How to Retire Better, From Retirees Who Learned the Hard Way
Lessons from retirees on the biggest regrets of their postwork lives
4 min
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.
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Records keep falling in 2025 as harbourfront, beachfront and blue-chip estates crowd the top of the market.
A divide has opened in the tech job market between those with artificial-intelligence skills and everyone else.
JPMorgan Chase has a ‘strong bias’ against adding staff, while Walmart is keeping its head count flat. Major employers are in a new, ultra lean era.
3 min
It’s the corporate gamble of the moment: Can you run a company, increasing sales and juicing profits, without adding people?
American employers are increasingly making the calculation that they can keep the size of their teams flat—or shrink through layoffs—without harming their businesses.
Part of that thinking is the belief that artificial intelligence will be used to pick up some of the slack and automate more processes. Companies are also hesitant to make any moves in an economy many still describe as uncertain.
JPMorgan Chase’s chief financial officer told investors recently that the bank now has a “very strong bias against having the reflective response” to hire more people for any given need. Aerospace and defense company RTX boasted last week that its sales rose even without adding employees.
Goldman Sachs , meanwhile, sent a memo to staffers this month saying the firm “will constrain head count growth through the end of the year” and reduce roles that could be more efficient with AI. Walmart , the nation’s largest private employer, also said it plans to keep its head count roughly flat over the next three years, even as its sales grow.
“If people are getting more productive, you don’t need to hire more people,” Brian Chesky , Airbnb’s chief executive, said in an interview. “I see a lot of companies pre-emptively holding the line, forecasting and hoping that they can have smaller workforces.”
Airbnb employs around 7,000 people, and Chesky says he doesn’t expect that number to grow much over the next year. With the help of AI, he said he hopes that “the team we already have can get considerably more work done.”
Many companies seem intent on embracing a new, ultralean model of staffing, one where more roles are kept unfilled and hiring is treated as a last resort. At Intuit , every time a job comes open, managers are pushed to justify why they need to backfill it, said Sandeep Aujla , the company’s chief financial officer. The new rigor around hiring helps combat corporate bloat.
“That typical behavior that settles in—and we’re all guilty of it—is, historically, if someone leaves, if Jane Doe leaves, I’ve got to backfill Jane,” Aujla said in an interview. Now, when someone quits, the company asks: “Is there an opportunity for us to rethink how we staff?”
Intuit has chosen not to replace certain roles in its finance, legal and customer-support functions, he said. In its last fiscal year, the company’s revenue rose 16% even as its head count stayed flat, and it is planning only modest hiring in the current year.
The desire to avoid hiring or filling jobs reflects a growing push among executives to see a return on their AI spending. On earnings calls, mentions of ROI and AI investments are increasing, according to an analysis by AlphaSense, reflecting heightened interest from analysts and investors that companies make good on the millions they are pouring into AI.
Many executives hope that software coding assistants and armies of digital agents will keep improving—even if the current results still at times leave something to be desired.
The widespread caution in hiring now is frustrating job seekers and leading many employees within organizations to feel stuck in place, unable to ascend or take on new roles, workers and bosses say.
Inside many large companies, HR chiefs also say it is becoming increasingly difficult to predict just how many employees will be needed as technology takes on more of the work.
Some employers seem to think that fewer employees will actually improve operations.
Meta Platforms this past week said it is cutting 600 jobs in its AI division, a move some leaders hailed as a way to cut down on bureaucracy.
“By reducing the size of our team, fewer conversations will be required to make a decision, and each person will be more load-bearing and have more scope and impact,” Alexandr Wang , Meta’s chief AI officer, wrote in a memo to staff seen by The Wall Street Journal.
Though layoffs haven’t been widespread through the economy, some companies are making cuts. Target on Thursday said it would cut about 1,000 corporate employees, and close another 800 open positions, totaling around 8% of its corporate workforce. Michael Fiddelke , Target’s incoming CEO, said in a memo sent to staff that too “many layers and overlapping work have slowed decisions, making it harder to bring ideas to life.”
A range of other employers, from the electric-truck maker Rivian to cable and broadband provider Charter Communications , have announced their own staff cuts in recent weeks, too.
Operating with fewer people can still pose risks for companies by straining existing staffers or hurting efforts to develop future leaders, executives and economists say. “It’s a bit of a double-edged sword,” said Matthew Martin , senior U.S. economist at Oxford Economics. “You want to keep your head count costs down now—but you also have to have an eye on the future.”
Records keep falling in 2025 as harbourfront, beachfront and blue-chip estates crowd the top of the market.
A divide has opened in the tech job market between those with artificial-intelligence skills and everyone else.
