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.

The Obligatory Apology Post

This is the blog post I never planned to write...

Today I was overwhelmed with inspiration to let the words flow and hit "publish" with a glorious grin on my face after what seemed like a little, teensy hiatus, if you will. And then, I signed into my account and realized the horrific truth: my last blog post was over six months ago.

So now this is the part where I write the obligatory sorry-I-couldn't-write-I-was-backpacking-through-Europe-volunteering-at-food-banks-and-deworming-orphans-in Somolia post. Anyone get that Legally Blonde reference, or am I the only one who has watched that movie 94 times?

But the real truth is: I was a miserable mess. I admit, I have signed into my blog over the past 6 months. I even have several drafts just hanging out, but I could never finish them or hit the button to send them out into the world. And why is that? Because just about everything I started to write took a drastic turn to Negativeville, a land no one wants to visit, and will certainly never hitch a ride to willingly.

Looking back, I must say I am thrilled with my ability to hold back on the posts and realize even though I really wanted to continue writing to show my committment, the fact that I was having trouble pulling myself out of the black hole of discontent was not going to help anyone, nor encourage return readers.

And, why you might ask was I a miserable mess? Well, the worst part is I feel like I don't have a full, legitimate reason for the unhappiness. Although I certainly did have very valid reasons, and I quite understand that most of them had to do with not feeling fulfilled in my career, the specific reasons are far too involved, convoluted, and just plain not worth it to get into here. Sounds so...dramatic and existential, huh?

But, now, I am fulfilled, over-the-asteroid-belt happy, challenged, motivated, ambitious, fun-loving, joyful and feel like I'm tap dancing on a rainbow after winning the lottery whilst surrounded by Labrador Retriever puppies in a pub in Ireland. In other words, I feel like myself again.

It all boils down to a comment I received on my last post all those six months ago...The post was entitled, the oh-so-high-browed title of "I just want to work out of a coffee shop for f#%ks sake!" One reader, and fellow writer, asked the simple question, "What are you waiting for? Go!"

After that, I put my head down and forged ahead to make my dreams a reality. Some days were harder than others, sometimes it seemed overwhelmingly daunting, but finally opportunity has met my preparation and the two became fast friends. I am proud to say that now I am officially on the path I have dreamed of often - running my own business and exploring the many facets of life that intrigue me - to finally, and fully, Live 1000 Lives.

For the first time in my life I can honestly say I am ready and willing to enjoy every step of the journey because the path I'm on now is the right one for me.

Cheers to you, Reader, and here's hoping you're liking the view on your path as well.

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.

My larger carbon footprint has prevented me from toppling over...

I love the environment and stuff, but yes, I fully admit I'm a bit lost when it comes to figuring out what is best and most helpful for our Mother Earth short of walking everywhere barefoot, living in the dark when it's actually dark and eating only what I grow. I'm sure a hardcore environmentalist just read that and fainted. But anyway, I digress. Typical.

So, I know about these carbon footprint things and mine was probably pretty decent for a while. I was a big public transportation girl, but now I've been gifted an amazing gift. My nana's car, an 11-year-old Mecury. I am now driving to work and I must say, this shining beacon of a car has saved me from my latest near fall into the pit of insanity. I don't quite know what a pit of insanity truly is, but I spend a lot of time crawling out of it.

So now that I'm a driver again, I started to think about what a different feeling I have every morning. When I was taking public transportation, I walked around with my shoulders up to my ears, my eyes darting left and right. I had a constant stream of anxious thoughts of the possible delays at every turn and even yelled at a German tourist over his "unattended bags." It actually turned into quite a pleasant encounter, so stop judging. Now in the morning, I spend a good part of my time laughing at talk radio, or singing along with new hits, or old favorites (at the top of my lungs, naturally). I really think this morning singing has lowered my blood pressure and allowed me to ease into my day in a much happier way. A way that has allowed me to calm my impulsivity and save myself from drastic life-altering decisions that I am oh-so-inclined to make.

So a big thank you to the Universe/Karma/Mother Earth (and Nana) for sending me this gift. I know not everyone has the opportunity to pick their commute poison. My next car serenade goes out to you and I promise I'll recycle.