Note: this piece initially appeared on Medium on July 24, 2019. I pressed "publish" as my flight for Colombia was boarding and I was leaving my life behind. I've made a lot of dumb decisions in my life. This wasn't among them.

A Beginner's Guide to Screwing Up Your Late 20s

Ok, deep breaths.

Last week, I quit the most incredible job I’ve ever had to embark on one of the riskiest adventures I can imagine.

I worked at NationBuilder for nearly six years, helping the world’s leaders use technology to build powerful relationships with people — build movements. It was a lot of fun. It was insanely heavy. The mission is powerful, the culture is a unicorn of transparent communication and community, and the work is hard in all the right ways.

I met presidential candidates from the United States to Panama. I was trusted by major issue advocacy campaigns to build their communication engines. I was trusted by the company to talk to the press internationally — from National Public Radio and Yahoo! News to Germany’s Berliner Zeitung — about the thing I care most about in the world: how people who really care about something can make it happen. I learned how to sell, I closed lots of business, I sat on panels, and I felt important.

In the years I spent at NationBuilder, I fell in and out of romantic love on three separate occasions. Most recently, after more than two years of incredible moments with a badass lady I saw a forever with, I fell into the thing you’re supposed to do when that seems true and you’re in your late 20s: I got engaged.

Damn, that all felt good.

Until, ya know, it didn’t.

Who cares about the narrative?

About two months ago, a Prep school in Connecticut hosted my ten year reunion. I’m sure someone was there, but I sure as hell wasn’t.

For the last ten years, I’ve built a narrative about myself (for the record, I don’t feel bad about this — after all, we all have a story along these lines). It’s a hyper-conscious fairytale I told to my own soul, and I distributed it through the world as loudly — though subtly — as I could.

Mine goes something like this: Oh Will? Yeah he’s that adopted kid from a rich suburb who dropped out of college when he was 19 after he met his birthparents. It all looked lost and then he battled back and now he seems to be doing really well.

Two things are true:

  1. This is a story designed for people I haven’t seen in a decade. No one I’ve met recently cares what I did when I was 19, where I’m from or whose blood runs through my veins. If I learned one thing from my last relationship, I learned the definition of real, true love. I learned about moving beyond the narratives into honest vulnerability. No one cares who I was. They care who I am today, and they care who I’ll choose to be tomorrow.
  2. The story is complete bullshit anyway. I was never in a tough spot by any stretch of the world’s definition, and today I’m kinda-successful-professionally-I-guess-but-like-not-really. I didn’t invent Facebook or anything.

But for seven years, that narrative actually served me quite well. I felt directed toward some emotional True North and so I took aggressive, calculated risks. I was unbelievably driven to find success (whatever that meant) and, at some level, I did.

Then it changed. With a noble resume, an unearned blue checkmark next to my name on Twitter and a fiercely manicured Instagram profile, I achieved the optical illusion I was striving for.

My daily internal dialogue transformed from the lofty longing of ambition (when I get “there,” I’ll feel good) to an artificial crutch of anxiety (please don’t do anything to mess this up).

My feeling tone shifted from aggression to complacency; from demand for progress to an uneasy satisfaction with plateauing.

And then I realized I was 27, I hadn’t made meaningful emotional or personal progress in years, and I had about six decades of life ahead to reflect on unnecessarily stunted mediocrity.

The narrative had to change.

No, the narrative had to vanish completely.

And so I forfeited the party thrown in honor of all the stories 230 kids from a Prep school in Connecticut have been telling themselves for ten years. I blew off my high school reunion.

Right around my 28th birthday, I scrapped the story. I exited the parts of my life that felt inherently tied to a false narrative. I left my relationship, I left my job, and I left my life.

What’s next?

In my six years at NationBuilder and four years in elected politics, I learned what defines successful leaders. In truth, it’s not software, money or high profile relationships. Those things sometimes win elections, but they seldom win transformative change. Successful leaders — much like successful people — are defined by two things: selfless love for others and a willingness to be vulnerable.

I can’t succeed as a human — I can’t take pride in my life at 80 years old — without both. This blog is an attempt to punch through the glass of my narrative and lean heavily into my deepest vulnerabilities and insecurities.

Right now, I am stepping onto an airplane that will land in Cartagena, Colombia. I speak no Spanish and I have the financial security for about six frugal months. I will bow out of the narrative game, I will confront honest vulnerability, I will explore a new continent city by city, and I will, brick by brick, build back into an understanding of myself, the people I truly love, and the structure of my next decade.

I have no doubt my experience of my late 20s mimics that of many of my contemporaries. If this sounds familiar — if something feels a little broken about your internal dialogue and you’re entering an emotional phase of maturity just barely powerful enough to recognize it — I truly hope you follow along with me.

Click here to listen to the Baggage Claim podcast on your platform of choice.

Will Conway


Former political software guy. Now a traveler and adventurer, which isn't a job, and host of the @heybaggageclaim podcast, which really isn't either. Travel stories no one tells.