In 2016, I found myself at rock bottom—heartbroken, broke, and unsure of where life was taking me. How did I end up here? I felt so lost and alone. It was during this time that a friend introduced me to a transformative exercise—it opened my eyes, clarified my thinking, and, in many ways, set my life in a completely new direction.
What started simply as a personal development exercise has evolved into something much bigger. My friend G and I took this exercise and turned it into a workbook we called Staying Uncomfortable. The name reflects a simple truth: growth rarely happens in comfort. By leaning into the discomfort of self-reflection, we began building frameworks that provided us with direction, focus, and the clarity to design lives that felt intentional and aligned. (Some of those early conversations, which now feel like time capsules, can be found on YouTube here.)
The exercise itself is straightforward but demands honesty. It invites you to sit down, quiet the noise, and ask yourself some essential questions:
• What are the five things you’re most grateful for?
• What are your ten proudest accomplishments?
• Why do you believe you deserve success?
• What are the 30 things you want to achieve in the next decade?
• What are the five things you’re most grateful for?
• What are your ten proudest accomplishments?
• Why do you believe you deserve success?
• What are the 30 things you want to achieve in the next decade?
From there, it’s about narrowing down—identifying the priorities for the next five years, three years, and then the single year ahead.
Over time, this exercise has taken on new life for us. At the end of every year, G and I write letters to our future selves—a reflection on where we’ve been and a vision for where we hope to go. It’s a powerful ritual. We reflect on the promises we kept, the ones we missed, and the unexpected moments that surprised us along the way.
As you are planning for 2025, I invite you to try this exercise for yourself. Take out 15 to 20 minutes of uninterrupted time—no screens, no distractions. Write it all down. Be honest. Be ambitious. The rewards of this exercise are immense. It will anchor you, challenge you, and illuminate the path ahead with greater focus and intention.
The future belongs to those brave enough to imagine it——have an awesome week ahead, and I’ll see you next week.
KD
