The Washington PostDemocracy Dies in Darkness

Retirement regrets: What retirees would say to their younger selves.

One bit of financial advice to a younger self: Skip the timeshares. (iStock)
Placeholder while article actions load

I’ve spent my whole life talking to myself.

“No, Michelle you don’t need to stop and get food. Go home and cook and save money.

“No, Michelle you shouldn’t buy that dress. You can wear what you have to the party.”

“No, Michelle you can’t spend that raise. Put it toward your retirement savings.”

I’m pretty good at fussing at myself. And yet, I still have some regrets. I would have more in my 401(k) had I not been so afraid of investing in equities. For years, my retirement account was too conservative overloaded with fixed income investments with low returns compared to the S&P 500 Index. I could just kick my scared younger self.

With the help of a financial planner and increasing my retirement savings over the years, my 401(k) is doing well. But my portfolio would probably be worth 20 percent to 30 percent more had I not been so risk-averse.

Last week I asked: If you could, what retirement planning advice would you give to your younger self based on what you know now?

I’ve been overwhelmed with comments from retirees who wish they could go back and talk to themselves. But the advice doesn’t have to be wasted. There’s still time for others to learn from our mistakes. Here’s what some retirees say are their biggest regrets.

John Heenehan of Madison, N.J., would give a lot of advice to his younger self. “Though that jerk surely wouldn’t listen, even to me," he wrote.

Here’s his lecture list. It’s all in his words, but well worth reading to the end.

-- Resist the siren call of credit cards. We quickly racked up credit card debt totaling $16,000 – nearly $34,000 in today’s dollars. No names but one of us had to give up our credit cards, leaving us to spend only the cash in our purse. That’s a hard discussion we should have had early in our marriage. Like, on our first date.

Read more: Ready to pay off your credit cards? Try the ‘Debt Dash’ method

-- Don’t buy more house than you need. A house isn’t an investment. It’s a home.

Read more: Yes, you should pay off your mortgage before retiring.

-- Subscribe to some reputable investing publications and learn how to invest. If you take an investment class, it might be bait the teacher uses to get customers. Assume the teacher, no matter how affable, is not worthy of handling your life savings.

-- Invest in good stocks or stock funds and leave them alone. For years. You don’t need bonds until you’re within a decade or so of retirement.

Read more: A Wharton professor puts stock market plunges in perspective

-- Never, ever try to get rich overnight. Remember the adage: “Bears and bulls make money. Pigs get slaughtered.” Instead think, “grow rich slowly.”

-- When you change jobs, transfer your 401(k) into an IRA – not into your new company’s cramped and probably crummy 401(k) plan. Then your investment choices aren’t limited to a few funds.

-- Work at being good at your job to maintain income and savings continuity. Continuously develop your career and your network by joining a professional organization – and serve on its board. (Since 1978, I’ve had nine jobs, 10 if I count working for myself. This includes five friggin’ layoffs and moving through five states across most of the country. Moves are costly. Still, I reached my retirement saving goal at 62 and retired because we stayed true to our savings plan and invested wisely. But I likely could have retired years earlier with fewer moves.)

-- Learn how to laugh at yourself. Being self-effacing goes a long way to making friends at work, including with your boss and even some of the office jerks.

-- Learn what you really need. And experiences with loved ones beat out a lot of stuff you really don’t need, even if your neighbors feel they can’t live without it.

-- And no timeshares! (Yep, we fell for it.)

Markus Berber of Mering, Germany, has two major regrets. “I started saving too late,” he said of his first regret. “As drivers we have mastered the skill to maneuver around a blind corner. No one questions the need to slow down even though you don’t see the danger yet. The retirement sign is posted at the end of that blind corner. My second regret is not having started earlier with a healthy lifestyle that gives me daily happiness. ‘Health is not everything. But without health everything is nothing.’ (A tag line for a health insurance company in Germany.)”

Ray Villegas of Maumee, Ohio, also has two major regrets --- trying to time the market and not putting money in a Roth IRA.

“I had just started a new job and my employer matched up to 5 percent of my pay,” he wrote. “About five years after I started investing the market had a correction and I got out. But I got out somewhere near the bottom. I did get back in but long after the market recovered so I entered paying a premium. I should have just stayed in and dollar cost averaged at market lows. My second regret was not understanding the financial benefits of a Roth IRA compared to the traditional IRA. A lesson that I’m reminded of each time I make a withdrawal and pay the taxman.”

Read more: Here’s how much more you’ll be able to save for retirement in 2019

“I planned for retirement,” wrote Susan P. from Honar, N.Y. “I have a Roth and a 401(k) and I started in my 20s. My regret -- I didn’t expect to be completely disabled at age 52. There went my short-term savings, my health insurance and my earning potential. I had disability insurance, but it ends at two years if they think you can do anything -- even if it’s unlikely that you actually can do something. The devil is in the details. I should have had my own disability insurance rather than an employers only policy.”

From NerdWallet read: Disability Insurance: Why You Need It and How to Get It

Read more: Insurance mistakes people make at every age

Wendy Rice from Colorado wrote, “Set joint financial goals early on for younger self and spouse to commit to. Understand the miracle of compound interest and auto pay self (pay yourself first). Even if only $5 to $10 to start with from every paycheck, it won’t be missed or noticed.”

Alan K. Homer of Mesa, Ariz., wrote, "To my younger self, I would give the mantra, ‘Save early, save often.’ The matching of the contributions from your employer and the compounding effect of time and average annual stock market returns will make retirement attainable and with a sustainable income. Good thing I listened. I can retire at 60 at my discretion. More likely I will still be working, but on my own terms.”

Nancy Johnson of Fresno, Calif. wrote, “Don’t ‘save’ experiences for retirement. Travel now, spend more time with friends, enjoy hobbies, read challenging books, go to concerts and plays, see great art, volunteer time, find enjoyable regular exercise, donate to causes that touch the heart and help the earth – whatever enriches your inner life. Savor as many of these experiences now, even on a limited budget. Accidents, unexpected illnesses, family obligations and other unanticipated crises may completely change what’s possible in retirement.”

If you’re a good saver but have trouble spending read: How to live it up without going broke before you die

Your thoughts

What’s the biggest pre-retirement mistake you made? Send your comments to Please include your name, city and state. Put “Regrets” in the subject line.

Retirement rants and raves

I’m interested in your experiences or concerns about retirement or aging. What do you like about retirement? What came as a surprise?

If you haven’t retired yet, what concerns you financially?

You can rant or rave. This space is yours. It’s a chance for you to express what’s on your mind. Send your comments to Please include your name, city and state. In the subject line put “Retirement Rants and Raves.”

Ross from Arlington, Va., had some great observations about a column I wrote earlier this year: This is how it feels to be a millionaire and still feel broke

“You mentioned a middle-aged woman who had a sizable nest egg and yet she was still suffering retirement anxiety, wondering whether she had saved enough," he wrote. “I can empathize (And no, I’m not looking for sympathy) as I occasionally feel the same way. My wife and I are both professionals, in our early 60s. Retirement is near. We have, I believe, done well managing debts and saving. Our home will be paid off in about two to three years. We have no other debt – zero, no car payments, no student loans, etc. All are paid off. We own a couple of rental condos. In both cases the rent covers the mortgage, condo fees and taxes. We have a long term nursing care insurance plan. No children to worry about. And our brokerage account is in the mid-seven figure range.”

But even having saved well he has doubts.

"Sometimes I think, ‘Have we done enough?’ Will we be able to maintain our lifestyle? What cuts will we need to make? I know 99 percent of people out there would call me nuts and tell me to shut up. But still, it gnaws at me. The problem with retirement as I see it, unless you are so wealthy as to be part of the uber rich class, you’re bound to wonder about whether you made the right choices. And you’ll never find out until it’s too late if you made the wrong choices. That’s the nature of saving and retirement. The best analogy I can come up with is a baseball game. If you are leading by one or two runs going into the 9th inning, you may think you have done well, but are you winning or are you at risk of losing? But if you are leading by, say, 15 or 20 runs, then you are definitely winning (and part of the uber rich) and have no worries. That’s the dilemma. Maybe you think one or two runs ‘should’ be enough to win, but you won’t know until it’s too late.”

Read more:

Is $1 million enough to retire? Why this benchmark is both real and unrealistic.

Are you ready for retirement? Here’s how to know.

3 myths about this early retirement movement

Note to readers: The personal finance and retirement newsletters won’t be sent out on the Dec. 24, 27, and 31. The newsletters will return starting Jan. 3. Happy Holidays.

If you’re viewing this post online sign up to automatically receive Michelle Singletary’s newsletters right into your email box: "Your Retirement" on Mondays and "Personal Finance" on Thursdays

Read and share Michelle Singletary’s Color of Money Column on Wednesdays and Sundays in The Washington Post. You may also see the column in your local newspaper.

Follow Michelle Singletary on Twitter @SingletaryM and Facebook.