I'm always told that the geometry behind going from $\mathcal{O}$ to $\mathcal{O}(1)$ is like going from the cylinder to the Mobius strip. $\mathcal{O}$ here is the structure sheaf on $\mathbb{P}^1=\text{Proj} \mathbb{C}[x,y]$, and $\mathcal{O}(1)$ is obtained from it by the standard twisting construction.
However, I can see how the Mobius strip is obtained from the cylinder by cutting it open and gluing it back together with a twist. However, I have no idea how to take the trivial line bundle (as a "geometric object") on the sphere (Let's think about $\mathbb{P}^1$ as the Riemann sphere), cut it open, and twist it? Has someone ever attempted to make some sort of visualisation of how this would work?
For the record, here is is an expansion of my comment and a summary of the answers to the question I linked to.
First, let's see how $\mathbb{P}^2 \setminus \{x\}$ is a line bundle on $\mathbb{P}^1$. For concreteness, give $\mathbb{P}^2$ coordinates and take $x = [0:0:1]$. The $\mathbb{P}^2 \setminus \{x\} \to \mathbb{P}^1$ is a line bundle, where the fiber above $[z_0,z_1] \in \mathbb{P}^1$ is the line $\{[z_0:z_1:\lambda] : \lambda \in \mathbb{A}^1\}$.
To see that this line bundle is $\mathcal{O}(1)$, consider the global section $$[z_0:z_1] \mapsto [z_0:z_1:z_0].$$ It has exactly one zero at $[0:1]$, so the degree of this bundle is $1$, hence it is $\mathcal{O}(1)$.
A more geometric way to describe this is as follows. Remove a point $x$ from $\mathbb{P}^2$ and consider a line $L \subset \mathbb{P}^2$ disjoint from $x$. Then projection away from the point $x$ onto $L$ is a map $\mathbb{P}^2 \setminus \{x\} \to L \cong \mathbb{P}^1$ which realizes the line bundle $\mathcal{O}(1)$.