Recently I was hit by the great tech layoff wave of 2023 and have been looking for my next adventure. As part of that, I’ve been working on a new portfolio.

This process reminded me of some advice I gave my former direct reports while I was head of design at Amperity:

You should feel good if you look at your old work and hate it.

A lot of designers told me they felt bad when they were looking at yesteryear’s projects. But my reply is, chin up, that is fantastic news. It’s a signal that the designer you are today has grown from the designer you were, and today-you can handily critique the work of yesterday-you. Regrets are just the lampposts to light our path forward, revel in them and celebrate that you’re now smarter than you used to be, more experienced than you used to be, and have more tools in your tool belt than the old you.

Instead of focusing on pain and embarrassment, celebrate the fact that you can now see mistakes or opportunities you once could not!

On the flip side, if you look at your work from a few years back and have no feedback for your former self, that might be a time to introspect a bit and ask if you’ve stopped deepening and widening your skillset.

The great news is, I have a lot of hate for my old work.