Why Letting Go Is So Hard
Your brain is wired to hold on. To people, outcomes, possessions, ideas about how things should be. This made sense evolutionarily—attachment to food sources and tribal bonds kept your ancestors alive.
But in modern life, this same wiring creates suffering. You cling to relationships that have run their course. You obsess over outcomes you can't control. You white-knuckle expectations that reality keeps refusing to meet.
Both Buddha and the Stoics diagnosed this problem millennia ago. Their solutions are practical, not mystical.
What Attachment Actually Is
First, let's be precise. Attachment isn't caring about things. You can love people deeply without attachment. You can want good outcomes without attachment.
Attachment is the refusal to accept reality when it doesn't match your preferences.
It's the "should be" that fights against "is."
- "He should apologize."
- "I should have gotten that job."
- "This shouldn't be happening."
That tension between expectation and reality is where suffering lives.
The Buddhist View: Holding On Creates Pain
Buddha's Second Noble Truth states that suffering arises from craving and attachment. Not from wanting things—from clinging to them.
Here's the distinction: You can prefer something without needing it. You can want an outcome without falling apart if it doesn't happen. You can love someone without requiring them to be a certain way.
Attachment adds neediness to preference. And neediness hurts.
Think about the difference between these two mental states:
"I want this job and I'm doing my best to get it."
vs.
"I need this job. If I don't get it, I'm a failure. I can't be okay unless this works out."
Same desire. Completely different relationship to it. The first allows engagement without suffering. The second guarantees suffering whether you get the job or not.
The Stoic View: Focus Only on What's Yours
The Stoics approached attachment through a different angle: the dichotomy of control.
External things—other people's opinions, whether your business succeeds, whether traffic cooperates—are not "up to you." They involve luck, other people's choices, factors beyond your control.
Getting attached to external things means handing your peace of mind to forces you can't influence. It's a losing game.
Epictetus: "Seeking to control what is not in our power while neglecting what is in our power causes anxiety, frustration, and distress."
The Stoic practice is brutal in its simplicity: want only what you can actually control. Your effort, your choices, your character.
You can prefer external outcomes. But if your wellbeing depends on them, you've given away your power.
Practical Technique #1: Notice the Should
When you're suffering, look for the hidden "should."
- You're angry at traffic. Hidden should: "Traffic should be moving faster."
- You're hurt by a friend. Hidden should: "She should have been more considerate."
- You're anxious about the future. Hidden should: "Things should be certain."
Once you see the should, you can question it.
Says who? Why should reality conform to your preferences? Has arguing with reality ever changed it?
This isn't passive resignation. You can still take action—leave earlier, have a conversation with your friend, prepare for uncertainty. But you stop demanding that reality be different than it is.
Practical Technique #2: The Stoic Premeditation
Before engaging with something you care about, remind yourself of its nature.
Seneca recommended this for possessions: "When we consider the nature of what we have, we should think of it as something borrowed."
The Stoics would look at their belongings, their relationships, even their own bodies and say: "This is on loan. I may lose it. That's its nature."
This sounds morbid. It's actually liberating. When you accept that loss is part of having, you can enjoy what you have without the anxious clinging that ruins enjoyment.
Before a difficult conversation: "This might not go how I want. That's possible."
Before a project launch: "This might fail. I've done my best, and the outcome isn't in my control."
Before time with loved ones: "This moment is impermanent. Everyone I love will die or leave. Let me be present with them now."
Practical Technique #3: Impermanence Meditation
This is a Buddhist practice that can be done in five minutes.
Sit quietly. Bring to mind something you're attached to—a person, a possession, an outcome, an identity.
Now gently remind yourself: this will end. Not as a threat, but as a fact.
The person you love will age and change. The possession will break or become irrelevant. The outcome you're craving will eventually be in the past. The identity you cling to is already shifting.
This isn't depressing if you let it land properly. It's clarifying. It shows you what matters right now. It loosens the grip of grasping so you can actually experience what you have.
The Difference Between Letting Go and Not Caring
This is important: letting go doesn't mean becoming cold.
Buddha loved his followers. Marcus Aurelius loved his children. They weren't emotionally detached in the sense of not caring.
They were detached in the sense of not clinging.
You can love someone fully while accepting that you can't control them. You can work hard for an outcome while accepting that success isn't guaranteed. You can appreciate something deeply while holding it lightly.
Actually, holding lightly allows for deeper appreciation. When you're not anxiously gripping, you can actually experience what's in front of you.
When Letting Go Feels Impossible
Some attachments feel welded to your identity. You can't imagine being okay without this person, this job, this outcome.
That's the attachment talking. It convinces you that you need the thing to be okay. But people have lost everything—and become okay. Sometimes more than okay.
Viktor Frankl, in Nazi concentration camps, lost his family, his health, his profession, his possessions. He later wrote that even in those conditions, one freedom remained: choosing his attitude.
You are more adaptable than your attachments want you to believe.
A Daily Practice
End each day with a brief inventory:
What did I cling to today? Where did I fight with reality? Where did I demand that things be different than they are?
No judgment. Just noticing.
Then consciously release the should. "Traffic should have been faster"—released. "She should have been nicer"—released. "I should be further along"—released.
This isn't pretending things don't matter. It's practicing the skill of holding them lightly.
Over time, the grip loosens. Not your capacity to care—your compulsive need for things to be a certain way. That's where freedom lives.