Walk It Back Ep. 1: Stay or Go? (A Classic Dilemma)

Two rejections and a Craigslist ad that could change everything.

This is the first episode in a series about the real choices that shaped my life — the ones that led me here, to this very moment. Except this time, we’re walking it back and YOU get to decide which path to take. Free will and fate, past and present, tangled together to tell a new story.

Step into my shoes. Expand your perspective. Stretch your heart’s capacity to feel. And maybe along the way, you’ll start to hold all the versions of your former self with a little more compassion (or at least throw them a bone of gratitude once in a while).

Thanks for being part of this experiment. Now, let’s see where the story takes you.

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The first day of the rest of your life… now what?

The year is 2006, and you’re a wildly optimistic 22-year-old.

There’s just one minor problem: You have no idea what to do with your life.

You know you want to help people, but don’t know how. And unlike your friends, you didn’t line up a job before graduation. So now, you’re living at home, working at your family’s doughnut shop in Pennsylvania.

The regulars at the shop, old men who love to give out unsolicited advice and borderline-inappropriate compliments, scoff at your naivety: “Sociology major? Pfft! You’re gonna be as broke as the people you’re tryin’ to help!”

They might not be wrong. But at this point, you’d take any job — anything that isn’t this.

So you buy yourself some time. You spend a few months volunteering on farms across Ireland and Wales, pulling weeds, chasing bulls, waiting for clarity.

It doesn’t come.

Then, near the end of your trip, as you’re raking hay on a homestead in Southwest Wales and wracking your brain about what comes next, it hits you: Teach for America. A random city placement. A two-year contract. Helping kids. And the kind of high-stakes environment where you’d be too busy to have an existential crisis.

That’s it. That’s the plan. (Or at least Plan B, which has now officially become Plan A.)

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When you get back to the States, you immediately apply. A few weeks later, an email lands in your inbox inviting you to a phone interview.

You’re a nervous wreck. Your thoughts are much more fluent in writing than in speech — especially when you’re being evaluated. But somehow, you pass.

Next round, they invite you to teach a trial lesson at your alma mater. You have to design a science lesson and teach it to a classroom full of other interviewees.

Gulp.

You spend a week preparing and walk in confident. Despite your tendency toward chronic self-doubt, you feel good about your performance. You nailed it. One more in-person interview at the end of the day and you’re home-free!

Or so you think.

A few days later, you’re notified that you’ve been rejected.

Not once, but twice.

Because your college boyfriend ghosts you and moves to New York City without you.

You’re discouraged and broken-hearted and confused and shit out of ideas.

Because you didn’t have a plan C — no one told you you’d need one. And now, your dad is telling you that you need to start paying rent.

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If you’re going to pay rent, you reason, you want it to be somewhere that you want to live. You start weighing your options.

A year ago, you took a road trip across the country with your brother. Standing barefoot on a blustery Baker Beach in San Francisco, watching the golden sun sink behind the Golden Gate Bridge, you turned to him and said, "I’m going to live here someday."

You just didn’t expect someday to come this soon.

So, you do what any lost 22-year-old does in the mid-2000s: You open Craigslist.

Somewhere between “Free Couch (must pick up ASAP)” and “Roommate Needed: Must Love Ferrets,” you see it:

"Harvest Workers Wanted – Santa Rosa Crush Facility. No experience necessary."

You know nothing about winemaking. But a Mapquest search reveals that Santa Rosa is only 90 minutes from San Francisco, the place you really want to be.

And that’s a hell of a lot closer than Scranton.

This could be it: your escape route. It’s a seasonal job — only a few months. No long-term commitment. Just enough time to figure out what’s next.

You could take it.

Or… you could stay.

Because as tempting as it is to leave, you don’t actually have a plan. No safety net. No network out there. Barely any savings. Simply a gut feeling and the notion that California = better.

And that ain’t nothin’… but is it enough?

Cast your vote, and we’ll step into that story next week.

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Paid Subscriber Bonus: The Director’s Cut

If the fictional version wins (the choice I didn’t make IRL), paid subscribers will get both versions — the made-up one and a behind-the-music-style post with the real story.

Want the full story, no matter what?