Great leaders don’t get it right every time. They get better over time. In this episode, I tackle one of the most critical questions a founder will ever face, “When is the right time to sell?”

I walk through five clear signs that test your timing, valuation, and mission alignment.

Are you burned out or is the assignment complete? Has growth turned into maintenance mode? Are silent warning signs showing up in your health, marriage, or spiritual life? Are you tempted by a hot market and peak multiples? Or are you waiting too long and risking enterprise value, succession strength, and legacy impact?

Selling too early can cost a mission. Waiting too long can cost value. The right exit strategy requires clarity, wise counsel, and alignment with purpose.

Tune in to this episode of The GuideLight, walk through the five signs with me, and make sure your next move protects both your business and your calling.

Enjoy the podcast? Subscribe and leave a 5-star review!

Jason Trent is the founder of Guidelight Legacy Advisors, where he helps business owners prepare for, execute, and transition through the sale of their life’s work. With over 25 years of experience as an owner, operator, and advisor, Jason understands that an exit is never just a transaction—it is a defining leadership moment that affects identity, family, culture, and legacy. Unlike traditional M&A firms that focus solely on valuation and close, Guidelight Legacy Advisors works upstream, helping owners build transferable businesses and downstream, helping them navigate the personal and strategic realities of life after exit. Through his advisory work and The Guidelight Podcast, Jason equips leaders to move from success to significance with clarity, conviction, and purpose.

Connect with Jason Trent:

Websites:
https://guidelightlegacy.com/
https://guidelightpodcast.com/

Social Media:

LinkedIn: https://www.linkedin.com/in/trent-jason/

https://www.linkedin.com/company/guidelightpodcast

Facebook: https://www.facebook.com/people/The-Guidelight/61575862355860/

Stay Connected. Stay Inspired.
Let’s build deeper, stronger relationships—one meaningful connection at a time.

👉 Explore all things JTrent Connect:
linktr.ee/JTrentConnect

Great leaders don’t get it right every time. They get better over time. In this episode, I explore how moments of misalignment can become powerful turning points, and why real leadership growth starts with refocusing your aim, not carrying shame.

I reflect on the true meaning of “missing the mark,” a phrase rooted in the language of archery. Most leaders don’t wake up trying to make poor decisions. We lead with good intentions, but distraction, pressure, and misplaced focus can pull our aim off center. When that happens, the solution is to refocus on the target.

I share lessons drawn from leadership, faith, and even the trail why looking at what you want to avoid often leads you straight into it. Strong leaders learn to set their eyes on what matters most: purpose, identity, truth, wisdom, culture, and stewardship. These anchors help leaders adjust their aim and move forward with clarity.

Learn how realigning your focus can help you lead with clarity, conviction, and renewed purpose. Watch this episode of The Guidelight.

Enjoy the podcast? Subscribe and leave a 5-star review!

Jason Trent is the founder of Guidelight Legacy Advisors, where he helps business owners prepare for, execute, and transition through the sale of their life’s work. With over 25 years of experience as an owner, operator, and advisor, Jason understands that an exit is never just a transaction—it is a defining leadership moment that affects identity, family, culture, and legacy. Unlike traditional M&A firms that focus solely on valuation and close, Guidelight Legacy Advisors works upstream, helping owners build transferable businesses and downstream, helping them navigate the personal and strategic realities of life after exit. Through his advisory work and The Guidelight Podcast, Jason equips leaders to move from success to significance with clarity, conviction, and purpose.

Connect with Jason Trent:

Website: https://guidelightpodcast.com/

Social Media:

LinkedIn: https://www.linkedin.com/in/trent-jason/

https://www.linkedin.com/company/guidelightpodcast

Facebook: https://www.facebook.com/people/The-Guidelight/61575862355860/

Stay Connected. Stay Inspired.
Let’s build deeper, stronger relationships—one meaningful connection at a time.

👉 Explore all things JTrent Connect:
linktr.ee/JTrentConnect

Transitions take time and that’s where leadership is tested.

In this episode, I reflect openly on why navigating transition requires awareness, patience, and a willingness to lead people, not just processes.

I share why change may look simple on the surface, but transitions affect identity, purpose, and trust beneath the surface. Drawing from proven transition frameworks and real leadership experience, I explain why resistance often uncertainty asking for clarity.

The three phases every transition moves through are endings, neutral zone, and new beginnings. I talk about why leaders must name what’s ending, create safety in the in‑between, and reinforce meaning before expecting momentum. Transitions succeed when leaders communicate clearly, anchor people to purpose, and model steady faith through uncertainty.

If you’re leading a team or growing a brand, watch this episode of The Guidelight to learn how thoughtful leadership can turn difficult transitions.

Enjoy this episode? Give us a review and leave a 5-star rating.

Jason Trent is the founder of Guidelight Legacy Advisors, where he helps business owners prepare for, execute, and transition through the sale of their life’s work. With over 25 years of experience as an owner, operator, and advisor, Jason understands that an exit is never just a transaction—it is a defining leadership moment that affects identity, family, culture, and legacy. Unlike traditional M&A firms that focus solely on valuation and close, Guidelight Legacy Advisors works upstream, helping owners build transferable businesses and downstream, helping them navigate the personal and strategic realities of life after exit. Through his advisory work and The Guidelight Podcast, Jason equips leaders to move from success to significance with clarity, conviction, and purpose.

Connect with Jason Trent:

Website: https://guidelightpodcast.com/

Social Media:

LinkedIn: https://www.linkedin.com/in/trent-jason/

https://www.linkedin.com/company/guidelightpodcast

Facebook: https://www.facebook.com/people/The-Guidelight/61575862355860/

Stay Connected. Stay Inspired.
Let’s build deeper, stronger relationships—one meaningful connection at a time.

👉 Explore all things JTrent Connect:
linktr.ee/JTrentConnect