The Lawyer’s Well-Being Brief…The Monkey Trap and the Cost of Not Letting Go
“So many of our dreams at first seem impossible. Then they seem improbable. And then, when we summon the will, they soon become inevitable.”-Chrisopher Reeve
Welcome (back) to the Lawyer’s Well-Being Brief! Each week, I share insights and practical strategies to help us cultivate well-being and thrive — both personally and professionally. Live well! Lawyer well!
There’s an old story about a villager trying to catch a monkey.
The villager drills a small hole in a tree or gourd and places food inside — something the monkey really wants. The hole is just big enough for the monkey to slide its hand in. When the monkey grabs the food, though, its clenched fist is too large to pull back out.
The monkey is now trapped.
At any point, the monkey could simply let go of the food and be free. But it doesn’t. It holds tighter. The desire to keep what it has outweighs the awareness of what it’s losing — its freedom.
And so the villager returns and captures the monkey with ease.
This story isn’t really about monkeys.
It’s about us.
What We’re Holding Onto
In wellbeing, we often talk about adding things:
Better habits
More motivation
Stronger discipline
New routines
But just as important — if not more so — is what we refuse to release.
We hold onto:
Old identities that no longer fit
Thought patterns that once protected us but now exhaust us
Roles we’ve outgrown
Expectations that aren’t even ours
Comforts that quietly cost us our health
Like the monkey, we grip tightly because letting go feels risky. Familiar stress can feel safer than unfamiliar peace. Even when the “food” is hurting us, it’s known — and that can be enough to keep our fist clenched.
The Hidden Trade-Off
The monkey doesn’t realize it’s making a trade:
Food for freedom.
We make similar trades every day:
Busyness for rest
Control for connection
Perfection for progress
Approval for authenticity
Short-term relief for long-term wellbeing
The trap isn’t that the hole is too small.
The trap is that we don’t question whether what we’re holding is worth the cost.
Wellbeing Begins With Release
True wellbeing often starts not with effort, but with awareness.
What if the question isn’t “What do I need to add?”
But instead:
“What am I unwilling to let go of?” Letting go doesn’t mean giving up.
It means choosing freedom over familiarity.
It means opening your hand — slowly, intentionally — and trusting that your wellbeing is worth more than what you’re clutching.
A Simple Reflection
Ask yourself:
What am I holding onto that’s keeping me stuck?
If I let go, what might I regain — energy, peace, time, freedom?
What would wellbeing look like if I loosened my grip, just a little?
The hole has always been wide enough. Freedom was never taken from us.
It was waiting for us to open our hand.
Forward Always!
