I have never lived a year in which I wasn’t working on multiple things at once.

Not because I couldn’t focus, not because I was unsure of my path, but because I have always understood that the world moves too fast to rely on a single plan. For the past 20+ years, no matter what my primary role was, I was always nurturing side projects, developing new skills, and engaging with ideas beyond my day-to-day work. Even now, in what I consider the best role I could have imagined – my work with the Ottawa Community Foundation – I continue to give my energy and attention to the things that are close to my heart: leadership development, strategic consulting, web development, technology integration, coaching and mentoring, educational initiatives, and now, real estate. None of these are distractions. They are the threads of a larger story, one that is constantly evolving, one that ensures I am always growing, always engaged, and never at the mercy of a single path.

This is not just personal preference; it’s conscious strategy.

The idea that a single job, project, or plan will carry us safely into the future is one of the most dangerous assumptions we can make. Businesses that thrive in uncertainty don’t rely on one big play – they structure their bets across multiple time horizons. McKinsey’s Portfolio of Initiatives framework is built on this principle: that organizations need a mix of short-term wins, medium-term growth, and long-term moonshots. But, in my opinion, this isn’t just a corporate strategy – it’s the smartest way to manage a career and a life. If businesses can’t afford to put all their eggs in one basket, why should we?

I feel that most people approach their careers reactively.

They focus on their current job, their next promotion, or, at max, a single side project. They assume that if they work hard and stay the course, the right opportunities will present themselves. The problem? If you’re always waiting, you’re always behind. Industries shift. Job markets change. Even our own interests evolve. The people who stay ahead aren’t the ones who wait for change; they’re the ones who prepare for it. And the best way to stay adaptable isn’t to hedge your bets – it’s to structure them. A Personal Portfolio of Initiatives ensures that while you’re delivering results today, you’re also building what comes next.

For me, this has never been about chasing distractions – it’s been about being intentional with my energy. Over the years, I’ve learned that not every initiative needs to be a massive leap. Some are small, familiar, and low risk: learning a new tool, refining a workflow, mentoring someone. These keep me sharp and valuable in the work I’m already doing. Others are slightly riskier – stretch projects that expand my skill set and credibility, like speaking engagements, consulting work, or new collaborations. And then there are the big bets: the ones that may not pay off immediately (or at all) but have the potential to redefine my future – like my continuing work in youth leadership development. These are the initiatives that open new doors, create unexpected opportunities, and keep me from becoming stagnant.

The difference between corporate and personal strategy is speed. Businesses plan in five-year cycles, but individuals move faster. In my world, short-term plays are the things I can start seeing returns on in months. Medium-term bets unfold over a couple of years, shaping my trajectory in tangible ways. And the long-term ones, the moonshots, are the things that may take years to fully come together, but could be game-changers. Without this structure, it’s easy to get stuck. People often focus so much on the present that they neglect the future – or they dream of the future without building the steps to get there.

I believe that a portfolio approach forces balance.

What I’ve come to understand is that a well-structured portfolio isn’t chaotic – it’s intentional. It allows me to take calculated risks while maintaining stability. It ensures that if one door for something I love or enjoy closes, another is already halfway open. It creates a rhythm between growth and security, between what pays the bills today and what will create the future I actually want. Too many people wait until they need a new opportunity to start thinking about it. They wait until their job is no longer fulfilling, until an industry shift forces a reinvention, until burnout makes them question everything. But the best time to build your next thing isn’t when you need it – it’s when you don’t.

A company that only focuses on today’s revenue eventually finds itself irrelevant. Likewise, a person who only focuses on today’s work eventually finds themselves unprepared. The businesses that thrive, and the professionals who stay ahead, understand the same truth: sustainable success isn’t about betting on one thing. It’s about running multiple plays – thoughtfully, strategically, and always with an eye on what comes next. Because the best investors don’t put all their money in one stock. The best businesses don’t rely on a single product. And, similarly, the best professionals don’t gamble their entire future on a single play.

So, if I can ask, what’s in your personal portfolio?