Interview conducted by Chanèle McFarlane
Photography by Keidi Janz

Here’s what we know for sure about Jacqueline Leung: she’s not one to back down from a challenge.

From a lay-off to a shorter than anticipated stint in New York City, her career began with some tough hurdles. Yet, she remained resilient, landed a great job in Toronto and successfully worked her way up the corporate ladder in the marketing industry...until, of course, she got the entrepreneurial itch.

Now, Jacqueline is taking on a new challenge. As the Founder and Editor-in-Chief of Pressed, she’s on a mission to make the news easy to understand and follow, from a Canadian perspective. Pressed sends daily emails with the top 5 news stories written in real words - equipping you with everything you need to know to hold your own in conversations.

Jacqueline’s story is the perfect reminder that no matter what hurdles (or lemons!) come our way, things will always work themselves out as long as you remain confident, resilient and, of course, willing to do the work.

Here’s Jacqueline on being grateful for mistakes, finding balance and knowing your worth:

Tell us about a time that life handed you lemons. Did you make lemonade?

The moment that stands out to me the most is the moment I was let go from my job. I remember kicking and screaming (almost literally) in my car and calling my mom to tell her I was officially a failure. I was completely blindsided and didn’t know what to do next. Three weeks later, my mentor at the time offered me my former job back. The support really helped me pull myself (and my confidence) back together; enough to move to New York for a quick stint before finally landing in the corporate world, where I spent several years climbing the ladder. About four years later, I ditched the corporate life to start my own business. I am grateful for every step, and misstep that has led me here.

**Describe your ideal work environment to get sh*t done.**

Near natural light. I need to be close to a big window where I can see mother nature - rain or shine. Also, I have to have a fresh cup of coffee nearby plus a fully charged phone and laptop. I also prefer to be around people than by myself at home. I like working at the library or in co-working spaces where I have the option to talk to people around me.

After that first year, how did you scale your business and continue to grow?

I had to raise money. You need a lot of resilience and hustle to start a business. But you need money to grow. I was able to raise a round of pre-seed (angels, family & friend) funding to get us to our next milestone. The funding allowed me to hire a team and really set up my business (and finances) in a more “official” way. It made everything really real.

How do you measure success in your career?

In my startup – numbers. Dollars, users, click rates, etc.

In my career – how happy I feel. Since I started Pressed, there hasn’t been one morning that I’ve dreaded going to work. Of course, I’ve often dreaded tasks I have to complete, but actually getting up to go to work? I’ve never been happier.

"You have to believe you’re worth it before you can convince other people to believe in you.”

How much of your success as an entrepreneur has come from taking risks versus playing it safe?

Being an entrepreneur is really risky. I’d say 80% risk and 20% being smart about when to play it safe. For example, I had to leave a really good corporate job – the money, the friends, the stability – to start Pressed. That was really risky. Every step after that is risky too. As a startup founder, I’m essentially trying to start something that hasn’t been proven – so I’m constantly throwing different things against the wall, hoping that something will stick. Playing it safe has also played a role, however. For example, as a team, we have so many good ideas that we want to execute. But we can’t risk everything we’ve built on one idea. We have to plan.

Who is a fellow Toronto-based female entrepreneur that inspires you and why?

Erin Bury. Because she’s so different from me! I admire how positive she is (dare I say, always?) and you can’t help but rub off on some of that positive energy when you’re around her. I deal with a lot of anxiety on a daily basis, so having Erin as an advisor and friend really helps balance my emotions and keep things in perspective. She also works so hard, has accomplished so much, and manages to look great all the time.

What would you say is the biggest mistake you've made and how did you rectify it?

It’s difficult to call anything a mistake. Every day, I’m forced to do something I don’t know how to do, so mistakes are inevitable. To me, they’re all learnings. I guess my biggest learning so far happened last Christmas when I listened to too many outside voices and didn’t listen to my gut – I spent money and a lot of time executing a Christmas campaign for Pressed. I knew in my gut that we weren’t set up for success. And I knew that I didn’t want to involve outside partners until we had a better formula. But we did it anyway. As I expected, the campaign missed the mark. What I learned is that I know my business best. I take advice from my advisors very seriously but it’s also okay to disagree and push back. Another thing I learned is how to move on fast. I had to just understand that some things aren’t going to work and be brave enough to try again.

What is your best negotiation tip?

Don’t sell yourself short. Of course your service is worth that much money. Of course that blog wants to feature you. You have to believe you’re worth it before you can convince other people to believe in you.

What is a personal or professional challenge that you're faced with right now?

I’m trying to do a better job at merging my personal and professional life together. I’ve stopped doing a lot of the things I love because I think it’s the way “startup life” is supposed to be - all consuming. But I’m working hard on bringing some of those personal things back. If I want to run this marathon, I need to make sure I take care of my mental health.

What is one thing you wish you knew before becoming your own boss?

I wish I knew how much support was waiting for me on this end. Yes, being an entrepreneur is hard, but there’s a whole community ready to help you succeed. I am especially grateful for support from the Ontario government, in the form of grants and affordable education. I am also grateful for the startup community in Toronto and Kitchener/Waterloo. The tight-knit community reminds me that I’m not alone. If I knew all of this ahead of time, it would have made my decision to quit my job much easier.