The Case for Pretirement: Test Retirement While You Still Have a Salary

Market Mood

Oil hits $100, markets hit the floor – Iran's new Supreme Leader vows Strait stays shut, and three straight days of red

The quick scan: U.S. markets suffered their third consecutive day of losses as Brent crude oil settled above $100 per barrel for the first time since the Iran conflict began. Iran's new Supreme Leader, Mojtaba Khamenei, declared the Strait of Hormuz will remain closed as a "tool to pressure the enemy," obliterating any hope of near-term resolution. The IEA's record 400 million barrel emergency release – more than double the amount released after Russia invaded Ukraine – was met with a collective market shrug. Energy stocks were the lone bright spot in an otherwise brutal session.

S&P 500: -1.52% to 6,672.62 – The index fell to its lowest level since November, breaking through technical support levels that had held since late 2025
Dow Jones: -1.56% to 46,677.85 – Goldman Sachs (-4.47%), Boeing (-4.29%), and 3M (-3.91%) led the carnage as financial and industrial stocks bore the brunt of inflation fears
NASDAQ: -1.78% to 22,311.98 – The tech-heavy index had the worst day among major indices, though Oracle provided a rare bright spot earlier with strong cloud infrastructure earnings.

What's driving it: Brent crude settling above $100 per barrel reignited sticky inflation fears and forced traders to price out any near-term Federal Reserve rate cuts. Over 72% of U.S. stocks declined, with losses concentrated in industrials, discretionary, and technology. Airlines were hammered – Southwest dropped 7%, United and American both fell over 4% as fuel costs surge. Morgan Stanley shares sank 4.1% after capping withdrawals from private credit funds, adding financial stress to energy anxiety. Meanwhile, Stryker confirmed a cyberattack from pro-Iranian hackers (the Handala group), sending cybersecurity stocks like CrowdStrike and Palo Alto Networks higher. Energy Secretary Chris Wright confirmed the Navy isn't ready to escort tankers through the Strait yet: "All our military assets are focused on destroying Iran's offensive capabilities."

Bottom line: Three straight down days, oil above $100, and Iran's leader saying the Strait stays shut – this isn't temporary volatility, it's a fundamental repricing of inflation risk. If you've been waiting to rebalance into energy positions or defensive sectors like utilities (which held up today), the message is getting clearer: until the Strait reopens, oil pressure isn't going away. The Fed meeting next week just became far more complicated.

"Pretirement": The Sabbatical That Shows You If Retirement Will Actually Work

The scoop: In Singapore, retirement is treated as a destination – a fixed date at 65 when the "doing" ends and the "being" begins. You save, invest, and wait for the clock to run out.

But the modern economy doesn't follow that script. For many, retirement won't be a choice made at 65 – it will be forced upon you much earlier from market fragmentation, digital upheaval, or an industry deciding you're redundant before you feel finished.

Jason Leow, writing in the Business Times, saw this coming in 2009 when he left journalism. He imagined himself in his 50s, laid off because the industry couldn't navigate digital disruption, being told he had "only ever been a reporter."

His response? Build his own social safety net while still employed – train as a psychotherapist, qualify as an executive coach (PCC-accredited with the International Coaching Federation), launch side businesses while holding corporate roles at Shell, GIC, and consulting firms.

But the breakthrough came from what Leow calls "pretirement" – taking a sabbatical to test whether retirement actually works before you're forced into it permanently.

"A spreadsheet cannot simulate the anxiety of a Tuesday morning with nowhere to go," he writes.

The Risk No One Talks About

The hardest truth about retirement isn't running out of money – it's being forced out before you're ready, financially or psychologically.

Market shifts, technological disruption, corporate restructuring – the economy often decides you're done before you feel finished. Without a trust fund or welfare state to cushion the blow, you need your own plan.

Leow's approach: skill up in something evergreen. "I reckon psychotherapy and coaching will always be needed because human communication cannot be replaced by automation." These weren't hobbies – they were "essential experiments in resilience."

The strategy: trial small businesses while you still have salary to cushion failures, just to see which one sticks. Not as retirement fantasies, but as actual income-generating options.

Most people don't do this. They treat retirement as a financial exercise – calculating burn rates, projecting withdrawals, optimizing asset allocation. All necessary, none sufficient. Because retirement isn't just a math problem – it's an identity crisis waiting to happen.

The Pretirement Experiment

Leow advocates for "short pretirement" – a sabbatical to test reality if you can afford one. It's the only way to know if you can lean on your side business for income and whether you're ready for the professional engine to stop.

During his own pretirement, he confronted uncomfortable truths. He still valued the reach of business with scale and visibility, liked having a platform to write and influence. While possible independently, a corporate role offered more leverage – at least for now.

That required what Leow calls "a technical audit of the self" – introspection many dismiss as navel-gazing. But without it, you risk severe psychological disconnect when the professional engine slows.

He's increasingly bothered by the "trendoid" phase of purpose-seeking that keeps telling people to "be, not do."

"No, sir. I am happy doing. I am happy being busy. As long as I enjoy the work, that is purpose."

If a role provides scale and keeps him busy, that's a successful outcome – a data point, not a moral failing.

Prepare, Not Predict

Leow's biggest lesson came from his time at GIC, Singapore's sovereign wealth fund: prepare, not predict.

GIC doesn't waste time trying to predict the exact moment of market shifts. It prepares portfolios to survive them. The same philosophy should apply to retirement.

"Retirement is a phase we have to invest in by preparing well for it," Leow writes. "It is not something that just happens because we are getting too old for the economy. It is a strategic pivot we execute because we have already built the ground we intend to stand on."

If you refuse to know yourself – honestly and literally – you'll be miserable when that pivot is forced upon you.

The Desktop vs. The Real Thing

Desktop exercises for retirement – running scenarios, stress-testing withdrawals, modeling longevity risk – are useful but incomplete. A spreadsheet shows whether your money will last, not whether you'll be okay when Tuesday morning arrives with nowhere to go.

Pretirement – even a few months – reveals what spreadsheets can't. Do you enjoy the freedom or feel untethered? Does the side business generate viable income? Do you miss the corporate platform? Can you structure days without external demands? These require lived experience, not intellectual answers.

What "Prepare, Not Predict" Actually Means

You can't predict when your industry implodes, your role gets eliminated, or health forces early exit. What you can do is prepare multiple options so when the shift comes, you're not starting from zero.

Build evergreen skills that can't be automated. Trial businesses while you have salary stability. Take sabbaticals to test whether your plan works in practice. Conduct brutal self-audits about what you actually need versus assume you need.

Most importantly: know whether you're wired for "doing" or genuinely want to stop. The trendy narrative about slowing down might be terrible advice for people who thrive on activity.

Retirement forced upon someone who loves working but hasn't prepared alternatives is a disaster. Retirement forced upon someone who's built multiple options is just another transition. The difference is preparation, not luck.

Actionable takeaways for L-Plate Retirees:

• Trial your side business while you still have a salary, not after you retire. Leow launched psychotherapy and coaching practices while holding corporate roles at Shell, GIC, and consulting firms – treating them as "essential experiments in resilience" to see which would stick. Starting from scratch after retirement, without income cushion and with skills untested, is high-risk. Test while you have financial safety.

• Take a pretirement sabbatical if financially feasible – even 3–6 months reveals critical truths. A spreadsheet can't simulate the anxiety of Tuesday mornings with nowhere to go. Short sabbaticals expose whether you can actually lean on side income, whether you're psychologically ready for the professional engine to stop, and whether freedom feels liberating or untethering. These aren't hypotheticals you can answer intellectually.

• Conduct a technical audit of yourself: do you actually want to stop "doing"? The trendy narrative about slowing down and "being instead of doing" might be terrible advice if you're wired for activity. Leow realized he's happy being busy and values having a platform for scale – that's purpose for him. Know whether you're someone who thrives on engagement or genuinely wants to wind down, because forcing the wrong model on yourself guarantees misery.

• Build skills in areas that can't be automated – human interaction remains evergreen. Leow chose psychotherapy and coaching specifically because "human communication cannot be replaced by automation." As industries digitize and AI disrupts knowledge work, focus on capabilities that require human judgment, empathy, nuance, or relationship-building. These create portable income options that survive technological shifts.

• Apply GIC's investment philosophy to your retirement: prepare, not predict. You can't predict when your industry collapses, role gets eliminated, or health forces early exit. Preparing means building ground to stand on before the pivot is forced – multiple income options, tested skills, psychological readiness. Predicting the exact timing is impossible and wastes energy. Preparation makes the timing irrelevant.

• Be honest about what you'll actually miss from corporate life – platform, scale, visibility matter. Leow realized during pretirement that he still valued the reach of established organizations versus running small independent practices. Many retirees underestimate how much they'll miss the infrastructure, resources, network, and visibility that corporate roles provide. If you need those things psychologically, plan for ways to access them outside full-time employment rather than pretending you won't care.

Your Turn

If you could take a 6-month sabbatical right now to test whether your retirement plan actually works in practice, what would scare you most about trying it – and does that fear tell you something important about whether you're actually ready to retire? When you imagine Tuesday mornings with no meetings, no deadlines, and no external structure demanding your attention, does that vision feel liberating or anxiety-inducing? If the "be, not do" retirement narrative feels wrong for you but everyone around you insists slowing down is the goal, how do you build a retirement that honors your need to stay busy and engaged without apologizing for it?

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

If this exploration of "pretirement" – testing retirement while you still have income – helped you think differently about preparing for forced exits versus waiting passively for age 65, consider supporting L-Plate Retiree on Ko-fi. Translating one person's strategic approach into broader lessons without making sabbaticals sound mandatory for everyone requires balancing aspiration with reality.