Why the Retirement Journey Metaphor Fails: Planning for Life's Unpredictable Moments Instead

Markets closed for Christmas – time for reflection, not trading

The quick scan: U.S. markets were closed Thursday for Christmas Day, giving traders a break after five consecutive winning sessions that pushed the S&P 500 to record highs. With markets shuttered, portfolios sat untouched while families gathered, presents were opened, and the relentless ticker finally paused.

What's happened so far this week: Through Tuesday's close, the S&P 500 had climbed to 6,932.05 (up 17% for 2025), the Dow reached 48,731.16, and the NASDAQ stood at 23,613.31. Gold hovered near record highs above $4,500 per ounce, while the VIX "fear gauge" remained near its lowest levels since last December, suggesting investor complacency heading into year-end.

Bottom line: Christmas offers a rare pause in the market's relentless rhythm – no gains to celebrate, no losses to worry about, just stillness. For L-Plate Retirees, this enforced break mirrors what we're exploring today: retirement isn't a smooth journey with predictable rest stops. It's a series of unpredictable moments, some peaceful like today, others requiring immediate action. The question isn't whether we can map the entire route – it's whether we're prepared for whichever moment comes next.

Life Doesn't Follow a Map

The scoop: There's a phrase retirement commentators love: the retirement journey. It sounds wise and comforting, suggesting a predictable path with clear milestones – perhaps you retire at 65, travel in your early 70s, slow down by 80, and gracefully coast into your sunset years.

It's also complete fiction.

A retirement expert in Australia recently confessed something refreshing: she's been using lazy language for years. The retirement journey metaphor, she now realizes, promises something most people will never actually experience – a logical, linear progression through predictable life stages.

Real retirement looks nothing like a journey. It's more like a mosaic of moments, some planned, most not. Health crises that force early exits from work. Relationships that end or begin unexpectedly. Jobs lost to retrenchment, found through necessity. Parents or partners who need care. Inheritances that arrive. Property that must be sold. Life, as John Lennon reminded us, is what happens when we're busy making other plans.

Consider three real examples from Australia. Ian, 68, was retrenched a year ago and has applied for countless jobs without success – possible ageism keeping his resume from the top of the pile. He's now taking odd jobs through his service club while his wife's income covers essentials. Their retirement plans? On indefinite hold.

Sarah, 58, felt on track to retire in a few years when a breast cancer diagnosis forced her to leave work much earlier than expected. She faces uncertain medical bills, an unclear prognosis, and no idea whether she can work again.

Rob, 75, was enjoying cycling trips and visiting kids overseas with his wife Heather until dementia changed everything. He's now a full-time carer, trying to understand aged care rules and make accommodation decisions. "What retirement?" he asks.

These aren't rare edge cases. Australian Bureau of Statistics data confirms that more than 20% of Australians leave their most recent job and retire due to health issues, retrenchment, or family circumstances beyond their control. The journey metaphor fails because it assumes control we simply don't have.

Why the journey metaphor persists

Since Australia's Retirement Income Review was published in 2020, superannuation funds have struggled with the Retirement Income Covenant – delivering better outcomes as members transition from accumulation to decumulation. One major barrier might be that the target is simply too overwhelming. Getting ordinary Australians to look at their super savings and engage with how it will provide support over a hoped-for 30-year retirement feels paralyzing.

What if we approached financial planning differently? By breaking it down into manageable moments rather than comprehensive decades-long plans?

Consider six common life events: health issues, relationships ending or beginning, losing or finding work, family wealth transfers, unexpected windfalls, and property decisions. At what age does each occur? Apart from empty-nesting, every one of these retirement-defining moments can happen anywhere between 16 and 99. There's no useful median age. Yet there are specific rules and strategies that maximize income when these situations arise.

The assumption that life-changing moments will conveniently arrive at ages 60, 67, 70, or 75 – specific retirement trigger ages – is fantasy. But the need for information and support to manage these big money moments is massive.

Reframing the conversation

A moment-based framework could transform how funds, advisers, and retirees approach later life. Instead of insisting on comprehensive 30-year plans that feel daunting and disconnected, what if we offered responsive support for the situations people actually face?

First principle: just because you can do something at a certain age doesn't mean you should. Downsizer contributions become available at 55, super access at 60 – but these are triggers, not mandates. Rules create opportunities to use when timing suits your circumstances, not obligations to act immediately.

Second insight: retirement is no longer "a thing." We don't treat our first three decades as one monolithic phase. We differentiate between childhood, adolescence, and young adulthood, respecting the huge differences in needs and experiences. Later life deserves the same nuance. The needs of someone at 60 differ dramatically from someone at 90, yet we lump them together as "retirees."

Third realization: retirees don't need to know everything to get started. There's no requirement to understand the entire superannuation system – just the bits relevant to their current moment. Which rules apply right now? How do things change if certain events occur? This creates more relevant, less overwhelming conversations.

What packages might look like

Industry participants could offer clusters of support around changing needs: relationship status shifts, health dynamics, work transitions, inheritances, family loans, property decisions. Instead of comprehensive "whole of life" plans that feel too vast, retirees could engage with packages that address their specific moment.

This approach suits emerging hybrid advice models perfectly. Digital tools combined with adviser support could create responsive packages containing just the rules that matter for people facing specific life dilemmas.

Does this suggest a shakeup for comprehensive financial advice? Certainly. But perhaps that's necessary. Engagement remains an ongoing challenge, possibly because we've asked retirees to commit to full 30-year plans when five-year models suit their circumstances and temperament better.

The snakes and ladders reality

Life in later years resembles a game of snakes and ladders more than a journey. We rise. We fall – sometimes dramatically. Hopefully we rise again, finances intact and definitely wiser. This isn't pessimism; it's realism that enables better preparation.

When we stop pretending retirement follows a predictable path, we can focus on what actually helps: building flexibility into plans, understanding rules that apply to common life moments, and creating support systems that respond to circumstances rather than age milestones.

The woman who recently admitted her "ah ha" moment about retirement language wasn't rejecting planning. She was recognizing that the most useful planning acknowledges unpredictability. It's not about mapping every year from 60 to 90. It's about being ready for the moments that matter – the ones you can't see coming but will need to navigate when they arrive.

Retirement isn't a journey. It's a series of nows, each requiring different knowledge, different strategies, different support. The question isn't whether you can envision three decades ahead. It's whether you're prepared for whatever this particular moment requires.

Actionable takeaways for L-Plate Retirees:

• Stop planning for an entire 30-year retirement at once. Break retirement into manageable five-year segments or life moments (health changes, work transitions, relationship shifts). This makes planning less overwhelming and more relevant to your current circumstances.

• Understand that age-based triggers aren't mandates. Just because you can access super at 60 or make downsizer contributions at 55 doesn't mean you should. These are opportunities to use when timing suits your situation, not obligations requiring immediate action.

• Focus on rules relevant to your current moment, not the entire system. You don't need to master all superannuation, tax, and pension rules. Identify which specific rules apply to your situation right now, then learn what changes if certain common events occur.

• Consider "moment-based" advice packages instead of comprehensive plans. Look for advisers or services offering targeted support for specific life events – relationship changes, health transitions, work shifts, inheritances, or property decisions – rather than insisting you need a complete decades-long strategy.

• Build flexibility into whatever plans you do make. Rigid long-term plans often fail when life throws unexpected moments at you. Create strategies that can adapt when health, relationships, work, or family circumstances change suddenly.

• Accept that retirement is more snakes and ladders than linear journey. You'll rise, fall, and hopefully rise again. Finances that acknowledge this unpredictability – through emergency buffers, diversified income sources, and contingency planning – serve you better than perfect roadmaps for decades ahead.

Your Turn:
Looking at the past five years, which unexpected "life moment" most significantly changed your retirement trajectory or planning?
If you could access advice packages for just one specific life situation (health crisis, relationship change, work transition, inheritance, or property decision), which would give you most peace of mind right now?
Does planning for a full 30-year retirement feel empowering or overwhelming to you – and if overwhelming, what smaller time frame would feel more manageable?

👉 Hit reply and share your thoughts – your answers could inspire fellow readers in future issues.

If this moment-based approach to retirement planning resonates with you, consider supporting L-Plate Retiree on Ko-fi. Your contribution helps us keep challenging conventional wisdom and exploring the messy reality of retirement as it's actually lived – not as glossy brochures pretend it unfolds.