Looking back at twenty–odd years involvement in LaTeX development and maintenance the author highlights the (in his opinion) most important milestones and pitfalls. - What are significant events that came at the right moment? - Which important events came at the wrong moment? - What were the biggest failures and why? From this data the article attempts to draw conclusions as to how the future of LaTeX could be shaped in a way beneficial to everybody involved and what needs to happen to make this possible.