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Retirement lessons learned over my career

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By Elliot Raphaelson
Posted on April 15, 2025

I worked 34 years before retiring and have been retired from full-time work for 29 years. I have made some good decisions and some not so good, and I hope you can learn from both. First, I will discuss what I believe were good decisions.

  1. When you look for full-time employment, see if you can find an employer that offers a defined benefit plan. Although most employers no longer offer defined benefit plans, unions are now being more aggressive and are insisting on them. Since I retired at 58, I have received over $700,000 in pension payments from my defined benefit plan.
  2. If your employer offers a defined contribution plan, such as a 401(k), always contribute at least as much as necessary to obtain the maximum employer match. By making maximum contributions to my plan and receiving a 50% match, when I retired at age 58, the account was worth several hundred thousand dollars, which I rolled over into an IRA account.
  3. Whenever your yearly taxable income is lower than usual, convert your traditional, non-Roth retirement plan into a Roth account. [Ed. Note: This will increase your tax that year, but you’ll pay tax at a lower rate provided the conversion doesn’t raise your tax bracket.] Try to avoid pushing your taxable income into a higher marginal tax bracket.
  4. If you have reached your required beginning date — which means you are required to take required minimum distributions (RMD) from your traditional retirement accounts — use the qualified charitable deduction (QCD) to make charitable contributions before you take any yearly RMD. This will reduce the amount you have to withdraw to meet your RMD by the amount of your charitable contribution. [Ed. Note: Do this in a year when you itemize deductions so you can take advantage of the charitable deduction.]
  5. If you have earned income from self-employment, make sure you take all legal tax deductions, including premiums and Medicare premiums, as deductions on their tax returns.
  6. If you have a hobby or skills you enjoy, try to find a way to turn these hobbies and skills into profitable side income.

For example, even though I was employed full-time at a major bank for 23 years, I was able to earn substantial income with considerable tax deductions as a college instructor, a freelance writer and book author. I was able to earn almost as much in these activities as I earned in my full-time positions.

Because I had already been making retirement planning presentations at my bank, Dow Jones hired me as a consultant to conduct retirement planning seminars for its employees.

Not all my decisions were optimal. The following are some maxims that I didn’t always follow. If I had, the results would have been more favorable.

—Always make your new contributions to retirement accounts to Roth accounts rather than traditional accounts.

—Establish retirement accounts for non-working spouses with contributions from your earned income. Using this option, you can create an additional IRA for your spouse using the same maximum annual limit.

—Allocate more than 50% of your retirement account assets to equities. I generally allocated no more than 50% of my retirement accounts to equities. Allocating more than half of your retirement assets to stocks will maximize growth, especially for young workers.

Elliot Raphaelson welcomes your questions and comments at raphelliot@gmail.com.

© 2025 Elliot Raphaelson. Distributed by Tribune Content Agency, LLC.

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