• Nearly 1,200 Americans shared with BI their financial regrets.
• Many of the baby boomer respondents said they had regrets about preparing for retirement.
• This is part of an ongoing series about boomer regrets.

Millions of Americans facing retirement are worried they won’t be financially prepared — or fear that they’ll have to work forever.

Some are already there. Finances and retirement were major themes in the roughly 1,200 responses Business Insider received from Americans between the ages of 48 and 90 who filled out a voluntary survey about their biggest regrets. (This is part two of an ongoing series.)

Many of the respondents in the baby boomer generation said retirement — how to invest and how much one needs — is a black box. Some wish they’d hired a financial advisor, while others regretted expensive purchases. Others said they took Social Security too early or retired without a long-term financial plan.

And then there are those who suffered an unexpected setback such as a cancer diagnosis, a job loss, or a divorce and wish they’d been better prepared for an emergency.

We want to hear from you. Are you an older American with any life regrets that you would be comfortable sharing with a reporter? Please fill out this quick form.

Gary Lee Hayes, 70, wished he’d been more regimented with his savings and investments. The California resident briefly served in the Navy, got a degree in public administration, and worked in mental health and handyman positions. He had little financial literacy growing up and said he didn’t focus on building his career to be more lucrative.

Two of Hayes’ main money regrets are not investing in Verizon stock early on and not saving at least 10% of his income each month. He also said he was somewhat too liberal with his spending throughout his life, though he said he didn’t purchase anything too far beyond his means. He also avoided putting money into his 401(k) and said he should have chosen more stable investments instead of short-term ones.

“You can’t expect that you’re all of a sudden going to win the lottery,” said Hayes, who receives $1,846 a month in Social Security and lives in government-subsidized housing. “You can’t expect that someone’s going to pass and leave you an inheritance that will make your life more comfortable.”

Some older Americans wish they’d had more investing knowledge

A major theme among BI’s survey respondents was that they lacked knowledge about investing. For some, this meant not saving enough; for others, it meant falling into some common investing mistakes.

New research from Vanguard suggests people changing jobs put less into their 401(k)s, often without realizing it, and can lose out on as much as $300,000 throughout their careers.

Another theme among survey respondents was they waited too long to start saving. Two separate surveys from Transamerica Institute and Charles Schwab found that, on average, boomers waited until age 35 to start saving.

Nancy Seeger, 64, who lives outside Cleveland, said she made investing mistakes that had long-term repercussions on her finances. Seeger, who has two master’s degrees, worked for many years as a teacher and health librarian. She was laid off earlier this year from her $74,000-a-year job and while she’s not ready to fully retire and is still looking for work, she worries she won’t be able to land another decent-paying job given her age.

She told BI she wished she could have saved more when her children were young and started retirement funds earlier. While she had some savings, she began consistently putting more into her investments at age 50.

She also didn’t realize that because she has a pension in addition to receiving Social Security when she retires, she would be affected by a little-known Social Security provision that would lower her monthly check. Between her pension of $713 monthly and Social Security, which she expects will be between $1,200 and $1,400 monthly, she’ll have just enough to cover her rent.

“I was fortunate to get a small inheritance from my parents and an aunt, which saved me, but it’s unlikely that I will be able to do the same for my children, and that bothers me a lot,” Seeger said. “I had hoped to travel, and I wanted to leave money for my kids, but both of those goals are compromised now.”

Seeger said she has few regrets and “let life come to me,” though she’s planning to take a part-time job when she retires to supplement her income. She’s still digging herself out from bills from undergoing cancer treatment in 2022, and because she has a few months until turning 65, she can’t get on Medicare and has to pay her health insurance out of pocket.

“I’ve had a lot of unexpected things happen, but I’ve also come to understand that the unexpected things impact everybody, and you can’t really plan for them,” Seeger said.

It’s difficult to prepare for the unknown

While $1 million for retirement may be sufficient for some Americans, it could be too little for others.

Bank of America’s Financial Wellness Tracker suggests that Americans ages 61 to 64 should have about 8.5 times their current salary in savings. Someone with $1 million in savings at 65 can safely withdraw $40,000 in their first year of retirement, Bank of America said.

For some, saving just 1% more could have significant financial rewards down the line. If someone making $50,000 annually contributes 5% of their salary to retirement, they would save nearly $60,000 less after 30 years than if they’d contributed 6%.

Nevenka Vrdoljak, the managing director in the chief investment office for Merrill and Bank of America Private Bank, told BI that calculating how much you need for retirement requires difficult estimations of life expectancy, spending in retirement, and retirement resources.

“Changes in government benefits can affect expected income,” Vrdoljak said. “Fluctuations in investment returns make it difficult to estimate how much savings you will have in the future.”

With cancer rates rising and diagnoses coming earlier in life, another difficult calculation is how to prepare for time off work and quickly mounting medical bills.

“The need for long-term care can cause more than financial strain in retirement. It can place a burden on loved ones,” Vrdoljak said. “Investors with substantial assets may prefer to self-insure against this risk. But for many other investors nearing retirement, long-term-care insurance can help mitigate the risk and cost of care.”

PJ White, 69, never had aspirations for a high-income career — but she never expected to be homeless.

Throughout her career, she worked for a lab supply company, retail companies, and as a secretary at law firms. She married at 21 and bought a house, but she divorced a year later, which set her back financially.

While she said she often lived hand to mouth, she wished she had been more cautious about spending on leisure and clothes — what she called “play money” — and set aside time to learn about investing. She said it was rare she had savings left over each month, and her peak income was about $41,000. She left work in 2008 to care for her partner’s mother.

“The money would come in and out it would go,” White said, adding she rarely put money into her 401(k). “I didn’t think about the retirement aspect because it was so far down the road, but here I am now wishing that I had.”

She recently lost her home because she and her partner couldn’t afford to pay property taxes. They now live in a camping tent in San Diego. She lives on about $1,500 in Social Security each month as they fight to get their house back, but she said much of her money goes to court fees. She’s received some assistance with groceries through her new health insurance company, but she hasn’t secured an affordable housing unit yet.

“He doesn’t make any money at all, so it’s all on me, and I’m feeling it,” White said of her partner. “I’m showing symptoms of stress, and I don’t have anywhere to go, no one to turn to.”

Are you an older American with any life regrets that you would be comfortable sharing with a reporter? Please fill out this quick form or email nsheidlower@businessinsider.com.