Jennifer Weatherhead Harrington: Today’s Notable Young Entrepreneur

Inspiring Canadians fall in love with travel, one stylish carry-on at a time, Jennifer Weatherhead Harrington is the chic travel expert and creative force behind Travel & Style, the premiere resource for smart and stylish travellers who love to explore.


Describe what you do in less than 140 characters. Go.
I make people want to travel to far-flung destinations through words and pictures.

What was the inspiration for your career route?
My grandmother always said how important it was to meet new people and see different things since I grew up in a very small community in Nova Scotia. After studying journalism I moved to Toronto and landed a digital editor job at ELLE Canada magazine. It lead me to my love of all things digital and travel and to starting my own travel site,, just over three years ago because I couldn’t find a website geared toward women who wanted to travel well and stylishly. Now I’m focused on growing my site, digital content creation and of course visiting as many new countries, and remembering my grandmother’s advice to see as much as possible!

What is the most memorable milestone in your career so far?
I have two. Having lunch with Oscar de la Renta at his home in Connecticut. He was so genuine, attentive and obviously an extremely talented designer, but I noted his warm soul the most. I later met him two more times in New York and he remembered me each time. It always stuck with me that such a successful person remained so kind, thoughtful and tuned in. 

The second would be doing live TV as a travel expert. The moment when I was seen as an expert in something I was so passionate about was a milestone for sure.

Where do you see yourself in 5 years, 10 years, 20 years?
I’m more of a five-year-plan kind of person. In the next five years I see myself continuing in the travel industry in many facets, but definitely on the digital content creation side. In 10 to 20 years? Who knows! I want to keep as many doors open as possible.

Do you have any advice for other young professionals?
Long hours, pushing yourself, and teaching yourself will get you farther in your career than anything else. And being kind. Kindness is such an important aspect to me, in your career and in life in general.

Do you support any charities? If so, which one(s) and why is it (or they) important to you?
A couple of trips to Africa opened my eyes to the plight that African wildlife is under. I remember being in awe of a herd of about 35 elephants in the Mara in Kenya. Then my ranger told me that herd was so small. It used to be over a hundred strong, but poaching has depleted the elephant population. After staying at the ol Donyo lodge in Tsavo, Kenya (owned by award-winning conservationist Richard Bonham), I learned about his foundation Big Life Africa and have been a supporter of it ever since as they try to protect elephants and other Africa wildlife from poaching.

What is one major challenge that youve had to overcome in your career? How did you overcome it?

I was always shy, despite wanting to be outgoing. Truly, travel helped me overcome that shyness. It forced me to talk to others and put me in uncomfortable situations.

What does the word notable mean to you?
It’s something or someone worth talking about.

Screen Shot 2017-02-23 at 5.03.42 PM


Where is your favourite place to wine/ dine in your city and why?
I’m currently obsessed with Bar Reyna in Toronto. Their cocktails are amazing and the food is delicious. Plus they have a great patio that feels like a secret little nook in the city!

Whats the most visited website on your Internet browser? The most played song on your phone?
Aside from my own travel site, it’s a tie between and 
Most played song… I rotate through three: Africa by Toto (I’m not a fan of 80s music at all, but this has been a favourite since I was a child), Live Forever by Oasis and Yeah by Usher.

Who’s one person you think everyone should be following on social media?
Anthony Bourdain because he’s the coolest man on the planet, and if you ever need inspiration to do something crazy, he’s the guy. For travel, Sam Horine @samhorine is an incredible photographer.

Whats your favourite country to visit and why? And whats the next one you plan on travelling to?
I have a few. I love Kenya for the nature, the people, the animals, the feeling of how vast the world is when you’re on the plains. I always feel at home in the U.K. I’ll never tire of going to Ireland and eating brown bread. And Peru, I’ll always want to go back and try to beat my hiking time up Huayna Picchu. 
For where I’m going next, it will likely be Hawaii in the U.S., but it’s constantly changing. Japan and Norway are in the very near future.

What gives you the greatest FOMO?
People’s travel photos on Instagram and Snapchat! I love seeing them, getting ideas, seeing friends go to amazing places, but it makes that travel itch go crazy.

Whats your guiltiest pleasure?
I have so many! Celine Dion, Twinkies, Snapchat, and watching tasty videos of food that I’ll likely never make (I’m a vegetarian and I watch food videos on how to make burgers, ribs, etc. all the time).

Whats something you wish you didnt spend so much money on? Whats something you wish you spent more on?
Phone chargers! I lose one on every trip and then I’m always paying a premium. I will always wish I could spend more on travel. I don’t think that will ever change in my life.

And finally, what does success look like to you? Work, play, or otherwise…
I’m not a ‘sit still’ kind of person. I always want to be learning, trying something new… And I like to do all that in a collaborative environment, with other creative, positive people. Surrounding myself with positive people, who push me out of my comfort zone, both personally and professionally would be success to me.