The Hero's Journey - 425 Magazine Women to Watch interview with Lindsay Angelo

Women to Watch - Lindsay Angelo

By: Shelby Moyer, 425 Magazine

Lindsay Angelo found herself in a dream career with Lululemon, but it wasn’t until she struck out on her own that she began to see the world in technicolor.

That iconic scene in The Matrix where Neo has to decide between taking the blue pill — and staying in the fictional world — or the red pill — and journeying into the real world — is a classic story arch for The Hero’s Journey. 

The Hero’s Journey is a storyline used by a plethora of filmmakers in which the protagonist answers a call from the universe and leaves the ordinary world to go on a journey to a new world. They face setbacks, and there’s usually some intense battle (maybe with a fire-breathing dragon) but, in the end, they come out victorious with lessons they use to make the ordinary world a better place. 

It may sound a little dramatic, but The Hero’s Journey is exactly how it feels to branch out as an entrepreneur and start your own business, said Lindsay Angelo, a growth strategist and public speaker who launched her own consulting company after leaving Lululemon. 

“There’s this scene from the Wizard of Oz where the house is flying, and the picture is in black and white, and then the house crashes down, and Dorothy opens the door, and she enters this new world of technicolor,” Angelo said. “I make that analogy because that’s been the world of entrepreneurship for me. It’s allowed me to (see) this new and beautiful world of technicolor.”

Angelo started getting glimpses of this when she was 14 years old in Vancouver, British Columbia. One day her aunt brought over microwave mitts, and Angelo thought, “I could make those.” With help from her business-minded mom, Angelo started churning out microwave mitts, and the two shopped them around to local stores and sold them to friends. Then, as the year 2000 approached, she bought rolls of silky fabric with “2000” printed in glittery script and started making millennium scarves. 

“I remember being totally enthralled by entrepreneurship,” Angelo said. “It just completely lit me up, and it was at that point that I realized I love being an entrepreneur.”

After graduating from George Mason University in Virginia, she got a job working for an angel investing firm, assessing start-ups, and helping start-ups refine their business concepts and ready themselves to pitch to investors. From there, she onboarded with a financial tech start-up and helped grow the company over two years before leaving to get her MBA. 

Looking back, Angelo realized that her sweet spot was working with small, scrappy companies, but after getting her MBA at Simon Fraser University in British Columbia, she went on to work as a strategist for BC Hydro, one of the largest energy suppliers in Canada, and eventually landed a place on the strategy team at Lululemon. 

When she started at Lululemon in 2012, e-commerce was just starting to pick up steam, and the company was doing $1 billion in annual revenue.  Her team focused on growing the company overall — from geographies to product concepts — and as a strategist, she was essentially helping draw the blueprints for the future of Lululemon. 

“Part of strategy is deciding where to place your bets on the different ways you can grow the company and why that makes sense based on the context you’re operating within and the environment you’re operating within,” she said. 

On paper, being a strategist at Lululemon is a dream job for an MBA graduate, but Angelo started to feel that entrepreneurial itch again and she wanted to explore her career options outside of the typical 9-to-5 corporate path. 

It took six months for Angelo to really build up the courage to break out on her own, but by the time she left Lululemon in 2017, she had been doing some public speaking on the future of consumerism and strategy, and she was seeing demand for speakers offering insight. Plus, several professionals from her network were leaving their own corporate nests, so she decided to dive into this brave new world along with them. However, Angelo said, that doesn’t mean it wasn’t a little terrifying. 

“I think I’d lived a life of achievement up to that point,” she said. “My dad has achieved so much in his life, and I’d lived a life as an achiever in a lot of different ways. So, the fear of not achieving, for me, was really big.”

In the scheme of The Hero’s Journey, Angelo was answering her call. She was venturing away from the safety of the world she knew and was entering into undiscovered territory. The first year was a hustle, and she spent most of that time reconnecting with people in her network. Lululemon rehired her right away to do some strategy work and she started building up a client base. Currently, about 60 percent of her business is centered around advising — helping companies from start-ups to major corporations with innovation, growth, and story-telling. The other 40 percent of her time is spent in the speaking realm, sharing insights at business conferences. 

“I’ve learned a lot about myself. Entrepreneurship tests you in ways that nothing else does,” she said. “Everyone’s purpose is different, but you have to find what makes you see the world in technicolor. In the Wizard of Oz, there’s still trials and tribulations and there’s the wicked witch. There’s still really hard stuff you come across — similar to being in the black-and-white world — but your lens has shifted.”

She added: “I think we’re all creators at heart, and I needed the freedom to create new things. I think a big part of my purpose is to bring new concepts and ventures to the world that leave it a little better than it was before. … I didn’t always have the space to do that. In the corporate world, your brain is packed with other things.”

Angelo likens finding that perfect-fit career to finding your inner lion heart. When Angelo was a little kid, she had what she calls her lion heart sweatshirt. It wasn’t actually a lion. In fact, it was a bear sliding down a rainbow. But anytime she wore it, she felt the most like herself. And that what this career shift has been: rediscovering her inner lion heart. 

“Having experienced that shift from black and white to this,” she pauses. “At this point in my career, I wouldn’t go back.”

So here’s our charge for you: Reflect on your career. Does it light you up? Are you seeing the world in technicolor? If not, it might be time to take the leap. Choose the red pill. It’ll change your world.