Five Years Ago


My buddy Ray and I recently started an exercise to flex our creative muscles: We’re giving each other writing prompts each Sunday and publishing the results on Friday. The only catch? A self-imposed 500-word limit. This week’s prompt: Write a letter to your five-years-ago self.


As you read this, your life is perfectly average. You go to Blazers games when you can, but you’re still looking for that first girlfriend to join you. You lost 100 pounds a few years ago and work out regularly, but you’re still overweight. You mastered your job, but you’ve been there three years and can’t imagine three more. The good generally outweighs the bad, and your biggest concern on any given day is whether the Blazers won last night or what you’re making for dinner tonight. Like I said: Average.

So don’t freak out when I tell you what’s about to happen. Take a deep breath. Say it out loud: “It’s going to be fine.” Because it is.

In another few days, that average life will feel like it belonged to someone else entirely. You’re about to read a Seattle Times article on two college graduates who left the rat race to travel the world, and the baseline for what you demand from life will shift forever. You’ll imagine yourself in exotic locales around the world, but that’s just the start. You’re about to embark on a scavenger hunt for something you can’t quite define, and you’ll collect meaningful memories, lasting lessons, a stronger sense of self, and so much more along the way.

With dreams of seeing the world, you’ll apply to programs that would send you to Morocco, San Antonio, and New Orleans. If that’s not weird enough, you’ll get into each program but ultimately turn them all down. (It’s a long story.) You’ll travel to New York, Boston, New Orleans, Vancouver, B.C., and Chicago. You’ll start running and dragon boat paddling. You’ll work on essays and blog posts until 2-3 a.m., just because you love the process and craft of writing. You’ll move to Seattle and, after 15 months, return to Portland’s warm embrace. And you’ll take three jobs in three years.

That sounds like a lot–and it is–but you’ll be fine. Every experience will teach you something that you’ll carry with you; good or bad, be grateful and stay positive.

Not that the advice matters now but, whatever you do, make “special” the starting point. Don’t share a “good” essay when you have a “great” one in you. Don’t take a job for money or security. If you have a “decent” workout, get back on the treadmill until your legs start shaking. No matter what, don’t be afraid to demand more from yourself; more often than not, you’re up for the challenge–even when you’re tired, overwhelmed, frustrated or heartbroken. You’re going to grow in ways you can’t imagine, and five years from now, you’ll say, “This is the life I never knew I wanted.”

There’s more, but I don’t want to spoil too much. You have to write the story yourself, and while it might not feel like it, you already know the words. Just start writing.


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