My Mistress of the Night: Moonlighting

I would highly recommend starting out your soon-to-be smashing success of a business on-the-side as I did.  Have yourself a mistress from your full-time job (but just from work, not, like, a real mistress, don't be trashy). Moonlight, work weekends, use any free time you have, even if it's an hour a day, to do your side work.

Many people have asked me how I was able to go from the 9-5 to life as an entrepreneur. Well, first step. I learned how to spell e-n-t-r-e-p-r-e-n-e-u-r. Check! Then, I figured out what I was willing to live with and live without when it comes to lifestyle choices. What is the minimum amount of money you can live on to cover your bills, eat, save a little and enjoy life. Figure out the lowest possible number and then strive to get a few small regular clients/contracts to reach that number. Once you have that in place and can feel comfortable that you can actually sleep at night without stressing, then I say take the plunge. Then, everything else you make on top of that, will be extra. *When figuring out this number, MAKE SURE you account for taxes you will have to pay quarterly. Be sure to over-estimate, so again, anything you over-estimate will have been sitting in a savings account earning a tiny amount of interest.* A great resource to figure out how much you need to live on is at Tim Ferriss's blog. Tim Ferriss is the author of 4-Hour Workweek and 4-Hour Body, two fantastic reads that will get you thinking differently! Check out his monthly expense calculator that will help you figure out exactly how much money you need to live on per day. Breaking it down to the day level makes branching out on your own much less daunting.

So how to find these contracts? Reach out to former employers, volunteer with a charitable organization for a small amount of hours at a discounted rate, ultimately: find a need and fill it.  Check Craigslist.org in your area. There are gems hiding in the gigs section for most large metro areas.  For my first contract, I had been moonlighting on a freelance basis for many months on the side of my full-time job. The work kept coming along and was challenging and fulfilling. After months of demonstrating my commitment, I simply asked if they would be interested in signing a contract to guarantee hours for both their benefit and for mine. Never underestimate the power of asking, no matter how crazy it may seem! And, even if the answer is no, at least you know you tried and know the definitive answer. Better than wondering, in my opinion.

While you are searching for opportunities, make sure you create a starter website, and starter "brand" to have a place to refer potential clients. I say starter because as soon as you are ready to take the full-on plunge, you no doubt will want to re-brand (as I currently am). But, if you work on it carefully and work something out that you like, or can live with for a year or two, perfect!

I'd say, the most important things to have in place are:

1.) Savings (3-6 months)
2.) All necessary equipment (software, hardware, etc) to do the job you want to do
3.) At least one guaranteed contract of work: enough to cover a basic, reasonable cost of living and taxes
4.) A company name, website and if you are able to ahead of time: a logo, business cards and all social media accounts
5.) A running to do list of what needs to be accomplished quickly once you jump in
6.) Professional affiliations paid for and up-to-date, as well as a few networking events on the calendar

Those are the basics. Could you do more? Absolutely. But, sometimes, it becomes too difficult to work full-time, freelance and actually live with the limited amount of hours every week. While in this stage, though, here is a great resource from Jennifer Blanchard of Procrastinating Writers Blog: the un-schedule.

So, all in all, make sure you make the time to transition. Depending on your current situation, even six months of set-up time will get you into a great position to make your business your full-time endeavor.

The Start to my Empire has not been with a Bang, but a Sniffle.

Marie Killen/Getty Images

On February 16, 2011 at 6:15pm EST, I drove away from my place of full-time employment blasting Whitesnake's "Here I Go Again." Shall I remind you of the lyrics? No problem.

Here I go again on my own
Going down the only road I've ever known
Like a drifter I was born to walk alone
And I've made up my mind
I ain't wastin' no more time
[Insert 80's Hair Band Scream]



That's right. Because as of February 17th, I officially embarked on beginning my own business and being my own boss. It was certainly a magical moment. Sometimes it feels like it happened fast, other times when I really reflect on the process, I realize that close to a year of moonlighting, prepping, researching, planning, strategizing and work-filled weekends went into this grand moment. And that made it all the more special. As much as I wanted to jump right in immediately, I instead did the pre-planning that will sustain me for longer, and lead to a more successful endeavor.

While I did a good deal of planning, there is still a lot to do. I knew it was time to fully immerse myself in my business when I legitimately was running out of time in the week. I did a lot of work on the weekends for larger projects and a bit of work most mornings and some evenings. And that, was just for one client. To actually focus on myself, I just didn't have the time to work on everything in the way I wanted.

I was all ready to take the weekend off and jump right into taking care of business when, despite all of my enthusiasm and eagerness to check-off items on my to-do list, I was hit with the flu. The kind of flu where you wake up and open your eyes, but then after 15 minutes of keeping your eyes open, you fall back to sleep because you are so exhausted from blinking.

So alas, my business has not started with a bang, but a sniffle. But at least I've taken care of item one on my list: signing up for my own personally- sponsored health insurance. Sweet irony.

Next up on the list? Creating an LLC and an accounting department of one.

I just want to work out of a coffee shop for f#%ks sake!

Courtesy of Scott Feldstein

Ok, the crazy is back. Full force. And it's all because I really want to work on my laptop at a coffee shop while listening to moody, melodic folk singers. Is that seriously too much to ask?

I was already dreaming of this and then my mom went ahead and gave me a Starbuck's gift card and that's only fueling my desire. It's like she gave me a few free days of office rent. Yes, I count coffee costs as rent because you have to pay for a coffee in order to use the WiFi and a table. Okay, maybe you don't technically have to, but it's pretty cheap and trashy if you sit there all day, no coffee, with a laptop/fax/copier/scanner/printer set-up whilst screaming BUY, BUY, SELL, SELL on your...cell. Please note that the only thing I know about the stock market is that my Uncle Bob (everybody has one) works in trading and that my boyfriend once explained futures to me and despite that conversation and my 347,862 questions, he's still speaking to me.

To top it all off, I'm in the middle of reading The Four-Hour Work Week by Timothy Ferriss and it's like that time I walked by the homeless man in New York and caught myself walking slower and slower because I really liked what he was saying about enjoying life. I almost wanted to yell out in support, but I got a little closer and saw the crazy in his eyes, not my type of crazy, the scary other type where it's possible I'd be skinned and worn as a pretty Christmas jacket. No, but, I really like what this Timothy guy has to say. I suppose I'll finish reading before I go all gangbusters into my four-hour work week that as of right now would leave me in a precarious situation of being fired, broke and preaching on the streets about enjoying life. Wait a second...shit.

So, Perfection is...Ugly?

Marilyn sure had it right when she said, "Imperfection is beauty, madness is genius and it's better to be absolutely ridiculous than absolutely boring."

Oh, who am I kidding? I still can't help but strive for the perfection part. I give myself some room for mistakes and refrain from sticking bamboo shoots under my fingernails when I skip a workout (every day for three weeks) or drink one too many at the bar (read: take those sucker restaurateurs for all their worth at happy hour), but typically I expect a lot of myself. So much so that it is often hard to keep up with my personal demands. Demand a lot equals deliver a lot...until I can only go so long until I crash and enter into the dreaded tub-of-cookie-dough-eating, less-than-enthusiastic, Do I have to shower again? sloth phase. It's quite a cycle.

Back in the day, I always tried my hardest and almost always met my expectations. I rarely ever failed as a young Kate and that screwed me big time for when I entered my 20's and started effin' things up left and right. Looking back, I also see I started risking more, hence more opportunities for failure, but at the time, it was beyond confusing to not get it right all the time. I developed my cycle of perfection madness back then and it always ended the same way: the inevitable health crash. I'd work to the brink of my ability, burn myself out, struggle to pull myself back to calm and once I was "safe," I'd get physically ill. Whether a sore throat, fever, migraine, or issues with "el estomago," I'd be a wreck. And when my health wasn't "perfect," it would stress me out even more. HELLO?! How did I not put this all together? Too busy charting out the path to world domination before the age of 25, I suppose. Thankfully I missed that deadline and am starting to mellow the f#@k out.

So where did this all come from? Recently, I read a great article, The Dark Side of Perfectionism Revealed, courtesy of a tweet from @stevepavlina, that made me take a deeper look into my perfection obsession. A look, that combined with other recent epiphanies, might just help me kick the habit away for good.  Bottom line: extreme perfectionism is just not good for your health. Cue the heavenly light and singing of angels. Setting such high goals on a continual basis leaves so many opportunities for life to get in the way of plans, as it so often does, and ruin your perfect record. Funny how in my attempt to get everything right, I just so happened to ignore such a basic, easy, simple, no-I'm-serious-you-didn't-get-that? truth.

There's no doubt I'll still strive for the best - it's part of what makes me, me. But something else that makes me, me is an ability to laugh at those perfectly imperfect moments.

And you know what? I love to laugh.

Unlocking my Identity.

No, seriously. I need to go to the DMV and all my goddamn "important papers" are locked in my big-girl responsible-adult safe to protect them from water, fire and thieves who are too lazy to run away with a 20 pound metal-ish, slightly awkward box. To which I say, F#CK you nature/life cycles/Mother Earth/karma/insert higher power here for making me deal with my current identity crisis in such a literal way.

I woke up this morning, after nearly an hour of searching last night, and first thing I did was grab a flashlight to look around my entire apartment for two small bronze keys on a ring. One, because it was way to early for actual bright light, and two, because I have looked every single possible spot at least twice and now needed to "check the corners." I don't know why I put that in quotes either.

As I walked around on my vision quest, I couldn't help but laugh at the absurdity of the timing. I'm at the height of my every seven to nine month cycle of extreme life questioning and yes, even, soul searching. Luckily for me, this time around it only involves my career and certain interpersonal relationships, or lack thereof, of the acquaintance/casual friend variety. Read: my inner Sally Field is screaming, "Do they like me? Does anybody really like me???" Thankfully this doesn't apply to my family, bf and close friends - they are very familiar with my brand of crazy and love me just the same. But, still, a girl, especially a TOUGH BIATCH, okay fine, big empathetic softy like me, has to wonder why my kindergarten friend-making skills are not up to par as of late.  All this going through my head. All because I lost a pair of keys.

I wish I could wrap this up by telling you I found the elusive Holy Grail and life truths revealed themselves, but I'm still keyless. With any luck, when I find those keys, a light will shine down, angels will sing and I'll find my way. Or maybe, I'll just be able to finally register my car and get my new license. And that would be pretty great too.

You are extraordinarily special. Just like everybody else.

Being the typical Gen Y’er filled to the brim with pop culture references and propensity for extreme multi-tasking, I learned early on that I could be anything, do anything and go anywhere in the world simply because, I was me. That’s right. Just because I was myself and offered the world my presence on a daily basis, I was taught I was special and that there was no one else in the world quite like me. Movie after movie. TV show after TV show. Fable after…you get it. It was like the burgeoning child entertainment industry banded together to make me feel so great so that I couldn’t look away from the next half-hour program, or resist playing a favorite VHS (in your face, BETA!) until the tape wore thin. This world of programming didn’t ignore that in life, problems happen. Sometimes they are small and sometimes they are big — sometimes so big they are worthy of a “very special” episode. But, no matter what, each problem was easily wrapped up in 30 minutes, a to-be-continued episode or within a three-act structure showing us the world was once again ours to storm and conquer.

Being the naive, innocent, idealist I was (and, yes, still am), I believed it. Yes, right up until my first real-world exciting opportunity in the form of the ever-coveted New York City television network production internship. It was thrilling. It was my first step in my soon-to-be wildly successful, fame-tinged, money-out-my-Laubotin heels career. During our orientation, I met scores of people. People just like…me. Dozens of young women and men going out there to claim their right to be anything, do anything and go anywhere. Yes, me and all of the unique, special people exactly like me. The numbers of career dopplegangers multiplied as I moved through college and into the real world. As time went on I realized getting that dream job was not going to be as easy as I thought. And then when I landed my dream job(s) over and over and over again they were not really the dreams I imagined. Damn it, childhood entertainment programs, this is not what you led me to believe. It's a rough day when you first realize your life may not be everything you planned.

This realization sent me into a bit of a rut. What's the point? What if I'm not good enough? I can't deal...oh shut up. I seriously couldn't believe what I was hearing. Yes, hearing. I talk to myself...roughly every three seconds. These negative thoughts crept in and once they get in they are annoying little f#cks to get out. Woe is me.

And that's when my crushing, heart-breaking lesson came in handy (that phrase sounds so perverse). But, seriously it did. I'm just like everybody else. Everyone gets moments of negativity. Everyone feels overwhelmed from time to time. Everyone struggles. And, everybody hurts...sometimes. R.E.M. in the house. I could either wallow in my self-pity and do nothing, or get a frackin' grip and make things happen. Yeah, your novel might take years to write. But, ready for another cliche in your face? Nothing worthwhile is ever easy. So keep on moving. Keep on working. Keep on keeping on. This is your life you are wasting by spending time...worrying about wasting your life.

And you know what else? Yes, everyone is special, even if there are many other wonderful people just like you. Now let's all hug and encourage each others dreams. Mister Rogers is smiling down upon us.

Imposter Syndrome

Be brave enough to admit who you really are.

I am a writer. Go ahead, say it out loud, it feels nice, if not a little uncertain.

I have been gearing up to start my writing career for over a year now. I’ve read hundreds of articles, started many idea journals and have spent countless hours in bookstores carefully inspecting every hardcover and paperback that assures to unlock the secret of writing success. All of this preparation and yet, this is my first official article since my decision to be a writer.

Why do I want to write? This is a question I have asked myself on many occasions when I’m frustrated over the fact that, well, I haven’t actually written a thing. For starters, I love paper. Stationary, buck slips, greeting cards, photo albums and of course, the most beautiful: a newly bound, crisp novel. When I walk into a bookstore I feel calm. I lose all sense of time and feel my typically tense shoulders relax and lower. I take deeper breaths when I’m surrounded by tall shelves and beautiful display tables of recently discounted paperbacks. I can’t get enough of the smell of freshly printed paper and cherish the moment when I find the right book for me. I’m often hesitant about diving in and creasing the perfect binding because, to me, a new book is beautiful and so full of possibility.

Clearly any career counselor would tell me that this passion for paper and reading would almost demand that I write for my profession. I’ve demanded it of myself as well, but something has always held me back. Now I have discovered that “something.” I am afraid of being an imposter. I hold works of writing up to the highest standard and treasure the art of a well-crafted piece of fiction, a beautifully told memoir or a non-fiction biography.

So, what if I don’t measure up?

During one of my feel-good writing escapades, I attended a three-hour seminar on how to write your first memoir with author, Sue Shapiro. I thought a little inspirational speech would propel me into the career of my dreams, and help me realize my potential. While sitting in the audience, I enjoyed the class so much and experienced such excitement over writing that I could barely keep my legs from shaking. I felt motivated, if not completely compelled to run to my laptop and start writing my story. That is, until the question and answer session of the evening.

“Hi, Sue. I’m such a fan! I’m currently working on my second memoir and wanted to ask you how you deal with the pressures ofalienating your friends and family through your writing?”

Wait. One. Second. I have to alienate my family and friends in order to write? My excitement turned to dread and a realization that I would never want to jeopardize any of my most trustworthy relationships. Why it didn’t occur to me at that time that this was the opinion of just one audience member? I do not know. Or do I? Of course, it was yet another excuse that held me back from my fear of being a person that perhaps I was not meant or destined to be in this world. I braced myself and listened to the rest of the questions and answers hearing multiple times about all of the accomplishments of the room full of writers in the audience. Could they tell? Could they sense that I was not really one of them?

As the session ended, the moderator encouraged us to purchase one of Sue’s books in the hallway for her to sign. Well, sure, why not? She was a pretty cool woman and I had a feeling I would like her writing based on her self-deprecating, yet oddly optimistic sense of humor; quite similar to mine, in fact.

I made my purchase, The Five Men Who Broke My Heart, and walked over to the crowded table where writers continued to praise themselves and their literary accomplishments. People, this woman is here to promote her writing, not to help the world discover yours. I was feeling a little bit better at this point; at least I wasn’t desperate…yet. I walked closer to Sue, admiring her more than ever. This woman was actually doing what she loves and lives for; all the while I was wasting 40 hours per week creating excel spreadsheets and tracking other co-workers creative endeavors at my media project coordinator “career.” I was next in line and was embarrassed to realize my hand had formed a sweat imprint on the first page of what had moments before been a pristine paperback.

Sue looked up and caught my eye. “Imposter. Imposter!” she yelled, if only in my mind. In actuality she looked at me genuinely in the eye and smiled. I smiled back, much more at ease until she asked the dreaded question, “So, are you a writer?”

I did the equivalent of a face plant with how I stumbled over my words. As I struggled with what to say, my mind wandered to the moment in A Christmas Story when Ralphie could barely tell Santa his need for his most desired present, the Red Ryder BB gun. Should I just shout out “football” to Sue and be on my way? Or would that leave me wanting to crawl my way back up the slide to say what I really meant? I want to be a writer and I plan to be a writer, but does that give me the right to say that I am?

So I did my best, “Well, I’m starting to write and I aspire to be a writer.”

“It’s the best thing I’ve ever done,” she told me with confidence and signed the inside cover with flair. Not too bad. Must have pulled it off okay, or maybe she was just used to dealing with whack jobs having existential meltdowns like me. She handed me my newly purchased book and I walked away. I opened it up to look at her signature and was surprised to see a little more.

“To Kate, A fellow writer. Good luck & good karma. –Sue”

While I’m sure this phrase has made its way into many books she has signed, looking back, it was just the boost I needed. I mean, if a real, live, professional writer couldn’t tell I was an imposter; maybe, just maybe, I wasn’t one after all.


Note: I wrote this article years ago, but felt it was appropriate to kick things off on this blog. I hope you enjoyed my first "official" piece as a writer.