Dear Monday
Dear Monday is a podcast about the decisions that change the shape of your life. Most people talk about opportunity in terms of upside — growth, freedom, financial potential. But far fewer conversations sit with what lives underneath those decisions: the obligations, the constraints, the commitments that are difficult to unwind once they're made.
This show exists in that space.
Each episode explores the realities behind ownership — business ownership, franchise investment, career exits, and other high-stakes commitments that reshape financial and personal life.
I spent years inside franchise ownership and deal advisory — walking prospective owners through the discovery process and watching how the industry was designed to move people toward decisions, not through them. Dear Monday is what I built for the moment in between.
The conversations are reflective, structured, and grounded in one principle: Clarity before commitment.
Rather than motivation or hype, Dear Monday offers disciplined thinking about risk, responsibility, and the long arc of a decision. The kind of thinking that belongs in the room before a contract is signed.
Because once it is — the real work begins.
Episodes
35 episodes
S2E9 Clarity Before Commitment: How Do You Know When You’re Ready to Go Again?
This season has followed three different kinds of threshold moments.One woman standing at the edge of ownership. One woman trying to leave a successful career. One woman rebuilding after disruption she didn’t choose.All three have...
S2E8 Clarity Before Commitment: Do You Actually Want the Life, or Just the Decision?
The research is done. The FDD has been reviewed. You’ve talked to owners, run your own version of the numbers, attended discovery day. A yes is forming — you can feel it.And something is still making you pause in a way you can’t quite na...
S2E7 Clarity Before Commitment: How Do You Know When You’ve Waited Too Long?
There is a version of waiting that is responsible.The timeline is moving. Real things are accumulating — runway, readiness, a foundation for what comes next. The plan is being built. The condition is specific and the endpoint is real.
S2E6 Clarity Before Commitment: What Are the Obligations Nobody Mentions?
Every major ownership decision has something in common.It doesn’t matter if you’re evaluating a franchise, planning a corporate exit, or rebuilding after a disruption you didn’t choose. The process around you — the brokers, the advisors,...
S2E5 Clarity Before Commitment: Where Do You Go When the Ground Shifts?
She didn’t choose this.The role ended. The plan she trusted no longer held. The ground moved without her permission. And now she’s not standing at the edge of a decision — she’s standing in the aftermath of one.This is Renee. And ...
S2E4 Clarity Before Commitment: What Are You Pretending Not to Know?
She already knows.That’s what makes Allison different. She’s not waiting for information. She’s not in the discovery process the way Erin is. She has the plan, the research, the numbers she’s been running quietly for months. She knows wh...
S2E3 Clarity Before Commitment: What Does Your Yes Actually Commit You To?
You're closer to yes than you've ever been. The research is done. The fear has changed shape — gotten quieter, more specific. Something has shifted. But before that yes lands, there's a question worth asking: what are you actually sayi...
S2E2 Clarity Before Commitment: What Are You Waiting for Someone to Tell You?
You've done the research. You've read the FDD, run the numbers, talked to current owners. By every reasonable measure, you have what you need to decide. And you're still waiting. In this episode, TuRhonda Freeman names the ...
S2E1 Clarity Before Commitment: The Moment Before the Decision
Dear Monday is back — and this chapter is different.After three years working inside some of the most consequential decisions women make — consultations, due diligence, the conversations that happen when an opportunity stops feeling exci...
S1E25 Foundations: Anchored w/ Coach Tish
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
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S1E24 Foundations: Break the Cycle
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
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S1E23 Foundations: A New Normal w/ Isabelle Covington Lay
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
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S1E22 Foundations: Be Relentless!
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
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S1E21 Foundations: Growing in the Dark w/ Nicole Denae
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
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S1E20 Foundations: It Is Well!
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E19 Foundations: Demolition Day w/ Joi Worthy Johnson
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E18 Foundations: Watch What You Say!
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E17 Foundations: What Did You Learn?
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E16 Foundations: It's Only Up From Here!
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E15 Foundations: Go
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E14 Foundations: Group
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E13 Foundations: Growth
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E12 Foundations: Goals
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E11 Foundations: Gratitude
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
S1E10 Foundations: Every Vision Needs GOD
This episode is part of Season 1 of Dear Monday—the foundation of the show. These conversations centered on facing life’s demands with courage. As Dear Monday evolves, newer episodes focus on clarity before commitment and the decisions that...
