Stepping Into 2026 With Confidence

There’s something about seeing Chicago from 103 floors up that puts everything into perspective. Over the weekend, I took my kids to Skydeck Chicago, and let me tell you — their faces alone were worth the elevator ride. From the moment we stepped into those clear observation boxes, they were glued to the view. Watching my kids take it in with that mix of curiosity and quiet confidence gave the moment a whole new layer… they were in absolute awe.

And honestly? So was I.

Up there, with views extending into four states, I felt a quiet shift. Maybe it was the height, maybe it was the stillness, or maybe it was seeing my kids take in the world from a new angle — but I found myself reflecting on how often life invites us to step out of our comfort zones. Sometimes courage doesn’t arrive with a big moment; sometimes it starts with simply saying yes to the next step, the next adventure, the next opportunity to see things differently. Up in the sky, the reminder felt clear: growth happens when we’re willing to look beyond what’s familiar.

After our Skydeck adventure, we headed over 30 floors down to the Metropolitan Club of Chicago for Breakfast with Santa. It was the perfect cozy contrast to our sky-high morning — warm, festive, and filled with that holiday sparkle only kids can truly bring to life. If you haven’t been, the Club is truly something special. For over 50 years it has been a place where leaders, creatives, and changemakers gather high above the city to connect and recharge. Between the energy, the views, and the community, it’s a place that makes you feel right at home.

As we head deeper into the holiday season, I’m holding onto the spirit of that day — the wonder, the perspective, the gentle nudge to keep stepping forward. May we all find moments that lift us a little higher, remind us of our strength, and bring us back to what truly matters.

Whitney Reynolds
Whitney Reynolds is the host and owner of The Whitney Reynolds Show on PBS.
www.whitneyreynolds.com
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