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.
Dear Monday
S1E20 Foundations: It Is Well!
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
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 shape what Monday requires.
How do you declare that IT IS WELL in every season of life? How do you set the expectation that something good will come out of your current circumstance? What do you say in the face adversity, uncertainty and fatigue? That's exactly what we're talking about on this episode.
HIGHLIGHTS FROM THE EPISODE:
- Putting expectations in its proper place
- A Biblical example of declaring "It Is Well"
- A therapist's tips for setting expectations for yourself (and nobody else)
Today, raise your level of expectancy, because IT IS WELL!