Winter is Coming: Rewirement Over Retirement

A friend of mine retired a couple of years ago. Except she didn't call it retirement. In a Facebook post that stopped me mid-scroll, she announced her "rewirement."

Not retirement. Rewirement.

That one word—that clever little shift—completely changed the energy around what she was doing. Retirement sounds like winding down, stepping back, becoming less. Rewirement sounds like rebuilding, reconnecting, becoming different. Same life stage, entirely different intention.

And as someone staring down the barrel of my own Winter season (though hopefully not for another decade or so), that reframe hit me hard. Because here's the thing: Winter is coming. For all of us. And how we prepare for it—and what we choose to call it—matters more than we think.

A Canadian's Guide to Not Freezing Your Ass Off (Literally and Metaphorically)

I'm Canadian. Born and raised. I've survived minus-40-degree Prairie winters where your nostril hairs freeze the second you step outside, and I've weathered East Coast snowbelt storms that bury your car so thoroughly you don't see it again until April.

And like our ancestors who settled and colonized this land learned very quickly: you have to prepare for winter.

You don't just hope for the best when you live somewhere that can literally kill you if you're not ready. You winterize your car. You stock your pantry. You get proper boots and a decent coat. You check your furnace. You salt your walkways. You know where your snow shovel is (and you have a backup because the first one will break at the worst possible moment).

The people who thrive through Canadian winters aren't the ones with the most money or the biggest houses. They're the ones who prepare. Who take the threat seriously. Who understand that winter can be beautiful and cozy and full of skating and snowmobiling and hot chocolate by the fire—but it can also be cold and ruthless if you're caught unprepared.

Sound familiar?

Winter is Coming (And the Starks Were Right)

If you've watched Game of Thrones, you know the Stark family motto: "Winter is Coming." While everyone else in the Seven Kingdoms was busy with politics and power plays, the Northfolk stayed vigilant. They understood Winter wasn't just a season—it was an ever-present threat that demanded respect and preparation.

They looked like paranoid killjoys to everyone else. Right up until Winter actually came and proved them right.

The Winter of our lives carries that same weight. It's not a maybe. It's not an if. It's a when. And unlike the seasons we've passed through—Spring, Summer, and Fall—Winter is our long term. This is the season we don't get to restart or redo.

Whoever was able to forgo some comfort in the short term to provide long-term benefit, ease, and care? They're the ones who will truly thrive in Winter. The ones who spent their Summer years only focused on immediate gratification? Well, they're in for a rough time.

What Seasons Teach Us About Preparation

Here's what living through multiple seasons teaches you: what you plant in Spring, tend in Summer, and harvest in Fall determines what you eat in Winter.

You can't suddenly decide in December that you want fresh vegetables and expect your garden to comply. You needed to think about Winter back in May when you were planting seeds. You needed to water and weed through July's heat. You needed to preserve and store in September's abundance. Sure we have grocery stores that have an endless supply of these things now, but the metaphor applies to many more things especially when it comes to our health and our finances.

Our lives work the same way:

Spring decisions (your education, early career choices, foundational habits) set up possibilities for later seasons.

Summer investments (building relationships, developing skills, saving money, maintaining health) create the resources you'll draw on in Fall and Winter.

Fall harvesting (leveraging your career peak, deepening important relationships, making smart financial moves, seriously addressing health) determines what you bring into Winter.

You can't arrive at 65 or 70 and suddenly wish you'd built strong friendships, maintained your fitness, saved money, or developed interests outside of work. I mean, you can wish it—but wishing doesn't make it so.

The Two Pillars: Health First, Finance Second

Let me be blunt about something: your health is the core fact. Your financial resources are secondary.

I know, I know. Everyone talks about retirement planning like it's all about the money. And yes, money matters—a lot. But all the money in the world doesn't buy you a new body when yours stops working. And if and when it does, it will cost you more.

I've watched people hit their sixties and seventies with healthy bank accounts but bodies that won't let them enjoy any of it. They saved and saved and saved, planning for exotic travel and golf and grandkid adventures. But they didn't invest in their physical health with the same diligence they invested in their RRSPs. So now they've got the money but not the mobility, the breath, the energy, or the pain-free existence to actually live.

Conversely, I know people who are ridiculously healthy at 70—still running, still hiking, still dancing—but stressed about money because they didn't plan. They've got the capacity for adventure but not the cash to fund it.

Both situations suck. So, the goal, obviously, is to have both. But if you're in your Fall season right now and you're finally getting serious about Winter prep, start with your health. Your body is the vehicle that will carry you through Winter. Maintain it now.

Rewirement: What It Actually Means

So let's come back to that word: rewirement.

My friend wasn't just being cute with language (though she was definitely that). She was signaling something important: Winter isn't about shutting down. It's about rewiring for a different purpose.

Traditional retirement was built for a world where people worked until 65 and died at 70. You got five years of golf and grandkids, and that was it.

But we're not living in that world anymore. If you retire at 65, you could have 20, 25, maybe even 30+ years ahead of you. That's not a five-year victory lap. That's potentially another entire life phase as long as your entire career.

So the question isn't "How do I wind down?" It's "How do I rewire?"

Rewirement asks:

• What do I want to contribute now that I'm not locked into a career for income?

• What skills and interests have I neglected that I can finally develop?

• How do I want to show up in my community, my family, the world?

• What kind of elder do I want to be?

• What legacy am I building through how I live these years?

It's not about doing nothing. It's about doing things that matter to you without the pressure of doing things that pay the bills.

How to Prepare for Winter (Even If It's Already October)

Okay, enough metaphor. Let's get practical. Whether Winter is two decades away or two years away, here's what you need to be thinking about:

1. Your Physical Foundation

What you need to do NOW:

• Move your body regularly (strength training is non-negotiable for aging well)

• Address health issues instead of ignoring them (that knee pain won't fix itself)

• Build habits around sleep, nutrition, and stress management

• Get regular check-ups and actually follow through on recommendations

• Maintain or build cardiovascular fitness (your heart needs to last)

Why it matters: Every year of mobility, independence, and pain-free existence you can preserve is priceless. The 70-year-old who can still hike, travel, play with grandkids, and live independently? That person invested in their body decades earlier.

I'm training for a marathon at 55 not because I love running (jury's still out), but because I'm building the physical resilience I'll need at 75. I'm literally running toward my future self.

2. Your Financial Reality

What you need to do NOW:

• Actually look at your retirement savings (denial doesn't help)

• Work with a financial planner if you haven't already

• Understand what you'll need and whether you're on track

• Make a plan to close the gap if you're not

• Consider what "enough" actually means for your lifestyle

Why it matters: Money doesn't buy happiness, but financial stress in your seventies is miserable. You want enough to cover basics plus some joy. Define what that looks like for you, not some generic retirement calculator.

3. Your Social Infrastructure

What you need to do NOW:

• Nurture friendships outside of work

• Build community connections that aren't tied to your career

• Invest in family relationships (if they're healthy)

• Join groups, clubs, or activities where you belong

• Be the kind of friend/partner/family member you'd want in your life

Why it matters: Loneliness and isolation are two of the biggest killers in older age. Not metaphorical killers—actual, measurable contributors to disease and early death. The people who thrive in Winter have rich social lives. Start building that now.

4. Your Sense of Purpose

What you need to do NOW:

• Develop interests and hobbies that have nothing to do with your paycheck

• Explore what you care about beyond your job title

• Consider how you want to contribute (volunteering, mentoring, creating)

• Ask yourself what would make you excited to get out of bed if work wasn't the reason

Why it matters: I've watched too many people—especially men, honestly—retire and completely lose their sense of identity and purpose. They were their job. When the job ended, they didn't know who they were anymore. Don't be that person.

5. Your Adaptability Muscle

What you need to do NOW:

• Practice learning new things (keeps your brain plastic)

• Get comfortable with change and uncertainty

• Build resilience through challenging yourself

• Let go of rigid ideas about how things "should" be

Why it matters: Winter will bring changes you can't control: health issues, loss of loved ones, technological shifts, societal changes. The people who adapt survive. The people who cling to "the way things were" suffer.

The Short-Term/Long-Term Tension

Here's the uncomfortable truth: preparing for Winter often means making choices in Fall (and even Summer) that don't feel good in the moment.

It means:

• Skipping the fancy vacation to bulk up your savings

• Going to the gym when you'd rather sleep in

• Saying no to overtime to preserve your health and relationships

• Eating boring, healthy food instead of comforting garbage

• Investing time in friendships when work feels more urgent

• Addressing the marriage that's slowly dying instead of ignoring it

These choices feel like sacrifices right now. But they're investments in your future capacity for joy, health, independence, and connection.

The tragedy is watching people hit their sixties or seventies with deep regret: "I wish I'd taken my health seriously." "I wish I'd saved more." "I wish I'd invested in my friendships." "I wish I'd dealt with my marriage when there was still time."

You can't get those years back. You can't undo decades of neglect in a few months.

But if you're reading this and you still have time? You still have time.

What Winter Can Be (If You're Ready)

Here's what I want you to know: Winter, when you're prepared for it, can be absolutely magnificent.

It can be the season of:

• Freedom from having to prove yourself

• Time and energy for things that actually matter to you

• Deep, meaningful relationships with people you've invested in for decades

• Wisdom and perspective that only come from living through all the seasons

• Contribution and legacy that isn't tied to a paycheck

• Cozy, intimate joys (like actual winter evenings by the fire)

• Adventure and exploration on your own terms

But all of that requires preparation. It requires treating Winter as something to actively ready yourself for, not something to ignore until it arrives and hope for the best.

Your Winter Prep Checklist

If you're in your Fall season right now, here's your homework:

This month:

• Book a full physical with your doctor

• Make an appointment with a financial planner

• Start or restart a strength training routine

• Reach out to one friend you've been meaning to connect with

• Write down three things you'd love to do in your Winter years that aren't dependent on work

This year:

• Get serious about any health issues you've been ignoring

• Create or update your financial plan for retirement

• Join one group/club/activity where you can build community

• Develop one hobby or interest that has nothing to do with your career

• Have an honest conversation with your partner (if you have one) about what you each want your Winter to look like

Long term (ongoing):

• Treat your body like the precious vehicle it is

• Live below your means and save the difference

• Invest in relationships, not just your career

• Keep learning, growing, and challenging yourself

• Build a life you won't want to retire from—one you'll want to rewire into something even better

The Bottom Line

Winter is coming. That's not pessimistic; it's realistic. And realistic preparation is what allows you to actually enjoy Winter instead of just surviving it.

You can make Winter a season of cozy fires and meaningful contribution and hard-won freedom. Or you can make it a season of regret and struggle and wishing you'd done things differently.

The choice is yours. But like my East Coast ancestors learned: you can't wait until December to start preparing for winter.

Start now. Winterize your life. Build your reserves. Strengthen your foundation. Deepen your connections.

And when Winter finally arrives? You'll be ready to make it spectacular.

What are you doing right now to prepare for your Winter season? What choices are you making today that your 75-year-old self will thank you for? Drop a comment—I'd love to hear what Winter prep looks like for you.