An easier proof, starting from jafe's idea:
Let $d(n)$ denote the number of letters used in writing down a number $n$. Let $S_0=\{4\}$, and recursively let $S_{n+1}$ be the set of natural numbers $k$ for which $d(k)\in S_n$. (Equivalently, $S_n$ is the set of numbers such that repeating the step $n$ times reaches $4$.)
Claim: $S_n$ is finite for all $n\geq 0$.
Proof (by induction over $n$): Obviously, $S_0$ is finite. Now, let $n>0$. By assumption, $S_{n-1}$ is finite, and thus has a maximal element $M$. Note that there are at most $26^k$ numbers with exactly $k$ letters, so there are at most $1+26+26^2+\cdots+26^k$ numbers using at most $k$ letters. For each $k\in S_n$, we have $d(k)\in S_{n-1}$ and thus $d(k)\leq M$, so in particular $S_n$ can't have more than $1+26+26^2+\cdots+26^M$ elements, and thus is finite.
Now assume there was an $x$ so that the series always terminates after at most $x$ steps: Then clearly $S_x=\mathbb{N}$, a contradiction.
In particular, this generalizes to every language where $d$ has only finitely many fixed points and loops.
If it can't be assumed from the question, a quick proof that $4$ is always reached*:
Let $n$ be a number with $k$ digits (so $k\leq \log_{10}(n)+1$). Split the string representation of $n$ at each point where a new digit (or "eleven"/"twelve"/"...teen") is "mentioned" (so "one thousand twelve-hundred and thirty-eight" becomes ["one thousand ","twelve-hundred and ","thirty-","eight"]). If $n$ is less than one centillion, then each element of the list will contain at most 32 letters ("three hundred quattuordecillion and"). Otherwise, the upper bound for each component will be $32+\log_{10^{303}}(n)=32+\log_{10}(n)/303$ (ten letters for "centillion" are needed for every factor $10^{303}$). There will at most be $k$ elements in the list.
So in total, $d(n)\leq (\log_{10}(n)+1)(32+\log_{10}(n)/303)$, which is less than $n$ for all $n$ larger than some constant $N$ (it can easily be seen that $N\leq 100$). In particular, repeatedly applying $d$ will always reach a number below $100$. The longest number below $100$ is seventy-seven with $12$ letters. It remains to check that $1,2,\ldots,12$ all reach $4$.
*The above proof doesn't require that, but if it isn't, the result is pretty meaningless - of course, if there was a number that never reaches 4, then there is no $x$ such that applying $d$ for $x$ times always reaches $4$