Retirement Maxxing: How Small Decisions Help You Build a Better Future

A new word has been trending online lately: maxxing.

Mar 13, 2026

10 min

The basic idea is to pick a corner of your life and optimize it ruthlessly. Sleep maxxing. Health maxxing. Productivity maxxing. In its more extreme corners, people are attempting to optimize their actual physical features. Go ahead and Google "looksmaxxing" if you are curious and have a strong constitution. One influencer named Clavicular — a 20-year-old from Hoboken who claims to have taken a literal hammer to his face to coax a chiselled jawline — has become the reigning king of this particular rabbit hole. Medical experts would prefer you not try that at home.

The Globe and Mail published a comprehensive explainer on the whole phenomenon. The Republican National Committee put out a press release praising Donald Trump for "jobsmaxxing" the economy. The Department of Defence posted a soldier with the caption "lethality maxxing." It has become, as one writer put it, the suffix that just will not quit. Retirement Maxxing: because chin waxing, I mean maxxing, was already taken.

And yet, buried beneath all the absurdity, the underlying impulse is not entirely ridiculous. Humans want to optimize things. We always have. The real question is whether we are optimizing the right things. Then, as these things sometimes happen, three articles landed in my inbox in the same week and refused to leave my mind. Maxxing. The psychology of future selves. A golfer named Max Greyserman, who sits just one-tenth of a stroke from the top of his sport. I am not a woman who ignores signs. The connection was obvious once I saw it: retirement might be the most important time to apply this kind of thinking. Not the obsessive version involving ice baths and fourteen supplements before breakfast. The practical version. Thoughtful maxxing that quietly stacks the odds in your favour over decades.

Retirement isn't just one decision; it's hundreds made over the years, each guiding your future self toward either financial dignity or a Shaggy tribute tour you never signed up for.

The “Shaggy Problem”: How Your Retirement Decisions Today Determine Your Financial Security Tomorrow

You remember Shaggy. The reggae artist. Enormous hit. "It Wasn't Me."

When it comes to retirement, it absolutely was you.

Every decision you make today is writing a letter to your future self. Some of those letters are generous and thoughtful. Others arrive decades later, like a bill you forgot to pay, from a creditor with excellent memory and zero sympathy.

The seventy-five-year-old version of you hopes the fifty-five-year-old paid attention. The eighty-five-year-old version would very much like functioning knees, a dignified income, and the ability to say "I planned for this" rather than "I did not think it would go this fast."

It went that fast.

That's why the most useful habit you can develop right now is what I call the future-self test. Before making a major financial or lifestyle decision, pause and ask: how will this look from the other end?

Will I still think this tattoo is a good idea when I’m ninety? Will I regret staying in a house that is too large and too expensive for another decade? Will my future self thank me for delaying CPP, or curse me for taking it early because waiting felt uncomfortable?

Or as the Beatles asked rather memorably: “when I'm sixty-four, will you still need me, will you still feed me?” The song is charming. The financial planning version is considerably less so if you have not thought it through.

The future-self test is not complicated. It is just the habit of writing better letters.

What Sports Analytics Can Teach Us About Smarter Retirement Decisions

Speaking of decisions that come back to haunt you, let's discuss probabilities.

A recent New York Times article about golfer Max Greyserman stopped me mid-scroll (Lindgren, 2026). Not because of the golf — though the golf is fascinating — but because of what it revealed about the gap between what the data says and what people actually do when the stakes are high.

Greyserman's scoring average is less than one-tenth of a stroke per round away from the elite level. One-tenth of a stroke. Not a full swing, a putting mistake, or a collapse on the eighteenth. The difference between obscurity and greatness in pro golf is about the time it takes to find your reading glasses. Which, as we've established, were on your head the entire time.

Hockey analytics have demonstrated that teams trailing late in a game should often pull the goalie much earlier than the traditional last-ninety-seconds rule. Research indicates that pulling the goalie around the eight-minute mark can significantly boost the chances of scoring, as the extra attacker alters the odds. However, most coaches still wait until the final minute or two. Why? Because if you pull the goalie at eight minutes and lose badly, it can look like you lost your mind. The math checks out, but the optics are terrifying.

Soccer offers a similarly uncomfortable example. A widely cited study analysing thousands of penalty kicks found that about one-third of kicks are aimed straight down the middle of the net, yet goalkeepers stay in the centre only around six percent of the time (Chiappori, Levitt, & Groseclose, 2002). Shooting directly down the middle often provides good odds because the keeper has already committed to diving one way or the other. But if the goalkeeper stays put and makes the save, the kicker seems to have tried to outsmart the odds and failed. The math checks out. The optics, however, are still terrifying.

Retirement is filled with these moments. And most people make their decisions based on the optics.

Common Retirement Decisions Canadians Get Wrong — And What the Data Actually Says:

Working a couple of extra years often delivers significantly better retirement outcomes, yet people retire early because they feel emotionally ready. Delaying CPP can greatly increase guaranteed lifetime income, yet many choose to claim early because waiting seems risky. Downsizing can free up cash and lessen financial stress, yet people stay in large homes because selling feels like giving up. Using home equity wisely can boost retirement income, yet many retirees dismiss this option because of a stigma rooted in outdated beliefs rather than current data.

In each case, the emotionally comfortable choice is not the one with the best long-term odds. Fear of loss, fear of regret, fear of looking foolish — those emotions sprint ahead of rational thinking every single time. That is why the future-self test matters. Math is universal, but money is deeply personal, and the goal is to let one inform the other before it is too late.

The Psychology of Retirement Saving: Why We Treat Our Future Self Like a Stranger

The second New York Times article examined the psychology of how we connect with our future selves (The New York Times, 2026). The findings are humbling. Psychologists have discovered that people often see their future self almost like a stranger, which explains why saving for retirement can seem somewhat punishing. It feels less like helping yourself and more like sending a cheque to someone who shares your cheekbones but whose problems seem distant and abstract.

Research led by Hal Hershfield found that when people feel more connected to their future selves, they save more and make consistently better long-term financial decisions (Hershfield, 2011). Retirement planning is not just about spreadsheets and withdrawal rates. It is about being genuinely generous towards the person you are becoming. It is a love letter, written in small decisions, over a very long time.

So, write a good one. Your future self is counting on you.

How to Optimize Your Retirement: A Practical Framework for Canadians

If retirement maxxing were a lifestyle trend — and I am formally proposing that it should be — it wouldn’t involve bone-smashing or extreme jawline enhancement. It would look more like this.

Health Maxxing: Why Strength and Mobility Are Financial Assets

Move your body. Lift weights now and then. Walk up hills. Muscle strength is one of the most underrated assets for retirement that nobody discusses at dinner parties. Research from the National Institute on Aging confirms that strength training improves mobility, balance, and healthy longevity (National Institute on Aging, 2023). These are the very factors that influence whether your later years feel like a gift or a burden. People hesitate over the cost of a gym membership while ignoring the significant long-term benefit of staying upright, independent, and capable. Skipping exercise to save a few dollars is like stepping over a hundred-dollar bill to find a quarter. As Aunt Equity likes to say: be careful not to get out over your skis. (Yes, that was an exercise metaphor. You’re welcome.)

Income Maxxing: How to Build Reliable Cash Flow That Lasts

Build reliable income streams so you can sleep at night without one eye on the market. Pensions, annuities, dividends, home equity, and carefully structured withdrawals — these all play a role in a well-crafted retirement income plan. The goal isn’t to maximize a single number – it’s to reduce the worry behind all of them. If your retirement plan currently makes you watch financial news at midnight while eating crackers over the sink, something has gone wrong and we should talk.

Purpose Maxxing:Why It Matters for Your Health and Longevity

Retirement is not a forty-year holiday. Humans need purpose, connection, and something worth getting out of bed for — especially on days when nobody expects you anywhere and the morning is entirely, terrifyingly yours. NIH research consistently shows that social engagement and a sense of purpose are linked to better health and longer life (National Institute on Aging, 2023). Purpose is what makes a retirement that feels like freedom different from one that feels like a long Sunday afternoon with nowhere to go. Somewhere along the way, society decided that aging meant quietly fading into the background. Retirement is when you finally have permission to dye your hair a vibrant colour, volunteer somewhere meaningful, start a project that genuinely excites you, or do all three at once and totally surprise your grandchildren. Purpose is not optional. It is the foundation.

Decision Maxxing: How to Overcome Emotional Bias

Use data when the stakes are high. Emotions are useful for choosing dessert but much less reliable for planning a thirty-year income. Don't swat away analytics like a fly at a family picnic just because they suggest something uncomfortable. Run projections. Stress-test your plan. Understand probabilities. Pull the goalie early if the math indicates so, even if it looks odd at the moment. Because appearing odd now and being wrong later are not the same thing. Not even close.

The Ending That Brings It All Together: Small Decisions That Compound Over Time

Here’s what three articles about “maxxing” our future selves, and golf, taught me about retirement. Clavicular is out there taking a hammer to his face in pursuit of optimization. Max Greyserman is grinding for one-tenth of a stroke. Hal Hershfield is reminding us that we treat our future selves like strangers when we should treat them like people we love. And somewhere between all three of them is the retirement insight that really matters: the best decisions compound quietly. Tiny improvements in health, income strategy, purpose, and decision-making build up into dramatically different outcomes over decades. Not because of one dramatic move, but because of many small, sensible ones made with the future in mind.

Your future self isn't a stranger waiting to judge you. They are the person you are intentionally becoming, shaped by every decision you make today.

Perform the future-self test before making risky decisions like pulling the goalie, shooting down the middle, or getting a tattoo that might lead to an awkward chat with your colonoscopy technician (this is for you, JK). Consider whether your fifty-five-year-old self is being kind to your seventy-five-year-old self. Look at what the data says, not just what feels right.

Retirement maxxing isn't about perfection. It's about making small, sensible decisions consistently and thoughtfully over time. Think of it as compound interest for your future self. Einstein allegedly called compounding the most powerful force in the universe. He was talking about money, but he might as well have been talking about the small, steady choices that create a retirement worth living. Your future self will be deeply grateful—having functional knees, a dignified income, and a tattoo they still absolutely love.

And when you turn sixty-four, and someone asks how you got there so gracefully, you won't need to channel your inner Shaggy.

You just smile and say: It was me!

Sue

Don’t Retire…ReWire!

P.S. Aunt Equity approves.

Ready to start retirement maxxing? Here are two things you can do today.

Run the future-self test on one financial decision you have been avoiding. Just one. Write down what your seventy-five-year-old self would think of the choice you are leaning toward. You might be surprised what comes up.
Move your body and find your people. Join a pickleball club, a walking group, a trivia night, or a bridge league. Laugh often. Sweat occasionally. Your future self needs both, and your colonoscopy technician will be thrilled.

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Sue Pimento

Founder | CEO

Writer, author & presenter focused on financial literacy and retirement strategies. I advocate for the health, wealth & purpose for retirees

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Jul 8, 2026

7 min

The Biological Clock Nobody Talks About

Biology is ageist. There. I said it. Young people have a biological clock that ticks toward new life. It is loud and urgent, and it comes with its own well-funded industry of apps, doctors, and anxious dinner-party conversations. Ours ticks too, but more quietly. Less “the nursery won’t paint itself” and more “the knees are filing a formal complaint.” Same clock. Wildly different countdown. Young people race toward a beginning. We are racing toward… what, exactly? That is the part nobody warned us about in the brochure. I have been thinking about this clock a great deal lately, not in the abstract, philosophical, this-would-make-a-good-dinner-party-topic way. In the personal, slightly unsettling, why-am-I-like-this way. Because somewhere between turning seventy and watching my brother nearly run out of time entirely, I started to suspect that the clock is not just ticking quietly in the background of my life. It may be driving much of my behaviour, and not always in directions I am proud of. At seventy, I have become mildly obsessed with squeezing every drop out of life. Partly because of the birthday. Partly because 33-year-old entrepreneur Steven Bartlett recently declared that a couple of glasses of wine can derail several days of optimal living, causing poor sleep, missed workouts, reduced productivity, and full-scale biological chaos. The internet, predictably, exploded. One side applauded his discipline. The other suggested he put down the smartwatch and pick up a personality (Bartlett, 2025). Then broadcaster Greg James offered a counterpoint worth sitting with maybe measuring every step, calorie, and heartbeat is not making us happier. Maybe it is making us anxious (James, 2025). Let that idea marinate. It hit me harder than I expected. If I call balls and strikes here, I may have become a card-carrying member of Team Optimize. I teach fitness classes. I went back to school. I write books. I hike mountains. I track protein. I have voluntarily reached the age when discussing fibre intake is considered a contribution to the dinner conversation. Normal retirement behaviour, said no one ever. Apparently, I have a track record with this sort of thing. I have written before about my addiction to home improvement, the kind that finds a project the house did not actually need. Self-improvement, I am beginning to suspect, is the same compulsion wearing a different outfit. What I am exploring here is whether I am actually growing, or, as I am increasingly suspecting, just optimizing out of panic. So, I started asking myself an uncomfortable question, one that keeps circling back to that same clock. Am I pursuing excellence, or am I negotiating with my biological clock? Researchers studying aging have found something fascinating about how that clock changes us. As people become increasingly aware that time is finite, their priorities shift: less interested in accumulating and more interested in meaning, less interested in status and more interested in relationships, and less interested in “someday” and more interested in today. Psychologist Laura Carstensen’s landmark work on socioemotional selectivity theory suggests that it is not age itself that changes us. Rather, it is our perception of the time we have remaining (Carstensen, 2006; Carstensen et al., 1999). I am not sure I have made that shift. Not fully. If I am honest, I wonder whether all the doing, the relentless forward motion, is less about passion and more about outrunning something. Maybe I think that if I keep running, Father Time will not catch me. I can smell a fool’s errand a mile away, and yet here I am, lacing up my shoes … possibly while listening to a podcast on slowing down. I have a theory about this. I call it FORO, the Fear of Running Out. Most people assume it means Fear of Running Out of money, and money is certainly part of it. But lately I think money is just the socially acceptable thing we admit to worrying about. The less acceptable version is the fear of running out of time, energy, relevance, and chances to matter. FORO does not always show up as worry. Sometimes it shows up as motion. Another course. Another project. A new certification nobody asked for. A calendar so full it functions less as a planning tool and more as an alibi. If I cannot stop the running out, I can at least look busy while it happens. That is not ambition. That is panic, wearing a blazer and carrying a planner. Then something happened that stopped the clock cold … or at least kept me from ignoring it. Recently, one of my brothers suffered a massive heart attack. One moment, life was proceeding as planned. Next, he was in intensive care fighting for his life. Thankfully, he survived a quadruple bypass and is now on the long road to recovery. I am still processing it. Watching someone you love close to the edge clarifies things faster than any amount of journaling ever has. Suddenly, nobody is talking about productivity hacks or sleep scores. The conversation gets very simple. More time. More laughter. More family dinners. More life. His clock nearly ran out. Mine, presumably, has not. The question is what I plan to do with the difference. And I sat with that, quietly, for a while. Because his heart attack did not just scare me. It held up a mirror. If the people who matter most to me were sitting across the table right now, would they say I have been present, or would they say I have been busy? I am not sure I want to hear the answer. But I think I already know it, because my wife Bonnie and my dog Dottie have been telling me for a while now, in their own ways. Bonnie has not complained, not really, though I have noticed the particular quiet of someone who has learned not to wait up and has become quite good at saving me half a plate of dinner without asking what kept me. That quiet has nothing to do with her and everything to do with me. Dottie has taken a more direct approach. She has started leaving passive-aggressive stuffed toys outside my office door, which I choose to interpret as a formal grievance filed by a ten-pound dog with excellent comic timing. Both have been waiting for me while I try to sort this out. But patience, like biology, has its limits. Here is where I have landed, at least for now. Retirement, at its best, should be a contact sport: full-bodied, fully engaged, leaning into life with both hands. But there is a trade-off in the pursuit of optimization that no one puts on the inspirational poster. By filling every available hour with the next worthy initiative, I risk alienating the very people for whom “more life” was supposed to be. That is not ambition. That is a quietly self-sabotaging way of running out the clock on the wrong things. I do not have a tidy resolution. Maybe it means resisting the urge to add more simply because I can. What I keep coming back to is this: presence, being genuinely and unhurriedly present with the people I love, might be the optimization I have been overlooking all along. Not because it is hard to measure, but because it is hard to schedule, and even harder to admit I have been avoiding it. What I want, at the end of the day, is to be as present as humanly possible. Not present in the mindfulness app, remember-to-breathe sense. Actually present. Available. Unhurried. With Bonnie. With Dottie. With the people who have been waiting for me to look up. I am not going to pretend I have made this shift. I have not. But I have started doing something that feels different from doing nothing while thinking deeply about it, and I will take the small win. I dropped one school course this term. I have started leaving my phone in another room during dinner, which Dottie has not noticed, but Bonnie absolutely has. I am trying to ask myself, before I say yes to the next worthy thing, whether I want it or whether some part of me is still trying to outrun a clock that cannot be outrun. Some days I catch myself in time. Other days I sign up for the nine-week certificate anyway and figure it out later. Progress, not perfection. If you are reading this and recognize yourself, or someone you love, the invitation is not to overhaul your entire life by Tuesday, or to ask them to. It is to ask the same question I am still learning to ask. The next time your calendar fills with another worthy thing, pause and ask who benefits from that time. If the honest answer is mostly you, and mostly in a way that keeps you safely too busy to sit still with the people who love you, that might be worth a second look. Not guilt. Just a look. Which brings me back to the clock, because it always does. The biological clock of aging is not warning us that time is running out. It is reminding us that time is valuable, and that the people keeping time with us deserve more of it than the leftovers. Young people hear the clock and ask, “When should I start?” Older people hear the clock and ask, “What am I waiting for?” I think I finally know the answer. It is not another course. It is not another goal. It is them. Turns out the clock was never my enemy. It has been my alarm, going off for months while I kept hitting snooze and signing up for another nine-week certificate instead. The good news is I have finally found a project worth finishing. The bad news is it does not come with a certificate of completion, only my loved ones and whatever time the clock decides to give me to enjoy them. Biology may be ageist, but it is also, infuriatingly, right. Sue Don’t Retire…ReWire! My Book is Now Available for Pre-Order I hope you will consider pre-ordering a copy of Your Retirement Reset for you, a friend or loved one. It's available September 8, 2026 published by ECW Press - You can now order at Indigo or Amazon. And if you love supporting Canadian booksellers, please also check with your local independent bookstore. Most can easily order it for you.

Jun 24, 2026

8 min

GRANDSPLAINING...It's as Bad as it Sounds!

Summary: "Grandsplaining" is a playful term that captures the all-too-familiar situation where younger generations offer unsolicited advice to older family members, often in a manner that is as condescending as it is unhelpful. This behaviour can be perceived as disrespectful and potentially creates awkward communication barriers, emotional strain, and family tension. Rooted in ageist stereotypes, it can even undermine elders' self-esteem. Here, we explore alternatives to grandsplaining, including the radical concepts of genuinely listening, asking open-ended questions, demonstrating empathy, and avoiding assumptions. These suggestions aim to help adult children support their older family members—not merely swoop in with a "fix-it" attitude. The Disrespectful Impact of Condescending Advice on Seniors When I helped older Canadians navigate financing their retirements, I often witnessed what can only be described as "grandsplaining in the wild." Conversations between adult children and their elders usually felt less like dialogues and more like lectures—one-sided advice sessions that left everyone gritting their teeth. The younger relative, likely well-meaning, would offer suggestions like, “You should downsize and buy a condo,” “Sell and rent,” or, the pièce de resistance, “Move in with family!” Judging by the withering looks from their elders, it was clear this approach wasn’t winning any "Favorite Child" awards. The older family members often felt patronized, as though their decades of life experience had been conveniently forgotten. The advice was condescending, painfully obvious, and usually impractical or unwanted. The dynamic reminded me of the cringeworthy experience of being "mansplained." And that’s when it hit me: this is “grandsplaining.” Unfortunately, grandsplaining can turn retirement planning conversations into a crash course on how not to communicate! Fortunately, with a little effort (and much less lecturing), families can turn this ship around and build stronger, more respectful relationships. What is "Grandsplaining"? In an age where communication flows freely across digital platforms, I define "grandsplaining" as a colloquial expression to describe a situation where younger generations offer unsolicited advice to older individuals, often patronizing or condescendingly. Grandsplaining typically involves a younger person explaining something to an older individual in a way that belittles their experience or intelligence. The term combines "grand" (suggesting age or status) and "splaining" (a slang term for condescendingly explaining something). While the intention behind such advice may often be well-meaning, the delivery can be patronizing, reinforcing stereotypes about aging and competence. This behaviour can significantly undermine the dignity and autonomy of seniors, leading to feelings of frustration, resentment, and a sense of being marginalized. Understanding the nuances of grandsplaining sheds light on intergenerational dynamics in these conversations. We must find a better, more respectful, and effective way to communicate with our elders considering retiring. The phenomenon of grandsplaining can manifest in various contexts, not just financing retirement—whether it’s discussing technology, lifestyle choices, healthcare options, or even social norms. For instance, a grandchild might explain how to use a smartphone app to a grandparent, assuming that the older generation cannot understand it despite their own lifelong experience with technology in different forms. Communication Breakdown In an era where financial literacy and retirement planning are more crucial than ever, "grandsplaining" has become a significant barrier to effective communication between generations. Retirees often feel overwhelmed or dismissed when their relatives provide unsolicited advice, especially if it contradicts their wants or financial strategies. This can lead to a reluctance to engage in discussions about finances, creating a rift that undermines the potential for collaborative planning. When adult children dominate conversations with preconceived notions of financial management, it stifles the opportunity for seniors to express their feelings, share their knowledge, and collaborate on effective retirement strategies. The Generation Gap in Financial Understanding Adult children may rely on outdated financial paradigms that no longer apply to their elders' realities. The economic landscape has changed dramatically over the past few decades, with shifts in real estate markets, a lack of formal retirement plans, and longer life expectancies. This generational gap can lead to misguided advice that does not consider modern challenges such as retiring with debt, little or no pension income, or rising living costs. Emotional Strain and Family Tension When relatives impose their views, it can evoke frustration, resentment, or inadequacy in their elders. This dynamic can shift the conversation from one focused on financial empowerment to one steeped in emotional conflict and shame. Instead of fostering a supportive environment for discussing retirement goals, grandsplaining can create adversarial relationships where seniors feel belittled or pressured, further complicating an already sensitive topic. Erosion of Autonomy When relatives try to impose their methods or strategies, it can undermine the seniors’ independence, making them feel a lack of control over their finances. Financial decisions are deeply personal and often intertwined with individual circumstances, goals, and values. This loss of agency not only affects financial outcomes but can also impact the mental well-being of older adults, leading to feelings of incompetence or anxiety about their financial futures. The Context of Ageism The implications of ageism are particularly concerning in a rapidly changing world characterized by technological advancements and unprecedented changes in social norms. While younger generations may genuinely wish to assist their elders in navigating these changes, their actions can reinforce negative stereotypes rather than empower seniors. Grandsplaining highlights the generational divide, creating an "us versus them" mentality that hinders collaboration and mutual understanding. Grandsplaining is deeply intertwined with ageism, a pervasive societal attitude that discriminates against individuals based on their age. Ageism manifests in various forms, including stereotypes that depict older adults as technologically inept, resistant to change, or incapable of learning. These stereotypes can lead to the marginalization of seniors within families and communities. Not cool! When younger generations adopt a condescending tone, they inadvertently reinforce ageist stereotypes that portray older adults as out of touch or incapable. This affects individual relationships and perpetuates societal narratives devaluing older individuals' contributions and wisdom. The Impact on Relationships Grandsplaining can strain relationships between generations, fostering resentment and conflict. For many seniors, unsolicited advice can infringe on their autonomy, making them feel infantilized or disrespected. I've seen firsthand how parents can react defensively to younger family members and sometimes withdraw altogether from conversations. When assistance is delivered condescendingly, it can backfire. The resulting tension may prevent meaningful conversations about important topics, such as healthcare decisions or lifestyle changes, which are crucial for seniors' well-being. The Psychological Impact on Seniors Being on the receiving end of condescending advice can also lead to diminished self-esteem and increased feelings of inadequacy. Seniors may begin to internalize the belief that they are not capable of making sound decisions or understanding new concepts, which can further exacerbate issues related to aging, such as cognitive decline and depression. Encouraging Respectful Communication with Seniors Addressing the issue of grandsplaining requires a concerted effort from both younger and older generations to cultivate respectful communication. Here are several strategies to foster more positive intergenerational interactions: 1. Actively Listen: Younger people should prioritize active listening when engaging with seniors. This involves hearing what the older person says and validating their experiences and perspectives. Younger people can create a more respectful dialogue by acknowledging their knowledge and expertise. 2. Seek to Understand: Younger generations must approach conversations with empathy. To quote Stephen Covey's wise words, "Seek first to understand, then to be understood." Recognizing seniors' challenges, such as health issues or technological gaps, can foster a sense of compassion. This approach can help bridge the generational divide and promote more constructive conversations. 3. Avoid Assumptions: The tendency to assume that older adults are out of touch or incapable can lead to grandsplaining. Instead, younger individuals should avoid making assumptions about seniors’ knowledge or abilities. Asking questions like “What do you think about this?” or “How do you feel about that?” can empower seniors to share their insights and experiences. 4. Offer Support, Not Solutions: Ask questions like, “What does a successful retirement look like to you? How do you plan to finance your retirement? Do you want to stay in this home? Are you open to moving? If so, where? Do you have enough in savings? How can I support you in having an independent and dignified retirement”? 5. Understand the Bigger Picture: Don’t assume that the traditional strategies of downsizing, selling, renting, or moving in with family are reasonable solutions for your elder in today’s economic environment. These retirement strategies are problematic for today’s seniors. In most cases, downsizing only works financially if the retiree is willing to move to a smaller, more affordable community. Most seniors want to stay in their communities and not move away from family, friends, churches, or familiar shops and services. Selling, renting, or moving in with family requires the sale of their significant appreciating asset. Given today's longer life expectancies, it's not always a wise choice. 6. Humour: By skillfully using humour, you can turn potentially patronizing situations into moments of connection and shared joy, ensuring that conversations with elders remain meaningful, respectful and memorable. For example, you could start the conversation this way; "The last thing I want to do is give you advice. That would be ridiculous. You’re the wise sensei here—I’m just the clueless apprentice trying to save enough downpayment to buy a shoebox of a house." This approach humorously flips the script, poking fun at the presumptuousness of unsolicited advice while emphasizing the elder's experience and wisdom. People often feel judged or vulnerable when discussing finances or significant life changes. Humour shifts the dynamic, showing that you approach the conversation as an ally, not an adversary. For example: "Talking about budgets isn’t fun for anyone—I mean, who loves math? But it’s worth it if we can figure out how to turn this retirement conversation into Canada Day rather than Labour Day!" This playful approach lowers barriers, making the discussion feel collaborative rather than critical. Laughter fosters connection. Sharing a laugh creates a sense of camaraderie, making it easier for people to open up about sensitive topics. When elders feel that you’re not judging them but partnering with them—and can make them smile—they’re far more likely to trust your intentions and take your advice seriously. Humour invites the other person to join the conversation, breaking the ice and encouraging them to share their thoughts. It sets a tone that the conversation is a dialogue, not a lecture. Example: "You’ve been making great financial decisions for decades. I’m here to ensure we don’t accidentally end up with a basement full of K-tel Veg-O-Matics… unless that’s the plan?" This allows them to laugh, respond, and engage while respecting their autonomy. A word of caution. Humour is only effective when paired with genuine respect and sensitivity. Pay attention to your elder's reactions and adapt if they seem uncomfortable or unamused. The goal is to build rapport, not to win laughs at their expense. Using humour skillfully, you can turn potentially patronizing situations into moments of connection and shared joy, ensuring that conversations with elders are respectful and memorable. Before You Go Good financial planning thrives on clear communication, but grandsplaining tends to turn productive discussions into monologues that undermine elder autonomy and trigger emotional static. To create a more harmonious environment, families should swap their megaphones for listening ears and embrace a collaborative approach that respects seniors' wisdom and frames younger relatives’ financial theories as conversation starters, not TED Talks. After all, when it comes to navigating retirement planning, a little less "know-it-all" and a bit more "let’s figure it out together" can go a long way. Think of it as building a bridge, not a lecture podium—because nothing says "family unity" like tackling compound interest together! Don’t Retire…Re-Wire! Sue My Book is Now Available for Pre-Order I hope you will consider pre-ordering a copy of Your Retirement Reset for you, a friend or loved one. It's available September 8, 2026 published by ECW Press - You can now order at Indigo or Amazon. And if you love supporting Canadian booksellers, please also check with your local independent bookstore. Most can easily order it for you.

Jun 17, 2026

8 min

The Grace to Fail: My MBA Journey (Part 3)

I have a confession to make. My wife Bonnie and I are addicts. Not the kind that requires an intervention, exactly, but close. We are addicted to home improvement. We are always planning the next upgrade, the next project, the next thing to tear apart and make better. It gives us genuine pleasure and a profound sense of accomplishment. Bonnie leads most of these endeavours. She is remarkably capable with power tools and can pull off a tool belt like she is strutting down a Home Depot runway (aisle). Our shared obsession has even spawned a series of Facebook posts called the 2 Capable Women, where we document everything from felling trees to the deeply humbling art of Ikea assembly. So there we were, driving in traffic, and Bonnie was telling me about her next project: removing the circa-1960 wood panelling and replacing it with modern shiplap. Mid-conversation, she went quiet for a moment and said, almost to herself, “I guess I need to allow myself the grace to fail.” I nearly drove off the road. You must understand something about Bonnie. She is a self-declared perfectionist. Not casually. She is committed to being a perfectionist at being a perfectionist. So, hearing those words come out of her mouth, unprompted, while discussing a renovation project, was like hearing your accountant quote Oprah. It stopped me completely. The truth has a certain ring to it. I heard that bell loud and clear. Because sometimes wisdom does not arrive in a lecture hall or a leadership book or a TED talk. Sometimes it arrives in a car, in traffic, from the person sitting next to you holding a coffee and thinking about shiplap. That phrase has not left me since. Many of us do this. We replay mistakes endlessly, convinced that self-criticism is somehow productive. We lie awake revisiting conversations and missteps, assuming that if we beat ourselves up long enough, we will emerge wiser. All we accomplish is a thorough self-beating followed by self-flagellation. Lots of noise. Zero progress. Zero calories burned. This is not just a problem for people climbing mountains or starting businesses. It plays out in perfectly ordinary moments. You send an email and immediately wish you had worded it differently. You make a comment at dinner that lands wrong and spend three days replaying it. You make a small error at work and carry it around like luggage for a week. The inner courtroom convenes regardless. Most of us are not failing spectacularly. We are just living, occasionally getting things slightly wrong, and treating that as evidence of something deeply and permanently wrong with us. It is not. It is just Tuesday. I have been thinking about this a lot lately because I am in the middle of my MBA at the Sprott School of Business. I wrote about My MBA at age 69 in Part I and Part II. Back in graduate school after four decades in the workforce, opportunities to feel uncomfortable, uncertain, and occasionally like you have wandered into the wrong building are plentiful. A recent assignment on crafting Team Charters and enhancing my leadership skills inspired me to write a personal manifesto for my graduate studies and to take a closer look at myself. You can read mine here. While working through it, I made a surprising discovery. Most of the commitments I was making to myself had nothing to do with school. They were about life. Read the instructions carefully. Ask for help sooner. Pay attention to what your emotions are trying to tell you. Trust your experience. Hold yourself to your own standards. And this one, which stopped me cold, and sounded very familiar: Allow yourself the grace to fail. There was that bell again. Those six words turned out to be the most important thing I wrote. Not because failure is something to celebrate, but because the willingness to risk it is the price of admission for virtually everything worth doing. Failure is not a topic most of us rush toward. It is about as pleasant as stubbing your toe in the dark. Yet every meaningful thing I have ever done required me to risk it. Starting a new career. Leading a sales team. Launching a business. Climbing a mountain. Writing a book. Going back to school at 69. None of it came with guarantees. All of it came with uncertainty, mistakes, and moments where I genuinely wondered whether I had lost my mind. The jury is still out on some of those. The irony is that failure and growth are inseparable. Dweck (2006) found that people who view setbacks as learning opportunities rather than evidence of inadequacy are more likely to persevere and ultimately succeed. Duckworth (2016) agreed, and in Grit, one of my favourite books, long-term success depends less on talent and more on the willingness to keep going after things fall apart. Neff (2023) added that people who respond to failure with self-compassion rather than harsh self-judgment show greater improvement and are more likely to try again. The friction produced by failure is often exactly what generates learning, but only if we give ourselves enough grace to stay in the game. I see this everywhere. Professionals are staying in jobs they no longer enjoy because starting over feels too risky. Retirees hesitate to try something new because they might not be good at it right away. Students who will not ask a question because they do not want to appear uninformed. And if I am being honest, I see it in myself. Every time I hesitate to contribute to class because everyone else seems younger and sharper. Every time I catch myself wondering whether I belong in the room. One exercise has helped me enormously. When I catch myself spiralling into negative self-talk, I imagine my five-year-old self standing beside me, listening. Would that little girl feel encouraged? Not a chance. So why do we think inner dialogue helps us? A recent example: I made a point in a meeting that got a polite nod and complete silence. You know the silence. The one that could mean anything from “interesting” to “what on earth did she just say?” I replayed that moment for two days. Eventually, I asked a colleague how the meeting had gone, and she said she barely remembered it. The forensic investigation was conducted entirely in my own head. I am not suggesting we lower our standards. We should hold ourselves accountable, learn from our mistakes, and strive to do better. But there is a meaningful difference between accountability and cruelty. Between reflection and rumination. Between learning from a mistake, and building a summer cottage on top of it, and checking in every long weekend. I worry about what this means for the generation behind us. Research by Professor Gabriel Rubin at Montclair State University found that despite living in one of the safest periods in history, Gen Z perceives risk virtually everywhere (Rubin, 2023). They have grown up knowing that at any moment, someone has a phone. One stumble, one terrible dance move, and the clip is posted before you catch your breath. Permanent, searchable, shareable public failure is something entirely new, and the consequences are showing up in surprising places. Monocle magazine noted young people standing completely still on nightclub dance floors, phones in hand, unable to lose themselves to the music. The club has become a stage, and the crowd has become the content. Instead of dancing, people film. Instead of connection, there is performance. This is not a small thing. Dancing is how humans have always signalled availability, built trust, and found each other. It requires a willingness to look slightly absurd. If we have raised a generation so terrified of being captured mid-stumble that they will not move to the music, we have handed surveillance culture a victory it does not deserve. Calculated risks lead to new opportunities, foster innovation, and teach lessons that comfort never could (Rubin, 2023). Risk aversion makes short-term sense. As a way of life, it quietly closes doors that were never meant to stay shut. Give yourself and the young people around you, explicit permission to be unpolished in public. To dance badly. To say the wrong thing and survive it. The phone will always be there. So, fortunately, will the music. Here is what I keep learning inside this MBA: wisdom arrives disguised as failure. The assignments that challenge me teach me more than the ones that come easily. The questions I most resist asking are usually the most important. I did not expect graduate school to teach me this. Then again, I did not expect to be here at seventy. I no longer think in terms of Wins and Losses. Those categories are too simple. I think in terms of Wisdom and Learning. Success builds confidence. Setbacks build insight. Both move us forward. Read that again. So the next time you find yourself at two in the morning replaying something you said three days ago, ask whether your five-year-old self would find your internal monologue useful. If the answer is no, offer yourself a little grace. Which brings me back to Bonnie. Last weekend, she pulled off that 1960s panelling. Every last piece. It was messy and uncertain, and at several points she was unsure what she would find underneath. There were surprises. There were moments of doubt. She kept going anyway. By the end of the weekend, the shiplap was going up, clean and bright and exactly right. She did not do it perfectly. She did it anyway. And it is beautiful. That is the whole lesson, right there, delivered by a woman with a pry bar and a tool belt, on a weekend in June. Failure is not the enemy. Most of the time it is just fear wearing a funny hat. And if you are lucky, it will teach you something genuinely worth knowing. Sometimes it comes from a research paper. Sometimes it comes from your wife, in a car thinking out loud about shiplap. Either way, listen for the bell. Writing my manifesto was one of the most clarifying things I did this year. Not because it solved anything, but because it forced me to decide, on paper, who I was going to be when things got hard. I want that for you, too. So I created the ReWirement Manifesto: a simple template for anyone navigating a new chapter, a big transition, or simply a Tuesday that did not go as planned. It is not a bucket list. It is not a vision board. It is a set of honest commitments you make to yourself, in your own words, that you can return to when your inner courtroom calls you to order. Download your free ReWirement Manifesto template here. Fill it in. Keep it somewhere you can find it. And the next time you are staring at a wall of 1960s panelling, wondering if you are in over your head, remember: the grace to fail is not a consolation prize. It is the whole point. Don’t Retire…Re-Wire! Sue My Book is Now Available for Pre-Order I hope you will consider pre-ordering a copy of Your Retirement Reset for you, a friend or loved one. It's available September 8, 2026 published by ECW Press - You can now order at Indigo or Amazon. And if you love supporting Canadian booksellers, please also check with your local independent bookstore. Most can easily order it for you.

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