How to Retire Better, From Retirees Who Learned the Hard Way

Thousands of Americans retire every day short on cash, friendships and plans.

Many retirees say they realised too late how they could have prepared for a more financially secure and rewarding postwork life. They would have focused on saving more money to cover the higher cost of living. Or they would have put more time into building relationships, taking better care of their health or cultivating new pursuits.

One reason retirement is so hard to prepare for is we often lack models of postwork life to emulate, retirees and financial advisers say. Though our culture is awash with images of professional success, we are a little hazier on what retirement success looks like and what it takes to achieve.

To sharpen that picture, we asked retirees about what they would do differently if given a second chance. Their regrets offer insights that can help people think and plan better at every life stage.

“Regret makes us feel bad, but it can help us do better,” said Daniel Pink, who researched people’s relationships to regret across a range of areas for his book “The Power of Regret.”

Here are three lessons retirees say they wish they had known sooner.

Investing for retirement means more than money

Jim Pilzner, a retired entrepreneur, regrets not setting goals for himself when he retired about four years ago. Now 78, he found there is only so much golf to play and only so many lunches to go to.

“I would counsel my younger self, and any other active, achieving person to recognise what drives them and what success really means,” said Pilzner.

He eventually figured out that the two things that motivated him most during his career—taking action and learning new things—were the same recipe he needed for retirement.

So this spring he enrolled at University of Nevada, Reno with two classes (earning a 4.0) and will be full-time in the fall. He is studying for a degree in political science and history.

Retirees frequently don’t realise how much their career provided a sense of identity and self-worth. Many fail to grasp the need to plan for a different source of purpose in retirement, said Betty Wang, a financial adviser in Denver.

People carefully plan how they will spend money in retirement but often give far less thought to how to spend their time.

Jay Holt, 74, regrets not retiring sooner. He planned to spend his postwork years playing polo. But in 2015, he fell while playing and had to give up the sport.

The resident of Cincinnatus, N.Y., who retired in 2013 at age 64, now wishes he had had a few more years in which to enjoy this activity.

Relationships are the key to retirement

The best predictor of longevity, health and happiness in later life is the quality of your relationships. That is the finding of the Harvard Study of Adult Development, which has followed families for decades.

Dan Roberts, 72, in Idyllwild, Calif., wishes he had kept up with former colleagues for personal and professional reasons.

Roberts retired about 18 months ago. Soon after, his son and his family, who were living just two hours away, moved to New Zealand.

Roberts and his wife, Robin Roberts, said only two visits a year are doable on their budget. He said he would have been able to afford more-frequent trips had he kept the door open to contract work by maintaining both his relationships with former colleagues and a project-management certification.

“We miss our grandchildren terribly,” his wife said.

David Edmisten, an adviser in Prescott, Ariz., said clients sometimes regret delaying retirement for this reason. The extra years working come at the cost of missing time with family and friends and postponing trips, he said.

“Some even had people close to them pass away and regret not being able to spend more time with their loved ones while they still could,” Edmisten said.

Retirement is longer than you think

Arthur Parmentier, 69, regrets retiring at 65, rather than working a few more years, partly because he missed out on a few more years of contributions to his retirement account.

The Providence, R.I., resident claimed Social Security at 65, accepting a lower monthly benefit than he would have received by waiting.

“Had I waited two more years or maybe three, I would have been quite comfortable, but right now, I’m living on Social Security and trying not to touch my IRA,” said Parmentier. “I think now that I may live well into my 80s, so I have to be prepared for that and make sure my IRA will last me throughout those years.”

The life expectancy for a 65-year-old is 84 for men and nearly 87 for women, according to projections by the Society of Actuaries based on 2019 data. Surveys suggest many Americans vastly underestimate those numbers. Of 1,500 adults ages 45 to 80 polled by the Society of Actuaries in 2015, 41% of pre retirees and 37% of retirees underestimated their life expectancy by five or more years, while 14% of pre retirees and 18% of retirees underestimated it by two to four years.

Social Security allows people to start their retirement benefits any time between ages 62 and 70, and increases the payment for every month of delay.

For many, the math favours starting at 70, when monthly benefits before cost-of-living adjustments are 76% higher than at 62, according to Laurence Kotlikoff, a Boston University economist.

A person who postpones benefits until age 70 instead of 62 would have to live to at least 80 to come out ahead, said Kotlikoff, founder of MaximizeMySocialSecurity.com, which advises people on claiming decisions.

The Australian sharemarket rose during four of five sessions in the week ending 30 October, but the headline gain concealed a sharp divide between recovering miners, rate-sensitive property stocks and retailers hit by inflation and weaker trading updates.

The Australian sharemarket finished October with a positive week, although the route higher was anything but uniform.

The S&P/ASX 200 closed Friday 30 October at 8,908.1, gaining 112.9 points, or 1.28 per cent, from the previous Friday’s close of 8,795.2.

The All Ordinaries advanced 1.34 per cent to 9,025, while the more concentrated S&P/ASX 20 gained 1.11 per cent.

The benchmark rose during four of the week’s five sessions. It added 0.17 per cent on Monday and 0.46 per cent on Tuesday, before slipping 0.03 per cent on Wednesday. It recovered 0.50 per cent on Thursday and gained another 0.18 per cent on Friday.

The index briefly reached 8,933.3 but again failed to establish itself above the psychologically important 9,000-point mark.

The week’s central tension was between a resources recovery and a less forgiving domestic interest-rate outlook.

Materials gained 4.06 per cent, reclaiming part of the previous week’s heavy fall. Australian real estate investment trusts rose 3.77 per cent, financials gained 1.05 per cent and energy advanced 1.39 per cent.

At the other end of the market, consumer staples fell 5.13 per cent and consumer discretionary shares lost 2.35 per cent. Utilities declined 0.73 per cent and communication services eased 0.68 per cent.

Inflation changes the conversation

Australia’s September inflation data was the week’s pivotal domestic release.

Annual inflation of 4.3 per cent pushed market pricing towards another possible Reserve Bank increase and disrupted Wednesday’s early sharemarket rally.

By Thursday’s close, one widely followed market measure placed the probability of an increase in the cash rate to 4.85 per cent at approximately 80 per cent.

That pricing does not make an increase certain. It does, however, change the framework through which investors assess Australian businesses.

Companies dependent on discretionary household spending face renewed pressure on sales and margins. Property trusts, banks, developers and highly leveraged companies must be considered against the prospect of higher funding costs.

Banks present a more complicated equation. Higher rates can support margins, but they may also slow credit growth and increase arrears.

Miners recover

BHP gained 4.56 per cent across the week to close at $57.56, making a substantial contribution to the benchmark’s rise.

The recovery followed an 8.3 per cent fall during the previous week and helped lift the broader materials sector.

Northern Star Resources added 4.59 per cent, while Goodman Group advanced 6.85 per cent to become the strongest performer in the ASX 20.

The commodities picture was mixed. Gold fell approximately 3.12 per cent on the cited weekly measure, while Brent crude added around 0.68 per cent.

The Australian dollar was little changed at approximately US70.35 cents at the reference point.

Supermarkets and consumer shares retreat

The consumer-staples story was markedly weaker.

Coles fell 11.77 per cent after its first-quarter update, making it one of the largest significant-company declines of the week.

Woolworths lost 3.66 per cent and Wesfarmers fell 4.48 per cent to $76.69 as investors processed company trading commentary against the prospect of another squeeze on household demand.

The moves illustrate how quickly expectations can change when an apparently defensive company disappoints.

Supermarkets still benefit from the recurring need for groceries, but customers can trade down, shift between chains and reduce spending on higher-margin discretionary lines.

Wesfarmers carries exposure to several consumer categories through businesses including Bunnings, Kmart and Officeworks. A renewed rate increase would place more pressure on households already confronting higher prices.

The wider market’s biggest movements

Among companies outside the ASX 20, Mesoblast surged 27.32 per cent, SiteMinder gained 22.74 per cent and Zip rose 22.60 per cent.

The sharpest weekly falls included 4DMedical, down 33.51 per cent; Tuas, down 29.95 per cent; Catalyst Metals, down 17.47 per cent; and Champion Iron, down 13.35 per cent.

Those percentages require context.

The movements in BHP, Commonwealth Bank and other very large companies had substantially more influence on the index than similarly dramatic changes among smaller companies.

A 20 per cent move in a relatively small stock may attract more attention than a two per cent rise in a major bank, but the bank can have the greater effect on the market.

How the ASX 20 moved

The following list uses the S&P/ASX 20 constituents and five-session movements reported at the 30 October close.

Where the component feed did not publish a valid five-day comparison, no figure has been estimated.

BHP Group: Up 4.56 per cent

Commonwealth Bank: Up 1.66 per cent

Rio Tinto: Down 2.20 per cent

National Australia Bank: Up 0.48 per cent

Westpac: Up 0.08 per cent

ANZ Group: Up 1.92 per cent

CSL: Up 2.05 per cent

Macquarie Group: Up 2.19 per cent

Wesfarmers: Down 4.48 per cent

Woodside Energy: Up 1.43 per cent

Goodman Group: Up 6.85 per cent

Telstra: Five-day comparison unavailable from the cited component feed

Woolworths: Down 3.66 per cent

Fortescue: Five-day comparison unavailable from the cited component feed

Transurban: Down 2.40 per cent

QBE Insurance: Down 1.21 per cent

Aristocrat Leisure: Up 0.63 per cent

Northern Star Resources: Up 4.59 per cent

Sigma Healthcare: Down 0.36 per cent

Brambles: Down 1.20 per cent

The companies dominating the conversation

Coles was the week’s standout media-facing company for the wrong reason.

Its trading update produced an outsized repricing and drew attention across the grocery and retail sectors. Woolworths and Wesfarmers were also scrutinised as investors considered how stubborn inflation and another possible rate rise could affect sales volumes.

Bank of Queensland offered a more positive corporate signal.

The bank reported that its FY26 net interest margin had risen six basis points to 1.70 per cent, ahead of the 1.68 per cent expected by the market according to contemporaneous reporting.

Bank of Queensland shares rose 5.8 per cent on Thursday, while the major banks also rallied.

Endeavour Group finished Friday at $3.39, up 4.31 per cent on the day, and released the results of its annual general meeting.

The movement was notable during a week in which investors were highly sensitive to consumer-facing companies. The AGM result should not, however, be presented as the sole cause of the share-price increase without further supporting company guidance.

Mesoblast’s 23.4 per cent Thursday rise and 27.32 per cent weekly gain returned the biotechnology company to the centre of market attention.

For editors, it is important to separate the size of that percentage movement from its influence on the index. Mesoblast was an eye-catching performer, but it did not drive the ASX 200 in the way BHP or Commonwealth Bank did.

Qantas remained part of the broader market conversation as investors watched travel demand and company updates.

However, the primary-source review did not locate a fresh Qantas announcement that justified attributing a major weekly market movement to new company information. The airline should therefore remain on the monitoring list rather than being forced into the week’s causal narrative.

Is Australia’s IPO market reopening?

The official ASX new-listings pipeline remains active but selective.

ASX’s upcoming-floats page included formal applications with offer timetables extending through October and at least one anticipated listing on 30 November.

The exchange notes that its page covers companies for which a formal listing application has been received. It does not represent every company privately exploring a float.

The wider debate concerns whether Australia’s public market is sufficiently competitive when high-growth businesses can pursue capital in the United States or remain privately funded for longer.

ASX has previously raised possible reforms designed to improve the attractiveness of the local market. These include debate about reducing minimum free-float requirements and streamlining aspects of the admissions process.

An enhanced fast-track pathway for qualifying applicants can shorten the review process, reducing the execution risk created when market conditions change during a long IPO timetable.

That does not remove the more fundamental challenge.

New floats still require credible earnings or a convincing growth pathway, sensible pricing and enough genuine free float to support trading after listing.

Investors can already obtain diversified exposure through low-cost exchange-traded funds or buy established, liquid businesses. A float must therefore offer more than novelty.

The current pipeline suggests that the IPO window is open, but it is not indiscriminate.

What investors will watch next

The Reserve Bank’s next decision now sits at the centre of the domestic outlook.

Any change in cash-rate expectations will flow rapidly through banks, retailers, property trusts, listed developers and companies carrying substantial debt.

Investors will also watch whether the materials recovery can continue, whether BHP can hold its rebound and whether consumer companies provide further evidence of slowing demand.

Overseas, technology-sector volatility, commodity prices and the United States interest-rate outlook will continue to shape Australian trading.

The week’s 1.28 per cent headline gain was encouraging, but it was not a broad declaration of confidence.

It was a rotation towards miners, selected financials and property securities—and away from consumer businesses facing a more difficult inflation and interest-rate equation.

Market dashboard

S&P/ASX 200: 8,908.1, up 1.28 per cent for the week

All Ordinaries: 9,025, up 1.34 per cent

S&P/ASX 20: 5,214.7, up 1.11 per cent over five sessions

Best sector: Materials, up 4.06 per cent

Next-best sector: A-REITs, up 3.77 per cent

Weakest sector: Consumer staples, down 5.13 per cent

Major large-cap winner: Goodman Group, up 6.85 per cent

Major large-cap loser: Coles, down 11.77 per cent

AUD/USD: Approximately US70.35 cents at the weekly reference point

Gold: Approximately US$3,885 an ounce, down 3.12 per cent on the cited weekly measure

Brent crude: Approximately US$117.70 a barrel, up 0.68 per cent on the cited weekly measure