Ryan C. Bailey & Associates, LLC

09/08/2026

Most leaders run a better meeting with their team than they've ever run with their spouse. It's time to change that.

Read the Full CHEW → https://ryancbailey.com/the-weekly-meeting-you-run-for-your-team-but-never-for-your-marriage/

Many leaders could recite their Tuesday one-on-ones from memory — who’s on the calendar, what carried over from last week, which follow-up you still owe someone. Ask the same leader when they last had a real, structured conversation with their spouse about how the week actually went, and the ans...

09/07/2026

09/07/2026

A leader who needs to stay the most gifted person in the room has confused leadership with recognition.

Read the Full CHEW → https://ryancbailey.com/the-two-men-who-started-prophesying-without-permission-and-why-moses-was-glad/

The complaint reaches Moses secondhand, the way most leadership problems do. Someone ran to Joshua first. Joshua, fiercely loyal and probably more protective of Moses’ standing than Moses is himself, brings it straight to the top: two men, Eldad and Medad, are prophesying in the middle of camp ins...

09/06/2026

God runs towards you out of love. He was never waiting to see if you'd earn the welcome.

Read the Full CHEW → https://ryancbailey.com/the-father-who-was-already-running/

Picture the scene the way Jesus’ first listeners would have. A small village where everyone can see everyone else’s business. A father standing at the edge of his own field, morning after morning, watching a road that has delivered nothing but disappointment for months. He’s watching. And one ...

09/05/2026

A teenager who never sees you give doesn't just miss a financial lesson — they miss watching what it looks like to actually believe money isn't the point.

Read the Full CHEW → https://ryancbailey.com/teaching-your-teenager-to-handle-money-what-generosity-at-home-actually-looks-like/

Your teenager has never once watched you decide to give something away. Not because you’re stingy — you give plenty, quietly, often automatically, a check written or a transfer made somewhere they’ll never see it happen. You’ve just never done it where they could actually watch, and a money ...

09/04/2026

A parent's love for their child doesn't shrink as the child grows up — it simply changes shape.

Read the Full CHEW → https://ryancbailey.com/the-manual-i-wish-existed-for-this-weird-in-between-stage/

My twin boys just turned 21. My daughter is 18. All three are believers. All three have jobs they love. All three are now facing taxes, buying their own things, and living with the consequences of their own choices — real adulthood, arriving in real time. I wish someone had handed me a manual for....

09/03/2026

The world does not fall apart the moment you stop holding it together, because you were never the one holding it together in the first place - God has been holding it together since the beginning of time.

Read the Full CHEW → https://ryancbailey.com/rest-isnt-a-reward-its-a-confession-you-are-not-the-one-holding-this-up/

You checked your phone one more time before turning off the light. Nothing was actually happening — no fire to put out, no message you were genuinely waiting on. You checked it anyway, because some part of you doesn’t fully believe things keep running smoothly if you stop watching them for eight...

09/01/2026

A leader who only hears the loudest voice in the room has mistaken volume for value.

Read the Full CHEW → https://ryancbailey.com/call-on-the-quiet-one-first/

You already know who’s going to talk first in your 9 a.m. You could write the transcript before the meeting even starts — same opening line, same confident tone, same person filling the first thirty seconds of silence before anyone else gets a foothold. Maybe it’s you, maybe it’s someone els...