Stage 3: Reorientation

Designing your new normal

Retirement isn’t just a chapter break—it’s a full-on reinvention of who you are and how you want to live. After the honeymoon buzz and the pangs of disenchantment, many people find themselves in this third stage: Reorientation. This is where the pieces start to come together again. You begin to set more realistic expectations, explore what truly fulfills you, and shape a new routine that fits like a favorite pair of slippers.

Here’s where the fun begins. First, put on your designer cap and flex all that creative muscle living on the right side of your brain. It’s time to start crafting a lifestyle that puts you squarely in your happy place.

Secondly—and this part’s important—kiss the rat race goodbye. Not just a polite peck, but a full-on farewell. Let it go. If needed, sever old ties that are keeping you anchored to a version of yourself that no longer fits. Yes, you still need people in retirement. You still need connection and community. But staying too connected to your old workplace crowd can keep your head and heart tethered there, too. Keep the real friends—the ones who cheer you on in this new season. Let the rest go, and give them permission to let you go as well.

Rebuilding Your Social Landscape

Retirement often changes your social rhythms. Relationships may need rethinking. Stay intentional about keeping ties strong with family and friends. Communication doesn’t have to be high-tech or trendy—just meaningful.

Prefer the classics?

• A handwritten note, a cheerful card, or even a care package in the mail can brighten someone's day and deepen a connection.
• Good old-fashioned phone calls—landline or mobile—still do wonders for keeping the bonds strong.

Curious about new tools?

• If you're open to learning, technology offers handy ways to stay close to loved ones—email, video chats, even joining a family group on social media.
• It’s not about replacing the personal touch, just adding some new tools to your toolkit.

Mix and match.

• You might write letters to a grandchild who loves mail and hop on FaceTime with a friend across the country.
• Communicate in ways that feel right for both you and the people you care about.

Be mindful of preferences.

• Some friends might prefer phone calls; others may love a quick text or a photo shared online. Respecting their style (and your comfort level) can help make staying connected enjoyable and natural.

Embrace Flexibility and Flow

One of retirement’s greatest gifts? Time. Sweet, unstructured, gloriously flexible time. This is the stage where you learn to let go of rigid schedules and say yes to spontaneity. Sleep in if you like. Take a walk just because the sun is shining. Try something new—painting, birdwatching, baking, dancing, or maybe all of the above.

This stage is about building a life that suits you—your interests, your pace, your joy. It’s the moment when retirement stops being a concept and starts becoming your life.

Stage 2: Disenchantment

“Is this all there is?”

After the honeymoon stage of retirement—the travels, the new routines, the freedom—it’s common to feel a bit of a letdown. For some, this phase comes as a surprise. After all, wasn’t retirement supposed to be the reward for a lifetime of work?

My wife and I retired and spent the next six months in what felt like a perpetual vacation. For a while, it was glorious freedom from alarms, commutes, and deadlines. But over time, that sense of freedom gave way to something I hadn’t expected: restlessness.

I started to miss the structure of work—the challenge, the problem-solving, even the rhythm of a busy day. And yes, I’ll admit it: I missed the feeling of being needed, of contributing. It wasn’t about missing the “rat race,” but about missing purpose.

To complicate things, my wife loved her retirement. She thrived in the new lifestyle. I… didn’t. And that mismatch began to cause tension. We found ourselves bickering over little things. It felt like our marriage was being tested in new and unexpected ways.

Eventually, I went back to work, not full time, but enough to restore a sense of purpose and routine in my life. It helped tremendously, not only for me but for us as a couple.

Not everyone will go through this phase, but many do. It can feel a lot like the midlife moment when you ask yourself, “Is this really it?” The same question comes back in retirement: “Is this all there is?”

The reality is, when the novelty wears off, retirement can leave you feeling unanchored. Without goals or a clear sense of direction, some people experience boredom, frustration, or even mild depression. But here’s the good news: there are ways to navigate this stage without necessarily returning to work.

Ways to Reclaim Meaning and Momentum During Disenchantment:

🔹 Reconnect with Purpose
Think about what gave you a sense of fulfillment during your working life. Was it mentoring others? Solving problems? Creating things? Now look for ways to tap into those values in your retired life—through volunteering, teaching, creative pursuits, or community leadership.

🔹 Create a New Routine
One of the things people miss most after retiring is structure. Try establishing a daily or weekly routine that includes time for learning, movement, social connection, and rest. It doesn’t need to be rigid, but having a rhythm can ground your days.

🔹 Talk About It
If you’re feeling disillusioned, talk to someone you trust, your spouse, a friend, or even a counselor. Retirement is a major life transition, and it’s okay to need support while you figure it out.

🔹 Explore New Roles
Many people find meaning in new identities during retirement, as artists, community builders, caregivers, activists, or travelers. Ask yourself: What role do I want to grow into next?

🔹 Give Yourself Permission to Change Course
Just because you imagined retirement a certain way doesn’t mean it has to stay that way. You’re allowed to revise your expectations. Retirement isn’t one big destination—it’s a journey, and it can evolve.

You’re not alone if this stage catches you off guard. The honeymoon period is wonderful, but the disenchantment that sometimes follows is a real, human part of the transition. The key is to not get stuck in it. Let it guide you to the next phase—one where you redefine what success, meaning, and joy look like for you now.

 

Stage 1: The Honeymoon Phase

Congratulations—you’ve made it! After years of work, responsibilities, and deadlines, you’ve stepped into a new chapter: retirement. And right now, it may feel like a long-awaited vacation has finally begun.

The Honeymoon Phase is often a time of excitement, energy, and exploration. Freed from the daily grind, many retirees dive into long-postponed projects, trips, hobbies, or simply embrace the joy of sleeping in and doing things on their own schedule. This stage can be deeply satisfying, and it’s an important part of adjusting to your new lifestyle.

Here are a few ideas to make the most of your honeymoon phase:

🌱 Explore New Learning Opportunities

Now that you finally have the time, why not feed your curiosity? Whether you’ve always wanted to speak Italian, try watercolour painting, take a computer class, or study history, this is your moment. Lifelong learning helps keep your mind active and engaged, and today’s learning opportunities are more accessible than ever.

Community centres, local colleges, libraries, and online platforms like Coursera, Udemy, and Masterclass offer courses for every interest. Some universities even allow seniors to audit classes for free or at reduced rates.

❤️ Volunteer and Give Back

Many retirees discover a renewed sense of purpose by helping others. Whether it’s mentoring young people, supporting a food bank, serving on a community board, or caring for animals, volunteering not only helps others, it boosts your well-being, too.

It’s also a fantastic way to meet like-minded people and stay socially connected. Think about causes that matter to you and look for ways to get involved, even just a few hours a week.

✈️ Travel and Explore

If travel is on your mind, this is your chance to turn dreams into memories. Whether you’re envisioning cruises, cross-country road trips, European adventures, or short getaways to nearby towns, traveling offers new experiences, cultural discovery, and a sense of freedom.

Make a list of your must-see destinations, and consider building your travel around your interests—food, history, nature, or even genealogy. Not into big trips? Day trips and local explorations can be just as fulfilling.

💤 Rest, Relaxation, and Recharging

Not everyone enters retirement with a full itinerary—and that’s perfectly okay. Some people need a slower pace, especially if their careers were demanding or stressful. You might find yourself enjoying quiet mornings, reading, walking, or simply catching up on rest.

This "low-activity" path can be deeply healing. It’s not about doing nothing—it’s about giving yourself permission to breathe, reflect, and settle into a gentler rhythm.

A Time to Listen to Yourself

The honeymoon phase is often joyful, but it can also bring unexpected emotions. Some retirees are surprised to find that even amidst the freedom, they feel a little lost or unsure. That’s normal.

This is your time to check in with yourself. What excites you? What calms you? What gives you meaning? Be open to trying new things, but don’t pressure yourself to have it all figured out. You’ve earned the right to take your time.

Tip: Keep a journal during these early months. Write about what you’re enjoying, what’s surprising you, and what you’d like to do next. It’s a gentle way to keep your thoughts organized and your dreams unfolding.

Up next, I will  explore Stage 2: The Disenchantment Phase—what happens when the honeymoon begins to fade and reality sets in. But for now, enjoy this well-deserved season of renewal. Let yourself rest, explore, play, and dream.

You’ve only just begun.

 

Planning for Retirement: The Preretirement Phase

Let’s be honest—just the word "retirement" can stir up a whole mix of feelings. Hope. Relief. Excitement. And sometimes... uncertainty. If you're approaching retirement or helping someone prepare for it, you're not alone in wondering how to plan for this next big chapter. The preretirement phase—the time before the official “start” of retirement—is one of the most important parts of the entire journey. Why? Because the more thought and care you put into this phase, the more confident, free, and fulfilled your retirement is likely to be.

This stage is all about vision and preparation. It’s where your ideas, dreams, and maybe even a few anxieties begin to take shape. You’re not retired yet, but you're beginning to imagine what that life might look like. You might find yourself picturing lazy mornings with coffee and a book, or grand adventures across the world, or maybe it’s just the idea of finally having the freedom to say yes to what you want, when you want.

Envisioning Your Retirement Life

Start here. Not with numbers or spreadsheets (we’ll get to those)—but with imagination. Ask yourself: What does a good day in retirement look like? What about a good year? Would you like to travel? Volunteer? Take up painting, hiking, or mentoring? Your answers are yours alone—and there’s no “wrong” way to retire.

If you have a partner, now is a great time to have open, thoughtful conversations about what you both want. You may discover you have shared dreams—or that you’ll need to compromise in some areas. Either way, it’s better to explore those possibilities now than to be surprised later.

Create a “bucket list” if that helps, but don’t limit yourself to big, one-time events. Think about how you want to spend ordinary days, too. What kind of routines do you want? How will you stay connected, engaged, and joyful?

Getting Your Financial House in Order

Now, once you’ve got some vision and direction, it’s time to take a closer look at your finances. For many people, this is where anxiety kicks in. But it doesn’t have to. You don’t need to have every dollar mapped out right this second, but you do need a sense of what you have, what you’ll need, and how you’ll bridge the gap if there is one.

This is where professional guidance can be incredibly helpful. A financial advisor or retirement planner can work with you to look at your income sources (like pensions, CPP/OAS, RRSPs, or other savings), create a spending plan, and help you set goals that support the lifestyle you envision.

If you're not sure how to find someone trustworthy, start by asking friends, family, or colleagues if they’ve worked with anyone they’d recommend. Personal referrals often carry more weight than online reviews. You can also visit FP Canada or NAPFA to search for Certified Financial Planners in your area.

As you meet with advisors or planners, take your time. Interview more than one. Ask about their qualifications, their approach, how they’re paid, and whether they’ve worked with clients like you before. You should feel not only informed, but respected and heard.

If you're also considering working part-time or transitioning into a new kind of work during retirement, a career coach might be a great ally. They can help you explore meaningful second-act careers, flexible work options, or even entrepreneurial ventures that fit your evolving goals.

Keep It Personal, Stay Flexible

While numbers and plans are key, don’t forget that retirement is deeply personal. No two retirements are alike, and yours should reflect who you are. That means building a lifestyle that brings you joy, even if it looks nothing like the glossy brochures or TV commercials we often see.

You might find that your interests shift. That’s okay. Retirement isn’t a static state—it evolves as you do. What matters most is staying open, curious, and willing to adjust your plans as needed.

Maybe you'll join a community choir or start gardening. Maybe you’ll spend more time with grandchildren or get involved in civic work. Maybe you'll move, or stay put and renovate. Whatever you do, make sure it aligns with what feels fulfilling to you.

And if you’re still figuring that out—wonderful. This is your time to explore.

Start Now, Enjoy Later

The beauty of the preretirement stage is that it gives you the gift of time—time to dream, prepare, and set the stage for a life that feels rich in meaning. The more energy you invest here, the smoother the transition tends to be.

Don’t rush the process. But don’t put it off either.

Begin by asking yourself: What do I want this next chapter to look like? Then take a few simple steps forward. Call an advisor. Talk to your partner. Write down what makes you happy. These aren’t just tasks—they're acts of self-care. They’re small doors opening into a big, beautiful future.

And remember: you’re not alone. If you're looking for helpful tools or places to learn more, try visiting Retire Happy or the Government of Canada’s retirement planning hub for more resources and ideas to help you get started.

Next time, I will explore the Honeymoon Stage—that first exhilarating taste of freedom that follows your final day of work. But until then, take a breath, take stock, and begin shaping the retirement you deserve.