Great Software Requires Continuous Transgression

[W]hen you are doing something in a recurring way to diminish risk or doing it in the same way as you have done it before, it is clear why professionalism is not enough. After all, what is required in our field, more than anything else, is continuous transgression.

Professionalism does not allow for that because transgression has to encompass the possibility of failure, and if you are professional, your instinct is not to fail, it is to repeat success. So professionalism as a lifetime aspiration is a limited goal.

— Milton Glaser, 2001, at a talk given in London

When you sit down to design a piece of software, your instinct is not to fail, it is to repeat success.

That’s why software everywhere is plagued by the disease of sameness.

All to-do apps act the same. All calendar apps act the same. All email clients act the same — nearly identical to the first serious command-line apps from over 20 years before. Outlook and Elm don’t look that different.

Sidebars. Playlists. Table views. Folders. Threads.

Select lists which hide options instead of bulleted lists which lay them out, or live search/autocomplete fields which let the typing, keyboard-savvy user keep typing and savvying.

These are things we use without thinking, in many many places where they are inappropriate.

We need continuous transgression.