10 min
Retirement Maxxing: How Small Decisions Help You Build a Better Future
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. Want more insights like this? Subscribe to my free newsletter here, where I share practical strategies, real-world stories, and straight talk about navigating retirement with confidence—not confusion. Plus, all subscribers get exclusive early access to advance chapters from my upcoming book. For Canadians 55+: Get actionable advice on making your home equity work for you, understanding your options, and living retirement on your terms. For Mortgage Brokers and Financial Professionals: Learn how to become the trusted advisor your 55+ clients desperately need (and will refer to everyone they know). This isn't just another revenue stream—it's your opportunity to build lasting relationships in Canada's fastest-growing demographic.
