Retirees Share the One Thing They Regret Not Saving For

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Your financial situation in retirement depends not only on how much you saved but also on how well you prepared for the unexpected. Even with a solid plan, some retirees discover gaps that can upend their budgets.
Here, two retirees shared the biggest expenses they regret not saving for.
Healthcare Costs
Lesliee Antonette, now 67, developed an autoimmune disorder three years prior to her planned retirement at age 55. “I was in the process of building up my retirement job. Everything came to a halt as I searched for medical treatment. Retired for 15 years, I have outlived my pension,” she said.
She spent 10 of those years traveling the country and living with family as she sought treatment. “What should have been the beginning of the rest of my life became a struggle to stay alive to live — a life I did not want,” she explained.
Five years ago, she found a doctor who finally helped her create a treatment plan that has allowed her to reopen her business in a different state with different laws and standards. She works as an editor and a consultant for small businesses and startups.
“No one can predict the future but if I had the chance to give advice to my past self, I would say put every dime in savings, take fewer vacations and do not allow yourself to rely on Social Security.”
Taxes
Kyle M., age 55, a retired American in-house counsel for a technology company who now lives in Portugal, realized a little too late that his retirement calculations were “more general” than they should have been. Though he used several retirement calculators and consulted with a financial advisor, he wished he’d gotten more granular and considered his retirement vehicles more closely.
“I never really considered the impact of taxes as I was saving for retirement. I just went with the 401(k) that the company offered and put in as much as I could. I did think it was important to get the full company match, but I never considered that these were pretax dollars and what that would mean once we retired,” he said.
While he enjoyed seeing “the balance grow,” now that he’s retired, withdrawal strategies and tax implications are more of an issue.
“We have some rental income, but nowhere near what we were making when we were working, so every dollar feels like it should go to support our living expenses. I know that we need to pay our taxes, but those feel like they are supporting someone else, not our retirement.”
A Roth 401(k) Could Have Been Better
Kyle wishes he had looked into Roth 401(k) options when they were available. “Yes, those are after tax dollars when working, but we were working and had more income to pay those taxes.”
He feels that financial planners look at the pure dollar calculation and figure the marginal tax rate will be lower after retirement so a 401(k) works out to pay taxes later than while working. “But that isn’t how I look at things now that I’m allocating every dollar,” he said.
“If I had more in a Roth, all the dollars I see would be available to me for planning spending. The taxes would have been behind me now. I think there is something to be said for taking care of the taxes earlier than later.”
Because so much of their retirement funds are in a 401(k), he said, “I spend a significant amount of time looking at withdrawal strategies and tax planning.”
Retirement can bring surprises even for those who plan carefully. As these stories show, the best strategy isn’t just saving, it’s anticipating hidden costs so your future self is better prepared.