This is not a trick question: 'What do you *really* want?' 💫

Powerful Questions for Moving through Transition

Last week, I found myself in a room full of accomplished women balanced between the familiar and the unknown. I had the honor of co-leading a workshop on "Your Next Chapter: Thriving through a Career Transition" for the Healthcare Business Women's Association (HBA) SF Chapter.

Some of these 30+ mid-career professionals were eyeing the next horizon with eager anticipation, while others glanced back at their comfort zones, wondering if they should take that next step forward.

My co-presenter, Tanja Powers, shared a striking insight: most of us undergo at least seven significant life transitions as adults—from becoming a parent to changing careers to retiring. These pivotal moments often challenge our identity and priorities. We're all either in the midst of a transition or feeling the tremor of change underneath our feet.

To help unlock insights, we encouraged our participants to delve deep with these thought-provoking questions:

1. What do I *really* want? (Beyond societal expectations and "shoulds")
2. What do I want to be celebrating at my retirement party?
3. Whom in my network do I envy most, and why? What is this telling me?
4. How much of my identity is tied to my work?
5. Which habits, mindsets, or stories are no longer serving me?
6. What does work/life integration mean to me, and how do I value it?

These questions aren't just for those in transition—they're valuable for anyone, any day of the year. Some answers may come easily; others might require deeper introspection. The key is to notice what emerges without judgment.

If you feel stuck, consider what experiments you could try to learn more about yourself and your potential paths. (Reply to this email and I’ll send you my Experiment Design worksheet.)

From Reflection to Action:

Our participants left the session with pages of notes and a renewed sense of inspiration. They were reminded that they don't have to feel alone in the process in this in between.

Now it's your turn: Find a quiet moment to reflect on these questions. What surfaces for you? How might your answers shape your next steps?

Remember, every career or life transition, no matter how uncomfortable, is an opportunity for growth, self-discovery and re-connection to purpose. It's your chance to perfect your balance and enjoy the exhilarating view from the tightrope above.