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Flames and Coals: Leadership Lessons in Anger vs. Disappointment

The other day, I found myself in conflict with a company I’ve done business with for decades. Our dispute wasn’t monumental, but the company’s response was inflexible, bureaucratic, and dismissive of our long-standing relationship. When the conversation ended, I was angry and frustrated that years of loyalty seemed irrelevant to them.

What to Do at the Stoplight

What do you think is the number one question people ask me when it comes to homelessness? It isn’t whether someone is “really” homeless, nor is it about drugs or mental health. The question I get, above all others, is simple: “Hey Jack, when I pull up to the stoplight and someone has a sign… what do I do?”

From Crisis to Day-to-Day: Turning Emergencies into Manageable Problems

“Madam Chancellor, we have a crisis!”

Those words immediately trigger adrenaline, urgency, and sometimes panic. But here’s the truth: nobody actually solves a crisis. What we solve are problems.

Nothing is ever as good as you dream it, nor as bad as you imagine it.

I’m a major-league catastrophizer. Just ask my wife. My default is to run through the absolute worst-case scenario and consider all the ways a situation could go wrong. I tell myself it’s “just being prepared,” but honestly, it’s rarely helpful. The worst-case scenario I envision never actually happens, and meanwhile, I’ve stressed myself (and everyone around me) to exhaustion.

You might lean the other way as the optimist who envisions the perfect outcome. I do this too: picturing the ideal relationship, the flawless vacation, the dream job, or the ideal project. But in the real world, nothing is perfect. Chasing perfection wastes energy and drains resources, leaving you frustrated and your organization overextended.

A Fighter Pilot’s Guide to Staying Out of Trouble

I’m a fighter pilot. I don’t fly anymore, but once you’ve been a pilot, you never stop thinking like one. I used to launch 80,000 pounds of jet into the air in less than 6,000 feet of runway. With the afterburners lit, the ground shook, your ears hurt, and the jet guzzled fuel like there was no tomorrow.

It's Only 3 Feet.

What needs to be done about the growing homeless situation in America?

As the situation in Southern California is settling down, it is useful to take the time to understand how the military can be used in a domestic crisis. None of this is easy. Leaders are having to make decisions when none of the options are very good. They are having to choose what I call the “Least-Worst Option” and own it. Striking a balance between not being too impulsive nor being paralyzed is the goal: a timely decision that has a positive outcome. I know the pressure these leaders are under during any crisis. In this case, what adds even more pressure is the use of military assets on America’s streets. The background to making such decisions is not well understood by many. Let me try and briefly explain it so you can tell your friends.