Letting Go
August 10, 2025
Most normal people find skydiving frightening, and for good reason1. When you jump out of the plane, you put complete trust in your parachute2. Letting go of the aircraft becomes an act of faith3.
While such faith might seem crazy4, I’m convinced that this calculated, eyes-wide-open faith is a prerequisite to embarking on some of life’s most rewarding pursuits.
Fear
Fear is mechanism that is baked into5 the human condition; everybody must live with fear6.
There is no lack of things to be afraid of. Our existence is fragile7, and there are so many things that can go wrong8.
Utility
Fear can be a motivator to avoid dangerous and undesirable situations9.10
- When it snows and the roads are slippery, fear of collision makes it easy to drive slowly
- Fear of burglary (or worse) makes it easy to lock your doors at night
- After zoning out in a lecture, fear of embarrassment makes it easy to not ask a dumb question
This is good.
Detriment
On the other hand, fear can hold us back from doing things that would benefit us.
- Fear of drowning can make it difficult to learn how to swim
- Fear of rejection makes it difficult to ask your crush to go on a date
- Fear of disappointment can make it difficult to eat at an unfamiliar restaurant
Rationalization
Determining the degree to which a fear is useful or detrimental is a difficult equation and a subjective one.
Is a slim chance of a bad thing (e.g. fatality) worth overwhelming fear? It probably depends on the definition of “slim”. What about a large chance of a moderately negative outcome, but a small chance of an extremely good one?
The parts of our minds that calculate whether or not to be afraid aren’t very good at calculating or comparing these probabilities. There is a lot of noise in the equation. If we want to call our decisions rational, we have to put effort into understanding why we feel the way we do and make a decision only after deep consideration.
Evading Rationality
Our typical response to fear is avoidance. It hurts our pride to admit that we’re afraid, and we’ll naturally go to great lengths to fool ourselves and others into justifying and denying our fears.
The Icebergs of Evasion
We can divide evasion11 into two primary dimensions:
- Denial of fear (“I’m not afraid”)
- Justification of fear (“My fear is not a bad thing”)
For example, in terms of skydiving:
| High Denial | Moderate Denial | No Denial | |
|---|---|---|---|
| High Justification | “Why would I ever want to jump out of a perfectly good airplane? It would be dangerous, expensive, and not at all worth it.” | “I’m not sure how I feel about jumping. It would be dangerous, expensive, and not at all worth it.” | “I’m afraid of jumping because it is dangerous, expensive, and not at all worth it.” |
| Moderate Justification | “Why would I ever want to jump out of a perfectly good airplane? It seems dangerous.” | “I’m not sure how I feel about jumping. It seems dangerous.” | “I’m afraid of jumping because it seems dangerous.” |
| No Justification | “Why would I ever want to jump out of a perfectly good airplane?” | “I’m not sure how I feel about jumping.” | “It isn’t more danger than I’m willing to accept: I refuse to do it solely because I am irrationally afraid.” |
Think Harder, Think Deeper
Evasion is rarely productive. “None of the above” is never an option in life: by refusing to act, we condemn ourselves to living with the status quo.
If we don’t take the time to introspect, or even if we do and we don’t push deep enough, we will default to evasion.
Fear as a Prison
Fears are self-imposed mental boundaries. They are things that you tell yourself you cannot do12. If you fear many things, or if you fear things that would be good for you (or things that you “need”), life becomes an impossible puzzle to solve.
This is especially pathological because it’s a blocker of a positive feedback loop. Fear stops you from getting started, and getting started is usually the hardest part. Once you conquer fear you open your mind to what is possible, which makes everything easier. But until you do, you’re totally stuck and unable to progress. Bravery requires bravery. “Letting go” is the moment when you are afraid but you make the active decision to be brave.
Becoming Brave
Rephrasing
A slight shift in point of view can make a giant difference. When you permute the right piece of the puzzle, you might make a discovery which allows many other pieces to fall into place13.
I'm afraid of dying
I'm afraid of ¬(¬dying)
I'm afraid of ¬(living)
I'm afraid of not living life to the fullest
I'm afraid of not living life to the fullest (∧ living life to the fullest requires a slightly higher risk of death)
=> I'm more afraid of not living life to the fullest than I am of dying, so I'm willing to take calculated risks
I'm afraid of being rejected
I'm afraid of ¬(¬being rejected)
I'm afraid of ¬(being accepted)
I'm afraid of not being accepted
I'm afraid of not being accepted (∧ being accepted only can happen if I risk rejection)
=> I'm more afraid of not being accepted than I am of being rejected, so I'm willing to calculatedly risk rejection
to pursue acceptance
Cracking The Crust of Complacency
It’s natural and easy to grow comfortable with your situation14, and to stop pushing yourself to think in different ways. This is especially true in the age of the internet, where we can do increasingly more from our parents’ basements, without having to leave the house and feel vulnerable to risk.
Complacency is often rooted in the irrational unconscious fear of the unknown (leaving the house). The unconscious is rarely able to rephrase the fear and realize that staying inside of the house comes with its own risks and an opportunity cost of infinity.
The antidote to complacency is a habit of disrupting your current ways of thinking and pursuing a deeper understanding your fears.
Letting Go
Whether or not you can make a rationality judgement of your fear, you’ll likely come to a point where there’s an impasse, and, regardless of logic, you are face-to-face with your fear, and you have to make a discrete decision where you decide whether or not to go forward.
Jumping out of a plane is a romantic exemplar of this, but there are many more common and consequential decisions that follow this same format.
- leaving all your friends and everybody you know to go to a college you can’t afford and room with a person you’ve never met
- moving to an unfamiliar city
- leaving your job to go to another company
- getting married
- having children
- letting your children leave the house
In these situations, you must learn to transcend the ambiguities, let your dreams drive you past your fears, and just let go.
There is no promise that the universe will catch you, but that’s part of the journey; that’s what makes letting go so significant.
Holding on (refusing to let go) is act of complacency. It creates the illusion that you are in control, but ultimately results in no positive change.
Jump
Some of life’s most rewarding adventures are fear-inducing ones. If we are governed by fear, we can miss out on some of the best experiences life has to offer. Which are you more afraid of: having something go wrong in pursuit of this adventure, or never starting the adventure in the first place? Pain and failure and tragedy happen and are often beyond our control. They are horrible, but they are unavoidable. Perhaps the only way to justify this is to counteract the pain with so much meaning that the pain and risk of pain is worth it. Confront your fears, dissect why you have them, and blow the irrational ones out of the water. Risk is inevitable, stare it in the eyes and calculate it. Build a habit of being brave, of letting go when it makes sense. This will open up so many opportunities and allow you to truly live.
Modern skydiving equipment is incredibly reliable when correctly used and maintained, so in the right circumstances, skydiving can be quite safe (at least proportionally to the perceived risk). However, I think that some degree of fear is an appropriate response. ↩︎
“parachute” is used loosely here. More precisely, you are trusting your rig (your “magic backpack”), which is the harness-and-container system strapped to your body, usually with two parachutes (main and reserve) and associated deployment/cutaway systems. ↩︎
It might be faith in your own understanding of your gear, your rigger, your gear’s manufacturer, USPA’s statistics, God, or the ways of the universe. Whichever way you slice it, it’s faith nevertheless. ↩︎
I have no doubt that “crazy” is an accurate description of some skydivers. ↩︎
Meticulously developed and tuned over generations to maximize propagation. ↩︎
Everybody in their right mind, at least. ↩︎
Humans can have great resilience (relative to adversity), but are dually fragile. ↩︎
Endless permutations of pain, loss, failure, rejection, etc. ↩︎
This is, of course, the reason it was selected/developed by evolution. ↩︎
It might be worthwhile to note that a fear need not be rational to be useful. E.G. believing that there are satellites orbiting the earth that can detect your car’s speed and will instantly ticket you if you go over the limit. This isn’t the case (at least not yet), but it could be useful to believe this, because you would never be ticketed for speeding if you did happen to drive through a speed trap. ↩︎
The mental, chain-of-thought side of it, anyway. ↩︎
The phrasing (e.g. “I don’t want to”, “I’d rather not”, “I’m afraid of”) depends on the level of denial. ↩︎
Usually this happens at a time when you are stumpted (not moving any pieces), which makes it especially powerful. ↩︎
Assuming you’re lucky enough to end up in a somewhat comfortable situation. Though complacency probably applies to less fortunate circumstances too. Complacency (as used in the context of this post) is more like “giving up the upward battle” than “being genuinely fulfilled”. ↩︎