1) Grammar is dynamic. Rules are to be broken.
Good grammar is debatable, because language is mutable. Language is living and ever changing and who are you to decide when something is an error and when something has changed too fast for you to keep up with it.
If you had any sense of history, you'd spend more time listening to rap music and reading tweeners' texts to see where language is going. And if you're not careful, about where you put your energy, good grammar will derail your career.
2) Typos make us human
Spelling is not a sign of intelligence, and spelling is not an indicator of how good a job you do. It's just an indicator of how careful a speller you are. Spelling is overrated by people who are good at it. Most of the time it doesn't matter.
Take your rÃ©sumÃ©. Do you know what you'd need to do to send a resume without a typo? Pay three people to read it. Because here's what happens: you read your resume ten thousand times, and somewhere around the 50th reading, you are not reading words, you are memorizing them. So you won't catch typos. And if you're smart, you'll hire someone to help you write your resume, and that person is now the writer, not the copyeditor, so that person will miss typos, too. And you know what? Who cares? Because you don't want to work for anyone who thinks it's a good use of our time to have typo-free resumes. It's overrated.
3) Perfect writing is the result of demented, perfectionist thinking.
Yes. Perfectionism is an illness. So I am hoping that this post has a typo or two. Because I don't feel the need to obsess over minutiae before I tell people my ideas. Ideas are for debating. It doesn't matter if they're perfect since they can change.
If you find yourself terrified that someone will judge you because you made a grammatical error or a typo, then you need to get a life. You need to value yourself for something other than being perfect because perfectionism is impossible. And there must be something you're valuable for that you can really have, right?
4) Focus on shipping
Seth Godin has a great chapter in his book, Linchpin, about how it's important to ship. You can think and plan and scheme and strategize, but if you don't ship, nothing else matters. If you don't ship, you haven't done anything.
If you spend so much of your writing time worrying that the form is not perfect, then you won't ever write. You won't finish stuff. You'll always be working. But if you don't ship, you're not a writer - or a thinker. You're just a grammar maven. And even the grammar maven of all grammar mavens, the late William Safire, made fun of the Gotcha! Gang - the people who waited all week for him to make a mistake so they could tell him about it.
The New York Times has a great piece of commentary on the annoying people who pop up in social media as grammar vigilantes. If you had any doubts that you make yourself look like an idiot when you correct peoples' grammar, here's scathing commentary that should scare you into sending a few typos of your own.
(Disclaimer: The editor of Free Beer wants it understood that the views expressed in this post are Penelope's, not his.)