Where does your mind go when I tell you this:

You’re probably rolling your eyes, right?

It sounds like some convoluted Boy Scout motto, or the tagline on a Chevy 4x4 commercial, voiced by a John Wayne sound-alike over cinematic footage of an indestructible truck barreling across rugged tundra.

It feels motivational, but doesn’t make sense.

Right?

Wrong.

It’s the most important leadership lesson I’ve ever learned. And if y’all don’t know by now, I’m a professional bullshit sniffer. So hear me out.

👉 Good systems and good judgment are more important than precise plans.

👉 Mentorship f*cking rocks. Be one. Get yourself one.

And now — the story behind why this advice matters. 👇

If we’re lucky, we’re blessed with maybe one truly selfless professional mentor. I’m not talking about bosses, teachers, or coaches — I’m talking about people who have zero obligation to help us navigate our careers, but step up and do it anyway.

For me, that person is Frank Supovitz.

You know Frank as the guy who developed the first NHL Winter Classic outdoor game series, produced thirty-one (🤯) NFL, NHL, and MLB Drafts, and –ahem– ran the Super Bowl for a decade. No biggie.

So while you may not know his name, you definitely know his work.

I met Frank in 2014, right after he left the NFL and launched his own events and entertainment consulting practice. We shared a client — the Howard Hughes Corporation, who at the time, was redeveloping NYC’s Seaport District in the aftermath of Hurricane Sandy.

I had built them a cute little ice rink on the cobblestones of Fulton Street (if you’re new to this newsletter, building ice rinks was my career for a while), and they wanted to produce a star-studded, televised tree-lighting event, à la Rockefeller Center.

Enter Frank.

He was able to corral musical acts like Questlove and Bebe Rexha, I handled the ice stuff, and other than a particularly menacing gust of wind temporarily flattening an I Heart Radio promo tent, the event went flawlessly.

We said our goodbyes, and didn’t reconnect until two years later when that same client was embarking on a much larger project. 👇

I was stoked to work with Frank on the development of Pier 17. He was a big deal, and I felt honored to simply be in the room with him. He always asked the best questions, and had an uncanny knack for valuing the perspectives of everyone at the table.

So one day I nervously shot my shot, and asked Frank out for coffee, seeking some professional guidance.

He accepted, and true to his name, offered “frank” advice on the questions I had prepared for him. From that moment forward, I felt like I had an oracle of industry in my corner. Not because he needed to be — because he wanted to be.

Frank even wrote a letter of recommendation for my Harvard Executive School application. Who knows if I ever would’ve made the cut without that golden reference?

Frank is simply a good guy who genuinely enjoys helping people. And he’s spectacularly successful at what he does.

That’s why his mantra isn’t bullshit.

What’s that mantra?

“You can’t prepare for everything. But you can prepare for anything.”

While my relationship with Frank dates back a dozen years, it felt like everything came full circle at an event I hosted last month.

As part of this event, I interviewed Frank…

And in pure Frank-form, he quipped his famous line, which was met with (expectedly) skeptical faces.

“You can’t prepare for everything. But you can prepare for anything.”

Dude. We’re all successful entrepreneurs and senior executives. You can’t fool us with catchy riddles. What the hell does that actually mean?

Let’s break it down. 

The first line isn’t terribly profound: “You can’t prepare for everything.” It’s impossible to have a plan for every scenario, or anticipate every risk. I think we can all agree on that.

But that second line, “You can prepare for anything”, is what gets people leery. Aren’t “everything” and “anything” pretty much the same damn thing?

They’re really not.

You might remember this little nugget of sports history — in 2013, the lights went out at the Super Bowl. It was a full, stadium-wide power failure, mid-game, in front of 74,000 people and 115 million television viewers.

Frank was running the show that day. And he had zero plan for what to do in the case of a power failure. There was no playbook.

Yet, within 90 seconds, he worked his way through the systems he had developed:

So before thousands of people in the stadium could even begin speculating what might be happening (and, as massive crowds tend to do, panic), there was a calm voice on the backup-PA telling them exactly what they needed to know:

“Ladies and gentlemen, the stadium is experiencing a power failure, and everyone is perfectly safe. Please sit tight, and the game will resume shortly.”

So the true meaning of Frank’s mantra is this:

While you can’t have a specific plan for every specific scenario, you can absolutely build communication systems, decision-making hierarchies, and clear principles that always function — regardless of the scenario that actually gets thrown at you.

👉 Preparing for everything is the equivalent of handing someone a playbook, and praying that whatever they encounter falls within the pages of that book. Because if they encounter something outside those pages, they’re screwed.

👉 Preparing for anything is the equivalent of providing someone with guiding principles which inform their judgement, so they’re well-equipped to handle any range of scenarios.

I want you to think about the outcomes you’re responsible for at work.

Now I want you to imagine (another huge Frank-ism) all of the things that could negatively impact those outcomes. In other words — think about all the shit that can go wrong.

How many of those scenarios do you feel prepared to tackle? Or perhaps more importantly, how many of those scenarios does your team feel prepared to tackle?

Maybe you’ve thought about this, and you’ve got plans for how to handle most problems that arise in your business. That’s a good start. It means you’ve imagined these things might happen, and planned accordingly. Or maybe they already happened, you weren’t prepared, and now you’ve put a plan in place to handle it next time.

Be proud of that.

But then ask yourself — are you, or your team, prepared to handle complications that fall outside of the scenarios you’ve planned for?

Is there a set of core principles that guide decision-making? Do people feel confident making judgement calls? Are there systems in place to support people making those judgement-calls?

This goes beyond risk management and crisis planning. It’s the difference between a business where people show up and do their work, and a business where people show up and own their work.

And this is why Frank’s advice is so powerful. Because creating a culture filled with strong operating values, resilient systems, and vigorous accountability does a heck of a lot more than save you with the shit hits the fan— 

It seeds innovation by enabling you to take bigger risks.

Cheers! 🍻

-Kristin

P.S. — I don’t just write Drunk Business Advice — I bring it to life on stage. And I’d love to speak at your next event. Hit reply or click here to learn more.