Redefining Success at Every Stage

Achievements and happiness not a one-size-fits-all concept.

What motivates Canadian business founders today

According to research and our collective sense of loss shared on social media, we all struggle to find happiness and to feel like we are doing well. The hardest part? Personal definitions change as we pass through different ages and stages of life.

The boomer generation had shared values, making success or happiness definitions a lot more consistent for them. They don’t understand why younger generations see the world so differently. Content is so tailored to individual algorithms deciding what we see, hear or learn there are fewer opportunities to share ideas or develop relationships. No one argues how social media is a negative influence on how we perceive our own happiness and success.

So how do we measure those terms when the measuring stick is less a stick and more like a ball of yarn? How do we set goals or decide if we are doing well? If you had to write down three things that you are most proud of in your life, what would they be?

Do you see yourself as an outlier or simply from another time?

Simon Larocque discovered entrepreneurship at UVic and now defines success as “working on stuff I’m passionate about and grateful for all opportunities I’ve been given.” For a lot of Gen Z entrepreneurs like him, one of the biggest hurdles in figuring out what success and happiness really mean is the constant noise of social media “pushing everyone to measure themselves against others. I realized real progress comes from tracking my own growth and goals, not comparisons.”

According to Larocque, his friend shared this timely quote often attributed to Ernest Hemingway, but based on the Stoic beliefs of the Roman philosopher Seneca: “There’s nothing noble in being superior to your fellow man; true nobility is being superior to your former self.”

By sharing relationship-building events LampPost does double duty, meeting societal need and providing Larocque with a personal sense of purposeIn 2024, Larocque launched LampPost Victoria to address a need in the community for young people impacted by COVID isolation, those who had lost real-time social networks. Like Larocque when he started university, they were lonely, searching for friendships, but not knowing where to start. By sharing relationship-building events LampPost does double duty, meeting societal need and providing Larocque with a personal sense of purpose. Ultimately, he knows his definition of happiness and success will change along the way and that’s OK. No linear paths for this entrepreneur.

Is success an end goal or a constantly evolving reflection of values? Self-described zillennial (born on the cusp) Monique Sekhon always knew she wanted to be of service. Growing up in an extended immigrant family and encouraged to dream big, Sekhon never doubted she would become a positive force. Today as a trusted consultant, she makes the world better by improving health policies. She credits a funny source of inspiration for her core values in the “Anything is Possible” Barbie TV ad. As a youngster, Sekhon made that doll her mission. Persistence paid off and with Barbie recruited, Sekhon’s dreams took shape. She traces her sense of purpose to that “can-do” message. “I believed anything was possible,” she says. “I think that doll was my spirit animal!” Sekhon is curating her life and that freedom is key to feeling successful. “I grew up in a time of youth empowerment, how to make an impact and serve the community, so flexibility helps create that life,” she says.

personal definitions of success
Sources: Psychology Today, Survey Centre on American Life, Purdue Global

For millennial Jillian Climie, co-founder of The Thoughtful Co., “happiness is you, talking about what you do.” Her career began on Bay Street with a high-profile consulting firm in charge of corporate executive compensation. “I looked for what people wanted. In the beginning negotiating was mostly money. Salary, bonus, equity, but also titles and status,” she recalls. Climie explains her decision to relocate to Vancouver after three years: “My role seemed glamorous, but working 24/7 was taking a toll.” She made the move to Vancouver looking for her own version of success, seeking the laid-back West Coast lifestyle. At just 29 she landed at Lululemon as the senior manager of compensation and embarked on a demanding and all-consuming role. “I realized I put everything into my job and during COVID started asking myself whether I was making a positive impact on the world,” she says. “I didn’t feel good. I was missing real relationships.”

Leaving Lululemon was a tough decision, but Climie’s company now guides women and companies toward equitable compensation, so profit now aligns with purpose. She needed flexibility and control over her time, another millennial checkbox. “I mean I still work late or on weekends, but it’s my decision,” she says. “As an entrepreneur I’m so much happier. I have control over my own time.”

Recruiters and compensation professionals realize finding the right hire is not a one-size-fits-all game. A position was once defined by compensation, but now they need to consider who you want. Leaders create a stronger and more diverse workforce when they understand and act on what doing well really means.


Robyn Quinn is an award-winning storyteller. A public relations entrepreneur and small business owner of Big Bang Communications, she is happiest when her clients shine in the spotlight.