The Aerodynamics of Letting Go Part 5
The canopy above my head didn’t just fold. It vanished.
One moment, I was a god, carving silent arcs through the Alpine air, the world a toy-set village below. The next, I was a stone, wrapped in a fistful of limp nylon, plummeting toward it. The sound—a violent thwump like the world’s biggest wet towel being snapped—is something your bones never forget.
In those seven seconds of freefall before my reserve chute blew, a strange thought crystalized: This isn’t even my worst failure.
That might sound insane. But for a decade, I had been perfecting the art of the spectacular crash. Two failed startups before I was 30, incinerating not just my own savings but a gut-wrenching amount of money from people who believed in me. A relationship I loved, torched by my own insecurity and ambition. A book deal that evaporated overnight because I couldn't get out of my own way.
I wasn’t just failing. I was developing a signature style—going all-in, pushing too hard, and then holding on to the wreckage with a death grip long after it had slammed into the ground.
After that near-fatal paragliding accident, something shifted. Lying in a Swiss hospital bed with a renewed appreciation for gravity, I realized I’d been studying the wrong thing. I'd spent 10 years obsessing over success—the hustle, the grind, the climb.
But the secret wasn’t in the climbing. It was in the falling.
More specifically, it was in the physics of how to fall and get back up. Not with brute force, but with grace. I’d been trying to muscle my way through life. What I needed to learn was aerodynamics. What I needed to learn was how to let go.
And I discovered that letting go isn't a passive act of surrender. It's a dynamic, powerful, and deeply strategic skill. It has principles. It has physics. And the truth nobody tells you is that resilience isn’t about being tougher; it’s about becoming more aerodynamic.
Here are the three aerodynamic principles that changed everything for me.
Principle 1: You’re Confusing Drag with an Anchor
In aerodynamics, drag is the force that opposes an aircraft's motion through the air. It’s resistance. It slows you down.
In life, we experience drag as regret, resentment, and the ghost stories we tell ourselves about past failures.
- The business that went under.
- The partner who left.
- The promotion you didn’t get.
- The mistake you can’t forgive yourself for.
Most people treat this drag like an anchor. They believe they have to haul it behind them forever, a heavy, unmovable part of their history. We obsess over it. We replay the arguments in the shower. We second-guess the decision we made three years ago. We let the weight of yesterday’s weather dictate the flight path for tomorrow.
This is the biggest mistake you can make.
Drag isn't an anchor you have to carry. It's a force you have to manage.
Think about a high-performance aircraft. Engineers don't pretend drag doesn't exist. They obsessively design every surface to be as sleek and streamlined as possible to reduce its effect. They call it minimizing the drag coefficient.
You need to do the same for your life.
The Actionable Insight: You don’t eliminate the past, you streamline it. You do this by changing the story you attach to it.
My first startup failure was, for years, a story of humiliation. I’d lost $50,000 of my family's money. The drag was immense—I avoided family gatherings, ducked questions about my career, and carried a thick cloak of shame.
The streamlined story is different. That failure was a $50,000 real-world MBA in market validation. It taught me more than any business school ever could. It was the tuition for a lesson that directly led to my later successes.
The facts are the same. The drag profile is completely different.
Stop telling the story of what your failure cost you. Start telling the story of what it taught you. When you do that, the drag doesn't vanish—but it stops being an anchor and becomes the turbulent wake you’re leaving behind.
Drag is a memory. Thrust is a decision. Choose thrust.
Principle 2: Find the ‘Subtle Lift’ by Changing Your Angle of Attack
This is the one that will change your life.
In aviation, “Angle of Attack” is the angle between the wing and the oncoming air. A small adjustment to this angle can be the difference between climbing effortlessly and falling out of the sky.
When we face a setback, our default Angle of Attack is usually aggressive and head-on.
- “I need to work harder.”
- “I need to force this to work.”
- “I just need to push through this wall.”
We try to solve the problem by slamming into it with more force. This high-angle, brute-force approach creates enormous resistance. It’s exhausting, and ironically, it often leads to a stall (more on that next).
But here’s the secret, the part that feels like magic: in every crisis, in every failure, in every gust of wind trying to knock you down, there is a source of “Subtle Lift.”
Subtle Lift is the unseen opportunity hidden within the adversity. It’s the updraft you can’t see, but you can feel if you just adjust your angle.
- The layoff that forces you to finally start the freelance career you’ve been dreaming of.
- The brutal feedback that reveals a critical flaw in your product, saving you from a much bigger failure down the road.
- The breakup that clears the way for a relationship with yourself—and eventually, with someone who is truly right for you.
This isn’t just toxic positivity. It’s strategic repositioning. You stop asking, "Why is this happening to me?" and you start asking, "What is this making available for me?"
The Actionable Insight: When you hit a wall, don’t try to break through it. Change your angle.
For two years, I tried to revive my second failed startup. I kept pitching the same broken model to investors, convinced that more effort was the answer. My Angle of Attack was 90 degrees, straight into the granite wall of market indifference. I was burning out, fast.
The moment I let it go felt like the end of the world. But by surrendering the head-on fight, I changed my angle. I stopped seeing the situation as a failed company and started seeing it as a collection of assets. The "Subtle Lift" was a small piece of code one of my engineers had written, a side-project we’d almost ignored.
We took that code, built a new micro-SaaS product around it in six weeks, and it found a market immediately. The failure wasn’t the end; it was the crucible that burned away everything but the one thing that actually worked.
What problem are you attacking head-on right now? What if you tilted your perspective just 15 degrees? What unseen lift might you discover?
Principle 3: Master the Aerodynamic Stall
A stall is a pilot’s nightmare. It’s a sudden reduction in lift, causing the aircraft to fall. In my paragliding accident, the collapse of my canopy was an instantaneous, catastrophic stall.
In life, a stall is burnout. It’s hitting rock bottom. It’s the moment you look at the mountain you’ve been trying to climb and realize you don’t have the energy to take one more step. Your motivation is gone. Your momentum is zero. You are, for all intents and purposes, falling.
Our culture tells us that stalling is the ultimate failure. The advice is always: "Don't give up!" "Keep pushing!" "Hustle harder!"
I’m going to tell you something that goes against every productivity guru out there: Sometimes, the most strategic thing you can do is let yourself stall.
In flight training, they teach you how to recover from a stall. The first step is counterintuitive. You don't pull up. You push the nose down to regain airspeed over the wings, which allows you to generate lift again. You have to go down to go up.
A life stall is the same. It's not the end. It’s a critical reset maneuver.
When you hit that wall of utter exhaustion and defeat, your frantic efforts to "pull up" and "stay positive" only make the stall worse. You're trying to fly with no airspeed.
Embracing the stall means giving yourself permission to stop.
- To grieve the loss.
- To admit you’re burned out.
- To confess you don't have the answers.
- To let the project die.
- To just… be.
The Actionable Insight: When you’ve lost all momentum, stop trying to climb. Instead, focus on regaining airspeed.
Airspeed, in this metaphor, isn’t about hustle. It’s about energy. It’s about reconnecting with the fundamentals.
- Sleep.
- Walk in nature.
- Talk to a friend—not for advice, but for connection.
- Read a novel.
- Work on a hobby where the stakes are zero.
After my second startup imploded, I didn’t pivot. I went broke. I moved into a friend's spare room for six months. I delivered food. I stalled. For the first time in my adult life, I wasn't an entrepreneur. I wasn't a CEO. I was just a guy trying to figure things out.
And in that quiet, controlled descent, I regained my "airspeed." The pressure was off. My identity wasn't tied to a dying company. I started having ideas again, not because I had to, but because my mind finally had the oxygen to breathe. The stall wasn't a crash; it was a necessary dive to find a new thermal of energy.
The Takeoff Checklist
Letting go isn't about giving up. It's about giving up the things that are weighing you down so you can finally fly. It’s an active, aerodynamic process.
To recap, here is your checklist:
- Streamline Your Drag: Reframe the story of your past failures from a narrative of cost to a narrative of tuition. What did you pay to learn?
- Adjust Your Angle of Attack: Stop ramming your head against the wall. Ask: "What is this failure making available to me?" Find the Subtle Lift hidden in the headwind.
- Embrace the Stall: When you’re burned out and have zero momentum, stop trying to climb. Give yourself permission to descend, to rest, and to regain your energy (airspeed) before you even think about finding the next updraft.
For a decade, I thought resilience was about having a stronger grip. I was wrong. True resilience is about knowing when—and how—to open your hands. It’s understanding that the wind isn’t your enemy. It’s your partner. And that sometimes, the only way to catch the current that will carry you higher is to first have the courage to let go of what’s holding you down.
The sky is waiting.
So, I’ll ask you a question, and I genuinely want to know. What’s the one piece of drag you’re ready to streamline, starting today?
Leave your answer in the comments below. Your story might just be the updraft someone else needs to read.
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