An Invitation to Reflect: Coaching, Clarity, and Coming Home to Yourself

Yesterday, I listened to one of Elena Aguilar’s Bright Morning podcasts—a role play of a final coaching session for the school year. I tuned in for ideas to support the educators I coach, but I found myself unexpectedly pulled into the process. The questions asked weren’t just for others—they were for me.

At TeachWell, we often say we must model what we hope to cultivate. For me, that means staying coachable. Remaining open. Letting myself be a learner again.

Reflection is one of the most powerful tools we have. It reveals what’s working, what’s shifting, and what needs care. Increasingly, my reflections extend beyond work to include the whole landscape of my life—physical, spiritual, mental. The more whole I am, the more fully I can show up in service of others.

Here are a few reflection prompts from Elena’s podcast, along with some of my responses. I hope they offer you a mirror and a moment to pause.

What were your goals this year, and how did you grow toward them?

At the start of the year, I felt burned out. My goal was simple but urgent: to create space to reconnect with my values, regain perspective, and discern a path forward rooted in inspiration and intention. That pause helped me see more clearly why I do this work: to serve, to support healing, and to remain engaged in the ongoing struggle for justice. Public education continues to be a space where I live out that vocation.

Your turn: What intentions did you carry into this year? What have they revealed about you?

What was a day you left work feeling great?

One day that stands out began with both surfing and yoga—my favorite combination of movement and presence. Later, I spent time writing and led two coaching sessions where clients found clarity—not because of me, but through the reflective space we created together. That day was a convergence of creativity, embodiment, and meaningful connection.

Your turn: When do you feel most alive in your work? What conditions make that possible?

What beliefs about yourself have shifted this year?

This one challenged me. It took time to untangle beliefs from values. But with reflection, I uncovered both the light and the shadows. I believe in my experience—I’ve seen trends, reforms, and resilience. That belief brings steadiness and compassion. But I also wrestle with beliefs rooted in scarcity: that I haven’t done enough or reached enough educators. What shifted is my recognition that these shadows aren’t mine alone. They’re reflections of a broader system—one built on a culture of scarcity.

Naming that truth gave me space to breathe. It reminded me that my role is to define enough for myself, to respond with self-compassion, and to reclaim my sense of agency.

Your turn: What beliefs have served you this year? Which ones might you be ready to release?

Is there anything you regret from this year?

Regret is a heavy word—and a provocative one. I paused and leaned in.

I regret the moments when we couldn’t fully reach the educators we served. At TeachWell, our Tier One offerings—those all-staff wellness PDs—are the hardest to measure in impact. We recommit to them every year because we believe educator well-being is professional development. And yet, we know that for some, the content won’t resonate. From a data lens, a 15% disengagement rate might be expected. But from a human perspective, it still stings.

The regret, I’ve come to see, is rooted in care. We know educators’ time is precious. If our sessions didn’t feel like the best use of their time, we take that seriously. Beth Orton sings, “Regrets are lessons we haven’t learned yet.” I’m still learning how to hold space better, how to meet more people where they are, and how to keep our torch lit for integrating wellness into the core of education.

Your turn: What regrets—small or large—are inviting you to grow?

How do these reflections shape what’s next?

For TeachWell, we’ve made some big decisions. The most personal one: I’m staying in the work. What felt like burnout was, in part, disconnection from the educators who inspire me most.

Next year, we’re expanding our offerings in two key ways:
– More one-on-one coaching for school leaders—this is my personal area of focus.
– A strengthened Tier Two strategy, offering opt-in wellness groups and close partnership with leadership teams ready to weave well-being into their school culture.

We’ll continue Tier One work with a renewed emphasis on play, creativity, collaboration, and nervous system regulation. And we’ll move away from sessions that feel too didactic, too much like traditional PD. We want to keep modeling what we believe: that professional development can be humanizing, joyful, and sustaining.

Your turn: What are your next steps—not just in your role, but in your growth? What will you carry forward, and what are you ready to leave behind?

If you’re leading, teaching, parenting, or simply trying to stay connected to your values—reflection isn’t a luxury. It’s a lifeline.

Let this be an invitation to pause. To ask big questions. To answer them with honesty and care.

And if you’re curious about bringing this kind of work to your school or team, we’d love to talk. Visit www.teachwell.net  to learn more.