As Jeff Bezos heads off to Venice for a multimillion dollar wedding weekend extravaganza, coming off the heels of a democratic socialist winning New York City’s mayoral primary, I’m reminded of how I once booked a $20,000 first-class plane ticket and later commissioned $40,000 in custom airplane linens as a part of my day job during a particularly confusing chapter of my career.
These were obviously not for me, but for a client. However, still I made the call, typed in my credit card numbers, and watched the charges hit my expense report at the end of the month.
The first time, I hesitated. The CEO’s flight was in 2 days, and their corporate card hadn’t cleared. The only option left was mine: $20,381.17… over a quarter of my salary at the time. My fingers hovered over the confirm button longer than I’d like to admit. I double checked with the boss, and was castigated for my lack of fealty. Then I tapped purchase.
By the time the request for the linens came… Egyptian cotton, monogrammed, climate-controlled… I didn’t flinch. I’d learned my lesson: don’t question. Just execute.
1. These Weren’t Purchases. They Were Precautionary Architecture.
To the untrained eye, it looks like luxury. But when you’re close to power, you see it differently: it’s insulation. The $20K ticket wasn’t about reclining at 35,000 feet, it was about controlling light, sound, access, and variables. It was about ensuring the CEO arrived alert, and not aggravated.
The linens? They weren’t necessarily indulgent. They were a hedge. The last time the client got sick mid-flight, it delayed a board decision. The solution wasn’t more sleep. It was never losing sleep again.
The kicker: both were considered business expenses. Think about that next time you expense a cab home after a long day at the office.
2. This Is How Power Thinks: Remove the Variables, Not Just the Risk.
As someone who now designs strategic operating models and advises execs on transformation, I’ve learned this mindset isn’t confined to airplanes. It shows up in dashboards that cut decision making time. In org models that anticipate, rather than respond to friction. In retention programs that reduce churn by 25% because we stop guessing at what makes people leave, and engineer a proactive solution to make them stay.
3. I Didn’t Pay for the Ticket. But I Did Internalize the Logic.
The people whom I work with, the founders, family offices, public company boards, they don’t see friction as a cost. They see it as a threat. So they build systems around themselves to neutralize it.
My job? To translate that mindset to the rest of the organization. Not with $40K linens, but with clarity, infrastructure, and logic that cascades. With systems that make people feel seen before they feel exhausted and burnout.
4. You Don’t Need a Private Plane. But You Might Need a Paradigm Shift.
I didn’t write this to glorify the excesses of extreme wealth. I wrote it because I’ve seen how quickly the logic snaps into focus when the stakes are high enough. I’ve also seen what happens when companies try to scale without this level of clarity, and when they force adaptability instead of engineering decisiveness in their systems and processes.
What I learned that year, at the age of 23, between the first class ticket and the linens, is that elite environments don’t wait for dysfunction. They anticipate it, and outmaneuver it in advance. You can call it insulation, insurance, or just plain excessive. But it’s true.
I’ve carried that insight into every initiative I’ve led since. And no, I never did sleep on those custom linens. But I did start thinking differently about time, money, and power.
And, in the end, I learned that’s what they were really protecting.
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