I wonder whether this series is calculable or not.
Attempt:
$S=1/8+1/88+1/888+....=\dfrac18\displaystyle\sum_{k=0}^\infty\dfrac{1}{\sum_{n=0}^k10^n}$
where $$\displaystyle\sum_{n=0}^k10^n=\dfrac{10^{k+1}-1}{9}$$
then
$S=\dfrac98\displaystyle\sum_{k=0}^\infty\dfrac{1}{10^{k+1}-1}$
I have tried to calculate $\displaystyle\sum_{k=0}^K\dfrac{1}{10^{k+1}-1}$ for finite values but I failed.
What methods can we try?
$$\displaystyle\sum_{k=0}^K\dfrac{1}{10^{k+1}-1}=-1-K+\frac{\psi _{10}^{(0)}(K+2)-\psi _{10}^{(0)}(1)}{\log (10)}$$ where appears the generalized PolyGamma function.
It is not surprising that you have problems with it.
Edit
If $K \to \infty$, the limit is $$S=-\frac{9 }{16 \log (10)}\left(2 \psi _{10}^{(0)}(1)+\log \left(\frac{81}{10}\right)\right)\approx 0.13761477385452509205$$