Choosing Between Good and Good

So… many… salads…

Friends—

Some of life's trickiest moments aren't about choosing between good  and evil —that's actually pretty easy.

The real challenge? Choosing between good and good.

This past weekend, I found myself in that exact spot:

Do I go to Vegas to support my fiancée Jen at her daughter's dance competition?

Or...

Do I stay home for my son Matt's Junior Prom dinner—which, as I'd just remembered, was scheduled to happen at our house?

Someone was going to be disappointed. (Or so I thought.)

Now, this wasn't a casual commitment. Hotels, cars, the whole shebang had been booked for the competition weekend. Meanwhile, my son calmly assured me the dinner was in good hands: The chef—yes, an actual 5-star restaurant chef and brother of one of the prom attendees—was running the kitchen.

You may be screaming at me through your mobile device as we do at the unwitting idiot on screen who's about to walk into a clearly obvious trap:

“Jeremy, it's your son's LAST prom! Are you really about to be that guy who ends up on Dance Moms?”

Looking back, the answer seems obvious. But in the heat of the moment? It wasn't.

I stayed for the prom dinner.

Twenty-two teenagers in formalwear demolished a buffet like ravenous wildebeests, and I ended the night elbow-deep in dishes. 

And Jen? She had a magical weekend with sweet Annie and her army of smiling, twirling, glitter-covered dancers.

Everyone won.

We all face these “good vs. good” crossroads—especially when it comes to big life changes like real estate.

• Stay near friends or upgrade into the right-sized home?

• Downsize now while you're in control—or wait until it's urgent?

• Sell and cash out—or keep it as a rental to build wealth?

Here's the thing about crossroads:

It's often less about which road you take… and more about committing fully once you do.

Half-hearted decisions rarely serve anyone well.

Curious how I made my call?

I picked up the phone  and talked to my parents.

Yes, even with a big birthday coming up (hello, 50 ), I still lean on their wisdom—and honestly, I treasure those conversations more than ever.

So if you find yourself at a real estate crossroads, maybe it's time to talk it out.

I've helped over 2,000 families navigate their next steps. While I can't offer you a call with Dale and Dixie (though they'd be thrilled), I can promise a thoughtful, pressure-free chat.

Grab a time to connect and let's chat about your crossroads—whether it's by phone or in my cozy office.

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