In this episode of The Climb, Teko Bailey sits down with contemporary gospel musician and worship leader Theo Milford to talk about fear, obedience, and finally stepping into your calling. Theo shares the honest backstory behind releasing his debut album after nearly two decades of writing songs in private. Turning 40 gave him a jolt: he realized that leaving his music trapped on a phone voice note would be a quiet form of disobedience. The conversation hits the core tension many people live with—knowing you’ve been given something to carry, but sitting on it because of anxiety, timing, or doubt.

Theo walks through his upbringing in a pastoral home where music and worship were daily life, then traces his path from singing in groups to leading worship and developing his own material. He breaks down what changed for him over time: his focus moved from “Did I perform this right?” to “Was I obedient?” That shift reframed nerves, leadership pressure, and even the way he understands success.

The two also dig into rest and mental overload. Theo explains how his song “Sabbath” came from the lived relief of a weekly reset—stepping out of toil and re-centering on God and family. They connect the dots between anxiety in modern life and neglecting rhythms of rest that are both practical and spiritual. From there, the conversation moves into fatherhood, community, and discernment—how to build a small but trustworthy circle, and how prayer shapes decision-making when not everyone around you has your best interests at heart.

This episode is for anyone who has been sitting on a gift too long, anyone wrestling with fear masquerading as wisdom, and anyone who needs a reminder that obedience creates ripple effects far beyond you.

(00:00) Fear, obedience, turning 40

(01:19) Who Theo is today

(02:41) Growing up in church music

(03:57) Learning to lead worship

(04:39) Obedience over performance

(06:38) Why he wrote “Sabbath”

(08:46) Rest, anxiety, and modern life

(11:08) Fatherhood and priorities

(14:28) Encouraging men to step out

(16:45) Debut album details

(18:19) Staying grounded as a leader

(19:23) Community and discernment

(23:51) Favorite track and closing

About Theo Milford

Theo Milford is a contemporary gospel musician, worship leader, and songwriter based in the Washington, D.C. area. Raised in a pastoral home, he has led worship for nearly two decades across churches and music collectives. After years of writing in private, he is releasing his debut album, Altars and Answers, a 12-track project shaped by scripture, lived experience, and a renewed commitment to obedience. His work includes songs like “Sabbath” and “Rest,” centered on devotion, renewal, and hope.

Website: theomilfordmusic.com

YouTube: Theo Milford

About Teko Bailey

Teko Bailey is a husband, father, coach, and guide for men walking the path of faith and purpose. Through The Climb, he’s building a brotherhood of men committed to living fully, leading boldly, and climbing with intention.

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