The past few years have brought massive change, disruption, and transformation in both life and business. Many entrepreneurs are standing at a crossroads, asking: what is the right path for me in this next era?

In this episode of The Kelly Roach Show, Kelly shares insights from a Legacy Leaders mastermind conversation about making aligned business decisions rooted in discernment, not comparison. She unpacks how to balance ambition with peace, prune and simplify when necessary, and lean into God’s guidance as the ultimate compass for your entrepreneurial journey.

You’ll learn why bigger isn’t always better, how to create the right conditions for success in this season, and why giving yourself permission to evolve may be the most important strategy of all.

Timestamps

• 0:04 – The importance of discerning the right path for your next era

• 2:24 – The danger of “me too” marketing and how brands self-commoditize

• 3:38 – Stick to one business or pursue multiple paths?

• 5:54 – Why focusing deeply on one business may not be “settling” but strength

• 7:40 – Discerning between ambition, culture, and God’s calling

• 11:10 – Bigger isn’t always better: why small can be powerful and purposeful

• 20:40 – Kelly’s own focus for 2026 and the importance of pruning

• 22:28 – Creating the conditions for success in your current season

• 25:21 – Invitation to the Legacy Leaders mastermind event in Miami

Resources:

• Grab a copy of Conviction Marketing: Your Guide to Influence, Authority and Market Leadership Online: https://www.amazon.com/Conviction-Marketing-Kelly-Roach/dp/B09S259DWK 

• Grab a copy of Discerning the Voice of God by Priscilla Shirer: https://www.amazon.com/Discerning-Voice-God-Revised-Recognize/dp/1462774040 

• Legacy Leaders Mastermind: High-level strategic mentorship and community for $1M+ entrepreneurs: https://programs.thebusinessadvisory.com/legacy-leaders

• Legacy Leaders Miami Mastermind Event (Sept 26–27): Two-day in-person strategy and networking intensive at Miami Ironside: https://events.thebusinessadvisory.com/eventrsvp-4871