Ask anyone: I'm a planner.
If you had access to my early college journals, you could see my sweeping plans for life, in college, and beyond. If you had access to The BF, he could bend your ear for hours about my planner genes (especially if you plied him with tasty craft beers).
If you flipped through the various notebooks I've kept for the past five or six years, you'd find myriad plans for all sorts of projects, from painting the living room to launching a business to writing a book. Sorry, books. And if you could periodically scour the recycling bins in my apartment building, you'd find the rest of the lists, scribbled and squirreled away on scraps of paper here and there before they were either transferred to electronic formats or just discarded outright. (You would also be arrested if someone caught you, and old Eileen across the courtyard has a hawk eye for that kind of creepy nonsense.)
The next step is to bring in a confidante of some sort, a friend, my shrink, or even a random stranger in a line or on a plane. I say it out loud, make it more real, and see what happens. And then finally, a few of the ideas I take into real-real life: I book a flight to interview for a job I'm not even sure I want in a city I've never been to and, while I'm there, look at houses I'd buy if I lived there. (Disclaimer: while the notion looked nutty on the outside, and definitely to The BF, I could absolutely see myself going through with it going into it, or I'd never waste the valuable time of my potential employer or the real estate agent. That's just shitty.)
Most of the things I try on are lower-stakes than an expensive (for me) exploratory trip halfway across the country. I've become a huge devotee of thrift store shopping specifically because it lets you literally try out different looks for very little money. There were definitely expenses involved with me trying out various career options: I've thrown out more business cards than most people will have in a lifetime and spent crazy amounts of otherwise-billable hours writing copy or designing websites for myself that had to be scrapped six months (or weeks) later. And I'll not speak of the insane amount of money I've poured down the drain of acting headshots except to say that it would have come in very, very handy for weathering the current financial storm.
What used to stop me from doing anything new was the enormity of everything new. I couldn't quit my glorified cubicle job (it was a corner office, but the work was as odious as any cube monkey's) because how do you go from a job that not only pays you now, pays into the future and covers your health care but also is the sole ferry for your identity? I couldn't move to another state because my significant other was tied to this one. I couldn't be a writer because what the hell had I ever written outside of a letter or a :30 ad or a 3-minute sketch that anyone wanted to look at, much less pay for?
From the other side of the valley, here's exactly how: you don't quit your job outright; you go part-time, then freelance for five years, using the old hand in to cover you while you reach the other hand out to save yourself.
You test-drive Indiana and the Pacific Northwest with pilot visits and an open mind.
You start a blog. For no money. That no one really reads, for a long, long time, which is good, because it's sort of weird and herky-jerky for a long, long time.
You try stuff on, and you walk around in it, and you see how it fits.
Make no mistake, it can be as terrifying to try stuff on as it can to make one, bold, crazy leap. After all, when you leap, there's not a lot of time to think about the many, many ways things could go south. Which, surprise!, they do.
I'd say that things being what they are, you might as well. Because life is nutty now. Because it'll be over sooner than you think.
I have two little tools that have helped me with trying stuff on over the past 10 or so years.
The first is to have a credo. Or a mission statement, or a verbalized philosophy, or whatever else you want to call it. Mine is "To be a joyful conduit of truth, beauty and love." I came up with it fairly spontaneously doing an exercise from a book whose title I have, alas, long since forgotten. There were also some five-year plans and 10-year plans and lifelong plans I created along with it; those lists are mainly novelty items now, plan detritus, if you will. But that mission statement/credo thingy keeps me on the straight and narrow.
The other thing is to be prolific. If you can make a lot of stuff, or try on a lot of stuff, it takes pressure off of having to have ONE THING that really works for you. Obviously, you need to strike a balance: if you do too much, you spread yourself thin, and that's no good for figuring out anything. Plus, it'll drive you nuts. But throwing yourself into the trying on, in whatever way you can, that is a very good thing.
I'm trying on a few things for size right now. They have to do with ways to live my life as well as ways to make a living. And yes, I realize that given the current state of the global economy, this is something of a luxury. I have been both fortunate and frugal, and have no one to support nor answer to save myself. I do not discount the enormous freedom these things have given me to explore options, and I realize that most people, especially most people living in North America who are within 10 years of my age (47.5, as of this writing), don't live in this luxurious triangle of choice.
While I know it can be hard to come by, changing room is essential to most of us on the path. Just a little bit of private, move-around space for trying stuff on. Maybe it's not luxurious; maybe there's an item limit. Maybe it's makeshift. Maybe it's even shared, like the godawful spaces at Loehmann's where we all have to sort of let it all hang out by ceding each other some pretend private space.
But hey, just changing alongside old Jewish ladies and middle-aged Persian ladies and young ladies who just fell off the Turnip Express from Topeka will sometimes score you nod of approval (or a quick head shake of the other), sometimes there's even a little comradely advice or encouragement to be had in the company of fellow travelers.
I don't know how you find your room. All I know is that the alternative, to live a life where you deny your heart even a sliver of space to dream and your mind the tiniest room to roam, is mighty bleak.
Maybe start small: five square feet. Five minutes per day. An extra thirty seconds on the john after you've done your business.
In my own wackadoo experience, a little bit of room begets more.
And makes everything a little bit better...