Retirement Is Happening Everywhere

If you’ve ever read Carrick on Money, you’ll know that Rob Carrick has been a steady, trusted voice in Canadian personal finance journalism for over two decades. His columns were known for being clear, candid, and deeply reader-focused, demystifying everything from RRSPs to real estate to retirement itself.

Earlier this month, Carrick announced that he’s stepping away from the Globe and Mail after 26 years. For many readers, it marked the end of an era.

But his retirement is more than just a personal milestone. It’s part of a much broader pattern we’re seeing unfold across Canada:

Retirement is happening everywhere, in every industry, at every level.

From newsroom editors to electricians, small business owners to senior public servants, the country is in the midst of a massive generational shift. Baby boomers, the largest cohort in Canada’s workforce for decades, are transitioning out of their careers, often taking deep experience, leadership, and institutional knowledge with them.

It’s a moment that deserves not just recognition, but careful planning.

The numbers tell the story: every day, thousands of Canadians retire. According to Statistics Canada, nearly 1 in 4 Canadians will be over 65 by 2030, and that shift is well underway. The pandemic accelerated many people’s decisions to retire earlier than expected, while others are opting for phased retirements, sabbaticals, or second-act careers.

This trend is not isolated to any one region or profession. We see it in:

• Healthcare, where experienced nurses, physicians, and administrators are leaving a stretched system.
• Trades, where skilled workers are retiring faster than new apprentices are being trained.
• Family-owned businesses, where generational succession is often complex and emotionally charged.
• Corporate leadership, where senior executives are stepping down, sometimes without a clear plan for what (or who) comes next.

And, yes, even in media, where trusted voices like Carrick’s are passing the torch to a new generation of journalists.

Why Succession Planning Matters

Retirement doesn’t just impact the individual, it reshapes teams, families, organizations, and entire industries. That’s why succession planning is more important than ever.

For business owners, succession planning is about more than who takes over the job or the ownership. It’s about:

• Ensuring continuity of service or product quality
• Transferring knowledge and relationships
• Structuring the financial side of a transition to minimize tax and maximize value
• Preserving legacy while allowing for evolution

We often work with family businesses where retirement planning and succession planning are intertwined. It’s not just “When can I retire?” It’s “How do I make sure what I’ve built continues to thrive without me?”

Even for those in non-leadership roles, it’s worth thinking about who you’re mentoring, what you’re passing on, and what conversations might make your exit smoother for everyone involved. Thoughtful leaders need to bring this into regular conversations, knowing that it’s the whole team that is going through this transition, and plans need to be in place for everyone.

Carrick’s retirement is a great example of how this can be done thoughtfully. He used his final months not just to wind down, but to reflect, distill lessons, and prepare his readers for the road ahead. That’s succession planning in spirit, leaving things better for those who follow.

What We’re Seeing in Our Work

In our financial planning practice, this retirement wave is very real. Clients considering their next stage are asking these questions:

• “What does my cash flow look like if I retire next year?”
• “Can I afford to travel? Provide gifts to my children? Volunteer?”
• “How do I transition the business without giving away too much value or control too early?”
• “How do I know I’m emotionally ready?” (Well… they’re not asking this one as much. We’re asking, though!)

We’re also seeing people stay engaged after retirement, consulting, mentoring, starting foundations, or investing in community. Retirement today isn’t necessarily a hard stop. It’s a transition that can, and should be planned with intention.

On the business side, we’re helping founders and professionals:

• Clarify their personal financial readiness
• Evaluate succession options (family, employees, third-party sale)
• Set timelines and roles
• Coordinate with lawyers and accountants to build a tax-smart exit

The best transitions don’t happen overnight. They’re the result of years of preparation, open conversations, and structured planning.

What Comes Next

Rob Carrick’s retirement is a poignant reminder that even the most established voices eventually take a bow. What matters is how you prepare for that moment, and what you leave behind.

If you’re nearing retirement yourself or navigating what it means for your family or business, know that you’re not alone. This is a shared national moment. And with the right planning, it can be one of the most fulfilling chapters of your life.

Whether you’re five years away from retirement, already easing into it, or facing decisions about succession in your business, we can help you plan with confidence and clarity. Reach out to book a conversation with us, and let’s start mapping out what a thoughtful transition looks like for you.

Retirement isn’t just an ending. It’s the beginning of something new. Let’s make it really, really great.

Your Spring Planning Team

Practice Notes:

Julia will be on holiday starting July 25 and returning on August 12. We’re trying to spend Friday afternoons not working throughout the summer – cross your fingers for us! 

We hope you’re taking lots of time off and enjoying yourself!

Spring in the News:

Please check out our media page here for videos, podcasts, interviews and more.

Planning News Digest:

• Estate planning is one of the most loving things – Julia spoke with The Canadian Press on the basics of estate planning and how it isn’t about you, it’s about the people that you leave behind. Check out the full article here.
• The hidden risks of thinking through decisions –  Julia and our good friend Brooke Struck co-wrote an article on getting stuck in decision-making limbo and the hidden risks of playing it safe. Find out more here.
• Rob Carrick of the Globe & Mail bids farewell – Find out Rob’s eight lessons learned in 27 years of covering personal finance and investing in his farewell article here.

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