As someone who made this transition at age 40, I can speak first-hand to how purposeful and deliberate this decision needs to be.
I didn’t make the change because I disliked my job or because anything about my industry pushed me away. In fact, I loved what I did. I made the change because I wanted greater control over my schedule and how I spent my time. Then, and still today, I believed life is a journey, and I wanted the opportunity to experience more of what it had to offer.
By most measures, I had what many would call a stellar career. I reached the C-suite in my early 20s, enjoyed company cars, premium benefits, private access to major sporting events, a golf club membership, and a salary that placed me among Canada’s top income earners. I supported my family, lived debt-free, and worked in a demanding but meaningful role.
Walking away from that was not impulsive. It was considered—and it required an honest assessment of several key factors.
Family
This decision was as much about my family as it was about me. Becoming an entrepreneur changes everyone’s life, not just your own.
The challenge that comes with taking on debt, the loss of a predictable paycheque and benefits, and the reality of funding everything yourself—from vehicles to technology—requires a shift in how a family thinks about money and security. The hours are longer, the early years are demanding, and the traditional “9 to 5” disappears quickly.
Fortunately, my family was incredibly supportive and remains so to this day. In many ways, they became entrepreneurs themselves, working in our family businesses through school, university, and beyond. That shared journey made all the difference.
Financial Readiness
Leaving employment almost always means stepping away from financial certainty and taking on some level of risk. In many cases, it also means assuming debt.
You are betting on yourself—and that’s not something to gloss over. Financial fear is the primary reason more than 70% of Canadians say they want to be self-employed, yet only about 10% are. Preparation doesn’t eliminate risk, but it dramatically reduces unnecessary stress.
For many first-time entrepreneurs, franchising offers a structured entry point, reducing risk while still delivering ownership and autonomy. The right system can provide guidance, proven processes, and support while still allowing you to build something of your own.
Workload and expectations
Hard work has always been part of any meaningful career, and entrepreneurship is no different. The difference is ownership.
In the early stages, work is intense. Over time, as you develop systems and teams grow, independence and flexibility increase. It follows a bell curve. Your work, family, social, and personal interests often blend—and when done intentionally, that’s not a bad thing. It’s simply a different way of living and working.
Reducing unhealthy stress
Every job involves stress. Some of it is healthy and motivating. Some of it is not.
In many traditional work environments, unhealthy stress often comes from:
- Office politics
- Poor leadership or misalignment
- A lack of control over how and where you spend your time
Most people can recall moments when work demanded something unreasonable—missing family milestones, personal commitments, or moments that matter.
Entrepreneurship doesn’t eliminate stress, but it does eliminate much of this unhealthy kind. The trade-off is accountability. As an owner, it becomes your responsibility to build a business that doesn’t recreate the same pressures for your team.
Physical and mental readiness
Owning a business requires resilience. You don’t need to be young, perfect, or invincible—but you do need the capacity to handle uncertainty, responsibility, and sustained effort.
Strong physical and mental health make the journey more enjoyable and sustainable. Entrepreneurship is deeply rewarding, but it demands presence, energy, and perspective.
Preparing for the transition
Before making the leap, ask yourself:
- Are you financially prepared to live on less, at least initially?
- Does your family understand and support the transition?
- Do you have the mindset to move from specialist to problem-solver?
- Are you comfortable being a continuous learner?
- Are you ready to take control and responsibility for how you live and work?
Entrepreneurship is an incredible journey. It becomes even more rewarding when entered with intention, clarity, and preparation.
