Wild Card

Wild Card Questions

Dental Insurance for Seniors

terry, what’s the best insurance plan for seniors who are on medicare? looking at all options with no waiting period..

Debit Cards risks

My husband refuses to use a debit card even though most businesses do not accept checks anymore. He read a..

Form with Important names, accounts for kids

You mentioned on John Williams that you had.a financial information form to have for my kids. I can’t find it...

Cost basis of stock

I was employed by Walgreens for 36 years . I acquired over 15,000 shares thru payroll deduction, stock options and..

saving accounts

Could you please recommend a brick &mortar bank, S&K, credit union where a child could open an account for some..

THE VALIDITY OF THIS NEW SOCIAL SECURITY PERSONAL ACCOUNT PROCESS: LOG IN .GOV or ID.ME

Thank you for this platform to ask you a question. Several of us on Social Security just recently have been..

Personal organizer form

Read you every week and like your advice. In your 11/23/2025 you referred to a Personal Financial Organizer on your..

Personal financial organizer

Unable to locate where to access the personal financial organizer. You referenced it in the Sunday Tribune 11/23/2025. Couldn’t locate..

Personal financial organizer

You reference this in the trivia article today and I can’t see the link to it

Estate conversation timing

My husband and I are both 60. Our boys (twins) are 20. We likely will have substantial assets to pass..

personal financial organizer download

I am trying to find and print the “Personal Financial Organizer” as mentioned in your 11/23/25 email. Can you please..

SS & unemployment.

Hi terry. I’m 67 and collecting SS. I still work as a seasonal employee. Can I collect unemployment AND SS?..

Personal planner

Where do I find the 4 page form you mentioned on John Williams show for estate planning talk with children.

Identity Protection

Terry, It has been suggested that parents should subscribe to identity protection services not just for themselves but also for..

Cook County real estate tax increase

Can you do a segment on WGN- CC late tax bills and suburban 2025 tax increase for 2026? I got..

Stolen Retirement Money

Hi Terry, My dad has retirement accounts at Fidelity. Somehow his account was hacked maybe through a sophisticated operation where..

Sharing Financial Position with Adult Children

Hello. Appreciate you and have followed you for a very long time. Thank you for all you do. I’m 60...

Retirement anxiety

Dear Terry. I hope you can give me some guidance. I am 61 and self-employed with a secure job. I..

2024 Taxes – Amended return waiting for refund

Terry, We filed our joint return for 2024 in April (electronically) and received our refund in a short time period..

Buying new car at age 73, should we finance or pay cash

Looking at buying NEW car, around 35k. We have plenty of cash, currently earning 4% in T-bills. Both our age..

money

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