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

Sue Pimento

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

Sue Pimento

Founder | CEO

Focused on financial literacy and retirement strategies. Authoring new book on home equity strategies to help seniors find financial freedom

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Music, audiobooks, a class, a museum habit, a book club, anything that keeps your mind taxed in a good way and makes you feel curious again. Make "don't stand still" a rule. If you're avoiding something because you might look silly (a dance class, a new hobby, a new friend group), that's exactly the place to lean in, gently, but on purpose. Super Agers aren't chasing youth. (No one needs to see me in low-rise jeans again.) They're cultivating engagement. (Do you want to dance?) They move. They learn. They sleep well. They stay positive. They accept what is. They remain connected. They rely on the belt and suspenders. And most importantly, they don't wait for permission to live life to the fullest at any age. Yes, biology will win eventually. None of us gets out of this alive. But the real victory isn't in defeating what we can't control. It's in mastering what we can, for as long as we can, and living fully right up until biology takes its final bow. Don't Retire...ReWire! Sue Want more of this? Subscribe for weekly doses of retirement reality—no golf-cart clichés, no sunset stock photos, just straight talk about staying Hip, Fit & Financially Free.

6 min

Carney Cares. The Tax Code Doesn’t.

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Before making any financial or tax decisions, consult a qualified professional familiar with seniors' benefits, including GIS, OAS, CPP, and related clawbacks. Now that we've cleared that up, let's talk… Here’s a quick overview of what was announced. What the Canada Groceries & Essentials Benefit Program Covers Bigger Benefit Cheques: About 12 million Canadians will receive relief. Food Bank Relief: $20 million to food banks through the Local Food Infrastructure Fund. Food Supply: Immediate expensing for greenhouse buildings to bolster domestic production. Food Security: A national strategy including unit price labelling and enforcement by the Competition Bureau. Business Support: $500 million in supply chain support to help businesses absorb costs rather than passing them on to consumers. These ideas aren’t bad. Some are very sensible. Taken together, the Government estimates in its announcement that these measures would "provide up to an additional $402 to a single individual without children, $527 to a couple, and $805 to a couple with two children. They go on to say that at these levels, Canada’s new government will be offsetting grocery cost increases beyond overall inflation since the pandemic." On paper, this looks helpful. Unfortunately, paper has never had to buy groceries. But… You knew there was a “but” coming. Government announcements are legally required to include one. A Little-Known Tax Reality That Makes You Shake Your Head New research shows Canada's tax-and-benefit system disadvantages low-income seniors who work. The issue? It's hidden in the tax code. On January 28, 2026, a Zoomer Radio Fight Back discussion hosted by Libby Znaimer highlighted the issue. Guests included: • Gabriel Giguère, Senior Policy Analyst, Montreal Economic Institute • Jamie Golombek, Managing Director, Tax & Estate Planning, CIBC Financial Planning & Advice Their conclusion? Canada's tax system discourages low-income seniors from working exactly when they need income the most. Many seniors discover (usually the hard way) that a small side hustle doesn't always pay off. It can lead to higher taxes and benefit clawbacks. Work a little more, and Ottawa takes a lot more. Why Seniors Are Still Working Because the math doesn't add up. Either way. More than 600,000 older adults live below the poverty line. Meanwhile, rent, food, utilities, insurance, and property taxes are increasing faster than pensions ever did. More seniors are employed, particularly GIS recipients. MEI analysis indicates that GIS recipients with work income increased by 56% from 2014 to 2022, rising to 64% among those aged 65–69. These seniors aren't working for "fun money." They're working to keep the lights on and purchase medication. Reviewing the details reminded me of a long-standing issue in my research on income and cash flow for Canadians aged 55 and over.  Many Canadians can’t make ends meet and are forced to work well past 65. Yet Canada’s tax system punishes low-income seniors for working—exactly when they need income most. To understand why, we need to look at the Guaranteed Income Supplement. The Guaranteed Income Supplement (GIS) Program for Low-Income Seniors Here's how the GIS benefits work: • A non-taxable monthly benefit on top of Old Age Security for low-income seniors. • Roughly one-third of OAS recipients also receive GIS—over 2 million Canadians. • For a single senior with no other income, the maximum annual benefit is about $13,000. (Source: Government of Canada GIS website) The program has done meaningful work. Combined with OAS, CPP, and private pensions, Canada dramatically reduced senior poverty over the past half-century. But there’s a catch hiding in the design. Think of GIS as a hug that tightens when you try to stand up. The GIS Clawback Problem for Canadians GIS recipients can earn only $5,000 per year in employment income before clawbacks begin. After that, GIS takes back 50 cents of every dollar earned—before income tax and payroll deductions. A partial exemption applies to the next $10,000, where 25–37.5% is clawed back. The program helps seniors—right up until they try to help themselves. How the GIS Clawback Works Against Working Seniors Let me illustrate this. Meet Agnes.  She is about to learn more about marginal tax rates than any bookstore employee should.  Agnes is between 65 and 69 years old, lives alone, and receives OAS and CPP. Rising costs push her to take a job at a local used bookstore. She works about 15 hours a week at roughly minimum wage. Here annual gross employment income is about $13,000 Here’s what happens: • Her employment income triggers GIS clawbacks once she exceeds $5,000. • She pays income tax, CPP contributions, and sometimes EI premiums. • Between taxes and clawbacks, much of her earnings disappear. Simple version: Agnes works more hours but keeps far less than expected. When you keep 20 cents on the dollar, even capitalism looks confused. Agnes didn’t go back to work for the thrill of alphabetizing mystery novels. She did it to afford her prescriptions. A Canadian Tax System That Punishes the Wrong Thing If we’re going to test income, test investment income. Fine. Tax it. But employment income? Showing up? Working? The system treats that like misconduct. Once you add income tax, CPP contributions, and the loss of other credits, low-income seniors can face effective marginal tax rates of 70–80% on modest earnings. Nothing says “fairness” like taxing a bookstore clerk harder than a boardroom executive. As Gabriel Giguère of the Montreal Economic Institute has noted, "this level of taxation normally applies to wealthy Canadians—not seniors living in poverty."  In a well-researched economic brief, Giguère and Jason Dean, Assistant Professor of Economics at King’s University College at Western Ontario, present a compelling argument for policy change.   This comment by Giguère and Dean nicely sums up their key findings:   "For various reasons, including insufficient pensions to maintain their living standards, seniors are increasingly turning to work. Yet the current tax-and-benefit system merits reform as it undermines their efforts, with the harshest effect on low-income seniors." One-Time Credits Don’t Fix Structural Problems At Davos, Mark Carney famously said, “Nostalgia is not a strategy.” Fair point.  So why does our benefit system still behave as if retirement lasts ten years and ends with a gold watch? The system still thinks retirement lasts ten years and includes a gold watch. People are living longer. Many will spend 25 to 30 years in retirement. Some want to work. Many need to. A grocery credit helps. But a broken incentive structure still breaks people. Common Sense Tax Solutions the Canadian Government Should Consider 1. Raise the GIS earnings exemption The Montreal Economic Institute recommends raising it to around $30,000. Estimated cost: $544 million annually. Modest relative to the program’s size. 2. Exempt employment income from GIS clawbacks (at least partially) Keep testing investment income. Stop penalizing work. 3. Rethink retirement assumptions Policy built around “retire at 65 and earn almost nothing” no longer matches reality. None of these ideas are radical. They’re just… current. What to Ask Your Accountant About Your Tax Rate Get professional advice. Not generic advice. Not from Google. Not from your unemployed nephew. Ask specifically about: • Pension income splitting • Strategic RRSP contributions • Consulting or corporate structures where appropriate • Creative but compliant barter arrangements • CPP and OAS deferral strategies • Documentation. Lots of documentation. When clawbacks are involved, paperwork is your lifeboat. A Short, Honest Take Grocery relief is appreciated. The intent is good. But until Canada fixes a tax system that punishes low-income seniors for working, affordability will remain fragile. This isn’t about blame. It’s about aligning incentives with reality. Right now, it feels like we’re helping seniors swim by handing them bigger life jackets—while quietly drilling holes in the boat. And yes… I need to lie down. I feel another blog coming on. Apparently, exercising this much common sense counts as cardio. Sue Don't Retire...Re-Wire! Want more of this? 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