October 2026
Eventually, Everyone Wants Me To Stop Questioning
I keep noticing a point where advice asks me to stop questioning. Usually, it is the assumption I most want to examine.
I spend time talking through the advice I get.
Different conversations, but I keep noticing the same thing.
Eventually, everyone wants me to stop questioning something.
I can question the career. The business. The strategy. Sometimes even the conventional path.
But keep going and there is some assumption I am supposed to leave alone.
That is where I get stuck.
Because I don’t see why someone else’s success should decide where my questioning stops.
I don’t know whether I have always been like this, or whether AI has made it easier. I can take an assumption away and explore it without needing the person who gave me the advice to keep entertaining the question.
I can follow it further.
And quite often, I don’t agree with what it rests on.
A lot of it seems to be conditioning. Culture, school, religion, status, the things we absorb before we know we are absorbing anything.
I have plenty of that too.
But when I look at the life some of this advice points toward, I don’t always see much of what I actually want.
Aliveness. Joy. Creativity. Love. Abundance.
Sometimes the underlying assumption seems to be that a life organised around duty or sacrifice is inherently more meaningful than one organised around your own aliveness.
Maybe it is, for some people.
Maybe they genuinely choose it and love it.
I just don’t understand why that turns it into a universal answer.
‘You had a purpose greater than yourself.’
Okay.
But why does that end the questioning?
“The secret to living is giving.”
I don’t buy that shit.
There are assumptions inside that sentence. About the person giving. About why they are giving. About what happens to their own life in the process.
Calling it the secret doesn’t answer those questions.
It just makes asking them sound like a character flaw.
And that is the bit I keep running into.
The question stops being about whether the advice makes sense. It becomes about whether I am the sort of person who should be asking.
But I am the one who has to live the life it recommends.
So I want to know why.