Boomers Spill: Timing Your Retirement & Social Security for No Regrets!

• Over 1,700 older Americans have bravely shared their financial regrets, and the numbers keep climbing.
• Common sentiments include wishing they hadn’t retired too early, taking Social Security too soon, and depleting their savings faster than anticipated.
• This is part of a compelling series that dives deep into boomer regrets.

Have you ever pondered the perfect age to retire? Or the right time to start collecting Social Security? Maybe you’re wondering if part-time work will be in your future after retirement?

Millions of Americans are grappling with these questions, and recently, many have stepped forward to share their insights in a voluntary reader survey. In just the last two months, more than 1,700 individuals between the ages of 48 and 90 have opened up about their biggest regrets in retirement. This is a captivating continuation of a series that speaks to the heart of the issue.

A significant number of these respondents revealed their challenges and mistakes made during their retirement journey.

Among the regrets voiced were stories of retiring too early, tapping into Social Security benefits ahead of schedule, and running through retirement savings too quickly. Many shared how life’s unexpected events, such as losing a spouse or facing a medical crisis, derailed their plans. Several expressed a desire to have held onto their jobs longer or to have better anticipated the financial burden that sudden costs could impose. Yet, a few also discovered a newfound sense of community and self in their retirement years.

Here are some of their compelling stories.

We want to hear from you. Are you an older American with life regrets that you’re willing to share? Fill out this quick form .

Unexpected Financial and Medical Setbacks

Kathleen Rudd, 74, regrets her decision to retire when she did, especially when her health took a downhill turn.

After a fulfilling career managing a catering business and later serving as an executive chef, Rudd found herself with about $60,000 in her 401(k) by 2008. However, the Great Recession hit hard, slashing her account’s value by 40%, and it never recovered.

Despite having retirement accounts, she admits that in-depth financial planning wasn’t part of her retirement strategy.

“I don’t think retirement really crossed my mind until the last decade,” Rudd shared, reflecting on not having children or a legacy to consider.

At 62, she left her job with a salary of nearly $60,000 and started collecting Social Security early, receiving about $1,290 a month—roughly $400 less than if she had waited until she turned 67. Due to restrictions on Social Security earnings, she had to settle for part-time chef jobs that paid significantly less than her previous income until she turned 70.

Today, she finds herself with only $40,000 in savings and hopes to sell her Colorado home with her sister when the time comes. Medical issues, including a collapsed lung and a brain bleed, have further strained her finances.

“I never should have left that job; I should’ve stayed in the workforce longer,” Rudd lamented.

David John, a senior strategic policy advisor at AARP, emphasizes that the retirement expectations of older Americans often clash with the reality they face. Even those who plan meticulously may find themselves lost in the labyrinth of financial navigation.

“There’s a saying: ‘Act in haste, repent at leisure.’ That rings true for many here,” John remarked. “Retirement is like venturing into a foreign land. We can read about it, discuss it, but until we step into it, we don’t grasp its full reality.”

Retiring Too Quickly and Spending Recklessly

Misty Miller, 65, realized she pulled the plug on her career too soon—regretting her decision within just a week.

Having spent years as a paralegal and legal analyst, she retired at 58 with around $700,000 tucked away in retirement accounts. Living frugally, she drove the same car for 26 years and avoided luxuries, calculating her expenses for the decades ahead. She anticipated a monthly pension check of about $4,000. But once she retired, her frugality evaporated.

She withdrew funds from her 401(k) to purchase a beach house for $515,000. After selling that house in 2020, she moved to a $488,000 home in Sacramento, now facing property taxes five times higher than her previous residence.

“I’m house-rich but cash-poor, so I had to re-enter the workforce,” Miller admitted. “I lived frugally up until that point, and then I just lost my mind.”

With her living expenses and housing decisions trimming her retirement savings down to around $450,000, Miller returned to work for the state where she had previously been employed. She worries her pension will not cover all her expenses.

“I plan to keep working until they carry me out in a casket,” she said, adding she wishes she had never retired.

John from AARP points out three prevalent mistakes retirees often make during this transition. First, many withdraw more from their retirement investments than they should, leaving themselves strapped for cash later. Others, fearing they won’t have enough, work longer and save excessively, depriving themselves of enjoyment. Finally, many put off crucial financial decisions until it’s too late, neglecting to set aside an emergency fund or overly depending on Social Security.

“People need to make certain decisions as they age, but they often find themselves lacking the financial flexibility to do so,” John explained.

Cashing Out Social Security Too Soon

Sharon, 77, took Social Security too early, leading her to unretire to meet her expenses.

The Atlanta resident, who chose to use her middle name for privacy, retired in 2001 after a divorce and the loss of her parents. She took on temporary jobs during the 2000s and invested much of her inheritance, only to lose almost half of her $725,000 assets in the 2008 market crash.

“I became terrified of the stock market, unsure of what to do, and made a lot of poor financial decisions,” Sharon shared.

In an effort to recover, she opted to take Social Security at 62 instead of waiting until 67. Unfortunately, her financial situation worsened in her mid-60s, prompting her to return to teaching, albeit with a meager income. A string of health issues and home repairs has squeezed her $936 monthly Social Security check, and she has less than $100,000 in liquid assets.

“If only someone had told me not to take Social Security early or to invest differently,” Sharon lamented. “With proper guidance, perhaps I wouldn’t be facing this dire situation, considering that by 2030, I could easily run out of money.”

According to John, only about 22% of individuals had a financial plan before retiring, and just 33% established one afterward. “People often prefer vague worries over confronting hard truths,” he noted.

Returning to Work and Staying Engaged

For many older Americans, retirement missteps extend beyond finances. Numerous respondents revealed they returned to work after realizing that retirement could be unexpectedly lonely or monotonous. While some envision retirement as endless leisure on the beach or golf course, John highlighted that many still crave the structure of the workplace.

“So many individuals have social networks deeply embedded in their work lives, and once they exit that realm, feelings of loneliness can set in,” John explained.

On a brighter note, some respondents found rejuvenation after their careers ended. Many embarked on passion projects, using retirement as a time to rediscover themselves.

Cindy Kohli, 64, has relied on Social Security Disability Insurance since 1990 and receives compensation from Veterans Affairs. As a single mother, she struggled financially, making her share of mistakes along the way, but eventually developed her cost-saving strategies.

One of her most significant regrets was neglecting her own needs.

“I’ve always prioritized others over myself, even forgoing things like new clothes,” Kohli reflected. “In retirement, I’ve learned to put myself first.”

She now spends hours each week reading financial literature, engaging in pro bono paralegal work, and actively participating in her community.

“Strangely enough, my greatest challenge now is finding my own purpose, as it has always revolved around helping others,” she remarked. “Many complain that their limited income restricts their activities, but the truth is, they just need to adapt and find new avenues for enjoyment.”

Are you an older American with regrets you’d like to share? We encourage you to fill out this quick form or reach out via email at [email protected].