My 2 Worst Retirement Mistakes
Category: Uncategorized
December 8, 2025 — In my 19 years of writing these Topretirements Blogs there have been so many great questions and comments from our Members. So I have had plenty of time to think about the best ways to plan for retirement, and the worst ways. Tackling the negative side, here are my two worst retirement mistakes. In the grand scheme of things, they are not so bad, compared to many worse ones I could have made.
- Not contributing enough to Roths.
At the time it seemed like a no brainer – contribute to my IRA or 401(k) plan so that I always got the maximum match, or put in the most I could afford if there wasn’t a match. Put in $10,000, get a $10,000 deduction on our income tax. But, as I am finding out in my late 70’s, that bird comes home to roost in the form of Required Minimum Distributions (RMDs).
Comments on "My 2 Worst Retirement Mistakes"
Stevo says:
Never had the part D problem but I'm with ya on the IRA issue. Here is now I would invest my savings if I could turn back clock to 55. In order of importance:
1. Get the 401K employer match.
2. Sign up for a high deductible healthcare plan and max out an HSA.
3. Max out a ROTH IRA.
At 55yo I would only contribute more to the 401K if I had extra money to save after #1-2-3 were funded for the year. I also would NOT use the HSA for current medical expenses. It would become a long term investment account. What's better than putting tax free money (including no SS or Medicare tax from payroll deductions) into an account to get tax-free income in the future. To be used tax-free it has to be spent on qualified medical expenses but in 20 years you'll probably have lots of opportunity for that. After 65 you can use it for other reasons but it will be added to your income. Your spouse can inherit the account on death and continue to use it tax-free for medical expenses but any other person would have to treat the inheritance as income so be careful how you set it up. The HSA deductions will not show up on your yearly SS income because you don't pay taxes on it so be sure to talk to someone to see how that may affect you. I started this approach at 62 so it didn't do much to my predicted SS payments.
I believe the taxes paid on Roth IRA contributions now will be much lower today than 10-20 years in the future but who knows. Having that income sheltered from eventual taxes in the future can save you from Medicare IRMAA, a form of means testing too.
JCarol says:
Can't say I have any retirement mistakes or regrets, but it's early yet.
The changing fortunes of owning a small business necessitated frequent pivoting when it came to retirement savings. Sometimes feast, sometimes famine. Large chunks set aside some years, not a penny to spare in others.
IRAs comprise roughly 30% of my & my husband's retirement savings. 2025 & 2026 will be our first years of RMDs so we'll check with our accountant about best strategies for withdrawals.
If larger withdrawals don't kick us into higher tax brackets, it might be wise to take more than the RMDs and convert that money into ROTHS.