SiMPL #005 Always Plan for Failure – Plans Will Fail!

After a fast-paced week, it seems appropriate to tackle a topic not many people like to talk about: problem solving. A skill that seems to be fading over time, but one I think is a powerful tool for day-to-day situations. This is the story of two plans gone wrong, and how I managed to fix the course of one.

Plan Gone Wrong #1: The Water Outage

This weekend, there was a planned water outage in Panama City. Maintenance work was needed on a 1970s water plant that’s well past its prime. They laid out a plan—15 hours without water—but we all know how plans go. “No plan survives contact with reality” (Helmuth von Moltke). So at home, expecting failure, we planned for a 24-hour outage just to be safe. But, as you’ll see, even that wasn’t enough!

Everything started fine: the coffee was brewing (I have a vintage La Pavoni that demands respect and patience), my dog Ozzy was enjoying the morning, and I even had everything set up to help my mom do the web check-in for her Eurotrip… until we hit a snag.

Plan Gone Wrong #2: The Passport Calamity

My mom and her partner had planned this Eurotrip for months—Brussels, Sardinia, Pisa, Barcelona… I was slightly jealous of their itinerary. But as I sat down to help with their check-in, we discovered a major problem: her partner’s passport had expired. Just like that, their perfectly laid travel plan hit a wall, hard.

Activate Problem-Solving Mode!

To solve any problem, one must start by understanding the issue. As McKinsey’s Way reminds us: “Defining the problem is the first and most crucial step.” So I put on my consulting hat and started working.

Layer upon Layer of Failed Plans

Now, here’s where it gets fun (well, sort of!). We got the backup flight for her partner—it was a long journey, but at least he’d make it. Or so we thought! What was originally a 30+ hour trip quickly spiraled into something else entirely.

His flight got delayed by 30 minutes in Houston, and when he finally reached Amsterdam, his train to Brussels broke down midway. What should’ve been a 30+ hour trip turned into a 48-hour marathon of delays, hiccups, and “fun” surprises!

Meanwhile, back at home, the planned 15-hour water outage stretched into a 48-hour dry spell too! It was like the universe decided both problems should take exactly the same amount of time to fix. So there we were, without water, much like my mom’s partner without a smooth journey. Layer upon layer of plans that didn’t work, but hey, we managed to make it through!

By the time both the water came back and her partner finally made it to the wedding, it was as if the universe was saying, “Okay, now you’ve earned it.” After all that chaos, they sent me this picture that speaks on its own

Takeaways from Chaos

Through this chaos, I learned the importance of breaking problems into manageable parts. As McKinsey’s Way suggests: “Prioritize issues and focus on what will have the biggest impact.” Whether it’s a passport issue or a water outage, clearly defining and prioritizing problems is key.

And let’s be honest, not all life lessons come softly. Sometimes, they hit you like a bucket of cold water.

The Deserter: A Must-Read

One day, you’re young and carefree, and the next thing you know, you’re into podcasts and longform articles, right? Who am I kidding, I’ve been like this since I was a kid, ever since I discovered news talk shows and Reader’s Digest. Recently, I was chatting with a friend who said, “Hey, have you checked out The Deserter by The New York Times? You’ll love it.” Now, I don’t know about you, but The New York Times has become my go-to for US news, and their special coverage and deep dives? Incredible storytelling.

So, I went ahead and found it. The Deserter is a five-part series, and man, it’s gripping. It’s like a slow-burning thriller set against the backdrop of the Ukraine-Russia conflict. It tells the story of a Russian couple, Ivan and Anna. Ivan joined the Russian military thinking it would lead to better work and education opportunities. Instead, he got tangled in the brutal realities of war, corruption, and poor strategy. Talk about plans going wrong!

Meanwhile, Anna stays at home, raising their kid in a precarious and dangerous situation. The plot twists keep you on your toes, as Ivan navigates a system that’s crumbling around him, just like the failing military structure he’s part of. If you’re into war stories, spy intrigue, or just fantastic storytelling, this is your next must-read.

Check out The Deserter below. It’s available in text or podcast format, so take your pick!

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