8 Questions to Ask Before You Retire (Most People Skip Half of Them)

Oil fell, yields eased, and the Dow surged to a record as investors rotated out of tech and into almost everything else.

The quick scan: Thursday was the mirror image of Wednesday. Where Wednesday's Iran escalation drove oil higher and crushed equities, Thursday's Israel-Lebanon ceasefire agreement sent oil lower, eased bond yields, and triggered a broad rotation away from technology into banks, small-caps, and consumer stocks. The Dow surged to a record close. The S&P 500 extended its winning streak. The NASDAQ was the lone decliner as chip stocks continued digesting Broadcom's disappointing guidance.

S&P 500: +0.41%, to 7,584.31 – A tenth consecutive weekly gain now in sight; the longest such streak since 1985 if Friday's jobs report doesn't derail it
Dow Jones: +1.73%, to 51,561.93 – The standout of the session; financials, industrials, and consumer names all gained as oil's retreat reduced inflation fears. Lululemon fell 10% after cutting its full-year guidance
NASDAQ: -0.09%, to 26,830.96 – Essentially flat but fractionally negative; Broadcom continued unwinding after its after-hours guidance disappointment on Wednesday.

What's driving it: Two things moved simultaneously. The Israel-Lebanon ceasefire – separate from the US-Iran conflict but meaningful for regional stability – sent oil sharply lower, relieving the inflation pressure that has weighed on bond yields all week. Lower yields lifted rate-sensitive sectors: banks, real estate, small-caps. The Russell 2000 gained more than 1%. At the same time, the AI-driven chip trade paused: Broadcom's below-expectation Q3 AI chip revenue outlook reminded investors that even within the strongest thematic trade of the year, individual results matter. Ahead of Friday's May nonfarm payrolls – forecast at 85,000 to 100,000 – some of Thursday's gains may represent positioning rather than conviction.

Bottom line: The session's rotation – from tech to everything else – is a healthy signal for a bull market that has been uncomfortably narrow. When gains spread to banks, small-caps, and industrials, the rally has broader economic support. For L-Plate Retirees, Friday's jobs report is the week's final data point: a strong number is good news for the economy but may revive rate-hike talk; a weak number eases inflation concerns but raises recession fears. Either way, ten straight weeks of S&P 500 gains is the context in which both outcomes land.

Are You Actually Ready to Retire? The Checklist Most People Never Complete

The scoop: Here's a finding worth leading with.

Research from Age Wave and Merrill Lynch found that, of all the periods in a human life, we are happiest and most content between the ages of 65 and 74. Not childhood. Not the peak career years. Not the years when money was flowing in and life felt full of possibility.

The numbers are striking. Only 51% of people aged 25 to 34 say they often feel happy, compared to 76% of people aged 65 to 74. Contentment: 47% for the young, 71% for the retired. Feeling relaxed: 41% in your late twenties, 71% in your late sixties. Anxiety? It afflicts 37% of the 25 to 34 cohort. Only 12% of 65 to 74 year olds say the same.

The typical framing of retirement is one of loss – of income, of identity, of structure, of purpose. The data suggests something rather different: for most people who get the transition right, retirement is the best chapter of their life.

The operative phrase is "get the transition right." A separate study from the Employee Benefit Research Institute found that the percentage of retirees describing retirement as "very satisfying" dropped from 60.5% to 48.6% over a 15-year period. Experts suspect the culprit is either difficult financial situations or lack of direction and purpose. Both are solvable problems. Both require planning.

Here are eight questions that separate the people who run toward retirement from those who limp into it.

1. What will you actually do?

This is the question financial planning consistently underserves.

"Even if you're financially set to retire, you're now going to have many years ahead – especially if you're in your 50s or 60s," says Scott Draper, a certified financial planner at Thrive Financial Planning. "What is this next stage in your life going to be about?"

The retirees who are happiest tend to have a passion to pursue or a specific purpose in their life. Not necessarily a grand second act – it might be a regular volunteer commitment, a creative practice, a sporting pursuit, or simply seeing more of the grandchildren. What matters is that the answer to "what do I do today?" is already there when retirement begins, rather than something to work out afterward.

"Retirement is a great time to revisit old hobbies and dreams," says Kate Holmes, founder at Belmore Financial. Some of those passions might even generate income – more and more retirees pursue new careers or encore roles in retirement, on their own terms.

2. Do you have a daily routine?

This is the question that surprises people most.

Before retirement, structure is imposed: work starts at a certain time, meetings happen on a schedule, the week has a shape. After retirement, all of that disappears at once, leaving what might initially feel like freedom but can, without intention, quietly become aimlessness.

According to Northwestern Medicine, routines help people sleep better, reduce stress, use their time more wisely, and make daily life feel more purposeful. Successful retirees have a plan for their days – a regular commitment, a recurring social engagement, a physical routine. What that looks like matters less than its existence.

The practical exercise: before you retire, sketch out what a typical Tuesday looks like in your new life. Not the holiday version. A regular week. If the answer is vague, it's worth making it more specific before the transition begins.

3. Who is in your social support network?

This is the one people are most likely to underestimate.

Work colleagues may inspire a love-hate relationship, but they are almost certainly a significant source of daily social interaction. They provide stimulation, connection, perspective, and the simple experience of being in the world with other people on a shared endeavour.

After retirement, that source disappears overnight. And building a social network from scratch – particularly for people whose social life has been largely structured around work – is harder than it looks. The retirees who handle this best are the ones who have begun building those connections before they need them: community groups, sporting clubs, volunteer organisations, continuing education, faith communities.

4. Do you have a written retirement plan?

Not a savings target. A plan.

A plan covers what you'll spend – both monthly and the occasional large one-off – and where it will come from. It models healthcare costs explicitly, which are one of the largest and most volatile expenses in retirement. It addresses withdrawal sequencing and Required Minimum Distributions. It considers passive income, part-time work, and what happens to the portfolio if markets deliver a poor sequence of early returns.

And it accounts for what could go wrong: a bad market in the first years of retirement, an unexpected healthcare event, a family member who needs financial support.

The gap between having a savings balance and having an actual plan is considerable. Most people have the former and consider themselves prepared. The latter is what produces the financial confidence that shows up in the happiness statistics.

5. Have you considered the family dimension?

A retirement plan rarely affects only one person, but too often it's built as though it does.

A spouse is the obvious consideration. Their income timeline, their health, their own retirement plans, and the shape of shared life in retirement all require explicit discussion. The research on couples in retirement is clear: the transition goes better when it's been talked about in advance, including the parts that feel awkward.

Beyond a spouse, parents who are still living may need care and financial support. Adult children may return to the nest or need help. And the financial gifts most people give to family – supporting a child's house deposit, helping with education costs – need to be built into the plan rather than improvised against retirement savings.

6. Where do you want to live?

Housing is typically the largest single cost and the largest single asset in retirement. The decision about where to live is therefore not just a lifestyle choice – it's a significant financial lever.

Downsizing from a large family home to something smaller can release equity, reduce ongoing costs, and simplify daily life. This newsletter's weekend musing last week described exactly this process – the sell-down of 160 square metres of accumulated life in preparation for a 50 square metre apartment, though not for retirement. The practical and psychological dimensions of that decision are both real.

Could reducing your housing cost bring retirement forward? Could releasing home equity reduce the pressure on your investment portfolio? These are worth modelling before the housing decision is made emotionally rather than financially.

7. What will give your life meaning and purpose?

This question has research behind it that most people don't know about.

Oxford University found that people with a sense of purpose have a 15% lower risk of death compared to those who describe themselves as aimless – and critically, it doesn't matter when that purpose was found. It could be in a person's 20s, 50s, or 70s. The effect is consistent regardless of age, gender, or other wellbeing factors.

Purpose doesn't require a grand calling. It requires something that makes you feel that what you do matters and that you are needed. Volunteering, mentoring, creative work, community involvement, continued learning – any of these can carry the weight. The question is whether you've identified yours before the working life that has been providing it comes to an end.

8. Do you need support or a second opinion?

The things that go wrong in retirement – according to financial advisers – tend not to be investment selection or market timing. They are: lacking a solid financial goal, procrastination, ignoring tax strategies, and not knowing how to turn savings into reliable income.

All four of those are addressable with the right guidance. A financial adviser can stress-test your plan, identify the optimisation opportunities you're missing, and give you the kind of confidence in your numbers that makes the rest of the transition easier. The investment in getting it right at the start is almost always smaller than the cost of getting it wrong.

The broader point

The research says retirement is the best period of most people's lives. Not for everyone – the satisfaction figures have declined, and the reasons are known. But the structure for a happy retirement is not mysterious. Purpose, routine, social connection, financial clarity, and honest planning around the things that could go wrong.

None of those require extraordinary circumstances or unusual resources. They require intention, applied before the transition rather than after.

Actionable Takeaways for L-Plate Retirees:

• Answer the "what will you do?" question before you retire, not after. The financial question is necessary but not sufficient. The retirees who are most satisfied have a clear answer to how their time will be spent – specific activities, roles, commitments – before the working life that structured their days comes to an end.

• Sketch out a regular retirement week, not just the highlight reel. Plan a typical Tuesday. If the answer to "what do I do?" is vague, make it more specific. The routine that supports sleep, reduces stress, and makes daily life purposeful doesn't build itself.

• Start building your post-work social network before you need it. The work-based social network disappears overnight at retirement. Begin building community connections – volunteering, clubs, continuing education, faith communities – before those work connections end. Social capital takes time to develop.

• Write the plan, not just the savings number. A plan covers spending, healthcare, withdrawal sequencing, inflation, family obligations, and what happens if markets are poor in the first few years of drawdown. A savings balance is not a plan.

• Consider housing as a financial lever, not just a lifestyle choice. Downsizing, releasing equity, or reducing ongoing housing costs can change the retirement date and the portfolio pressure significantly. Model it explicitly before making the decision emotionally.

• Identify your source of purpose before you leave work. Oxford research shows that purpose reduces mortality risk by 15%, regardless of when it's found. The question isn't whether you need it – you do – but whether you've identified what form it takes for you.

Your Turn:
Of the eight questions, which one are you most confident you have answered well – and which one gives you the most pause when you think honestly about where you are?
The statistic that only 12% of people aged 65 to 74 experience frequent anxiety, compared to 37% of people in their late twenties, is striking. Does that match what you've observed in the retired people you know well?
The article suggests the two biggest causes of retirement dissatisfaction are financial difficulty and lack of purpose. If you're honest with yourself, which of those is the more live risk for you – and what's the most useful thing you could do about it in the next twelve months?

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

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