Dear Younger Me…
This episode is unlike any other I’ve recorded. It's raw. It’s vulnerable. And it’s a truth I never thought I’d share publicly.
It started with a prompt during a leadership mastermind call I’ve been part of for three years. Casey, our facilitator, asked us to do something different: write a letter to our younger selves.
Now, this group isn’t the sentimental, kumbaya type. We’re all high-growth founders, often strategizing our next big move or dissecting our KPIs. But that day? That day was different. We showed up fully human—no metrics, no decks, no masks.
One of the members shared his letter. Another asked, “What gives you your chip?” You know, that fire… the pain that fuels the purpose. That question cracked something open in all of us.
So today, I’m doing something I never planned on: I’m sharing the letter I wrote to my younger self with you.
Why? Because this podcast is a chronicle of the journey—not just the wins, but the wounds too. This letter is me saying, “Here’s how I made it. Here’s what I wish I had known.” It’s about Solomon’s Paradox—how we give better advice to others than we do to ourselves—and how writing to your past self can be one of the wisest things you’ll ever do.
You’ll hear about the “basket of chips” I carry (yes, guac not included 😅). You’ll learn why sometimes, we have to be thankful for the very things that almost broke us. And maybe—just maybe—you’ll be inspired to write your own letter, too.
Because what hurt us… might be the very thing that made us.
Let’s dive into the truth of the journey.
With vulnerability and fire,
j*
Click >>PLAY<< to hear all of this and:
[00:00] Why Writing a Letter to Your Younger Self Can Be Transformative
[01:45] What’s Your Chip? The Pain That Fuels Purpose
[04:12] Vulnerability in High-Performing Rooms
[05:45] Understanding Solomon’s Paradox in Entrepreneurship
[06:50] Why This Podcast Exists: Documenting the Journey
Listen to Related Episodes:
📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader. 📧
Click >>PLAY<< to listen now!
