Call It Serendipity

First, a big thank you to Jeff Gomez and Esteban Kolsky for filling in while I was traveling. If you missed their issues you can read them here: The Future of AI Isn't Better Stories. It's Better Storyworlds. and That Was a Great Conversation, but Nothing Changed.

My trip was great. If you can manage it, traveling is great for a mental reset and an injection of alternate perspectives. Especially internationally. We did a two week trip with a lot of it planned and some of it left open to allow us to make day-of decisions based on what we were feeling that day. Several times, even the day-of decisions needed to be reworked. Call it serendipity. Call it synchronicity. In most cases it worked out better than the original plan.

We had booked a musical in English at a theater in Amsterdam. The day of, I got an email saying someone in the cast was sick so they had to cancel the performance. I guess there was no understudy? My first reaction was simple: Well, this sucks.

Then we started looking for something else to see live, which is how I found Boom Chicago, an improv show in English. It was really just going out with a group of friends, but I consider the first time Jennie and I met was at Chicago City Limits in New York. This was an anniversary trip, so seeing improv in Amsterdam because the musical got cancelled fit the occasion better than the original plan would have.

The plan was good. What replaced it was already there.

Across the street

The night before, we'd taken a canal tour and had a great chat with a woman on the boat who happened to be a travel agent. She told us about a place to eat where you pick your fish out of a market at the door and they cook it for you. We called for a table that same day, they were full, and we let it go.

So on the night of the show that wasn't happening anymore, we picked a restaurant near Boom Chicago, walked over, took a look at it, and didn't want to eat there. We turned around. Across the street was Pesca, the fish place from the boat. They had a table. We had one of the best meals of the trip and then walked next door for the show.

The plan was good. What replaced it was already there.

I used the word serendipity a lot during the trip.Synchronicity got  plenty of use too. Looking back, though, I realized nothing about those evenings was actually random.

The restaurant recommendation was already in my head. The improv show connected to a memory we'd carried for decades. None of it was visible when the cancellation email arrived. It only became visible once the calendar had an opening.

That's the tradeoff with good planning.

A full calendar isn't a flaw. That's exactly what a plan is supposed to do.

The downside is that whatever occupies the calendar makes everything around it look like a distraction.

What surfaces after

A product launch slips, or a deal that was supposed to close in Q2 doesn't, and the immediate conversation is about what went wrong, which is where it should be.

But what often surfaces afterward isn't new information. Someone remembers a customer who would have happily done a case study if anyone had asked. Or there's something already true about the product that nobody said out loud, because the launch was going to say it. All of that was sitting there the whole time. It was behind the plan.

I wrote in Afraid of Running Out about people who hold onto one idea or one path because they're afraid it's the only one they'll get. Nothing like that was going on here. Nobody in these stories was clinging to anything. We liked the plan, the plan was good, and It simply occupied all the available attention.

The last day

We'd been staying at a hotel in Santa Margherita. Our hotel had an arrangement with the beach club directly across the street, so every morning was easy: chairs, umbrella, beach. The last day was a half day before the train to Milan, so we figured we'd get a few hours in.

The reservation hadn't gone through. No chairs.

A year ago that's the story I'd have told at dinner. Instead one of us remembered the rooftop pool. We'd looked at it on the first day and dismissed it. There wasn't much shade, so it didn't make sense for a full day. The beach was the right call for a full day, which is why we did it every day. For two hours before checkout the roof was better. A few open chairs, and just enough time to get in the water before we had to go.

The plan was good. What replaced it was already there.

By the last day we barely discussed it. Somebody said the roof and we went up.

I've worked on teams where a missed launch date wasn't treated like a crisis.

They'd been through enough of them to know the delay wasn't the story. The question was what became possible because of it.

I've been on teams where a blown date isn't a whole production. They've been through enough of them that it doesn't turn into an event. I've also been on the other kind, where every one gets handled as its own emergency, and then it's over and nobody carries anything out of it. I don't think that difference is temperament.

I think it's a difference in attention.

In The Wish List  I wrote that people who appear lucky usually spent time collecting options before they needed them.

I still think that's right. What I'd add after this trip is that collecting isn't the hard part. I had the restaurant. I'd had the Chicago City Limits thing for decades.

The harder skill is noticing how long I continue staring at the broken plan before I look up and see what else is already available.

Berkson's Bits

Communicating that you have nothing new to report is something to report. In all my years as a service provider and consultant, the most common complaint from end users and customers is "I don't know what's happening or when it will be done." Very often a lot of elements for resolution are out of your control. The end-user doesn't know that. Touching base with "I don't have anything new to update. Still, I want to let you know I'm paying attention and working on it" goes a LONG way. 

What I’m Listening to…

When Jennie and I first met one of our first dates was seeing the movie An American Tail. We had a bit of a long distance relationship and the theme song from that movie became our song. In honor of our anniversary trip, here’s Somewhere Out There. 

Two weeks isn't much of a test. Nothing was riding on any of it, and we'd built the trip with holes in it on purpose, a few days with nothing booked and room to decide in the morning. That isn't how my work calendar operates. The slots are full end to end, so when something falls out, the next thing slides into the gap before I've had a chance to look around.

It's easy to do this on vacation, when you have narrow constraints and low stakes. At home, and at work, it's more complicated. And it's harder to see while it's happening.

Founders and leaders spend enormous energy protecting plans. That's necessary. Execution matters.

But sometimes the opportunity isn't created by the plan succeeding.

Sometimes it's revealed by the plan failing.What I'd like to know is whether anyone catches it in the moment. Everything I've described here I only saw when I had time to think about it after I returned. The cancelled thing, and whatever turned out to be sitting behind it.

The story that was already true.

The thing that had been sitting there the whole time, waiting for the calendar to make room for it.

Looking forward to continuing the conversation...

Alan