Again, I’m on an airplane as this wings its way into your inbox. This past week, my kids got their summer reading and writing assignments, and I thought it might be a good time to share questions worth pondering with you, too. So, this week, I share five days of questions worth pondering as you unwind.
The Power of Distance
There's something magical about distance from our daily routines that creates space for deeper questions to emerge. Away from the barrage of emails, meetings, and endless to-do lists, we suddenly have room to wonder: “Is this the life I actually want to be living? Am I showing up in a way I’m happy with?”
For me, this question became unavoidable during my own transition out of the tech industry. The catalyst wasn't a crisis or dramatic moment—it was simply being asked if I was taking care of what I truly cared about. My immediate response was "Of course!" But as I sat with that question longer, really pondering it, I realized I had been so busy that I had stopped checking whether I was creating a life aligned with my values and the things I cared about most.
Questions Worth Pondering by the Pool (or Mountain, or Beach)
DAY 1: The Care Inventory
• What do I actually care about? Not just professionally, but across all the domains of my life—family, health, creativity, community, spirituality, personal growth. What do *I* care about (not what SHOULD I care about or what do others expect from me)
• Am I taking care of what I care about? This isn't about perfect balance—it's about honest assessment.
• What has been getting my time and energy by default rather than by choice?
DAY 2: The Meaning Deep Dive
• Why do these things matter to me? What's the deeper purpose behind my priorities?
• When I say I want to "take care" of something, what does that actually look like? How would I know if I'm succeeding?
• What would it look like to live more intentionally and aligned with what I care about?
DAY 3: The Honesty Mirror
• Where am I putting resources (time, energy, attention) that don't align with my stated priorities?
• What am I doing because I think I "should" versus what I'm doing because it matters to me?
• If I stepped back and looked at my life from the outside, what would I notice?
DAY 4: The Possibility Opener
• What assumptions am I making about what's "fixed" or "unchangeable" in my life?
• If I had permission to redesign one aspect of my life, what would it be?
• What would I try if I knew I couldn't fail? What would I try if I knew failure was just information?
• Where am I being plain stingy with myself?
DAY 5: The Future Self Check-In
• What does my 80-year-old self hope I'll do with this phase of life?
• What patterns do I want to break? What new patterns do I want to create now that I’ll appreciate in the future?
• What legacy am I building in the small, daily choices I make?
The Art of Vacation Introspection
This isn't about creating a new source of pressure or turning your relaxation time into a productivity exercise. It's about creating space for the kinds of questions that rarely get attention in our busy lives.
Some vacation days, the work of reflection will feel obvious and energizing. Other days, you might discover that spaces in your life you thought were rigid are actually quite flexible. Some days you'll rest. Some days you'll practice trust. Some days you'll realize this work is never "done"—it's always a journey.
The beautiful thing about vacation reflection is that it doesn't demand immediate action. It just asks you to wonder, to sit with uncertainty, to let questions marinate. Often, the answers come not through forcing them, but through creating space for them to emerge.
The Ultimate Vacation Question
As you watch the sunset, take that long walk, or simply sit in stillness, ask yourself: Is this working for me?
Not "Is this working for my boss, my family, my bank account, or society's expectations?" But is this working for you?
Be honest. Don't you deserve to know the answer to this question?
