Dear Friends -
Back in January, I wrote about how our comfort zone can shrink if we don’t keep stretching it.
That idea keeps popping up, especially whenever I talk to clients who feel stuck. The latest reminder came from Gary Vaynerchuk’s punch-y LinkedIn newsletter, “Let Me Delete Your Fear of AI.” His message: if you’re not carving out at least one hour a day to play with AI, you’re choosing to be left behind. His larger point? Most resistance isn’t about the tech—it’s about the fear of looking foolish while we learn something new.
If you caught my May edition, “Why Lifelong Learning Includes AI,” you know I’m already sprinkling AI prompts into these emails so you can experiment safely.
Today, let’s zoom out and talk about the larger pattern of saying no to new things as we age—and how to flip that script.
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The Problem in Plain English
Confidence drops even as experience rises. Only 26 % of internet users 65+ say they feel very confident with digital devices. pewresearch.org
Anxiety feeds the cycle. Research shows a negative self-view about aging increases “technology anxiety,” which in turn shrinks our willingness to try. bmcpublichealth.biomedcentral.com
Fear hides behind practical excuses. “It’s too expensive.” “I don’t have time.” “I’m waiting for the bugs to get worked out.” Often those lines mask the deeper worry: What if I can’t figure it out?
Left unchecked, that cocktail of doubt and delay can keep us from tools, experiences, and relationships that make Act Three richer.

Where Else Does “No, Thanks” Show Up?
Below are common arenas where many of us dig in our heels. See if any feel familiar:
Category | What We Skip | What We’re Missing |
---|---|---|
Tech | Generative AI chatbots, voice assistants, smart-home security, VR/AR headsets, electric cars | Saving hours on grunt work, safer homes, new ways to learn and travel |
Health & Fitness | Strength training beyond 3-lb weights, cold-water therapy, wearables that track recovery | Stronger bones, faster recovery, data-driven habit tweaks |
Money | Digital wallets, robo-advisors, crypto wallets for small experiments | Lower fees, diversified income streams, staying literate for the next decade |
Travel | Solo group tours, house-swapping platforms, riding e-bikes in new cities | Budget-friendly adventures, built-in communities, joy of exploring differently |
Creative Play | Podcasting, digital art tablets, online songwriting classes, 3-D printing | Fresh outlets for self-expression, new social circles |
Relationships | Purpose-driven dating apps, mastermind groups, language-exchange partners | Fresh connections, cognitive flexibility, deeper sense of belonging |
Everyday Life | Ride-share apps, self-checkout, meal-kit services, smart meters | Less friction, time savings, lower utility bills (85 % of seniors say tech can save both). |

A Three-Step Reframe
Adopt a Curiosity Hour. Block 60 minutes once a week to poke around a new tool. No goal beyond messing around.
Buddy Up. Pick a grandkid, neighbor, or colleague as your “tech sherpa.” Swap skills: they guide you through ChatGPT; you mentor them on negotiation.
Shrink the Risk. Choose the lite version first: watch a VR demo at Best Buy before buying a headset; set up Apple Pay for coffee only; do a free 7-day trial of a language app.
Mindset mantra: “I can learn anything—I just haven’t learned it yet.”

AI Prompt
Copy and paste this into your favorite AI platform:
“You are an experienced “Third-Act” transition coach who combines positive psychology with practical action planning.
Ask me 5 quick, reflective questions to uncover one core fear that’s keeping me from trying something new (e.g., a technology, hobby, or lifestyle change).
Summarize the fear in one concise sentence to be sure we’ve named it accurately.
Reframe that fear as an opportunity by listing three potential upsides if I move forward anyway.
Design a simple, three-step action plan I can complete in the next 7 days to shrink the fear’s power—each step should be specific, low-risk, and take no more than 30 minutes.
End by giving me a short mantra (10 words or fewer) I can repeat whenever the fear resurfaces.
Wait for my answers to step 1 before continuing with steps 2-5. Respond in a warm, encouraging tone.”
🔥 Hot Tip: replace “technology, hobby, or lifestyle change” with whatever feels most relevant—learning ChatGPT, lifting heavier weights, planning a solo trip, etc.—to make the prompt even more personal.
This Week’s Challenge
Email me one new thing you’ll try before next Sunday—whether it’s trying the ChatGPT prompt, a kettlebell swing, or booking an art class.
Staying curious with you,
Cara Gray
Third Act Consultant, CPRC, CEPA™️
P.S. Forward this to a friend who doesn’t tend to try new things.They can subscribe here and join us for the next editionl.
P.P.S. If you want to start planning your third act, set up a time on my calendar for a chat: Schedule a Chat with Cara