Financial Planning / Retirement

Financial Planning / Retirement Questions

Contribution to Roth IRA

Terry, We want to make a contribution to our son’s Roth IRA for tax year 2023. I understand max for..

Pay mortgage vs Save

My husband is 65 and working, I am 64 and have opted for early SS at 62 . We have..

Reverse mortgage

Hello. Would you please clarify whether someone can be forced out of their home if they use a reverse mortgage?..

IRA annuity vs. brokerage IRA

When my husband passed away our accounts(maybe 403-B’s) were put together into one IRA account for me. I thought is..

Social Security Benefits

Hi Terry, Listener on John Williams , I am at full retirement age 66 & 6 Months still working earning..

Signing up to early for Social Security

I signed up for social security at the age of 62. My birthday is May 20, 1959. I called Social..


I am planning on retiring end of 2025. I have a 401K with my employer and would like to invest..


My elderly mother has given her ss# and signature to strangers. We froze her credit. She has large balances in..

Retirement plan termination.

Greetings Terry, my wife’s employer ( a hospital not to be mentioned by name) is terminating their pension plan. We..

Wealth Planning/Shielding – Taxation –

Terry – love listening to you on WGN! I have a couple of questions that relate to my fear of..

Social security clawback

Just an FYI per your conversation on WGN. My husband’s last social security payment was held back. SS did not..

Will and living trust – who to go to

Hi Terry, Going to people who can help with Wills and Living trusts, who can you go to where it..

Just have a will

My wife just died no kids ! What should I do going forward . Most money is in cd’s and..

Retirement Advice

I’m 68+ and think I’m ready to retire. I have 375k in 401k . Thinking of rollover ? Do I..

Social security and whose to take first

So my question is can I take my social security now and when my husband dies can I transfer over..

What to do with the money

Hi, Terry – my husband and I came into a large sum of money, and would like some guidance on..

reclaimation of s.s. benefit after death

My Mom died on Feb. 22, she received her s.s. benefit on Mar.1st by direct deposit. On Mar. 27th they..

The difference between a 401k and a IUL

Is it better to have a IUL or 401k and what is the difference between the two

retirement checklist

Hi Terry, I am a 60 year old union ironworker, getting ready to retire at 62. I’d like to get..

Roth IRA conversion

I see a lot of advice regarding converting traditional IRAs to Roth. I honestly don’t understand it. Won’t most of..



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