This is an intuitive idea that I've used for a while, but don't know how to explain formally.
Suppose $(A,\prec)$ is some linear ordering, and each initial segment of $A$ has cardinality strictly smaller than $\kappa$ for some cardinal $\kappa$. Then $|A|\leq\kappa$.
This makes sense, since you can just take bigger and bigger initial segments whose cardinalities "approach" $\kappa$. But more formally, why is $|A|\leq\kappa$?
The statement is true. Suppose $(A,\lt)$ is a linear ordering and every proper initial segment of $A$ has size less than a cardinal $\kappa$. Then it follows that $|A|\leq\kappa$.
To see this, notice first that we may assume $A$ is infinite. Let $\gamma$ be the smallest cardinal such that there is a cofinal subset $B\subset A$ of order type $\gamma$. This is called the cofinality of the order $(A,\lt)$, and it follows that $\gamma$ is a regular cardinal. Note that $\gamma\leq\kappa$, since if $\gamma\gt\kappa$, then $\gamma$ would have a $\kappa^{\rm th}$ element, and so $A$ would have an initial segment with at least $\kappa$ many predecessors, contrary to assumption. Now simply observe that $A$ is the union of $\gamma$ many sets, each of size less than $\kappa$, namely, the predecessors of the elements of $B$. It follows that $A$ has size at most $\kappa^2=\kappa$, as desired.