Jeff Clapper’s query
I grew up flying in small planes with my dad. We usually cruised at about 9000 ft, which often meant a lot of bumpy flying in clouds. Sometimes I think about this as a metaphor for owning and leading a very small business like 8th & Walton, and I look enviously at leaders of larger companies with hundreds of employees and tens or hundreds of millions of dollars in revenue. Are they more akin to better equipped, pressurized planes that can fly more smoothly, high above the clouds, or am I misrepresenting or imagining the daily challenges these leaders face?
AI Response
That’s a powerful and honest metaphor—and a very apt one.
Flying Through the Clouds: The Small Business Perspective
Running a business like 8th & Walton is like flying a small, unpressurized plane. You’re closer to the turbulence—regulatory changes, employee departures, cash flow hiccups, market fluctuations. Every bump is felt directly, and there’s little insulation. You’re personally scanning the horizon, adjusting for weather, checking instruments, and sometimes fixing the engine while flying. It can be thrilling, deeply human, and at times exhausting.
You also get unmatched visibility. You see the terrain below—your clients, your team, the decisions being made—in vivid detail. You can land quickly, change course without a board vote, and take creative risks because you’re more nimble. There’s intimacy in the scale: team members know each other well, and your values can be felt across the business in ways that large organizations often struggle to achieve.
Flying High: The Larger Company Analogy
Yes, larger companies often resemble pressurized jets at 35,000 feet. They cruise above storms and appear to glide more smoothly. Their “altitude” (capital, headcount, brand reputation) provides lift and resilience. But that comes with its own cockpit of complexities:
Bureaucracy and slow response times can limit agility.
Internal politics and stakeholder balancing often replace your kind of direct control.
Culture dilution happens faster, and staying mission-driven is harder at scale.
Innovation and risk require navigating systems, not instincts.
At altitude, things may look calmer from the outside, but inside the cockpit, the stakes are often higher. A mistake can affect thousands of people. There’s pressure to sustain momentum and avoid being the next big company to stall or descend.
The Reality: Every Altitude Has Turbulence
No altitude guarantees smooth flying. Leaders at every level encounter storms—just different types. Where you might worry about landing a client to make payroll, they might worry about activist investors, managing thousands of people across time zones, or being paralyzed by institutional inertia.
And ironically, some leaders of larger firms look longingly at the freedom, meaning, and clarity that come from flying closer to the ground—where every decision matters and every win is personal.
Final Thought: Choose Your Flight Plan Intentionally
Your metaphor points to an essential truth: scale changes the flight experience, but doesn’t eliminate turbulence. The real question is where and how you want to fly—and with whom. Some leaders thrive at 9,000 feet, hand on the yoke, reading clouds. Others need altitude and autopilot to do their best thinking.
You’re not imagining the challenges—they’re real. But you’re also not misrepresenting the trade-offs. You just happen to be piloting a plane that lets you see the landscape below, feel the gusts directly, and still land in some of the most meaningful places.