The Jewish Observer
News from Middle Tennessee's Jewish Community | Wednesday, May 6, 2026
The Jewish Observer

Plan Your Happily Ever After...so that it’s not just a fairy tale. Lunch and Learn!

SCENE:Lunchtime in a local restaurant. 

 
CAST:My friend Emily and I are at a table. Sitting next to us are four cheery, loud-talking eighty-year-olds—Ted, Joe, Bill, and Don—and one much younger man, Gary, their financial advisor. 

ACTION:A discussion begins at the guys’ table. I pretend not to listen, but then subtly signal Emily to stop talking so I can hear better. 

GARY:“Okay boys, now that you are over 80, if you could go back and change anything about your life, what would it be? And no, you can’t say, ‘Don’t hire a financial advisor. 

TED:I’ll tell you what I’d change. No offense, Gary, but retirement is NOT A MONEY event—it’s a HEALTH event. Sure, money matters. But I’d spend less time checking my portfolio and more time checking my blood pressure. If I’d started early on, maybe I’d still be playing tennis instead of just watching it on TV. 

JOE:My turn, and my answer is simple: would stop postponing everything. My whole life I said, ‘I’ll do that when I retire.’ Hobbies - like mastering the computerCan’t take the time. Travel? Not nowTake up the guitar? Later 

When I retired, I found the things I’d like to do or learn have become really hard. Airports gates are always far from the check-in; guitars are crazy expensive, and don’t get me started on remembering my passwords. 

BILL:Well, if I change things, I know I would stay closer to the people who matter. I was always ‘too busy.’ Too busy to call my mother. Too busy to go to soccer games, dance recitals, family dinners. I fooled myself that I was doing it all for my family—but I missed a lot of family milestones while I was busy doing it.” 

Everyone gets quietas if each is checking that box, too. Then, it’s Don’s turn. 

DON:“All of that, yes. But mostly, I would be more intentional with my time. By 40, I should’ve asked myself what I really wanted. I chased money, titles, recognition… and somewhere along the way I forgot to ask whether any of it made me happy. Turns out, finding a good balance would have been a lot smarter than mregret.” 

I begin wondering how young, financial advisor Gary will respond to all this wisdomGary pushes back his chair and smiles. 

GARY:“You know, guys, I spend all day telling people how to save for retirement. But you four have just reminded me that retirement isn’t just about having sufficient money to live onIt’s about having more satisfaction than regret… and plenty of life left to enjoy it.”  

  I wanted to applaud. Emily smiled at me and said, That was awesome! I wish I’d had advice like that before I retired. Instead, I wasted the whole first year looking for new friends and trying to reconnect with old ones!”  

So… as we approach this May, make some midyear resolutions. Sure, call your mother on Mother’s Day - and make it more oftenGo to the kid’s recital. Take that walkAnd don’t wait too long to share lunch with old friends. 

Loretta   

loretta@coachingwithloretta.com

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