What Going Broke at 26 Taught Me About Gratitude
Originally shared November 21, 2024 in the Naked Sunday Newsletter. Adapted for the journal.
When I was 26, I went broke.
It started with a disagreement with my first business partner that destroyed our friendship. What followed was a long, drawn-out stalemate over the business that left me stripped of income and uncertain of what was next.
In the midst of it all, a family—clients of mine—took me in for a year. My own family helped bail me out of credit card debt. And I spent countless sleepless nights, running on sheer willpower for a year to push myself to the next phase of my life.
That was 11 years ago. Now, at 37, almost 38, I look back on that chapter as one of the most humbling and transformative experiences of my life.
It taught me lessons I’ll carry forever:
It showed me what really matters.
Losing “stuff” forced me to focus on what I still had: relationships. My now-best friend (and second business partner) stepped into my life during that time, and I met my wife. I learned that purpose and connection mattered far more than possessions ever could. The people who stood by me reminded me of my own strength and helped me see that I wasn’t defined by my circumstances.
It brought people into my life who believed in me.
That ugly fallout with my first partner was painful, but it opened the door to new, aligned relationships. I learned that when you stand for something bigger than yourself, the right people will show up to stand with you. Years later, I even reconciled with my first partner, which became part of a broader journey of healing and reconnecting with past relationships. It taught me the importance of forgiveness—not just for others but for myself.
It taught me the cost of conviction.
People say they care, but words are surface deep. You learn the sincerity of your beliefs when they cost you something. I was willing to work for nothing for an entire year—serving with no end in sight—because I believed in what I was building. It was painful, humbling, and at times, completely uncertain, but I kept going because I couldn’t let go of what I believed in. That conviction reshaped my life and gave me the clarity to lead with integrity and purpose.
It reminded me of the power of gratitude.
Living with that client’s family opened my eyes to generosity and what it means to be supported. It also helped me recognize how much I wanted a closer relationship with my own family, which became a focus of my growth moving forward. Gratitude shifted my perspective and showed me how to approach life with a deeper sense of connection.
At the time, it felt impossible to keep going. But now, I see that period as the crucible that shaped me into the leader I am today. It gave me the clarity to lead with purpose, gratitude, and sincerity.
What about you?
Have you ever gone through a season in your life that felt impossible at the time, but shaped who you are today? What lessons did it teach you?
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Until next time…
Love. Every. Body.
