From the Road Back to the Why
- Eliana Lipsky
- Jul 16
- 2 min read
Whether on the road or at home, finding purpose matters.
About a year ago, my family and I packed up our lives—four kids, one carry-on duffel and one backpack each, and a shared dream—and set out to travel the world for a year. We traded school lunches and morning meetings for rickshaws in India, back-alley adventures in Vietnam, and Shabbat candles lit in unfamiliar places. The adventure was equal parts chaotic and clarifying.

As we moved across continents, I found myself constantly tuning into what it means to learn—not just for my kids, but for all of us. Learning happened at border crossings and train stations, in broken-English conversations (and sometimes just through grunts and gestures). It happened in the space between what we expected and what we experienced. We weren’t tourists—we were students of the world.
Learning lives everywhere.
That shift in perspective was powerful. It reinforced what I’ve always believed:📍 Learning doesn’t begin and end in a classroom. It lives in every choice we make, every relationship we build, and every goal we set. Most of all, learning happens in every challenge we accept and every disappointment we overcome.
What this means for my work now
Now that we’re almost home, I’m bringing that lens back to my work—with more clarity, more urgency, and more heart.This blog marks a new chapter: one grounded in intention, built on reflection, and focused on impact.
While abroad, I continued coaching leaders and consulting on projects—sometimes from a guesthouse in Cusco, sometimes from a café in Osaka. I helped a Jewish organization design the first menopause education workshop series of its kind. I sat with leaders (virtually) as they asked the big, brave questions:
“What’s next for me?”“Why am I doing this work?”“How do I lead with both strength and empathy?”“Where am I taking my school?”
My answer always circles back to this:
👉 When we’re rooted in purpose, the path forward becomes clearer.
Why do I do this work? Because learners—from early childhood through adulthood—deserve the best educational experience possible.And to make that happen, we need transformational leaders who are deeply connected to their “why.”
Let’s build something lasting
I’m here for those ready to reconnect with their purpose—or redefine it. For school leaders, nonprofit founders, educators, and visionaries with an idea they’re still shaping.
I’m a strategist, a sounding board, and a guide—especially in the messy, meaningful middle.I love helping people and organizations ideate, align, and bring their “why” to life.
Let’s build something lasting. Let’s lead with purpose.And let’s keep students—always—at the center of it all.
📝 Coming soon to ELuminations: Thoughts on honoring transitions—and why they matter more than we think.



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