TBD 121: Pondering.
🏖️ A little bit of summer reflection to get you on track.
Again, I’m on an airplane as this wings its way into your inbox. This time, to the National Mountain Bike championships in Virginia. (Send it!) 🚴🏽 Summer is a great time for reflection but how we go about that can be fraught. I put together a five day guide with prompts to get you started.
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? How am I showing up?”
Sometimes those questions are too big and overwhelming, so I've broken out questions into five days pondering you can journal about, hold in mind, or discuss with a friend while you sip margaritas or linger over coffee.
5 Days of 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 might open some interesting conversations with those you're with. 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?
✨🎙️✨ The Evolution or Revolution Podcast
Hear stories of people who have questioned their own life paths and ended up making big changes. Hear how they did it, step-by-step, be inspired and start to hatch your own plan.
🌻 Work with me 1:1
Set up a 30 min call to talk about coaching and figure out how we unravel answers to your questions. Book time →
📚 Summer Reading Recommendations
These are good books I recommend for difficult times. Start reading →
⭕️ Women's Leadership Circle
Join this fall for connection, conversation and skills. We’ll meet five times to talk about peace, power and presence and develop supportive community. Apply now →