Letting go is easy when you don’t do 3 things
Missed last week? — Catch up on the archive here
Hey Reader,
Letting go is hard.
You’re still bitter about what happened at the job you left three years ago.
You’re stalking your ex’s Instagram at 11PM even though you know it’s over.
Or maybe you’re gripping the timeline you thought your life would follow, and mistaking the plot twist for failure.
We all do this. Holding on longer than we should.
It’s exhausting, and it’s sucking your energy dry.
So the solution is just move on, right?
But here’s the paradox: the harder you try to force yourself to let go, the tighter you grip.
So in this newsletter, I’m breaking down the three real blocks that stop you from letting go. And the backwards solution that worked for me when nothing else did.
(Covered this in thursday’s video — here’s the link if you want the video version)
Let’s start with Block 1.
I used to vape two packs worth of cigarettes a day. Remember those Juul pod e-cigs? And like everyone stuck in a habit they hate, I kept telling myself I should quit.
So I’d try to quit. Doing a big gesture of throwing it away, make it through a couple days… then cave and hit up the nearest gas station.
Each time I failed, the shame I felt got heavier.
Now I wasn’t just a smoker…
I was a failed quitter!
Until one day, I did something that felt completely backwards:
I admitted to myself I wasn’t ready to quit.
I told myself”
“You know what? I like vaping. I like the way it helps me focus. And pretending that I don’t like it is exhausting.”
And the moment I accepted that, something shifted.
The guilt and shame disappeared.
I instantly felt lighter.
And here’s the craziest part:
A few weeks later, I quit.
And I haven’t gone back since.
Because once I dropped the shame, I stopped needing the habit.
I wasn’t hiding anymore.
Which brings us to the first block:
Block 1: You’re not ready
Most people think they need to force themselves into readiness. But forcing it just creates more guilt and shame. And most addictions or bad habits are coping mechanisms for guilt and shame. Which means this type of shame around trying and failing perpetuates the exact behavior you’re trying to escape!
So if you can’t let go of something—maybe you’re just not ready yet.
And that’s okay.
The same pattern showed up when I let go of drinking.
People ask me all the time now:
“You know, I really should quit.. how’d you do it?”
My answer’s always the same:
You have to be genuinely ready.
Not “my wife wants me to cut back.”
Not “my doctor told me to stop.”
YOU have to be done.
Fed up.
Over it.
That’s the real secret to letting go.
When you’re truly done with something, you don’t need tricks or willpower hacks.
You just… stop.
Because there’s nothing left to argue with.
When you’re genuinely done with something and ready to let go, willpower and habit change techniques go out the window.
Because the habit wasn’t really about nicotine, it was about escaping the shame of being someone who couldn’t quit.
Once I stopped fighting myself, the grip loosened on its own.
So if you’re still holding onto that ex, that grudge, or that version of yourself you thought you’d be by now, maybe you’re not ready yet.
And forcing it just makes you grip harder.
The real shift happens when you stop treating “letting go” like a battle you need to win.
Which brings us to the second block
Block 2: You’re focusing on the wrong thing
Even when you ARE ready to let go, most people still can’t.
Here’s why:
They’re trying to release the emotion itself: the fear, the anger, the sadness. But emotions are automatic. They’re your body’s first response, and honestly? That’s not the problem.
The problem is the story you tell yourself about what it means.
Psychologists call this the difference between primary and secondary emotions.
Someone doesn’t text you back. You feel a pang of sadness. That’s primary—that’s just being human.
But then your brain kicks in with the narrative: “This means I’m unlovable. I’ll never find anyone. They were the one.”
That’s secondary. That’s the story. And that’s what’s actually crushing you.
You lose a job. The stress and disappointment? Pretty healthy and normal.
But then comes: “I’ll never find another one. I’m a failure. My life is over.”
See the difference?
Letting go isn’t about suppressing the emotion. It’s about releasing the meaning you’re piling onto it.
This is why journaling works.
Not as homework, but as a way to interrogate your own stories. You ask: “What does this actually mean to me? What story am I telling myself? Is that story even true?”
If you want my exact method for this, the one that’s helped thousands of people rewrite their narratives, our program My Best Journal will help you a ton.
Because once you drill down and challenge the story at its root, the whole thing shifts.
That failed relationship wasn’t proof you’re broken, it showed you what you don’t want and your next one will be clearer.
That decade in the wrong career doesn’t mean you’re starting from scratch, it means you’re building off the experience you gained.
When you rewrite the story, the weight lifts. You move from fear and shame to acceptance. Then willingness. Then action.
We’ve got one more block. And this one’s the biggest.
Block 3: You think letting go is quitting
If you grew up hearing “winners never quit,” you probably see letting go as weakness.
You’re supposed to push through. Grit your teeth. Never give up.
But there’s a difference between quitting and releasing what’s weighing you down.
Here’s a short story that illustrates this perfectly:
A professor once started a lecture holding a glass of water.
He asked the class, “How heavy is this glass?”
His students shouted guesses:
“8 ounces!”
“10 ounces!”
He smiled and responded:
“It doesn’t matter. The weight doesn’t change. What matters is how long I hold it. If I hold it for a minute, no problem. An hour, and my arm aches. A day, and I’m paralyzed.
The longer I hold on, the heavier it feels.”
Letting go isn’t quitting. It’s setting the glass down so you can move again.
So ask yourself:
What am I holding onto that’s actually holding me back?
What story do I need to release?
And am I ready?
If not, that’s okay. You’ll get there when you get there.
But when you do let go, you’ll realize something: the weight you’ve been carrying wasn’t protecting you.
It was just making everything harder.
Life Log
NO CAFFEINE
10 days in! 100 days caffeine-free challenge has been sitting in my journal as a “maybe someday” for five years, and I’m finally doing it. I’m vlogging the whole thing and hoping to turn it into a killer video.
What’s surprised me most? It’s been… easier than expected. Everyone makes quitting caffeine sound like hell, especially for someone like me coming off 700-1000mg a day for 15+ years. And yes, the first three days were brutal with headaches. But they’re manageable. You’re not gonna die. People say the 21-day mark is when life starts feeling amazing. Curious to see where this goes.
WHAT I’M READING
Read it in college and it hit hard. Listening to the audiobook on evening walks, and am hooked. It’s a novel about staying true to your vision even when everyone thinks you’re crazy. About not compromising your work for approval. Extremely relevant if you like what we talk about on the channel. Even more relevant if you’re a creative or an entrepreneur.
See you next saturday,
CK
