From Yossarian to Orr: Moving From Seeing the Problem to Solving It

January 2025 ¡ linkedin, republished ¡ View Markdown

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From Yossarian to Orr: Moving From Seeing the Problem to Solving It
There was only one catch and that was Catch-22, which specified that a concern for one’s safety in the face of dangers that were real and immediate was the process of a rational mind. Orr was crazy and could be grounded. All he had to do was ask; and as soon as he did, he would no longer be crazy and would have to fly more missions. Orr would be crazy to fly more missions and sane if he didn’t, but if he was sane he had to fly them. If he flew them he was crazy and didn’t have to; but if he didn’t want to he was sane and had to. Yossarian was moved very deeply by the absolute simplicity of this clause of Catch-22 and let out a respectful whistle. “That’s some catch, that Catch-22,” he observed. “It’s the best there is,” Doc Daneeka agreed.

For much of my life, I’ve felt like Yossarian from Catch-22. Trapped in systems that felt absurd, unyielding, and indifferent, I could see the problems clearly—how the rules worked against me and others, how progress was stifled by inefficiency and fear. But like Yossarian, I felt helpless to do anything about it. I raged, I resisted, and I tried to fight the system head-on. But the system didn’t budge.

It wasn’t until I started thinking more like Orr, Yossarian’s quietly brilliant counterpart, that I began to make real progress. Orr didn’t just see the problem—he acted. While others raged against the machine, Orr spent his time preparing. He crash-landed planes to perfect his survival tactics. He didn’t waste energy fighting battles he couldn’t win. He studied the system, found its cracks, and created a way out.

That shift—from seeing the problem to solving it—has been transformational for me.

The Lesson: Seeing Isn’t Enough

Yossarian and Orr both understood the absurdity of the system, but their responses couldn’t have been more different. Yossarian fought against it, growing increasingly frustrated and hopeless. Orr, on the other hand, accepted the system’s absurdity but refused to let it define him. He focused on what he could control, planned meticulously, and eventually outmaneuvered the system entirely.

For a long time, I was stuck in Yossarian’s mindset. I saw the flaws, the inefficiencies, the roadblocks, and I let my frustration and anger take the lead. I thought if I pushed harder, if I fought more, I could break through. But all I did was burn myself out. The system didn’t change—but I had to.

The Shift to Orr: What I’ve Learned

Here’s what moving from Yossarian to Orr has taught me:

  1. Calm Is a Superpower
  2. Focus on What You Can Control
  3. Learn the Rules to Rewrite Them
  4. Prepare for the Long Game

Moving Forward With Purpose

Many of us feel like Yossarian at some point—seeing the problems in our systems but feeling powerless to address them. It’s an overwhelming place to be. But we don’t have to stay there. By shifting our mindset and actions, we can move from frustration to strategy, from reacting to creating.

The journey from Yossarian to Orr isn’t easy. It requires patience, clarity, and focus. But the rewards are worth it. When we stop fighting against the system and start thinking our way through it, we create something far more powerful than resistance: real progress.

So, if you’re feeling stuck or overwhelmed, ask yourself: What would Orr do? How can you prepare, adapt, and quietly build your path forward? The answer might surprise you—and it might just set you free.