travel writer and Travel & Style co-founder Jennifer Weatherhead Harrington to find out how she got started and made globetrotting a profession — one that we have serious Insta envy over.

29Secrets: How did you get started as a travel writer?

Jennifer Weatherhead Harrington: I studied journalism in school and then started working in the magazine industry, working at ELLE Canada for about eight years. I was on the digital side while I was working there, starting as an editorial assistant and then a senior digital editor and one of the focuses was the travel section. That sort of struck my interest in general. I hadn’t travelled too much before”I had done a few trips here and there”but just the nature of working at ELLE Canada, there were always trips lined up for fashion shows, beauty junkets and that kind of thing, so I took any travel opportunities that happened. After about eight years I felt like travel was what I was really passionate about and I thought about starting my own travel site. There wasn’t really anything”at least in our Canadian market”for women who wanted to travel stylishly.

When did you decide to take the jump into doing this yourself? How did you make that transition?

I actually started it as a blog in 2010 under a different name”I was still working at ELLE at the time and it was kind of a side project. I started writing about the things that I wanted to write about and kind of got into the blog atmosphere and teach myself how to do that stuff. It wasn’t until about 2013 that I decided to switch it over to an actual travel website. So we made it more of a travel destination for women who wanted something that would be a bit more fashionable and have beauty, health and wellness and travel all in one. It was about three years ago that I left ELLE to focus on my travel site and freelance write on the side.

How has it been since you left?

It’s been great”it’s really wonderful to have the control over your own product. I take all of those things that I learned from my time in the publishing industry”I learned so much when I was at ELLE and it was an amazing experience and I really got to grow”but it’s so much more rewarding when you take what you learned and then put it into something that you started on your own. There are always growing pains and you have to learn how to do a lot of stuff on your own and you have no one to answer to”if something doesn’t get done, it’s kind of your fault and you have to deal with that, but the rewards of doing something on your own and the feelings that you get of having a project succeed and meet your expectations is probably one of the best feelings I’ve ever had in terms of my career.

What have been some of the things that you’ve had to learn as you’ve done this on your own?

Even when I was working at ELLE, if you’re in a digital space at all, you kind of need to teach yourself new things all the time because it’s constantly changing”that’s the exciting part of it. There’s always a new social platform, there’s always a new focus or trendy thing that’s happening. Whether it’s creating your own videos”that’s such a big thing right now”or learning how to use Photoshop and InDesign. You can always take classes and do that to upgrade your skills, but I’m the type of person who likes to figure things out on my own, so I would have to sit down and spend a few hours watching YouTube videos or reading up on how to fix something or how I’m going to do a particular layout.

What have been some of the ways that you’ve created a work-life balance when you’re traveling so much?

I would say it’s really tricky trying to take time, not just for yourself, but time with your family and friends. I’ve gone through phases in my career where I’ve been so focused on what I’m doing that I’ve slacked off in the friends and family department. Now I always make sure, whether I’m traveling or not traveling, that I have time to work out. Putting aside an hour a day”whether that’s meditating, yoga or going for a run”just making sure that I’m focusing on myself. It just gives you more energy to get things done instead of procrastinating and putting things off. For me, it can also be difficult to take an actual vacation. I’m always thinking, Oh, I want to stay at that hotel and I want to write about it. Sometimes it’s hard to actually go on a vacation and not make mental notes to write a review on the hotel or destination. I always try to fit in some time where it is an actual vacation. The other thing I would say is that I turn my phone off at a certain time of night, otherwise I will stay up all night looking at Instagram and not really turning my brain off. Even if you are in that social media space and you’re an influencer or blogger or even if you’re super-interested in it, it’s important to turn it off and let your brain settle.

That’s absolutely true”it’s so hard when you’re immersed in the digital world. On the travel side of things, how many places have you visited now?

I’m one of those people that keeps track and I have goals. I’ve been to 62 countries so far. I usually set a goal at the beginning of every year of how many new countries I want to get to. I remember in 2015 I didn’t get to many new countries. I travelled a lot, but it was all places I had been to before and at the end of the year it felt like I needed at least one new one. But I also really like going back to places. I feel that even if you’ve had a bad experience, you should always give it another try.

What have been some of your favourite destinations?

I would say Africa is really amazing. Kenya is probably the most magical place I’ve been. It’s a mixture of the people being really incredible and very friendly and outgoing and then just the wilderness”the vastness of these open planes. I’m a big supporter of protecting wildlife and, especially in Africa where it’s such a huge issue lately, getting to see the animals up close and really understanding the place that they’re in, it can be really eye-opening. It sort of put things in perspective. Other places are probably Peru”I’ve been a few times and I’m always blown away, it’s a really beautiful country. It’s one of those places that people need to get to before they limit how many people can get there. Sort of one of those bucket list things that I think people need to see. If they can get up there at sunrise and if it means waking up at 4am to make it up there to see the sun streaming over the mountains, it’s pretty quiet at that time and really beautiful. It feels otherworldly up there”like you’re not even on planet Earth. One other place that I’ve been most recently that I was completely blown away by was El Salvador. I wasn’t expecting that at all. I went to tick off another country in South America and I actually loved it a lot. They had these beautiful volcanoes that you could trek around”they had some active volcanoes that kind of added to the adventure element to it. Really safe and friendly country”I think people are put off and think it isn’t that safe right now, but I felt completely fine walking around by myself.

With that being said, you’ve traveled alone a lot, what are some tips for traveling alone”being safe, but also making the most of your time?

Research your destination and know where you’re going. As much as I love fashion and style, you don’t want to be sticking out too much or have too much bling on that calls attention. Being really aware with the destinations that you’re going to”that’ll make you feel more comfortable, too. You won’t feel like you’re sticking out or that people are looking at you. The other thing I would say is to research the neighbourhood, especially if you’re going by yourself, make sure you’re comfortable and safe being in those neighbourhoods. It’s always great to travel and feel like a local, but you also want to make sure you’re being safe and not constantly worried. Making sure you know where the best coffee shops are and good pubs that have really good ratings”research is really, really key when it comes to that. There are also so many forums on Facebook and other social channels where you can connect with other solo travellers (like this, this and this). They’re great because you can connect with solo female travelers who might be going to the same destination as you at the same time, or may have already been there or have already done some research. It’s a good spot for women to feel like they have friends or people looking out for them”it’s also a good way to meet new people and feel safer when you’re going to new places.

What are some tips on translating a love of travel into doing it for a living?

Everyone loves to travel, but you need to find a niche in what you’re going to write about. So many people who get to travel for work are also social media influencers, but they have a very niche market or niche voice or they’ve found a way to make their pictures a bit more unique. The other thing is that if travel is a passion of yours, just get your ideas out and discover your voice. Then you can research and see what people are doing and find a mentor”you may not know them in person, but you can consider them as one if you’re constantly reading their stuff and knowing what their style is, what countries they’re going to and why they might pick them”but you make your own vision. Then just get out there. The beauty of being in this day and age is that there are so many different avenues available. You can have your blog, but you can also have all these different social media channels and you shouldn’t have one without the other, really. All those are really great ways to get yourself noticed so you can start taking the trips that you really want to. When you travel, you have to use all of your senses, too. I find this really helps me keep all those details, when I get back my room, I’ll write out four or five points of what I’ve done”whether they made me feel a certain way or caught my attention”so I have at least a few fresh points of what I did. If you’re going to an amazing destination, it can be overwhelming. And if you’re on a press trip, they try to cram so much into three or four days so that you can see everything and it can be so much information to try to process.

Are there times where you’re booking the trip yourself?

When you’re starting out, press trips are really great because destinations will have things organized for you. But one of the downfalls of doing a press trip”whether it’s through a tourism board or a hotel”is that you could be with two or three other people or up to 20 other people and that can put pillars on the type of story you can write. I typically do individual press trips now and tourism boards are generally okay with it. They do realize that they want you to have the best experience that you can have and you’re going to write better stories and give them more coverage and it’s going to be more engaging. If you’re doing the stuff that you’re really enjoying, you’re going to be writing much better content. Sometimes I reach out to tourism boards, but sometimes I just like to go and figure it out on my own the way a real traveler would. More and more, I like to just experience it on my own without an agenda and then when I come back, I’ll have different angles. Also getting to see a place the way most people would travel.

Any tips on packing?

I only do carry-on and that’s definitely evolved. I’d say traveling has changed my style because I want to just be a carry-on. I used to go with giant bags with six pairs of shoes and so many shirt options”it was ridiculous. Over the years I’ve learned to be more minimal with what I’m packing. I’m always looking for quality pieces that are going to fit in different scenarios. The secret I would say for always doing carry-on is that you have to be ruthless with your shoes. Just be honest with yourself: You probably need one pair of heels, one pair of walking shoes and then I always wear my sneakers on the plane. I also like rolling all of my stuff instead of flat packing. I also look for materials that don’t wrinkle as much. When you roll really tightly it can get really wrinkling. Investing in a really good carry-on as well”ones that have little compartments to help keep everything organized can really change the way you pack. It also changes the way you shop when you get to your destination, so I know if I don’t want to check my bag, I’m only buying things that I really, really love”I’m not just picking up just trinkets or clothing items on a whim. The things I splurge on the most when I travel are jewelry items.

Where are you headed this year?

I have a few places in mind that I’d like to go to: Colombia is really high up on my list”it made so many of the top destination lists for 2017. I want to get back to Africa and see a few new countries there and probably go back to Kenya as well. I was thinking of going to Japan for the cherry blossoms.