Celebrating the 20 anniversary of Optics Express, this paper reviews the evolution of optical fiber communication systems, and through a look at the previous 20 years attempts to extrapolate fiber-optic technology needs and potential solution paths over the coming 20 years. Well aware that 20-year extrapolations are inherently associated with great uncertainties, we still hope that taking a significantly longer-term view than most texts in this field will provide the reader with a broader perspective and will encourage the much needed out-of-the-box thinking to solve the very significant technology scaling problems ahead of us. Focusing on the optical transport and switching layer, we cover aspects of large-scale spatial multiplexing, massive opto-electronic arrays and holistic optics-electronics-DSP integration, as well as optical node architectures for switching and multiplexing of spatial and spectral superchannels.