The Coach I Hired to Coach Me

The Daily CHEW™
Moving God’s love from head to heart for Christian professionals

A few months ago, Dan Rockwell and I decided how we’d actually spend our weekly coaching time: not leadership in general, but specifically what helps Christians get God’s love from head to heart — the thing I’m building my whole practice around right now. Walking into last week’s session, I caught myself running a quiet calculation. I’m the one studying this at the doctoral level. Dan’s expertise is leadership, not spiritual formation. How much was he really going to add here?

C.H.E.W. with Me

New here? What is CHEW? — a 30-second practice that grows into a day woven with God’s love.

C – Clarity: Wondering if the Expert Still Needed the Coach

It’s a specific kind of temptation, and it doesn’t show up as arrogance — it shows up as logic. I know this material better than almost anyone I know. Dan’s gift is leadership. So the math seemed to say: diminishing returns. That math is exactly the self-sufficiency I spend my working hours coaching other high performers out of and pushing them towards something better.

H – Hear: Iron Sharpens Iron

“Iron sharpens iron, and one man sharpens another.” (Proverbs 27:17)

This is not a verse about needing correction because something’s wrong with you. It’s a Father describing how sharpening actually works — friction against something outside you, not a blade improving itself in isolation. Stay with what is said: one man sharpens another. Not “the more skilled man sharpens the less skilled one.” The image has no exception clause for people whose job is sharpening others.

The Hebrew verb behind “sharpens” is chadad — the same word used for putting an edge on a weapon, not for polishing something already fine. And the phrase is literally “sharpens the face of his friend”: not just his ideas, but his whole countenance — his readiness to walk back into the room.

E – Exchange: What Dan Saw That I Couldn’t

By the end of that session I’d remembered something I already knew but needed to relearn: having a coach in some form has been indispensable to my practice for more than a decade, and it was never really about who knew more theology. Dan sees things I don’t see. He knows me well enough to spot exactly where I get in my own way, and he calls me back to who God actually designed me to be — not to a generic leadership template he’s running everyone through.

I’ve now done some version of this work for three decades. There will never be a point where I stop having blind spots, or stop needing someone outside my own head to ask the one question that unlocks what I couldn’t get to alone. A few weeks ago, right as I was deciding to go all in instead of coast, it was Dan — not me, not my own reflection time — who pushed me to block off a full day for my Ph.D. work so the focus would be real instead of squeezed into whatever was left over.

When I really believed that being coached was never about Dan outknowing me on the subject, but about him seeing me more clearly than I can see myself, the doubt in that session stopped being a question about his qualifications and became exactly the evidence for why I still need him.

Because God’s love works through others, not around them, how does that change who you let into your own leadership journey?

W – Walk: Name Someone Who Can Help to Sharpen You

If you already have someone — a coach, a mentor, an honest peer — tell them today, specifically, one thing you’ve been avoiding letting them see. If you don’t have anyone in that role, that’s this week’s real task: find one person with no stake in protecting your self-image, and ask them the question you’re afraid of the answer to.

Closing question: Who’s currently allowed to tell you something about your own leadership that you don’t want to hear?

With you on the journey,
Ryan

Ryan writes these with AI to help him say it better. Read more →

Ryan Bailey

Ryan C. Bailey helps Christian professionals live from the reality of God’s love in the middle of real leadership, work, and family pressures. For over 30 years, he has walked with leaders, families, and teams through key decisions and seasons of change, bringing together Gospel‑centered counseling, coaching, and consulting with practical tools like CHEW through Ryan C Bailey & Associates.

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