I got an email tonight with a great question and I thought I’d share my thoughts / gather some feedback.

Here’s the question:

One problem that I have always had  that after I design a website or Silverlight application I tend to start second guessing what I have produced.  Next thing you know I start tweaking a little bit here and a little bit there and in the end it ends up totally different when maybe it was fine to begin with.  It's almost as if it's not good enough and I am over critical. Do you have that problem?  If so, how do you deal with it or how do you recommend I deal with it?

Here’s my response:

That’s a great question. I’m certainly no stranger to overdesigning something that was good to begin with. On the other hand that refining process often makes things better not worse. So, I don’t have a perfect answer for  when to stop, but I do have some thoughts:

First, your instincts get better with time and you need to trust them. If you don’t have that “in the pocket” feeling about something, it’s probably good to keep exploring. You can always go back.

Second, it’s always a good idea to put some space between you and a design from time to time. I usually have two or three things “cooking” just so I get some perspective as I bounce between them. If you have the luxury of a time, taking a few days is great. Use that time to try to shift your thinking, find new inspiration, etc. When you go back, you’ll almost definitely see the design in a different light.

Third, backup as you go and keep a history of your iterations. Once you give yourself some space, go back and try to deconstruct your thinking. That will give you a chance to find the good among the bad. It will also help you understand yourself and refine your instinct.

Your response?

Wondering what other folks would say to this. Anybody have thoughts to share? How do you know when a design is good enough to stop?

Titilium

Very nice sans serif that works well for display. Comes in many weights. I’ve actually used this font a lot in WPF for display and had good luck with it. It’s a little square so it leaves the UI looking a little futuristic if you don’t manage the weights properly.

Raleway

Light weight font. Very friendly (because of a big x-height for those who came to the design fundamentals workshop). Feels a little bit like an updated light futura. It’s may be too thin for display in WPF and SL because of the platforms tendency to thin out typefaces at render time.

Miso

Really beautiful functional looking font. Comes in three weights (light, regular and bold)

Medio

A classic Bodoni style font. Very clean lines, classic and elegant.

Ubunt-title

Nice modern looking rounded sans-serif. Very modern feel. Friendly. Presumably created for the Ubuntu linux distro. Released under GNU.

Serif Beta

Serif beta is a temporary name for this font which is theoretically still not finalized (thus the beta) but it’s a very cool multipurpose serif.

League Gothic

Perhaps my favorite open source font out there right now (and, incidentally) the font I used for my slides at MIX10. Very cool narrow gothic based on Alternate Gothic No.1, a typeface from the 1920’s.

Chunk Five

A very “chunky” slab serif that is perfect for headlines. This is the font I used for the “Best Albums of 2009” app that I posted a few months ago.

Junction

This is a really nice humanist sans serif that would work great as a display font. It’s got a really unique shape for the lowercase “n” and “u” that makes it fairly recognizable.

New Athena Unicode

Very unique sans serif. Would make a great headline or display. Released by the American Philological Society and has good Unicode support plus some interesting open type features.

All fantastic books. There are other great books, but for me these are the essentials.

1.       How to Think Like a Great Graphic Designer by Debbie Millman  //  Amazon
This is the book to read if you want to understand the ethos of designers and understand design culture. Perfect way to begin to feel like you’re in the club.

2.       The Elements of Graphic Design by Alexander White  //  Amazon
By far the most organized thinking about design composition that I’ve encountered.

3.        The Elements of Typographic Style by Robert Bringhurst  //  Amazon
Not such breezy reading as the other two, but a very structured approach to typography, something that is normally left mostly to intuition.

Wow, MIX is here. I leave early in the morning so trying to gather up some stuff today. Also cramming to get my talk put together--should be a good one. Right now I have too much to say. That's a nice problem.

(download)

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getting-ready-for-mix-nxFyCmnqxdeppHDaiwpp.zip (3.29 MB)