If the place is one that’s open to creativity and its culture celebrates the novel, sending a “sardine that’s stuck in the mailroom” (of advertising agency lore) can delight and deliver. If it’s a place like so many others that values conformity above all else, it’s too risky.

Of course, you may find out the hard way how many employers proclaim they want self-starter/self-motivated types when they really don’t. Like one recruiter told me, “If I actually presented an innovator like the kind they say they’re after, he’d be canned in 6 months.”

If the company really wants you, they’ll forgive you about anything, from the unconventional to resume typos. If the company doesn’t, they’ll hold anything and everything against your candidacy.

Like another commenter, I also live in the Bay Area. Yet one thing I have never understood about Silicon Valley companies, new and old, is their obsession with resumes. Silicon Valley is supposed to be about creating the future, right? Why then do companies insist that if I want to join them, I have to introduce myself by saying “Here’s what I’ve done for others”?

You speak of transitions. That’s another problem with resumes. Perhaps I don’t want to do any more what I’ve been doing. I do want to change careers. However, resumes sentence you to only what you have done. (Heaven forbid you write anything less than tombstone chronological, which will cause red flags galore in the mind of some employers.)

I have personally decided to stop accepting and stop sending resumes to companies. Robert Scoble says he doesn’t. When I’m in my hiring manager role the last thing I want to talk about is “what have you done for others?” Instead, what I offer candidates is the chance to address “What can you do for me?”

Instead of writing resumes, submit business plans like entrepreneurs do. They’re all about the future! (And any employer who doesn’t want to talk to you about your future together gets screened out.)

I like to see leadership type of statements. It shows initiative, ambition and willingness to take on responsibility.

Well done

As you well know, the vast majority of resumes are parsed by machine, not by your skilled eyes.

If someone were to follow your advice and have a single page resume, they’d get ignored by most of the people searching resumes because those people use software that ranks you by the number of times keywords appear on your resume and NOTHING ELSE.

If you have C++ on your resume more than the inventor of C++, guess who gets the call first? It ain’t the inventor…

As a skilled professional, I don’t like the reality of this one bit. I’d go so far as to call it a real shame… but that’s how the world of resumes really works today and having a one-page resume is a good way to stay unemployed for a long time.