Overcoming a Deep-seated Fear of Difficult Conversations Story

Today, a client and I are celebrating her inspiring progress—overcoming a deep-seated fear of difficult conversations and learning to truly internalize positive feedback.

Despite 20 years across FAANG and startups, she was caught in a cycle: work intensely, burn out, question her worth, leave, repeat. Her career stalled, and the quality of her time with her kids began to degrade.

“People know me as a firefighter… I feel I’m too small to be worth anybody’s time,” she shared in our first session.

Through deep conversations about her working style and underlying beliefs, she had a realization that changed everything:

“Mindset is the main thing I need to work on.

She wrote her personal burnout playbook, tracking what drained her energy and how to pace herself. One evening, instead of working late, she sent me a picture of cookies she baked.

Then came the harder part—self-advocacy.

She saw she’d been “zigzagging through her career, kicking the can of difficult conversations down the road.”

So she began preparing differently, speaking up even when it felt uncomfortable in high-stakes situations.

“The negative consequences were bigger in my mind than in reality,” she realized.

So, positive feedback began to flow in. But she couldn’t absorb it—she’d detach and “forget about it 30 seconds later.”

Not allowing herself to feel success was a way to keep striving, she realized.

And that paved the way for a simple, yet profound breakthrough: “It’s OK to be happy. Celebrate in some way—get boba with my kids after a great review.”

Nine months into coaching, she feels clearer, calmer, and more confident. Her path to a promotion is clearer than it’s ever been—not because her technical skills changed, but because she did.

The journey to a leadership role is actually a journey of personal growth, courage, confidence that technical work alone cannot unlock.

When we build that courage, we begin to live with authenticity, autonomy, and the quiet power to shape the life we truly want.

Coaching can help us build that life.