I started this post years ago as a series of rough notes, and I’m attempting today to make it make sense, because I think the topic is crucial, even if I can’t explain it as clearly as I’d like.
It started from a presentation on discontent given by Chris Guillebeau.
If only X, I’ll be better. When I X.
This goal-setting and planning is common, but it can quickly give rise to dissatisfaction and lethargy, especially when you’ve been setting goals for years and have yet to see results.
“Most people think discontent is a catalyst for change. But it’s not a catalyst, it’s a companion. It’s not something that needs to be fixed. You’re not looking for a change, you’re looking for a challenge. Don’t push it away, embrace it. The challenging things that help us grow are never planned.”
On the surface, this isn’t hard to understand.
If you aren’t growing, you’re dying.
We only get stronger in challenging situations that feel difficult and frustrating – even impossible.
And they *are* impossible, for our current selves.
There have been some good studies and using uncertainty to develop antifragility; basically toughness or grit. Not the ability to persevere and survive, but to actively thrive in challenging situations.
Resiliency is not just “bouncing back” or “recovering” from setbacks or personal tragedy. It’s a gradual strengthening through adversity.
Emily Capito
According to Jonathan Fields in How to Live a Good Life, “Life’s greatest moments live in the space between desire and attainment. It’s not the getting that makes life good, it’s the seeking, even when that seeking demands not just action but surrender. The moment your object of desire becomes a foregone conclusion, the quest loses its potential to change you. Your life becomes a series of reruns, and that gets old fast.”
Vanessa Van Edwards takes it a step further with the metaphor of a tower: with the understanding that the tower is temporary scaffolding that takes time to build, but whose purpose is simply to get you high enough to take the leap into the new.
What do you need to jump?
- Quit everything that doesn’t make you say ‘hell yeah.’
2. Don’t stick with something after the joy is gone.
“You’re either building and climbing, or you’re jumping. Don’t forget to enjoy the climb, and when you’re ready, all you have to do is jump.”
What’s your tower?
Are you jumping or climbing?
How long have you been climbing this particular tower? Are you happy with where you’re at? Sometimes jumping from your tower takes more courage; it’s harder to go down than up. Most people stick with their choices out of habit or fear. Once you get so high up and can see how far you’d have to fall, what you’d have to give up, it can seem like too much.
However, the avoidance of uncertainty will not lead to growth, only stagnation.
If you feel complacent, bored, restless, it’s not a sign of unhappiness, it’s a sign that you need a challenge, that you need to set your sights higher. Pick goals that excite and challenge you. Not practical, reasonable goals. If it doesn’t excite you, you’ll give up too early.
There’s nothing wrong with building a tower and abandoning it once you can see further and find a new point on the horizon that ignites your imagination. You don’t owe anything to the tower you’ve built, and the illusion of safety and security might rob you of the zest and enthusiasm – the thrill of falling and failing and striving towards the Faustian “more” – that often makes the success and accomplishment feel worthwhile.

I’m a philosophy dropout with a PhD in Literature. I covet a cabin full of cats, where I can write fantasy novels to pay for my cake addiction. Sometimes I live in castles.
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