Hey there Reader,
Three Men and a Sailboat - The Great Dockside Debate
You ever witness something that feels like a comedy sketch unfolding in real life?
That was me recently—standing quietly (and quite proudly) on the sidelines as my husband, the seasoned sailor of the family, found himself... let's say in discussion with our adult sons over how to handle a sailboat situation. The twist? These once-little-kids-now-grown-men were confident they had the better plan.
I could feel the stubbornness radiating off the dock. Each man was convinced his way was the way. My husband’s face said it all: “Who are these children, telling me how to fix the lines?”
And yet—I held my tongue. I knew better. No advice. No encouragement. No referee whistle. Just me silently watching from the dock, amused and entertained, pretending to admire the view while watching this dynamic play out like a slow-motion " who knows best" performance.
The girlfriends? Oblivious. They were deep in conversation about something delightful and unbothered—probably what to look forward too after getting off the dock.
Each man had his way of doing things. My husband—the sailor in the family—watched as our sons, once little boys clambering around, now grown men, confidently debated each other on the best way to straighten out the ropes and lines that were crossed over. You could almost hear the internal dialogue: “Who do these guys think they are?”
But here’s the beautiful part: They figured it out.
No yelling. No egos (well... maybe just lightly bruised ones).
Despite generational differences, they worked through it. Sailboat secured. Pride mostly intact.
Through a few missteps, plenty of discussion (read: minor power struggles), and eventually laughter, they navigated the challenges and made the boat sail-ready. Watching them brought me so much joy. The boat stayed afloat, but even more importantly, so did our connection.
And isn’t that what we all want? To work through the messiness of communication and come out still tethered together?
That moment reminded me how important it is to make space for different perspectives, even when it's uncomfortable. Especially between generations.
And it hit me—this is what makes summer sweet.
A moment that could’ve become a power struggle turned into a lesson in balance, humility, and teamwork. One brought wisdom, the others brought ingenuity. Together, they made it work. That’s what family (and connection in general) can be when we let go of needing to be right and instead, stay open to learning from each other.
So often, we're divided by age:
Young folks thinking older people are outdated.
Older folks thinking the young are clueless.
But magic happens when both sides give a little, listen a little, and laugh a lot.
Bridging the Generational Gap
So often, we stay in our lanes—elders with elders, youth with youth—and the rich wisdom and energy between those groups never gets exchanged.
I was at a seniors’ group recently, listening to stories about aging, resilience, and how it feels to have the body slow down while the mind still runs free. And I found myself thinking: Why don’t we hear these conversations more often?
Why aren’t 20-year-olds listening to 70-year-olds talk about regret, love, forgiveness, or purpose? Why aren’t more older folks asking young people about what they hope for, what they’re afraid of, or what lights them up?
The truth is: we all need each other.
Young people need guidance, humor, and perspective from those who’ve seen life from a higher vantage point. Older people need the curiosity, innovation, and aliveness that the young carry so naturally. These connections are rejuvenating, enlightening, and deeply life-affirming.
So maybe this summer, we take a step toward that.
If you’re young, seek out someone older and ask them something real.
If you’re older, find a way to connect with someone younger—listen, share, laugh.
This month, let that be the spirit.
Plan for connection. Embrace the messiness of family projects. Invite people into your life who challenge your thinking and make you laugh. Be intentional about how you spend these summer weeks. They’re slipping by.
A few questions to ponder this week:
✨ Where could you hold your tongue and let others find their own way (and wisdom)?
✨ Are there opportunities to bring different generations together in your life this month?
✨ How might you plan for more meaningful (and fun) connection before summer ends?
Sometimes it’s not about doing something big.
It’s about showing up, staying quiet (when needed), and watching the beauty unfold.
You don’t need a sailboat or a perfect family dynamic to do it.
Just a willingness to show up, ask a few good questions, and let the winds of connection take you somewhere new.
This Week’s Thought to Ponder:
Where in your life could you benefit from a different generational perspective?
What might you gain if you invited that perspective in?
PS – If you’re navigating your own transitions—career changes, identity shifts, or even just needing help finding clarity—my coaching practice is built to support you through that process.
Let’s talk about where you are, and where you want to go.
.
What's happening in August:
- August has arrived and the summer is sailing by. No dates have been set for workshops, but I am available for the Free Clarity Connection call on some select dates and this is intended to help you get some initial focus on what is getting in your way and what can you do to move forward with confidence and clarity to help you get some positive results. See the Link above.
Staying Connected
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