At a recent talk at work, the speaker off-handedly mentioned something that stuck with me:
If I don't look back at my work a year from now and think it was crap, then I should probably be in management.
This guy is currently an individual contributor (IC) but had spent enough time as an engineering manager that this comment was not entirely tongue-in-cheek. The idea is that ICs should be improving themselves sufficiently to question previous work. In my conversations with other ICs, I have found this to be almost universally true. The more ambitious the person, the more crap things look in hindsight!
I first noticed this almost exactly a year after starting full-time work. From slides to presentation style to spreadsheets, I cringed at almost everything I had put out. One year later and that still held true. Whether it's in the approach taken or simply the speed of execution, the glances in the rearview mirror continue to be ugly. Progress is a funny thing.
Now in some ways this might seem obvious. Absolute improvement in a given domain probably follows an S-curve and if you're working across different domains, you're almost guaranteed to be in the exponential section of at least one of those S-curves. Despite knowing that in the abstract, it's hard to feel detached from your current work right now. Even if I hope to look back and pick apart all the ways in which my work was crap, I would be absolutely devastated to have someone else say that to me at this moment. Our egos cannot take the criticism in the same way until we've achieved some distance from work and become more confident in who we are.
That said, thinking about this in the abstract helps feel at least a little bit better about critical feedback for my current work. And if that stops being true then hopefully you're reading the musings of your future boss.