The question of whether an electron radiating its energy away during the interaction with a laser can reach the region of highest intensity with energy high enough to make a number of different phenomena observable is one of the most studied and most important in strong field quantum electrodynamics. Here a simple analytical estimate for an average electron energy evolution is proposed and benchmarked against particle-in-cell simulations. Furthermore, these results are used to estimate the electron and laser pulse properties required to make vacuum Cherenkov emission observable.