I traded my M-4 and combat boots for a keyboard and dress blues. It was the hardest “deployment” of my career.

When I moved from the Field Army to the Pentagon, I thought I was ready. I had spent over a decade and a half wearing the uniform, rising through the ranks from an enlisted soldier to a commissioned officer. I had years of tactical success under my belt. I knew the ground-level reality of the machine inside and out. I knew how to get 60 Soldiers to run in a tight formation, drag a convoy across an entire state, and win the 30/60/90 day cycle. The feedback loop in the field is immediate, visceral, and addictive. You make a call, you see the result, you adjust fire. 

I was a leader of men, and pretty damned good at it too.

Then, during my first week in the Pentagon, I walked into a meeting about a communications system that wouldn’t come out of the R&D program for another four years. My tactical brain screamed: “What are we doing? We have problems TODAY.”

But see, that’s the trap. And I got stuck waist-deep in the quicksand. 

During my 11-year tenure at the Pentagon, my primary directive was to be a part of the team who were building the Army’s capabilities for the next ten years. You do not build a generational warfare capability by worrying about what happens next Tuesday. 

When I was on the team building the Army’s initial Cyber Capabilities, we weren’t just procuring hardware; we were defining an entirely new domain of warfare. We had to recruit a completely different kind of Soldier, integrate them into a deeply traditional military structure that inherently resisted change, fight bureaucratic inertia, and anticipate adversarial capabilities that didn’t yet exist. 

Applying a field-artillery mindset to a cyber-strategic problem is a spectacular way to fail. You simply cannot out-hustle a decade-long strategic rollout with short-term tactical sweat.

The “Front Line Hero” Trap

I see this in the corporate world, too. “Front Line Heroes”, the ones who are the best individual contributors in the building, get promoted to the C-Suite and bring their 90-day goggles with them. They are so focused on the quarterly KPIs or the immediate “fire” that they forget to look at the horizon.

This is the great tragedy of corporate promotion structures. We take our best operators and penalize them with strategic authority they haven’t been trained to handle. The elite Sales Director who closed the biggest deals is handed the reins of the entire revenue organization. Instead of stepping back to build comprehensive compensation models or develop strategic partnerships, they panic. They revert to what they know. They start flying out to close individual accounts, undermining their own regional managers in the process. They mistake motion for progress. Congratulations, you are a VP now. Stop trying to run the cash register.

The shift from Tactical to Strategic is a shift in time-horizon:

• Tactical (The Field): Success is measured in weeks and months. You react to the terrain in front of you. It’s about Execution.
• Strategic (The Pentagon): Success is measured in 5, 10, and 15-year cycles. You aren’t reacting to terrain; you are shaping it. It’s about Endurance.

If you only lead for the next 90 days, you are just a glorified manager.

4th and 5th Order Thinking: Rejecting Surface-Level Fixes

To break this cycle, executives must adopt what my firm refers to as 4th and 5th Order Thinking. First and second-order thinking is easy, and it is where most leaders plateau. For example, a competitor drops their price (the Condition). We drop our price to match and save the deal (First-order solution). We retain the client for the quarter (Second-order result).

But what happens next? Third-order: our margins shrink, forcing us to freeze hiring in our customer service department. Fourth-order: client satisfaction plummets because our overburdened teams can’t support them. Fifth-order: we lose our market reputation as a premium provider, becoming locked in a race to the bottom that we ultimately lose. 

Strategic leaders map out the entire cascading sequence of consequences before they make their first move. They reject the dopamine hit of the saved deal to protect their decade-long market position.

Others-Oriented Leadership: Planting the Trees

When mapping out true leadership hierarchies, I rarely look backward at traditional historical military figures. To understand scale, I look at visionary business icons like Steve Jobs, architecting an entire technological ecosystem, or elite, culture-building sports leaders like Nick Saban. Saban didn’t win championships by obsessing over a single play; he built “The Process,” a relentless, self-sustaining system of standards that produced outcomes organically.

To be a true leader, you have to be willing to plant trees you will never sit under. This is the core of Others-Oriented Leadership. True organizational success isn’t achieved by chasing personal glory, winning the current news cycle, or securing immediate quarterly bonuses. It is achieved by prioritizing the vertical development, mentorship, and growth of your team.

My most cherished title isn’t Lieutenant Colonel, or Chief Executive, or even Chief Bourbon Officer — it’s “Pop Pop” to my 10 incredible grandkids. When I look at them, I am reminded daily that a true legacy isn’t about what you conquer today; it’s about the shade you provide for those who come after you. Your business, your command, and your people must be treated with that exact same reverence.

How to expand your “Field of Vision”:

• Audit your Calendar: If 90% of your meetings are about “Today’s Problems,” you aren’t leading. You’re firefighting. Pull up your schedule right now and color-code your meetings. Red for immediate crises, green for strategic design. If your calendar looks like a crime scene, you are the problem. Cancel the endless status updates. Force your team to write streamlined memos. Reclaim your time so you can actually think.
• Embrace the Slow Burn: Strategic wins don’t give you a dopamine hit every Friday. You have to learn to find satisfaction in moving the needle 1% toward a 10-year goal. The work is often unglamorous. It is drafting complex policy. It is fighting over a three-year budget projection. It is repeating the vision for the hundredth time to a cynical division head until the culture finally clicks. If you need immediate validation, step down and go back to the front lines.
• Stop Solving, Start Shaping: In the field, you solve problems. At the strategic level, you create the environments where those problems don’t happen in the first place. You are the architect of the ecosystem, not the mechanic of the engine. The highest compliment a strategic leader can receive is a quiet week, because it means the systems they designed are working flawlessly without their intervention.

It’s a hard pivot. It feels slow. It feels bureaucratic. I spent my fair share of late nights in the Pentagon wanting to tear my hair out over acquisition timelines, occasionally needing a pour of great whiskey just to process the sheer friction of bridging high-level strategic theory with practical execution. But if the leaders at the top don’t look 15 years out, the Soldiers in the field today won’t have what they need to win tomorrow.

Lift your head up. The horizon is further away than you think.

Look at your calendar for next week. If 90% of your time is booked for “Today’s Problems,” you aren’t leading—you’re firefighting. You’re still wearing your field boots in the boardroom.

Challenge: Carve out two hours this Friday. No Slack. No email. No fires. Just you and a yellow legal pad. Ask yourself: “What am I doing today that will matter in 2029?”

If you can’t answer that, it’s time to recalibrate. 

How do you force yourself out of the 90-day cycle? I’d love to hear your “horizon-scanning” tactics in the comments.