Across North America, elite universities are quietly reshaping how we think about midlife and retirement, not through research papers or policy, but by launching immersive programs for leaders in transition.

These are not degree-granting programs. They are life-design experiences helping accomplished professionals explore what’s next through a mix of structured reflection, peer learning, purpose-driven projects and community.

They’re gaining traction fast. In fact, there are now more than 20 midlife transition programs offered globally from Harvard and Cambridge, to Notre Dame and the University of Colorado Denver. The trend started at elite institutions, but it is expanding into a broader range of universities and colleges, proving that the need for purposeful transition support is widespread.

These programs offer something the financial services industry urgently needs: a broader view of retirement planning. Advisors who want to stay relevant in the era of 100-year lives should pay attention.

For decades, the dominant questions in financial planning have been when the client can retire, and how much they will need to get there — important, but incomplete.

Today’s clients are navigating more than a financial shift. They recognize that they’re stepping into unfamiliar territory, leaving behind roles that once defined them. And they still feel the pull toward continued purpose, contribution and growth. They’re not looking to stop. They’re looking to reset and reimagine.

That’s exactly where these programs begin.

A growing movement

I served on the advisory board of Yale’s Experienced Leaders Initiative. It’s a six-month hybrid program designed to help individuals in their 50s and 60s step confidently into their next chapter. These are people who’ve had successful careers but still have more to offer.

The structure is thoughtful: two immersive in-person retreats, live virtual sessions, curated peer groups and a capstone impact project. The goal is to help participants move from aspiration to action with clarity, confidence and community.

At Stanford’s Distinguished Careers Institute (DCI), a pioneering program now in its 10th year, participants explore three pillars: renewing purpose, building community and recalibrating health and wellness. The DCI model blends academic learning with reflective practice, offering tools like memoir writing, purpose pathways and life-design workshops.

University of Chicago’s Leadership and Society Initiative offers the Imagine Pathway, a retreat-based experience designed for leaders who are still working but want to begin reflecting on what’s next. With quarterly in-person gatherings, coaching and peer learning groups, participants create a “Next Chapter Compass” to guide their future.

Stephen Blewitt, the former chief investment officer and head of private markets at Manulife Investment Management is quoted on the University of Chicago’s website promoting the program: “It’s an opportunity to look at my life and be very introspective — about myself, what my values are and what I really want to do with the next 20 years,” he wrote.

These programs offer unique approaches, but shared goals: to support reinvention, foster intergenerational community and treat this life stage not as a wind-down, but a time for continued contribution.

Value for advisors

These programs signal what growth-minded, curious clients are craving: structure, exploration, meaning and peer connection.

They attract c-suite executives, board members, physicians and entrepreneurs — the same client groups advisors seek to serve. There’s an opportunity for advisors to apply the best practices these programs have developed to better serve their clients.

Three suggestions:

1. Create community: What if advisory firms offered their own reinvention workshops or life-design retreats for clients entering this stage?
2. Expand the conversation: What if financial planning included next-chapter visioning sessions, where spouses reflect on shared purpose, not just shared accounts?
3. Design for reinvention: Help clients build flexible financial plans that support experimentation, career pivots or impact projects, not just retirement withdrawals.

Advisors don’t need to be life coaches, but they can be catalysts. And they can help build the scaffolding that so many clients in transition are looking for.

Universities around the world are building what the financial industry still lacks: a structured path for people transitioning from success to significance. These programs remind us that retirement is no longer a finish line; it’s a new beginning.

Financial planning will always require rigour, modelling and sound advice. But to truly serve clients in the era of longer lives, we need to expand the playbook. We need to move from technical planning to holistic guidance, integrating purpose, health, identity and community into the conversation.

Over the past year, I’ve worked with board members and senior leaders from Canada’s largest pension funds, including OMERS, Alberta’s public sector plans and a major Ontario university. Each asked me to address the same pressing question: What does retirement look like when people live past their 90^th birthday, and no longer follow the old path of learn, work, retire?

A quiet but significant shift is underway. Pension funds are beginning to reframe retirement not as a financial endpoint, but a personal transition that calls for new types of guidance, flexibility and purpose. It’s time for financial advisors and institutions to take notice.

At a recent gathering of four of Alberta’s largest public pension funds, we utilized the Stanford Center on Longevity’s New Map of Life. It reframes longevity as a design challenge. Rather than seeing it as a burden, we treated it as an opportunity to rethink how retirement is structured.

The session surfaced three questions:

• How do we support midlife transitions, not just exits from the workforce?
• What new role models are needed for retiring well in 2025 and beyond?
• Can we move beyond one-size-fits-all solutions to create phased, personalized pathways?

Across Canada, pension leaders are taking action. They’re piloting new programs, redesigning communications and aligning strategies with the reality of longer, more dynamic life journeys.

There’s plenty of demand. One Ontario university recently launched a retirement pilot focused on health, identity and life transitions. A webinar drew nearly 250 participants. And a pair of follow-up holistic retirement planning workshops were overbooked quickly.

Although still in its early stages, the pilot demonstrates that there is a strong demand for holistic, relational retirement support that extends far beyond investment products and financial calculators.

OMERS: A scalable model for the future

While some institutions are still in the pilot phase, OMERS is actively scaling retirement innovation. With over 644,000 members, it is one of Canada’s largest defined benefit pension plans, serving municipal and broader public sector employees. It has embedded longevity into its member experience, making it a blueprint for transformation.

It has implemented several forward-looking initiatives:

• Its Retire Ready Impact Report found that while 79% of Ontarians are thinking about retirement, only 40% have a plan. Confidence is especially low among women. The report identifies four key pillars of readiness: financial, physical, mental and social.
• The Retirement Income Sources Hub is a digital tool that helps members navigate CPP and OAS decisions, and understand the value of guaranteed income. It’s a timely response to one of the biggest concerns among Canadians: outliving their savings.
• Preparing for Your 100-Year Life workshops introduced members to insights on longevity and explored the non-financial aspects of retirement, including identity, purpose and overall well-being. They also provided practical planning tools to help members navigate this life stage.
• OMERS’ Pension Blueprint Podcast dedicated its second season to exploring longevity, holistic planning and the evolving nature of retirement in today’s multi-stage life.
• Next Steps in the Evolution is a holistic retirement planning hub and immersive series of sessions designed with members to support life transitions that expand on pension education.

OMERS is continuing to pilot so it can reimagine retirement at scale, backed by research, leadership support and a strong member mandate.

The advisor opportunity

Advisors who find ways to engage on longevity and the evolution of retirement stand to gain a competitive advantage. The pension funds I’m working with represent the leading edge of a shift in thinking that resonates with a lot of Canadians.

This is a conversation they want to have with the financial services professionals they work with. The dialogue revolves around three themes

1. Longevity is strategic. It’s not just about how long clients live. It’s about how they live, work and evolve over decades of post-career life.
2. Retirement is a transition, not a destination. Clients need help designing this next chapter, not simply withdrawing from work.
3. Holistic planning is the next frontier. Purpose, identity and social connection are joining financial readiness as core retirement concerns. Advisors who meet these needs will deepen relationships and trust.

From emerging pilots in higher education to OMERS’ bold system-wide redesign, it’s clear that the future of retirement is relational, flexible and designed for longer lives.

Financial advisors who recognize this and approach it with curiosity, empathy and strategy will help shape the future of retirement, rather than just react to it.

After 36 years in banking, Mike Drak thought he was ready for retirement. He had a solid pension, a strong investment portfolio and decades of experience helping others plan for their financial future.

He had everything — except a plan for what came next.

“I thought retirement would be easy,” Drak told me. “But it wasn’t. I was in a dark place. I lost my identity. I had the money, but I didn’t have a plan for life after the office.”

This isn’t a story about poor planning. It’s about how you can do everything right financially, and still not be ready for retirement.

The victory lap

I first discovered Mike’s work in 2016 when I picked up a copy of his book, Victory Lap Retirement: Work While You Play, Play While You Work. I was wrestling with my own questions about what would come next after a high-pace career. Drak’s book challenged the idea that retirement was the end goal and introduced the concept of the victory lap: a phase of life in which you mix purpose, play and work on your own terms.

I reached out, and in the years since we’ve become good friends. We’ve shared ideas, supported each other’s work and even done a little fishing together.

Drak and I chatted earlier this month about his victory lap, and the importance of a holistic retirement plan.

“The system taught me how to save,” he told me. “But no one taught me how to live after work.”

Despite decades working in financial services, Drak was unprepared for the emotional reality of retirement. He went through what he calls “retirement hell,” a painful period of identity loss, disconnection and uncertainty. He realized that while the industry focuses heavily on building wealth, it leaves clients unprepared for what happens once the paycheques stop.

“I had enough money,” he said. “But I didn’t have a life plan. That part I had to figure out myself.”

Drak didn’t stay in the dark for long. In addition to Victory Lap Retirement, he published Retirement Heaven or Hell: Which Will You Choose? and Longevity Lifestyle by Design: Redefining What Retirement Can Be. Both are available for free at Booming Encore.

He began mentoring others, leading workshops and helping retirees build what he calls a “second life,” defined by purpose and possibility.

Advice for advisors

“Clients need more than a drawdown strategy,” Drak told me. “They need a blueprint for meaning.” He offered three recommendations for financial advisors:

1. Talk about life, not just money. Clients are rarely asked what they want life to feel like after work ends. Don’t stop at the retirement date or savings goal. Ask clients what their Tuesdays will look like. What makes them feel alive? How do they want to stay connected, creative and useful?
2. Prepare clients for the emotional shift. The first six to 12 months after leaving work can be disorienting and even depressing. Structure disappears. Social circles shrink. Identity fades. Clients may feel guilty bringing it up or have difficulty articulating their worries — especially if they’re on solid ground financially. Initiate the conversation. Tell them that the transition is difficult for a lot of people, and that retirement planning includes both a financial and emotional dimension.
3. Build your network of non-financial experts. You don’t have to do it all. Connect clients with retirement coaches, psychologists, health professionals and others who help people figure out what a victory lap looks like for them.

It’s not enough to prepare people financially, Drak told me. We must help them build a plan that includes identity, community, contribution and health. Advisors have a choice — keep selling plans for a retirement that no longer exists or help design second chapters that clients are excited about.

Drak is 70 now, focused on training for an oversized victory lap in the form of the Ironman triathlon in Ottawa this summer. In the decade since we met, he’s grown increasingly inspirational to me.

He doesn’t want to be seen as exceptional though. Drak’s retirement, in both its ups and downs, is a signal all of us should pay attention to. Retirement cannot be prepared for with products alone. Let’s ensure clients have the tools, advice and support necessary to thrive in a retirement that can last decades.

Most retirement conversations today centre on what’s next for Boomers and Gen X. How will we support them as they exit the workforce? How should we reshape products, portfolios and pension plans for them?

We also need to ask a more forward-looking question: What will retirement look like for today’s kids? And are we prepared to meet their needs?

A white paper published by Prudential Financial in January, Generation Beta: Redefining Life, Longevity, and Retirement, offers a glimpse into that future. It explores how children born between 2025 and 2039 — Gen Beta — may live, work and retire in radically different ways. It also reveals the cracks forming in today’s retirement systems.

This is not a future issue; it represents an existing strategic gap.

One of the report’s most striking insights is that 66% of respondents believe retirement will be fluid, meaning people will move in and out of it rather than treating it as a one-time event.

The traditional model — learn, save for 40 years, retire at 65 and draw from accumulated assets — was designed for a world of shorter lifespans and linear careers. It no longer aligns with today’s economic realities, workforce patterns or personal aspirations.

According to the report, 48% of parents believe their children may never fully retire. The perceived retirement target is US$1.88 million, but many doubt they will reach it. Four in five parents say saving for retirement should begin at birth.

These numbers reveal a growing awareness that our current systems aren’t designed for longer lives. They also highlight an urgent need for advisors to guide clients with a new approach to retirement planning.

Precautionary planning

An important behavioural shift is taking shape, especially among younger families. Parents are thinking differently about financial planning, for themselves and their children.

The most common financial regret among adults, according to the white paper, is not saving enough for retirement.

This signals the rise of what I call precautionary planning: a proactive, long-term approach to financial resilience shaped by economic uncertainty and new realities.

Add to that the declining trust in institutions, including financial services providers. People are turning to their peers, or taking planning into their own hands. They’re “doing their own research,” because the advice and direction delivered via conventional sources doesn’t reflect their real-world experience.

Advisors have an opportunity to help clients think more broadly about what they can plan for in the future — beyond just education and weddings. Those who do it well will build multigenerational relationships rooted in trust, longevity and foresight. They will provide guidance on more than just money.

The white paper describes a design exercise in which participants were asked to write postcards to their future grandchildren. The responses weren’t about wealth, assets or inheritance. They centred on values: curiosity, kindness and courage.

That makes sense. Living to 90 means that your kids are established financially when you pass. So, there’s less need to leave them an inheritance. Combine that with the expense of living that long, and you get a dramatically different kind of retirement income calculation.

For those with the means, retirement is less a financial milestone than it is a time for personal growth, reinvention and emotional legacy. More than half of respondents (55%) defined retirement as a time to spend what they’ve earned, not necessarily preserve wealth for heirs.

More than a financial plan

All of this challenges traditional models of accumulation and preservation. Today’s clients want more than a financial plan — they want to design a meaningful phase of life. Yet, most advisory models, products and communications haven’t caught up.

While 81% believe financial institutions have the power to reshape the retirement system, 57% say that current products are designed for a world that no longer exists.

Consumers are granting us both the permission and responsibility to lead. Successful firms will contribute to a more modern, flexible, purpose-driven retirement model.

Clients want solutions that are adaptable across life transitions (career breaks, caregiving, sabbaticals), personalized and holistic — integrating income, purpose, health and legacy.

This isn’t about abandoning traditional planning principles. It’s about expanding the playbook to reflect longer lives, nonlinear careers and more fluid transitions.

Three suggestions

Advisors who want to lead in this space can start by:

1. Engaging younger families on long-term financial resilience, not just RRSP and RESP contributions.
2. Exploring tools that accommodate multiphase careers and changing priorities.
3. Integrating conversations about well-being, values and life goals — not just income projections.

The future of retirement is already forming in the minds of today’s young parents. Advisors who act now will help shape what comes next. Those who don’t may find themselves planning for a world that no longer exists.

In my last Advisor.ca article, I shared how the traditional retirement model was built for a different era when careers were linear, retirement was a short phase and financial planning followed a straightforward accumulation-to-decumulation approach.

But longevity and evolving work patterns are rewriting the rules.

Over the past few years, I’ve worked with thousands of pre-retirees to help them see retirement through the lens of a longer life. Through workshops and one-on-one discussions, five retirement reframes have emerged — mental shifts that reshape how people approach retirement in a world where they can remain engaged for decades beyond 65.

For financial advisors, these reframes are critical to understanding how to effectively plan for retirement. They reflect how clients truly experience retirement, not just as a financial transition but as a multi-stage life shift that requires guidance beyond investments.

1. The longevity bonus: retirement is about redistributing time, not just extending it

Clients who recognize they could live to 90 or 100 rethink how they structure their time. The old model treated retirement as a finish line, but today’s clients are asking:

• What if I pace myself for a 60-year career instead of a 35-year sprint?
• Can I take career breaks, sabbaticals or shift to part-time work rather than stopping at 65?
• How do I blend work, learning and retirement over multiple phases?

For advisors, this means shifting from retirement readiness to life-stage readiness. Clients need financial advice to support a flexible approach to career transitions, phased retirements and shifting income needs. It’s not just about hitting savings targets for a retirement end date.

2. Holistic planning: retirement is more than a financial decision

Some of the most financially prepared clients I’ve met are the least ready for retirement.

Financial security alone doesn’t guarantee a fulfilling retirement. Well-being in later life depends on health, purpose and social connection as much as wealth.

Expand your retirement conversations to include purpose, engagement and social well-being. Questions to ask clients:

• How will you stay mentally and socially engaged?
• What will give you a sense of purpose when work no longer defines you?
• How will you continue learning and growing?

This shift is essential. Clients who plan holistically will thrive, rather than just survive in retirement.

3. Time affluence: free time isn’t always a gift

A retiree suddenly gains back 2,000 hours per year that were once dedicated to work. Many don’t realize that having too much unstructured time can lead to restlessness and even depression. One in three retirees struggle with depression due to the loss of structure and purpose.​

I’ve met retirees who feel lost within a year of stopping work. Others try to fill the void with too many commitments, leaving them overwhelmed.

The happiest retirees create structured flexibility by balancing leisure, purpose-driven work and community engagement.

Ask your clients:

• What will your ideal day look like in retirement?
• How do you want to invest your time in ways that are fulfilling?
• Do you need to financially prepare for volunteering, consulting or a phased professional wind-down?

Helping clients plan their time is just as crucial as planning their finances.

4. A positive view of aging: retirement is an opportunity, not a decline

Clients typically approach retirement in one of two frames of mind:

1. Excitement and possibility.
2. Anxiety and fear of becoming irrelevant.

What makes the difference? Their perception of aging.

Financial conversations often reinforce aging as a period of decline, focusing on risk, asset protection and long-term care. However, research tells us that a positive mindset about aging leads to better health, cognitive function and life satisfaction. A Yale study found that a positive view of aging can increase life expectancy by seven and a half years​.

Instead of simply preparing clients for risk management in retirement, help them see the positives of aging.

5. Curiosity and lifelong learning: retirement is an evolution, not a single decision

One of the biggest mistakes in financial planning? Treating retirement as a one-time decision.

The most successful retirees realize that retirement isn’t a static phase. Instead, they approach it as an experiment, testing new possibilities and adjusting along the way.

Encourage clients to plan retirement in three- to five-year increments rather than setting a rigid 30-year plan. A flexible financial strategy allows them to adjust based on health, interests and family dynamics.

Encouraging small experiments helps clients ease into new identities rather than making abrupt shifts.

Advisors as longevity guides

The old retirement model wasn’t built for today’s reality. These five reframes help clients understand the emerging retirement model. For advisors, it means:

• Helping clients define what retirement truly looks like so their financial plan supports their evolving lifestyle, work and purpose.
• Educating clients on how longer lives affect retirement timing, income and estate planning needs so they can make better financial decisions at every stage.
• Building financial flexibility into plans so clients can confidently navigate phased retirement, career pivots and evolving priorities without financial stress.

The best advisors don’t just plan retirements. They guide clients to navigate a longer, more dynamic life with purpose, flexibility and financial confidence.