If your plan’s in flames, you’d better be lit on fire

On not returning to the status quo

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #3. ✨

☀️ How was your week?

The view from my favorite local running trail

I signed up for my first running races in (checks watch) eight years. I’ll tackle the Snoqualmie Valley 10k in June, and the Orca Half Marathon in September. I’ve been reading

The Half Marathoner

here on Substack to psych me up for the miles ahead.

(Also: can we talk about how wild the foot-scanning technology is at Fleet Feet?! I know more about the intricacies of my instep now than ever before.)

I received the first photographic evidence of This Here Newsletter out in the wild. If you’re reading this in a fun location, perhaps with a fun beverage, do keep me updated!

Baby’s first hazy IPA

On to today’s letter!

If your plan’s in flames, you’d better be lit on fire

“If you feel like the tip of a match / Then strike yourself on something / Rough.” –Ezra Furman

I remember the moment I got hooked on John Mulaney’s stand-up comedy.

He was doing a bit in his Netflix special Kid Gorgeous about a former Chicago Police Department detective named JJ Bittenbinder. Apparently, Bittenbinder visited Mulaney’s Chicago elementary school auditorium each year for a primer on street smarts.

His age-inappropriate instructions for children dodging the perils of Stranger Danger—throw a money clip to distract a potential kidnapper! Punch out a taillight if you’re thrown into someone’s trunk!—sounded oddly familiar. As Mulaney delved deeper into the mildly-deranged details of Bittenbinder’s presentation, it dawned on me: I think this swaggering, mustachioed detective may have visited my suburban Chicago elementary school, too.

Between laughs, I grew to feel that nice-guy Mulaney (clean-cut in his tailored suit; headliner of a variety show for kids) could be a kindred spirit. We’re about the same age. We shared similar childhood experiences in the same metropolis, and attended the same university.

His wife was Jewish, like me and approximately half the people I’d grown up with. From the jokes he told, it sounded like they had a fun, easygoing relationship.

John Mulaney’s life seemed to be chugging along the Success Track. Then, two years ago, a derailment.

The headlines started getting ugly. First, the rehab stint for cocaine and prescription pills. Then, the breakup of his adorable-on-Instagram marriage, followed very closely by a much-more-famous new girlfriend…who happened to be pregnant with his baby.

It was the celebrity-news version of a car crash you couldn’t look away from.

When I saw that his latest stand-up special, Baby J, was streaming, I couldn’t click “play” fast enough. In some pretty fundamental ways, Mulaney’s previous life didn’t exist anymore.

So who was going to show up onstage?

When your plans go up in flames, you can react in one of three ways.

You can fizzle out. You can get burned. Or you can be lit on fire.

In all three scenarios, the setbacks you’ve experienced have left you raw; artifice has largely been stripped away. Your authentic self, whether you like it or not, is on full display.

When you fizzle out, you don’t have enough strength to channel that authenticity in a productive way—even after taking a long beat to grieve. You turn inward, using any remaining energy to lick your wounds.

When you get burned, your energy is channeled into lashing out at the ones who wounded you. Maybe your vulnerability makes you feel ashamed, overexposed. So any self-expression is done with the purpose of exacting revenge. (Think Taylor Swift’s comeback album Reputation, stuffed with lyrics designed to burn Kim and Kanye.)

When you’re lit on fire, you’re not driven by grievance. Your aim is to come alive again after a shattering loss, with self-expression as the vehicle for healing—and for finding and connecting with those who see your experience as a mirror.

In Baby J, John Mulaney is a man on fire.

For anyone who might’ve missed the headlines and still thought of him as “likable,” Mulaney dispels with that immediately, sparing no detail about the depths of his addiction.

After recounting an elaborate scheme he came up with to get cash for drugs, he notes, “As you process and digest how obnoxious, wasteful, and unlikable that story is, just remember: that’s one I’m willing to tell you.”

“It’s weird to be a recovering drug addict,” he continues. “You know, like, I’m doing great, but when I’m alone, I’m with the person that tried to kill me.”

He pauses to let the audience consider the gravity of this point, then admits: “It gives me a strange kind of confidence sometimes, because—look, I used to care what everyone thought about me. So much. It was all I cared about. All I cared about was what other people thought of me. And I don’t anymore, because I can honestly say: what is someone gonna do to me that’s worse than what I would do to myself?”

It’s a joke, but he means every word. I can tell, having been through my own gauntlet. You may go in as a people-pleaser, but you probably won’t emerge as one.

When you face life’s biggest challenges and squeak out the other side—without being flattened or becoming bitter—you’ve earned a quiet confidence you can’t gain any other way.

Chances are, that confidence will carry you in new directions.

Nora McInerny, author and host of the brilliantly-named podcast Terrible, Thanks for Asking, lost her husband and father to cancer in quick succession in her early thirties.

Her life upended, McInerny found herself unable to return to other aspects of the previous status quo—another defining characteristic of those lit on fire.

“I could have (and probably should have) gone back to my old day job,” she said in this interview. “But I just couldn’t. I was lit on fire. With the podcast and books, I want to make things that somebody can point to and say, ‘It felt like that.’ It’s not just about death, either. Any time something truly transformative happens in your life, it tends to set you apart from the rest of your world.”

Even with a world-class support system, being set apart is isolating. Intuitively, McInerny gravitated toward the best solution: sharing the details of her loss in order to build community.

As for me? I could easily put my head down, land another 9-to-5, and avoid writing or speaking about the thornier aspects of loss. It’s the path my previous self would’ve opted for.

But those losses lit me on fire. I’m a different person than I was before. At this moment, I find myself pulled in the direction of Mulaney and McInerny: toward openness and connection, both of which require risk-taking.

They also happen to be much more interesting.

💬 What do you think?

I’m curious to hear from you. Tell me about the last time you felt lit on fire—and what you did with that energy.

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie