How a Middle School Dream Turned Into a 27-Year Adventure

Have you ever set a goal that initially felt doable… only to find it would take you over two decades to complete?

Same.

When I was in middle school, I pinned a map to my bedroom bulletin board and started marking off the states I’d visited with colorful push pins. I'd already seen a fair number of them, thanks to family trips, so I figured I’d be able to see them all before graduating from high school. (Spoiler alert: I didn't meet that deadline.)

But here's the thing, I never let that dream go.

The goal evolved with me. From grade school summers on the back of my Dad’s motorcycle, for lobster off the dock in Maine…



…to introducing me to my favorite riding roads in the Smoky Mountains of Tennessee.


To the Georgia, Alabama state line...


By high school, I wasn’t just along for the ride—I was riding side by side with my Dad to the 95th Harley Anniversary in Wisconsin.


By college, I traded in my motorcycle to spend my summer in dusty parking lots across the country on the Vans Warped Tour.




This wasn’t just about travel—it was about becoming the kind of person who follows through, no matter how long it takes.

And last summer, I thought I’d finally reached state #49 when I stepped foot in North Dakota. I was already drafting my victory lap in my mind.



But then this April, while on a family trip to Boston, I realized something shocking: I missed an entire state! I'd never been to Vermont!

Cue the Google Maps search...

But here’s the magic part, when we arrived at our hotel that day, the stars aligned. I had access to a set of wheels, and the one state I still needed, Vermont, was a short 4-hour drive away. So I borrowed the keys to my parents’ truck, hit the road, and crossed that beautiful state off my list. 

Luck flickers in & out, but if you keep your flame lit, 
you’re always prepared when it shows up.

In just a few weeks, I’ll be standing in Alaska, my 50th state, right before my 40th birthday. That middle school dream? She aged with me, and now, it’s time to celebrate.

Here’s what I’ve learned about chasing long-term goals, and how you can keep your own fire lit:

So, what dream are you chasing right now?  Is it visiting all 50 states? Running your first 5K? Finally writing that book or starting a business?  Share it with me in the comments, I’d love to cheer you on. Because chasing a dream is always better with someone in your corner.

Whatever it is, don’t worry about how long it takes. Worry about how it feels to know you’re working toward something that matters to you. Keep putting in the miles, keep your eyes on the map, and never let your flame burn out.

I’m rooting for you.