What I Learned From My Summer Vacation
When I was a child, my parents formed close friendships with five other couples. Over time, this group became, let’s be honest, a bit of a clique. Six families, sixteen children.
In 2000, when the oldest of us “kids” were turning 21, we launched a new tradition: a week together on Long Beach Island, NJ. Our parents rented a house on the ocean, and we kids rented what could generously be called a “crash pad.” Inland, dated, and far too small, it was wall-to-wall air mattresses, creaky furniture from another era, and barely enough space to shimmy sideways past each other. Days were family time; nights were…well, exactly what you imagine late teens and early twenty-somethings get up to. And we always ended the trip with pizza on the beach, clinging to the last salty breath of summer..
The Gang, Long Beach Island, 2003
It was the best week of the year, and it stayed that way for over a decade.
We celebrated graduations, toasted first jobs, introduced significant others (some keepers, some not), and read every Harry Potter book release. And then came the babies. And babies do not belong in a crash pad.
So, we adapted.
First pivot: a few young families rented their own quieter house. They could pop in for beach days or quick evening catch-ups, but also sneak back for midnight feedings and nap schedules. That worked - for a while.
Second pivot: as the baby boom grew, the set-up shifted again. Instead of everyone squeezing into a few houses, we returned to vacationing with our families of origin. What didn’t shift, couldn’t last. Late-night chaos simply doesn’t pair well with bath toys and early bedtimes.
We held onto traditions where we could but let go of others. Casual late-night hangs evolved into earlier happy hours, which lasted for a while, until our group became too big to gather in a rental house without looking like we were hosting an underground rave.
This summer, we celebrated our 24th Annual Trip. Six original families have now expanded to 75 human beings, from their mid-seventies down to one-year-olds.
And our “best week of the year” now looks like:
Early evenings at the amusement park
Mini-golf logistics worthy of a military campaign
Rainy-day art projects
Pizza on the beach (still the last night, just not so late)
One sacred, kid-free night on the town
It doesn’t look the same. It shouldn’t. But it’s still the best week of the year.
And it’s not done shifting yet. The baby boom is becoming a teen takeover—and Harry Potter isn’t cutting it anymore. Snapchat, sarcasm, and eye rolls are becoming the new house rules. The crash pad may be gone, but the chaos just looks different.
The Tree Test
Here’s the thing: this tradition is like a tree. Its roots are deep—connection, ritual, friendship. But the branches have to bend with the winds of time. A rigid tree snaps. A swaying tree survives storms and keeps growing.
We didn’t have a strategy for adapting but, looking back, we were unconsciously practicing what Adaptive Leaders calls the 3 E’s of Change:
Essential: Being clear on what is so core to who we are that it will never change. Ending summer together - feet in the sand, generational overlap, time to talk about everything from the mundane to the transcendent.
Expendable: Asking what can we leave behind? What if we clung to too tightly would get in the way of the future we want. Farewell, air mattresses.
Emerging: Being curious and open to who we are becoming and allowing that to become the new norm. The joy of watching our kids form their own bonds. Shaping the week so they fall in love with this tradition the way we did, all while staying rooted in multi-generational friendship.
For You
If you’re leading through change, take the cue:
Name what is essential and non-negotiable.
Identify what’s expendable, even if it once worked.
Listen for what’s emerging—and grow toward it.
Because the crash pad may be gone, but the best weeks - and the best work - thrive on roots that hold and branches that stretch.
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If your organization is in a season of change and needs help aligning, adapting and moving forward. Let’s talk.