As André explains in his answer, your questions asks whether every linear order has countable cofinality. Let's consider a particular type of linear orders, namely cardinals. A cardinal is regular if its cofinality is equal to itself. André gave an example of an uncountable regular cardinal, namely $\omega_1$. The latter can be defined (depending on your axioms) as the minimal uncountable cardinal (the minimal one exists since the ordinals are well-ordered, and by Cantor's theorem $2^\omega$ is uncountable, so there are some uncountable ordinals).
Like any other ordinal, it consists of all ordinals smaller than it, all of which are countable. Because of the former property, a subset of $\omega_1$ (or any other ordinal) is cofinal if its union is $\omega_1$. Cantor's diagonal argument shows that the union of countably many countable sets is countable, hence $\omega_1$ has uncountable cofinality (and by minimality, it is regular).
Conversely, a cardinal like $\aleph_\omega$ is singular (not regular) since it is the union of $\aleph_0,\aleph_1,\aleph_2,\ldots$.
Unrelated, one may ask whether there is a scale for your partial order [thanks, ccc, for the correction]. This is a linearly-ordered cofinal set. We can assume (exercise) that any scale is well-ordered. Given a partial order $\alpha$, define its bounding number $\mathfrak{b}(\alpha)$ as the minimal cardinality of an unbounded set in $\alpha$, and its dominating number $\mathfrak{d}(\alpha)$ as the minimal cardinality of a cofinal set in $\alpha$. It's not hard to see (exercise) that $\mathfrak{b}(\alpha) \leq \mathfrak{d}(\alpha)$. Moreover, equality holds if there is a scale for $\alpha$ (but the converse is not necessarily true, see Asaf's comment).
ZFC is not enough to determine whether some simple and natural orders have scales, for example various orders on sequences. Usually, assuming CH an easy construction shows that there is a scale, whereas under Cohen's classical model there is none. The subject studying these properties is called cardinal characteristics of the continuum. For a highlight, check out Cichoń's diagram.