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Letting go by holding on
How I settle with the "Never enough" feeling
To be edited*
MOMMM I GOT A 97!!!
“That’s nice. What mistake did you make?”
“That’s such a silly mistake, you could have gotten a 100.”
“What did the top of the class get?”
…ouch mom…
Discontent sprouts from the discrepancy between expectations and reality. My parents have an ever rising bar of expectations for me.
Better grades, better job, better life. Do more, make more be More.
More, and more, and fucking more.
It never ends
Ironically enough, and although I struggle to acknowledge it, I do also ask more from them than what they provide.
More money for college, more acceptance of my life choices , more….
This pattern continues to the most important relationship too. My relationship with me. I never feel like I’m doing enough.
Whether it is a fact or not, it does feel very real and it is a recipe for misery. Always feeling like you’re falling short of something.
It feels like it’s just within reach but not quite reaching that goal. “If only I was just a little more disciplined, spent a little more time, pushed a little harder…”
And even when a set goal is reached, it feels like maybe the goal was not high enough and again meaning I didn’t do enough.
True story: On my last day of high school everyone was entangled in euphoria and nostalgia and whatnot. But there I was, with some oddly painted sadness on my face.
I again felt like I didn’t do enough. I didn’t study hard enough, I didn’t spend enough time with my friends, I didn’t create more opportunities for myself. More, more and more.
Oliver came in clutch with this one. Everyone say “Hi oliver”

Screenshot from the YouTube video
These are the words of Oliver Burkeman from THIS YouTube video.
The thing we don't realize about being finite humans is that our situation is actually much, much worse than we think it is and that this is tremendously good news.
We have this tendency to feel like mastering the situation of being a human in the 21st century is like a really difficult challenge. But I think actually when you turn your attention to things closely, you can see that it’s not really difficult to get on top of all your to dos. It’s actually completely impossible.
And in that transition from really difficult to completely impossible, there’s a moment of real kind of relief and relaxation. There’s a sense of a weight being lifted from one’s shoulder…
The zen master Houn Jiyu-Kennett - her philosophy of teaching students was not to lighten the burden of the student, but to make it so heavy that he or she would put it down.
Now this is just a start to the answer - you’ll have to stay with me for a minute to get to the bottom of this.
For some reason I don't just quite feel relieved by this. The logical path make sense. There are infinite things we can do as finite beings, True.
The bar for “enough” never quite seem to have a ceiling, also true.
Therefore no matter what, its never going to be enough so the only option is to let go of the burden
Let… let go…? what do you mean let go?
It’s not making much sense to me.
So like anyone, I went into a cave for 18 months in dead silence to figure out the answer.
Nah just kidding I asked an AI chat bot to do the thinking for me.
I asked Chat GPT to be my therapist and we had a pretty long chat. So I’m gonna spare you the details and instead break it down to the 4 unlocks in my process of letting go of the burden.
Logic ≠ Acceptance
Sure the logic make sense. it adds up. Thing is, our brains accept things faster than our hearts.
According to my therapist - there’s likely a part of me —maybe younger, maybe shaped by past experiences—that still holds onto the belief that if I just try hard enough, I can pull it off. That maybe you’re the exception.
But as we’ve seen the logical proof, it is impossible. Now I just have to sit down with this fact. Let’s see how we do that.
“What does “being enough” actually mean to me—on my terms, not someone else’s?”
That was a big unlock.
A- I never actually spent some time thinking what enough was for me. How could I know when Ive reached it if I never defined it?
B- uhm… “enough” doesn’t exist.
Going back to the last high school day thought - what if I spent more time studying and got the top grades, I would probably have had to give up some fun times with my friend and then I would be regretting that.
There is always going to be an opportunity cost to things
“No matter what I chose—studying harder or going out more—there would’ve been a regret. Because perfection is an illusion, and “enough” can’t be measured by doing everything. You’ve already experienced the emotional tax of chasing a horizon that keeps moving.”
Damn okay machine, touché. Let me try again with that definition of “enough”.
The “Enough” bar lowers in hindsight.
The ironic tragedy of life is that we live it forward but it only make sense looking at it backward. It makes it hard to be compassionate now.
The leaky “enough” bucket rarely feel filled in the short term. “I could have done more”
However when I look back at those moments, for instance the high school experience, I reflect back with a great deal of contentment happiness thinking “Yeah I did mostly good, Maybe it was not perfect but it was enough. “
,Looking back at how my parents raised me, was it perfect? Far from it. but with the benefit of hindsight I know that they did the best they could with the cards they were dealt with.
Okay feels like we are getting somewhere now. Finally.
I do feel like things are enough in hindsight. So I can manage to feel like ive done enough but with the caveat that I only do so about the past?
How do I make an un-miserable present then?
How to apply that in a helpful way in the present.
I’m just gonna let my therapist cook with this one
Let’s try an experiment—what if instead of trying to feel like you’re enough right now (which is hard because that muscle is underdeveloped), we practice acting as if you already trust that you’ll feel that way later?
💡 In other words:
“Even if I don't feel like this is enough right now, I trust that Future Me will look back and know I was doing my best. I’ll let him do the judging. Right now, I’ll just live.”
Let your future self be your witness—not your present-day judge.
You don’t need to fully believe in your present enough-ness. You just need to make peace with the idea that it will probably make sense later. That's already something.
Future me will look back thinking this is enough so present me can catch its breath, pat himself on the back and say it’s okay.
So.. that’s it… that’s the answer?
I have to trust my future self. Trust that he will look back at this moment in time and said yup you tried and you did enough.
How’s that different from “the burden is so heavy I have to put it down”?
Well that will have to do with the use of the amygdala vs the pre frontal cortex to reach your emotions rather than the logical part of your brain… is what I imagine someone who has a PHD in neuro science would tell you, but me, I have no fucking idea.
However if I had to guess: The first option is about letting go; mean it’s out of my hands with no control from me.
Second one is just me trusting me that I will be okay with me. Me having control serves me better than letting go.
My way of letting go of the burden is to hold onto the ever reinforcing belief that my future self will be the judge of present me.
Yeah stoicism bla bla bla by giving away control you achieve freedom bla bla.
I will actually have to spend 18months in a cave to settle with this one.
Not there just yet. But I trust my future self will.