While rumor has it there is a brain nestled somewhere behind them, one of the main things I provide those who hire me as a consultant is a new pair of eyeballs.
Same with editors. Same with interior designers. Same with coaches, shrinks, proofreaders (hoo boy, proofreaders!), trusted friends, non-trusted people who sit next to us on airplanes, stylists, headshot photographers, yoga teachers, bodyworkers, and feng shui consultants.
In fact, one of the exercises my favorite feng shui book in the world walks you through is Looking At Your Old Place with a New Pair of Eyeballs. (Not literally called that, but hey, I like literary symmetry and callbacks.) You're supposed to pretend you're a guest visiting your own home for the first time, or that you're you giving the nickel tour to a guest who's visiting your home for the first time, to see what you see. Because we humans are marvelous at adapting, which is useful when you find yourself in drastically reduced circumstances like a bison drought or post-war Vienna or seven stranded castaways here on Gilligan's Isle but is not so good when it comes to seeing your 47 years of accumulated crap, much less seeing what of it you can begin to release.
One reason I now realize I've been stuck so long in a particular place is that I was looking at it like Colleen of the Past, not Colleen of the Future or even Colleen of the Present.
Colleen of the Past likes things the way they are now, which is to say, the way things were then: this apartment, this circle of relationships, this job, this routine. Any changes are implemented slowly and are, for the most part, additive. Think closets that maybe get fuller instead of a wardrobe that occasionally gets thinned into usefulness. A thing is added and another thing, and everywhere-a-thing-thing, until yeah, you have a lot of clothes but you can't get at all of them and most of them look like whatever decade you turned 30 in. (I'm pretty sure that was a Marcia Wilke line: most people get new hairdos until they're 30, after which you can carbon-date them by it.) (I'm paraphrasing, of course.) (Oh, and to read up on Marcia, go to this page of marvelous writers and scroll in a downwardly direction.)
For me, some huge, usually uncomfortable thing has to come to bear before I will give a clear-eyed look to how useful a long-ago behavior or situation or what-have-you is suiting me today. Like a couple of leery-eyed misogynists from the Inland Empire checking out the rack or a shredded colon. And then I usually have to enlist outside help, a trusted friend, my shrink, a coach, to get a good, outside look at it. I've learned some tools that have helped me see some stuff in a new way. I harp on about Morning Pages (from Julia Cameron's The Artist's Way), but hey, they work. As do good shrinks and honest, longtime friends.
In a pinch, run your shit past that stranger on a plane. Provided you're non-threatening (no one's going to poke a bear 30,000 feet up), you might get some pretty eye-opening perspectives.
But look. Look look look. With fresh eyes and an open mind.
And, you know, a notepad or somesuch...