Hello Reader,​

What if I told you the issue isn't what you think it is?

You've been telling yourself it's the workload. Or the boss. Or the politics. You've adjusted your schedule, set boundaries, and tried switching teams.

And still, something feels off.

Here's what I've noticed after nearly eight years coaching executives: You don't trust yourself.

Not in the vague, motivational-poster way. I mean the daily, practical kind of self-trust that lets you:

• Make a decision and stand by it
• Say no without a ten-minute explanation
• Want something without apologizing for it
• Follow your intuition even when you can't rationalize it

Instead, you're second-guessing everything. Over-explaining every choice. Performing confidence while feeling uncertain underneath.

Pause here and answer honestly:

→ When was the last time you made a decision without seeking external validation?

→ What are you talking yourself out of wanting right now?

→ If you trusted yourself completely, what would you do differently tomorrow?

These aren't rhetorical questions. Actually sit with them.

Because the thing making you miserable isn't your circumstances. It's that you've lost trust in yourself, and that lack of trust is both the symptom and the disease.

You're brilliant at managing how others experience you as a leader. But you've completely lost touch with how you experience yourself.

Most leadership development focuses on the first part: executive presence, communication style, and impact on teams. We get really good at meeting others' expectations.

But the deeper work? That requires trusting that your desires matter. That your needs are valid. That wanting something different isn't a weakness.

I'm working with a senior leader right now impressive title, company, and everyone knows—who's drowning. He loves how people react when he tells them what he does. But he hates the actual work. He's so worried about what people will think if he steps back that he's second-guessing every move.

The irony? That constant self-doubt is exactly what's making him miserable.

You might see yourself here.

I wrote about the two dimensions of self-trust, why high-achievers are so good at self-gaslighting, and the practices that actually rebuild trust in yourself—even when you don't have the next move figured out yet.

If this landed somewhere uncomfortable, that's where the real work begins.

Want to go deeper? I recently joined Kimberly Benoit on the We've All Done It podcast to talk about midlife leadership transitions, finding purpose after 40, and what it takes to rebuild trust in yourself when everything you've achieved still leaves you feeling hollow.

Listen: Midlife Leadership Reset: Finding Purpose and Joy After 40
​Watch: YouTube version​

Warmly,

Chelese

703.825.0308
Chelese@ChelesePerryLLC.com
www.ChelesePerryLLC.com

Want to work together in 2026? Reader - if you want to work with me in 2026, here are a few ways that we can partner or meet for virtual webinars:  ​Harmonious Leadership Circles for women leaders ready for intentional self-leadership work (12-month program). The next cohort will be opening up in April.  ​Finding Your True North is an 8-week foundational program to discover your values and vision.  And 1:1 Executive Coaching for senior leaders seeking personalized transformation.  The deeper work of rebuilding self-trust happens in community. ​The Reclamation for women leaders will be opening in the fall (6 months, 8 spots).

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