A Letter to My Future Self: Beginning the 50 by 50 Journey

Chapter 2 | Breathing in the start of a new story | Embracing Creativity and Craftsmanship

What if you could send a message to the person you’ll become in four years? Today, I’m doing just that as I begin the journey of a lifetime—my 50 by 50 challenge. This isn’t just a box to check off my goals list. It’s the first step in a transformative process of becoming the person I aspire to be.

James Clear, in Atomic Habits, says, “You do not rise to the level of your goals; you fall to the level of your systems.” He argues that our identity is defined by the habits we cultivate, and who we are is a result of what we do every day. This journey isn’t about accomplishing tasks for their own sake; it’s about creating the systems and habits that shape a new version of myself—one capable of living fully and achieving big things.

Reflecting on Who I’ve Been

James Clear talks about our identities as the reflection of our habits. Over the years, my identity has been fluid, shaped by the chapters of my life. I’ve been a high school dropout and a college graduate. I’ve been a dad, a son, a brother, a firefighter, and a paramedic. I’ve been a member of a SWAT team. I’ve also been an athlete: a triathlete, rock climber, skier, and mountain biker. And at one point, I was even a smoker.

Each identity reflects a different version of myself, shaped by the actions, habits, and goals I pursued at the time. As I stand at the start of this new chapter, I’m reevaluating who I am today and envisioning the person I want to be by the end of 2028. This moment feels like a crossroads, where past achievements and setbacks blend into future aspirations.

The Catalyst for the Letter

I started therapy over a year ago, and during a recent session, my therapist asked, “Do you realize how far you’ve come?” At first, I didn’t understand. But then he listed off the ways I’ve grown and evolved since I started this journey. His words were a revelation.

When you’re constantly pushing forward, it’s easy to focus only on how far you have to go. Rarely do we take the time to reflect on how far we’ve come. That moment inspired this letter. It’s my way of documenting who I am today, the thoughts driving my goals, and the mindset I’m carrying into this process.

Hearing that external validation gave me a perspective I hadn’t taken time to appreciate—a reminder of the power of reflection. This letter is a way to pause, to capture this moment, and to send a message to my future self, ensuring that I never lose sight of where I started.

What I’ll Include in My Letter

This letter will capture a snapshot of my present self, laying the foundation for the person I want to become:

  • My Mindset: Why I’m taking on this challenge and what excites me about the journey ahead.

  • My Tools: The systems and habits I’ll build, inspired by books like Atomic Habits and practices like mindfulness and journaling.

  • My Support System: The encouragement I’ve received from friends, family, and mentors as I embark on this journey.

  • My Health: A baseline of where I stand physically and mentally today, including the challenges I’m overcoming.

  • Top Goals: The three goals I’m most excited about, along with the goals for each year that spark the most joy and fear.

  • Anticipated Challenges: Predictions for the hardest physical and mental goals and strategies I plan to use to tackle them.

  • Future Reflections: What I hope to believe about myself when I’ve completed all 50 goals.

By organizing my thoughts into these categories, I hope to give my future self a vivid picture of who I was and what I believed when I started this transformative process.

The Purpose of the Letter

This letter isn’t just a reminder of where I started; it’s a promise to myself. I’ll admit, I have no idea how I’m going to accomplish these goals, and I do have a fear of failure. Nonetheless, I’m at a point in my life where I feel like I’m already starting over, so why not take a huge leap of faith? It’s a chance to document the excitement, fear, and determination I feel in this moment and to give my future self a reason to pause and celebrate the journey.

Success isn’t just about reaching the destination; it’s about the transformation that happens along the way. This letter will serve as proof that growth is possible and a reminder of why I took that first step.

So, to my future self: When you read this, I hope you’re proud of how far you’ve come. You’ve done more than accomplish goals; you’ve transformed your life. Keep going.

What About You?

What would you say to your future self? I encourage you to write your own letter—whether it’s for one year, five years, or even ten years into the future. You might be surprised by what you discover about yourself and the clarity it brings to your goals. Share your thoughts in the comments or with someone close to you. Your journey is worth celebrating, too.

Chris Roper

Chris Roper is an adventurer, storyteller, and lifelong learner on a mission to complete 50 major goals before turning 50. As the creator of Reset and Roam, he shares his journey of personal growth, travel, and fitness while inspiring others to push their limits. Passionate about exploring new places, learning new skills, and embracing challenges, Chris documents his experiences with authenticity and insight. Whether hiking mountain trails, improving his photography, or working toward ambitious goals, he believes in the power of resetting, roaming, and redefining what’s possible.

https://www.resetandroam.com
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50 by 50: A Journey of Growth, Adventure, and Purpose