����ý

Retirement sounds great in theory. No more early alarms, meetings, deadlines, or pretending to care about office birthday cake. But when it’s actually your retirement on the horizon, the whole thing can feel a little murky.

You’ve probably got questions. Can I afford it? Will I be bored? Do I even want to retire right now? What if I regret it? What if I don’t?

Here’s the thing: being “ready” for retirement isn’t just about your bank account. It’s about your lifestyle, your habits, your relationships, and your expectations. It’s financial, emotional, and a little existential.

If you’re trying to figure out whether it’s time to make the leap, start with these six questions. They’ll help you get a clearer picture of what retirement might really look like—and whether you’re ready for it.

1. Do you actually know what retirement looks like for you?

We’re not talking about some vague idea of “freedom” or “doing whatever I want.” What does your daily life actually look like when you’re not working?

Are you traveling the world? Starting a side hustle? Babysitting grandkids? Going full garden gnome? Or are you just imagining yourself in sweatpants watching bad daytime TV for the foreseeable future?

Retirement works best when it’s not a black hole. If you don’t have at least a rough idea of how you’ll spend your time, you might find yourself more restless than relaxed.

Start thinking about how you want to feel in retirement. Engaged? Creative? Rested? Then build a version of retired life that gives you that—whatever that looks like.

2. Have you looked at your money from every angle?

Yes, this is the obvious one. But we’re not just talking about whether you’ve hit some magical savings number. You need to know how that money translates into actual spending power.

Have you figured out how much income you’ll have each month? Do you know when you’ll start drawing from government programs like CPP, OAS, or Social Security? Have you factored in inflation, market fluctuations, and that weirdly expensive hobby you just picked up?

Also, are you still investing like someone who’s 35? Retirement usually calls for a shift in strategy—from growth to income. Now’s a good time to make sure your investments are built to support your life, not just your portfolio.

If that all sounds overwhelming, this is where a financial plan—or a good advisor—can really help.

3. Have you and your partner actually talked about it?

One of you might be dreaming of early retirement and slow mornings. The other might be planning to work another ten years and still enjoying being busy. Surprise!

You don’t have to agree on everything, but you do need to talk about what retirement looks like as a team. That means discussing timelines, budgets, travel goals, and yes, how much time you actually want to spend together.

Some couples glide into retirement like pros. Others are suddenly around each other 24/7 and thinking, “Wait… this is too much togetherness.”

Have the conversation early. It can save you a lot of stress—and possibly a few awkward silences—later.

4. Are you carrying any debt that’s going to make this harder?

Let’s be honest. Retiring with debt isn’t the end of the world, but it does make things more complicated. Especially if it’s high-interest debt, like credit cards or personal loans. A small mortgage might be manageable, but if your monthly payments are eating up a chunk of your retirement income, that’s a problem.

Now’s the time to figure out what can realistically be paid down, what you can live with, and what needs a plan. You don’t want to be six months into retirement and suddenly realize your fun money is going toward interest payments.

Think of it this way: every debt you eliminate now is one less thing future-you has to worry about.

5. Do you have a handle on your healthcare costs?

Healthcare might not be the most exciting part of retirement planning, but it’s a big one. As you get older, it’s likely going to get more expensive—and it might not be as fully covered as you think.

Have you looked into what your provincial or national healthcare plan actually covers? What about dental, vision, prescriptions, or long-term care? Do you have supplemental insurance lined up? Or a budget cushion for the unexpected?

6. Are you mentally and emotionally ready?

This one’s huge—and it’s also the most ignored.

A lot of people think retirement will automatically feel amazing. Then they get there, and they feel lost. Turns out, stepping away from a career that gave you structure, purpose, and a reason to wear pants five days a week can be a weird adjustment.

Ask yourself: Do I feel excited about this next chapter, or just tired of my current one? Am I retiring to something or just running from work?

You don’t need to have every detail figured out, but you do need to be honest with yourself. The transition is easier when you’ve thought through the emotional side—not just the financial one.

Final Thoughts

Retirement isn’t a finish line. It’s the start of something new—and you deserve to enter it with clarity and confidence.

You don’t need to have it all figured out today, but asking the right questions now can help you build a future that actually fits your life.

If you’re still unsure, that’s normal. Take your time, talk to people who’ve been through it, and get support where you need it. Whether you’re a few months out or just starting to plan, the goal isn’t to have the perfect plan.

The goal is to feel ready for the life you’re creating next.

‍