If your old work doesn't make you cringe, you're not growing.
I personally couldn't agree with this statement more. When I create / work on something new, I take a look back at my portfolio and see if there is anything that can be replaced with new content. However, there is something to be said about seeing your progression and allowing potential employers / clients see how you've grown.
But why a cringe and a negative reaction?
Sure, if you don't see issues in your old work, you're not growing.
But for me, it's less a cringe and more of a knowing smile. ;)
Love this piece by Jarrod Drysdale.
Our old work often embarrasses us. It feels ugly. I love his response:
We tend to fetishize our current work and pretend it’s so much better now. But the design you’re excited about right now is headed for the same landfill before long. And that’s a shame, because our Old Loves got us to where we are now. Our current projects are giving us the practice we need to become even better designers in the future.
Thanks for posting my article. I see this negative reaction so much amongst designers and couldn't help writing about it.
Sometimes, what I did 2 days ago can be shocking!
I feel embarassed for the work I did yesterday
The fact that your old work looks bad to you is proof you have grown.
So stop putting your past self down, and be proud of what you can do now because of all that hard work.
I think this is important — believing you can do something is vital to being able to do it.
Every. Fricking. Time. It´s a huge problem when you have to select work for your portfolio.
My solution to this was having a 'Blog' and 'Work' page on my site - Work is filled with projects I'm 'somewhat' proud of and Blog is filled with unsolicited projects I enjoyed working on due to inspirations on Dribbble and Behance. Surprisingly enough, my first real gig came from unsolicited work on my Blog page and Dribbble. This is why when I see 'anti-Dribbble' posts on DN I smile, since in my case, I had a different experience than most people.
If you don't, it means you're stagnating.
Yes but I have found this diminishes over time as my ability level gets closer to my taste level.
This is explained brilliantly in the classic interview with Ira Glass: https://www.youtube.com/watch?v=ieEQ21mCOJA
I look back at my old work and it seldom feels good when I put it against the standard I currently aim for but it needs to be tempered by some context that work I did 10 years ago (or a year ago, whatever timeline) was trying to solve a problem or hit a target at that time and that I'd have used whatever tools and techniques were available at the time.
It doesn't mean my old work is "bad" or I haven't improved in that time, it sometimes means the current criteria for measuring that is different.
Old me 10 years ago would shit a brick to see new, improved me pondering using a load of framework cruft to make a simple website.
Constantly! I 'm scared of my current work, because it make me feel bad in some time.