Interview conducted by Chanèle McFarlane
Photography by Julia Park

As we hustle our way through our careers, we’re sure many would agree that taking time out to connect with like-minded women is a key priority. For the last 8 years, there has been one incredible woman who has created the spaces for diverse women in Toronto to do just that: Emily Mills.

As the Founder of How She Hustles, Emily leads a vibrant network of diverse women that connects through social media and special events. From brunches to pop-up shops and panels, she’s an expert at creating buzz-worthy events that sell out in a just a few days, leaving those unable to secure a coveted spot with serious FOMO as they watch the coverage across social media.

Most notably, How She Hustles led the award-winning project, HERStory in Black. When it was time to recognize Canada 150, Emily saw the perfect opportunity to include black women in the narrative. What started as a digital photo series of 150 black women turned into a hour long TV documentary, national press and recognition from the Prime Minister himself!

Here’s the thing about Emily: she’s an absolutely captivating communicator. Whether she’s speaking publicly at an event or writing social posts for her loyal network across Facebook, Twitter, Instagram and Linkedin, she has such a powerful way of using words to connect and inspire. Through becoming independent at 17 and the tragic loss of a family member, Emily was forced to see opportunity through adversity and today, we all get to benefit from the wisdom she’s gained from her life experiences.

After years of juggling her various events and projects alongside a demanding 9-5 communications job (we don’t know how she did it either!), Emily has now ventured into the world of entrepreneurship to pursue How She Hustles full-time - most recently being recognized on a list of 100 Accomplished Black Women.

Here’s Emily on growing through tough times, finding purpose through impact and embracing uncertainty in order to grow:

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

I’ve had to endure my share of tough times: Like moving out at age 17 then trying to juggle classes while paying bills, or reflecting on my life purpose after losing a beloved family member in a fatal accident. I’ve had to push through these defining moments and learn from the life lessons that came with them. Whatever life has thrown at me, I’ve had to lean on my evolving faith, see opportunity through adversity, trust the value in sharing my journey, and understand that I am here to help leave a positive legacy, however I can. That’s probably why one of my favourite quotes is, “Life is measured in impact, not duration.” It’s not how long we are here – but what we DO with the finite time we are given.

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

Music is a must. Uplifting R&B/Soul with a mix of classic Gospel, Afrobeats, Hip Hop, Reggae and House. Female singer/songwriters including homegrown talent like Jully Black. I also need some element of the great outdoors: I love the peace I get from the earth, water and sunshine. If that’s not an option, I love working in a space with vibrant colours and natural light. And above all else, I prefer to be surrounded by good vibes and energy. Good people are essential.

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

Since I launched How She Hustles in 2010, virtually every event has sold-out events over 8 years, I’ve spoken to audiences in Toronto and beyond and I’ve led many successful initiatives featuring diverse women. I was running How She Hustles while holding down a demanding full-time job in media and communications for many years.

Then earlier this year, I finally decided to follow my purpose and left my former place of employment to pursue my passion. Now that I’m focused on How She Hustles and my own brand exclusively, the results have blown my mind and I’m just getting started! In the last few months, for example, I’ve had a chance to meet Michelle Obama, was named to the 100 Accomplished Black Canadian Women list and spoke to a global audience through Twitter Canada’s #HereWeAre event (the video has been viewed over 68K times and counting). Some weeks, I’ve had a speaking engagement almost every day – a business opportunity I didn’t realize would have so much potential. All affirmation that I’m going in the right direction.I’ll continue to focus my work three areas: public speaking, communications consulting and expanding How She Hustles through women’s events and online spaces. Much more to work to do – and much more to learn – but I’m focused on getting my business in order and truly scaling up. Stay tuned.

“As things evolve, I’m learning to be more decisive, when to seek wisdom from others, when to hear my own voice and how to become more strategic as I hustle.”   

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

Transitioning away from my full-time job was a huge risk. I felt job security, had seniority and I knew my stuff. I held a coveted role and worked in a high-profile industry where black women are underrepresented. With my husband, we have two young boys to support. And yet, I still knew it was time to go after deep reflection. It was a definitely a risk – but a strategic one. I made this career change with a heart of gratitude and much respect for where I had been. But now I was ready for the next chapter - to use my knowledge, skills and voice to step into my own leadership – in my own way. To grow and lead a Toronto-based movement where diverse women can connect, inspire and empower each other more. The results so far? Speaking engagements. Sold-out events. Consulting clients. Awards. Media coverage. And above all else, women who feel like my efforts are helping them to be more authentic, entrepreneurial and bold. Every day is a journey, but I’m exactly where I feel I should be.  

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How do you measure success in your career?

Alignment with my purpose is what matters most to me right now. That means I’m successful when I do what I feel like I’m meant to do, while sustaining my family with my husband. To me, a project like HERstory in Black embodies the type of success that makes me most proud. I created this digital photo series of 150 accomplished black women through How She Hustles, then successfully pitched it to CBC, where I used to work.

The whole project was all about shining the light of black women making a difference in our city right here, right now; in the corporate world and in the community. It was about giving black women a platform to be recognized, celebrated and supported, and building bridges to other women who can rally around them so we all benefit and have new role models. It was an example of success because I feel like it had a positive impact on the national narrative around black women in Canada. It shifted the way our national broadcaster told stories about my community – and involved a very collaborative, innovative process between the corporation and my community. It made young women see new possibilities, it made older women understand the value of their trailblazing work, and it made black women from my generation understand the critical role we play in bridging the past and the future. More broadly, when women of all backgrounds tell me they feel more connected and inspired by my work through HERstory in Black or How She Hustles, that’s a great indicator of success.

Was there ever a moment that you questioned your decision to become an entrepreneur? How did you overcome it?

No questioning so far. While everything is far from perfect, my decision has been marked with positive signs every step of the way. For example? When I transitioned out of my former full-time job, my very last day of work was on a Friday.  By Monday morning, I was literally walking into Parliament Hill to meet with the Prime Minister’s Chief of Staff, who is known as the most powerful woman in Canadian politics. We met to talk about my journey as the founder of How She Hustles and the incredible women from HERstory in Black who are making their own mark in the world. If that isn’t affirmation that I needed to step into my purpose, I’m not sure what is. Imagine if I didn’t leave my job to pave way for that Monday meeting and everything that just keeps on coming?

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

There are many women who inspire me. But today, I’d say Aisha Addo from DriveHER – the ridesharing app by and for women. What inspires me most about Aisha is her quiet resolve – even in the brutal nay-sayers, unforeseen setbacks and odds that may appear stacked against her. And yet, I have complete faith that her story with DriveHER is far from over. Can’t wait to see where the journey takes her next. So many women who have spoken at How She Hustles events inspire me, too. For example, take a look at the line-up of wise women speaking at Startup & Slay, my October event for diverse female entrepreneurs. Wow. Walking inspiration.

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

Not sure I see it as a mistake but certainly a life – and business – lesson:

I underestimated myself. I thought it would take much longer for me to get traction – as a speaker, as a consultant, and with How She Hustles. I had undervalued the experience I had built up over the years. So when I left my full-time job there was a bigger avalanche of work, and a greater demand, than I had anticipated. Now, I’m doing my best to really get myself 100% set-up for success – to put all the supports in place to keep up with the pace of what’s to come. And to really capitalize on this momentum. I’m certainly not complaining – not a bad problem to have at all! I’m grateful and just need to work smart while life feels like it’s flying and I’m learning more every day.

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

Transitioning my How She Hustles network into a full-scale business is like having a huge canvas and the power to create a brilliant masterpiece. But that means I must have a vision. I can’t just throw around colourful paint around brushes. I have to figure out what should go on the canvas to create what I want to see - and what the market wants. Once I have a clear vision, I’m on it. And thankfully, I have an incredible community of supporters and mentors who are helping me figure it out – then go full steam ahead.

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

In my gut, I want to say … nothing. I feel like everything that is happening right now is meant. Even my uncertain steps and moments of stretch are important lessons. So my best answer would be, I wish I knew that embracing the uncertainty in every way is actually one of the best things that will help me grow.  As things evolve, I’m learning to be more decisive, when to seek wisdom from others, when to hear my own voice and how to become more strategic as I hustle.


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