This is a great conversation, and I think I'll write about it some day, maybe in my newsletter.

I think too often we conflate the final outcome (the thing we shipped) with our competency as designers, but that's inherently tricky. You're never designing in a perfect world, so you almost never ship the perfect thing. Usually there are compromises due to technical hurdles, new information from research, lack of resources, politics, etc.

The nice thing is that every company has these issues, so as long as you frame and communicate them properly, they'll understand, and maybe even be impressed with how you dealt with certain issues. For instance, pivoting and shipping Team Accounts v1, a mediocre product at best, which was just the best thing I could ship at the team, is the thing that impressed GitHub the most during my interview.

It feels better when something we've made is actually out there, especially when it's close to the form you wanted it to take, as if that validates the work we put in. But we're only human and all we can do is our best within a set of circumstances. So the advice I'd give is make the portfolio about the process. Be candid about the issues, and show me how you dealt with them. Because if I hire you, there are going to be issues you'll have to deal with too. I want people who make the best of whichever situation they're dropped in. Showing evidence of that can be way more powerful than just showing me that dope thing you shipped.