"If you want advice about how to get better at this, I'd say sit down at lunch and redesign the system. Do this like every day for a week (or month, or until yo

"If you want advice about how to get better at this, I'd say sit down at lunch and redesign the system. Do this like every day for a week (or month, or until you stop leaving work hating the state of things). Then, go talk to the business folks and really learn how the business functions. Then, figure out where your designs failed to meet these requirements, and use that as a guide for how to evolve things." Spot on. And to add to this you should also try to implement parts of your better designs outside of work. This will help you gain a concrete understanding of the trade offs in your design. Secondly, when you get requirement changes or feature additions at work, try and apply (even if just on pen and paper) those changes to your architected versions. Often this will give you an aha moment where you realise your favourite alternative has serious flaws.