When Plans Go Haywire

Like most good plans—whether in travel, work, or life—this one started with the best of intentions.

A few years ago, we took a family trip to a resort in Mexico while I was four months pregnant with our second kid. This was one of the first times we set out to have a real relaxing vacation (as opposed to a work trip that morphed into one), so we booked an all-inclusive resort that covered everything we’d need.

Of course, even at an all-inclusive resort, I’m the kind of person who gets antsy to get off campus in about 2 days. To switch things up, we decided to take a kid-friendly, lowkey tour of a local island, which included a water and nature park for our kid.

Back then, our lives revolved around our toddler’s nap schedule, so we planned the trip just right—or so we thought. Instead, everything went sideways. The bus was late. The boat was delayed. Our kid got more and more panicky. By the time we finally arrived, the park was about to close.

We were given a few choices: rush through the park in 20 minutes, come back the next day, or wander the island while waiting for the next shuttle. In another life, Jason and I would have shook off the misfire, walked down the street, and made do with an alternative game plan on the island. We’d have done a little shopping, wandered until we found a snack, maybe explored an unexpected corner and met some locals.

But this time, things were different. This time, it wasn’t just us. We were stranded on the side of the road with a cranky kid in a car seat. It was hot. I was pregnant. Our kid needed a snack. We didn’t have the supplies we needed, we didn’t have time to explore and just find out what we might find down the road.

So what we did instead was none of those things. My husband called another taxi, and we just…left. In other words: We pulled the ripcord.

Pulling the Ripcord

I was pretty quiet the whole ride back to the resort.

It sucks when plans fall apart—especially when you didn’t think you were asking for much in the first place. To me, this felt like such a low-stakes outing. Just getting off the resort for a single day shouldn’t have been so complicated. The fact that it was such a catastrophic failure made me anxious about our future (with two kids, not just one). After all, if we couldn’t pull off something this simple, what would happen when we tried to plan something bigger?

Back then, we didn’t have the vocabulary in our family then for what it meant to “pull the ripcord” and call things on the spot like that. But it’s a mindset we’ve really come to appreciate as a family in the years since.

As a high achiever, when things go sideways, it’s often been my tendency to try to salvage as much of the initial vision as possible, for as long as possible, both in work and personal matters. But this is also a quick way to drive yourself toward an unsustainable burnout mode (re: work stuff), or into a state of extreme frustration about things totally outside of your control (ie: kids just not cooperating). 

A few months ago, I was enjoying my morning coffee in Washington Square Park where I watched a family of five in matching outfits get portraits taken from a photographer. They were trying all of the classic poses. All kids in a row. One kid at a time. Then the entire family.

But none of the kids were having it. They squirmed, wiggled, wormed their way in and out of the frame. As the minutes ticked by (presumably eating into however long they’d paid the photographer), I watched the father’s patience boil over. He started forcing the kids into position, despite the tears. He pulled them aside, yelling at them in hushed words. He threatened to take away TV time, and even dangled the ultimate bribe—just one picture, right now, and there would be ice cream afterward.

Honestly, as a passerby, it was painful to watch. The tension was palpable, made even more ironic by the purpose of it all: a holiday card, meant to show off their picture-perfect, happy-go-lucky family.

Pulling the ripcord is a way to give grace back to yourself and the people around you—whether it’s your team, your family, or, in this case, your stubbornly uncooperative toddlers. It’s the mutual acknowledgment that this isn’t working, followed by the permission to say: Let’s call it here for now. We’ll regroup.

How to Recognize the Ripcord Pattern

Earlier this week, I had to pull the ripcord in a way I never expected. 

What started as a casual Sunday morning trip to a museum with my family morphed into a three-day stay at a NYC hospital. While I’m at home now, and on the mend, this unexpected medical malady has opened up a lot of questions about the impact of hard resets on my personal and professional momentum.

As a new startup founder, I’ve noticed that these early days of company-building are quite reminiscent of the early days of having a newborn baby. That’s to say, the high degree of around-the-clock nurturing that’s required to keep the thing alive is pretty all-consuming. 

The first two weeks are literally just a blur of happy discoveries and sleepless nights. At this early stage, with so much still left unknown and uncertain about both what I’m building and how I’m building it, I’ve felt at times like even leaving any bit of it alone for an hour at a time is akin to negligence. Even now, about two months into this endeavor, I don’t quite feel like this new creation I’ve been working on has even come close to being “sleep trained,” so to speak. So the idea of letting go of a project at this infantile state of development, even for just a week or two, is pretty scary.

But obviously a major health scare is so very clearly a moment for pulling the ripcord. Which is something that is crucial to recognize if you want any chance of surviving the calamity moments that are sure to come down the road.

As a solo founder, I feel this pressure acutely. But I’ve been working by myself for years, so I’m no stranger to the high and low pressures of self-motivated work. And by now, I have a really good sense of my own professional rhythms, hums, and ideal work cadence. Generating my own momentum has never been hard for me. But forced resets still suck.

I made the call in the hospital that I wasn’t going to work on any MuseKat stuff this week. But I kept generating and consuming content at my normal rate. Just, with less pressure to perform. (That was ripcord pull #1.)

The second was the canceling of plans. I had a bunch of stuff planned this week–project kickoffs, presentations, on-site visits, networking chats, a weekend event, even features I was supposed to push live on the site. I had to call all of those things too. And I had to let go of the weekly operating cadence I’ve been holding myself to for the past two months. (That was ripcord pull #2.)

But here’s what surprised me: Even while I was in the ER, the work didn’t just vanish. I noticed the emails were still coming in. A couple of intro requests that I’d sought out a few weeks back cleared my inbox. Some people told me they had started working on a few sidecar components of MuseKat work, anyway, despite my cancelling of plans. I got a lead on a lead gen channel, and a gallery partner. 

This past week showed me that stepping away doesn’t mean everything stops—it means falling back on a foundation. Maybe momentum isn’t as fragile as I thought.

That’s why learning to recognize a ripcord moment matters. Trust me on this, it’s better to get a few “at-bats” in low-stakes family vacation moments before the emergency room version shows up.