Bird by Bird: Some Instructions on Writing and Life by Anne Lamott

Though this is a guide intended for writers, I found this full of lessons that are applicable to my work as a designer.

You write a shitty first draft of it and you sound it out, and you leave in those lines that ring true and take out the rest. I wish there were an easier, softer way, a shortcut, but this is the nature of most good writing: that you find out things as you go along. Then you go back and rewrite.

I love her notion of a "shitty first draft". The first draft of anything - a book, a site design, an illustration - will 100% of the time be crap, and it's always reassuring to know that everyone deals with this. Get through the first draft, and it will improve and become clear each time you learn more and iterate.

If your character suddenly pulls a half-eaten carrot out of her pocket, let her. Later you can ask yourself if this rings true. Train yourself to hear that small inner voice. Most people's intuitions are drowned out by folk sayings. We have a moment of real feeling or insight, and then we come up with a folk saying that captures the insight in a kind of wash. The intuition may be real and ripe, fresh with possibilities, but the folk saying is guaranteed to be a cliche, stale, and self-contained.

I see the design-equivalent of this as taking inspiration from what is there vs. blindly following trends. Trends followed just for the sake of being the "cool thing to do" right now will feel inauthentic to your customers, and will become dated shortly after you launch (and maybe even before, and then, well, good luck getting out of that hole).

I am suggesting that there may be someone out in the world...who will read your finished drafts and give you an honest critique, let you know what does and doesn't work, give you some suggestions on things you might take out or things on which you need to elaborate, ways in which to make your piece stronger.

It's really never too early to get feedback on your work - the earlier you get it, the stronger your work will become. Even seek out those from outside the design field. They will bring a new perspective and will be able to point out flaws. Even if they can't necessarily articulate the reasoning in design terms - you can put it in design terms later and use that to dig into the root of why the design may or may not be working.