'Wealth doesn't erase your problems—it magnifies them': One serial entrepreneur's brutally honest take on making it

For most entrepreneurs, achieving financial success represents the culmination of years of hard work, risk-taking, and sacrifice. Yet for Emily Lyons, founder and CEO of multiple multimillion-dollar companies, the moment of "making it" brought unexpected psychological challenges rather than the relief she had anticipated.

"The first time I made real money, I cried in a parking lot," Emily Lyons shared in a candid LinkedIn post in October. "Not because I was happy. Because I was terrified I'd lose it."

This visceral reaction stemmed from Lyons' childhood experiences with financial instability. Growing up, she witnessed her parents' struggles with money, including eviction and having to count coins for subway fare. These formative experiences created deep-seated anxieties that persisted long after her financial circumstances improved.

"That kind of stress doesn't leave your body," Lyons reflected. "It just waits."

Building an Empire from $80

Lyons' journey to entrepreneurial success began in 2009 when she founded Femme Fatale Media Group at age 23 with just $80, a damaged laptop, and an ambitious vision to transform the event staffing industry. Operating from her Toronto headquarters, the company has evolved into a leading North American event-staffing and marketing agency with a network exceeding 20,000 event professionals.

The company now serves an impressive roster of Fortune 500 clients, including L'Oréal, Red Bull, Sony, and Grey Goose. Lyons' achievements were recognized when she received the Entrepreneur of the Year award at the CanadianSME Small Business Awards.

"I didn't have investors or a safety net," Lyons explained in a statement. "I had a dream, and I was stubborn enough to keep going."

Her entrepreneurial portfolio extends beyond Femme Fatale. Lyons Elite, her luxury matchmaking service, earned recognition as Canada's best matchmaking service for three consecutive years according to the Consumer Choice Awards. She also launched True Glue, a clean fake-lashes beauty brand in 2014, and established the Julia Lyons Foundation, a charity supporting individuals with cystic fibrosis, created in honor of her sister Julia, who passed away from the disease.

The Paradox of Success

Despite achieving remarkable financial success, Lyons experienced an unexpected psychological phenomenon. When her business flourished and her bank account showed "commas instead of panic," she discovered that prosperity didn't eliminate her underlying fears.

"Money didn't fix the fear," she wrote. "It just exposed it."

This realization led her to embrace the wisdom in the adage "more money, more problems," but with a crucial distinction: "wealth doesn't erase your problems. It magnifies them."

The anxiety accompanying her success became a catalyst for personal growth. Lyons had to reframe her relationship with wealth, learning to accept that "earning it wasn't a fluke" and that she "deserved to keep" what she had worked to achieve. Most importantly, she came to understand that "success wasn't something that would be taken away the second I stopped looking."

Understanding Imposter Syndrome in Entrepreneurship

Lyons' experience exemplifies imposter syndrome, a well-documented psychological phenomenon characterized by persistent self-doubt and feelings of fraudulence despite clear evidence of competence and achievement. Her honest reflection captures this internal struggle: "Turns out you can have everything you ever wanted and still not feel like enough. That's the part they don't put in the success stories."

Recent research from Cambridge International City Montessori School, Lucknow, published in January 2025, demonstrates that women entrepreneurs are particularly susceptible to imposter syndrome during the transition from traditional employment to business ownership. The study identifies cognitive restructuring, mentorship, networking, and social support as effective strategies for managing these challenges.

Lyons joins a growing number of successful female entrepreneurs who have openly discussed their experiences with imposter syndrome. Katrina Lake, founder of Stitch Fix, attributed her feelings of inadequacy to the absence of female role models during her formative years, despite leading her company to a $120 million IPO in 2017. Business writer and researcher Ali Kriegsman advocates for viewing imposter syndrome not as an individual weakness to overcome alone, but as a challenge that can be addressed through available resources and support systems.

The Path to Healing

Through her journey, Lyons arrived at a profound insight about the relationship between success and personal growth. Rather than viewing wealth as a cure for psychological wounds, she learned to see it as a tool for healing.

"Success doesn't heal you," she concluded. "It just gives you the resources to finally start."

This perspective reframes entrepreneurial success not as an endpoint, but as the beginning of a new phase of personal development—one where financial resources can support the deeper work of addressing underlying fears and building genuine self-confidence.