Coaching Styles: Compassion with Challenge

Anna and Zach describe the ideal coach as empathetic yet appropriately challenging, creating safe spaces to stretch clients.

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What do you do when the life and career you’ve built no longer work for you?

In this episode, I’m joined by Anna Holtzman, a former reality TV editor turned therapist, now life coach, who helps creatives and entrepreneurs release imposter syndrome and step into the next chapter of their careers. Together we share our own pivots and life quakes, and what it really takes to keep moving one step at a time. If you’re frozen in fear, stuck in the messy middle, or wishing life could go back to “normal,” this episode offers comfort, clarity, and the reminder you don’t have to do it alone.

Key Takeaways

Discern where your cheese has moved. The story of chasing cheese is a reminder that the old path may no longer serve you.
Embrace pivots as part of the path. Change can feel like failure, but it is often the exact step toward alignment and renewal.
Start with the smallest silly step. Action leads to motivation, not the other way around. Even tiny wins unlock momentum.

Episode Highlights

Parallel pivots that sparked a reunion and deeper conversation
Life in the before times versus surviving the after times
Unlocking journaling as a hidden practice of reflection
Reimagine identity by shifting from one brand to the next
Learn how to stop chasing the wrong cheese and pivot with courage
Fear, scarcity, and the power of “you’re not alone right now”
Face fear in your pivot and discover what opens on the other side
Find inspiration in real stories of clients choosing courage in chaos
How to build momentum with small silly steps that spark motivation
Calm fear and create clarity through journaling dialogues

Guest Bio

Anna Holtzman is a therapist-turned-coach who helps sensitive creatives and entrepreneurs move through the fear of visibility and finally launch the work that feels most true to them. After 15 years in TV and publishing—and many false starts on her own creative dreams—burnout and chronic pain led her to the nervous system tools that helped her unblock her voice and show up for the work she loves. Now she helps others do the same: melt through imposter syndrome, bring their creative visions to life, and share them boldly. She lives in Queens, NY with her husband, stepdaughter, and three orange cats, and she hosts the podcast How to Trust Yourself.

Anna’s Website, Instagram, Email, Podcast, Workshop