Taking the Plunge

I totally feel you on the soul sucking office - the bleak beige cubicle make me want to run the other way, but here i am sitting in one, writing you! So here's my question how did you transition from the office to writing full time? Can you talk about how, when, and why you started your career? For me that transition is the most daunting part.

I totally understand: leaving the security of a regular salary and health insurance for a career in which there are no guarantees of success sounds inane. When put that way, why would anyone take the leap? Well, I don't have any better answer other than to say that I've found enormous satisfaction in what I do...but I also recognize that I'm tremendously lucky in the level of success that I've achieved. As I've mentioned before, for every writer in my position, there are plenty of those with similar talent (or whatever word you want to use to describe what I do) who just aren't as successful.

So...how did I get here? I'm not sure that my story will be entirely helpful to tell, but I'll tell it anyway. I never intended to be a full-time writer. There, I said it. Not that I wouldn't have LOVED to be a full-time writer - there's a difference - I just never imagined how someone actually made a living at it. I'd always written for high school and college papers, had teachers and professors encourage me to keep at it, etc, etc, etc, but for a living...it seemed too ridiculously hard. I mean, seriously? People paying you to write? Ha! As if. In fact, at one point during my senior year in college, a few people suggested that I should pursue it (back when we were brushing off our finest suits and interviewing for jobs that would eventually bore us all to tears), and to this day, I remember thinking, "What an esoteric and unfeasible dream."

So, what I did instead, was act. :) I'm not kidding! You know, because breaking into the acting world is sooooo much easier than breaking into the writing world. Hee. Actually, first, immediately after graduating from college, I worked in PR. Hated it. Hated every freakin' second of it. That was probably because I spent most of my time stuffing gift bags and calling editors to push products that I thought sucked ass, but still, I hated it. I'd always loved to act and done a lot of it all my life...so...I quit my job (insert heart attack from parents), and hit the boards of NYC. I temped to pay the bills (and, after my parents recovered from their disappointment - I mean, they wanted me to be a banker at Goldman Sachs, not a secretary at Goldman Sachs, they generously offered to be of some financial help), and I eventually found some success in theater and commercials (hello, SAG card!). I'd made my way to Los Angeles and was busy draining my brain out there, when a college friend called and asked for some help launching a website. Maybe I was just fried from the LA sunshine or maybe I just needed to reverse the mental atrophy that had set in, but either way, I packed my bags and moved back to New York to help found and run the site. (This was during the internet boom.)

I wrote all of the web copy and press releases/kits for the site, as well as many of the articles that we had in the on-line magazine, and we got a lot of coverage in numerous national magazines (Self, InStyle, People, etc), so as it happened, a lot of our partners on the site approached me to write their web copy and press releases. So when the site was sold, I'd already built up a list of clients...and never really considered returning to the 9-5 grind. From there, I was fortunate to be hired at Rubenstein PR - a huge PR firm here in NYC - as their lead consumer writer and celeb ghostwriter, but on a freelance basis. So I had a built-in salary from Rubenstein (they paid me for three full days of work per week), plus my outside clients. (And this time, all I was doing was writing, which was 1000000000 times better than my first PR job.)

Ok, so, at the same time, my then-boyfriend finally came to his senses and proposed. I took this opportunity to begin to pitch bridal magazines and sites. I knew that I didn't want to write web copy/press releases forever, so I fired off some story ideas based on what I was going through with my wedding planning. As luck - and I do mean luck - would have it, The Knot was looking for a writer with ghostwriting experience to pen their second book, The Knot Book of Wedding Flowers. They liked my style, so had me draft a few chapters, and then they hired me. To write a freakin' book! I almost died.

The pay was crap and the situation itself turned out to be less than ideal (for long and varied reasons), but with that credit under my belt, I was taken a lot more seriously at the national mags. I landed my first feature at Bride's almost immediately, and from there, worked my way up to where I am now.

See...I told you that my story wouldn't necessarily help because there wasn't an exact moment when I took the leap. However, I still think that there are a few things to be gleaned. 1) I wouldn't leave your day job unless you had a plan - both financial and career - for the future. 2) To this end, I'd attempt to gather a few clips (or clients) before telling your boss to kiss your ass. This ensures that you'll at least have a little work (and some clout when pitching new places) and you won't be sitting on your couch for the next nine months wondering what the hell you were smoking. 3) There's probably never an ideal time to take this type of leap. At a certain point, you just have to jump. 4) Certain personalities thrive in the freelance world; certain do not. I say this not condescendingly; I say it from experience. I belong to a large writers group, and inevitably, the writers - talented as they may be - who deal poorly with rejection, with the ebbs and flows of the marketplace, with self-motivation, and with personalizing business when it's just business, are miserable...and don't succeed. Think about who you are before you hand in your resignation. If rejection bothers you, this isn't the route for you. I can't emphasize that enough. You will get 100 "nos" (at least) for every "yes" you get. That's a lot of "nos"...and each one can eat away at your self-esteem if you allow it to. By the time you've gotten 20 "nos," you're wondering what on earth made you ever think that you'd be successful at this - and you still have a lot more "nos" to go before you hit a "yes." I'm not trying to be grim: I'm being honest. If this is you, there's no shame in it. Not at all. I'd just suggest finding a way to work your love of writing into other aspects of your life, rather than ditching a safer path for something that will likely make you miserable (and chip away at your confidence).

All of that said, I count my blessings every day. And if you're the type of gal (or guy) who lets those nos roll right off of her back and then keeps chugging away, by all means...come join me!

So...who else is thinking of taking the leap? And how did others get their starts?