Letters to Our Younger Selves
Sometimes courage comes from the conversations we have with our past
This Week’s Courage Newsletter
"Life can only be understood backwards; but it must be lived forwards." - Søren Kierkegaard
Why wisdom requires both time and courage
Scare Your Soul Challenge: The Time-Travel Letter
Bottom line: Sometimes courage comes from the conversations we have with our past
Dear Courageous Souls (and Time Travelers),
So, I found myself sitting on a cold bench at Skidmore College, watching the sunrise paint the quad in shades of amber and gold.
Thirty years had passed since I'd transferred here from Tulane - scared, friendless, and completely without a plan.
I hadn't meant to come here.
I was in the Berkshires for a facilitation course, with an extra day to kill before flying home to Cleveland. Something pulled me to drive those 90 minutes to Saratoga Springs, to walk these paths again in the crisp morning air.
With each step, memories bubbled up like spring water:
The intimidating professors who became mentors.
The conversations I avoided out of fear.
The parties I attended trying to fit in.
The dorm, where I drank vodka alone in my room to boost my courage every time I had to speak publicly.
The chances I didn't take because I was too busy playing it safe.
Then, I did something that required more courage than I expected: I wrote a letter to my younger self.
"Looking down at my notebook that morning, I wrote what I wished I'd known:
Join everything that scares you - an empty dorm room never changed anyone's life
Stay sober; be the one trusted with secrets
Your GPA won't matter in ten years, but understanding how your mind works will
The most interesting people are usually the ones who terrify you at first
Smile. Meet people's eyes.
College will end one day, but friendships can last a lifetime
Here's what I realized: These weren't just life tips - they were invitations to daily acts of courage that my younger self wasn't ready to hear, but my older self now understands.
The science tells us something fascinating: When we engage in temporal self-reflection (fancy words for thinking about our past and future selves), we activate parts of our brain associated with personal growth and emotional regulation.
It's like we're building a bridge between who we were and who we're becoming.
This Week's Scare Your Soul Challenge: Your Time-Travel Letter
Find a quiet moment this week to write your own letter. Here's how:
Choose Your Moment:
Pick a specific time in your past
Remember how it felt to be that version of you
Let yourself feel both the wisdom and gentleness that time provides
Write Your Letter:
Start with "Dear younger me..."
Share what you wish you'd known
Focus on the small acts of courage that changed everything
Be honest about what you're still learning
Find Your Truth:
Look for patterns in your advice
Notice what still feels relevant today
Choose one piece of wisdom to act on this week
Remember, this isn't about regret. It's about recognizing that wisdom often comes wrapped in tiny moments of courage - moments we can still choose today.
With courage, compassion, and maybe a few bittersweet smiles,
P.S. Brave enough to share a piece of advice from your letter? Drop it in the comments. Sometimes the wisdom we think is just for our younger selves is exactly what someone else needs to hear today.