Six Years of Self-Employment

Today is the sixth anniversary of the day I left my full-time job.

I was 27. I had decided to leave my job one month earlier. I was then acting Development Director — the highest position in the fundraising and marketing branch of my small non-profit. I had worked there off and on since I was 19.

My coworkers were my family. I came to work everyday greeted by people I loved and who loved me (I think…). I worked with students with stars in their eyes; learned all about their hopes and dreams. Watching them party and study, party and study. There were good points. There were bad points.

I looked around my office that fateful day, and I realized… “I’m too comfortable.”

I was sooooooo comfortable. I loved what I did, and I was damn good at it. But I worked all the time. The work never ended. There was always going to be another giant project to sink my teeth into. I relished the work, but I also resented it. I gave too much too easily. I took it so seriously. It was my life.

My office featured a giant photo of me. It was perfect.

I took stock of my life that day. I realized that I was going to wake up and fifteen years would have gone by. By then I’d have a family. I’d be even more comfortable.

I started walking. My office was in North Berkeley. I walked through campus, and then down to Shattuck. I kept walking. I lived in North Oakland then (still do). I kept walking. Shattuck hit Telegraph. The sun set. It was Monday, March 30th, 2009.

I passed Lanesplitters. I went in. I had a slice of pizza with pesto, a side salad and a Racer 5. I was resolute.

My mom was the first person I called. “Mom, I’m leaving my job,” I said. “Oh, ok, honey.” She replied. “I’m not surprised.”

The next day I gave notice.

And then I was on my own. And the economy collapsed.

At the outset, I had $10,000 in a savings account and a lot of dreams. Let me enumerate them:


    I had recently painted the portrait of my BFF (best feline friend), the Guster. It looked slightly like a Van Gogh, so I bought I was convinced I would turn this into a good paying side gig.

  • Blogger, Vlogger and Internet Personality

    My main plan was this website. And I would promote products, build an audience and make a million dollars. I was sure I would make a million dollars. How could I not? I mean, if there’s one thing I am, it’s charming.

  • Tupperware

    For years I’d forced Tupperware products down the throats of my colleagues and friends. Now I would finally be able to branch out! If I was able to make, you know, $500/year selling Tupperware without trying — think of what I could do if I tried!

  • Silly Web Projects

    Even by March 30th, 2009, I had acquired a collection of domain names and plans for them. was to be a place for people to share stories of their hangovers*; a site where people can order shitty falafel sandwiches that would never arrive. I was on a mission to make the Internet a more hilarious place.

  • Consulting, Graphic Design & Web Design

    I sold my first website in 1996 and had sold them off and on ever since. I had expertise in non-profit marketing, communications and fundraising. No reason I couldn’t make some extra cash doing that, right?

Here’s what I actually did:

  • Watched Madmen

    Oooh…did I ever. I watched it all within two weeks. I stayed up till four watching it. I’d wake up and start again. It was awesome.

  • Shopped

    I am a good shopper. And I needed things. For my videos, I needed a green screen, the newest and greatest HD camera, a gorillapod, a tripod, and a selection of microphones. For Van Gogh My Pet, I needed letterpress cards and postcards (they ran about $0.50 each), more canvas, more paints. For Tupperware, I need more Tupperware! (DUH.) And I needed domain names. They were only $10! An affordable indulgence. And that was a great idea I just thought of. That’ll be sure to make a million dollars**.

    That $10,000 didn’t last that long.

  • Made a Giant Penguin

    Now, the whole let’s-spend-five-days-making-a-giant-penguin-thing wouldn’t have been such a waste of time if I didn’t actually have paying web work at the time that I was neglecting. But it sure was fun.

I did blog occasionally. I made a few silly videos that I was and am still proud of (especially Hanging with the Gus Man). And I did do some consulting, web and graphic design.

But most of all I incurred credit card debt, slept and dreamed.

Dreaming was my full-time job.

By mid-2010 I had maxed out my credit cards. I was freaking out. I knew I was destined to make a million dollars, but it wasn’t happening. What was I doing wrong??

I was lucky to have a life coach (Nicole of with whom I was trading web work for life coaching.

I think at a certain point even she was tired of listening to me dream and whine about not making enough money. I was laying on my couch when she said, crossly, “If you want to make money, I think you need to focus on your web work.”

“Really?” I was shocked. So much truth.

She was sure. That day my company, Artsy Geek was born.

Focus, Focus, Focus

It was the desperation of being completely out of money that made me finally focus my energy. I had no choice. I needed to survive.

And I had always been pretty good at making money. I’d had three part time jobs in high school. I hit the ground running. Gave classes to local business owners on social media. Networked, networked and networked.

Somehow I survived. I’m not sure how — the money didn’t instantly come in. At first there was a trickle.

I didn’t know what I was getting into. I didn’t know how hard it would be. I launched the company in November 2010, one and a half years after I left my full-time job.

Along the way I gave up all the other dreams on that list up there. I stopped blogging after realizing one day that I wanted to spend my free time outside away from the computer. I gave up art when my arm hurt too much after twelve or fourteen hour work days. I gave up any ideas that silly projects might one day make me some money. I gave up my dreams of making a million dollars. Even making a salary like I had at my job seemed so far away.

All I did was work. For years. And things started happening. I met Lindsay Gatz, our Creative Director, an amazing graphic designer and such a fabulous complement to my skills. That’s when things started really happening. We got a big office. We lost a big office. We got staff; lost staff. We acquired big clients and then lost some of them too.

There has been many a moment when I’ve reflected, “I surely must have learned all the hard lessons a business owner has to learn by now, right??”

I’ve learned that the answer to that will always be no.

There will always be more lessons.


Artsy Geek is now four and a half years old. She is a teenager, yearning to be an adult. She wants to grow up as fast as possible. She is already growing up so fast, but she wants to grow faster. I can’t keep up anymore. I have so much gratitude for the lessons, the long stress-filled nights and small victories.

I have dreams of what Artsy Geek will one day be. I have dreams of systems that allow my teammates to really succeed at their jobs. I dream of easy work days and peaceful nights knowing my clients are well taken care of.

I have finally matched the salary I had at my previous job. Every month I watch my credit card debt shrink as I aggressively pay for that year and a half of folly. I have gratitude for that too. I know that I wouldn’t be where I am — I wouldn’t be who I am — without it.

There are the weekends when I curse my fate as I work with developers to solve bugs in applications watching the sun shine and then set on a gorgeous Spring day. There are the mornings when I wish I could go back to those days where I had a steady paycheck and a family of coworkers to support me. There are the moments when my job is really, really hard. There have been a lot of those even in the past few weeks. And still I press on.

I wonder about why… why do I? How can I? How did I possibly make it this far and this long? I don’t know, honestly. But at this point, the business itself has more momentum than I could possibly stop. All I can do is dream of what I can make it into next. And enjoy the small things that come with running my own business and setting my own hours.

Every year I celebrate the day I left my full-time job. Today. I remember that long walk home. I remember the dreams of making a million dollars and the silly websites. And while I may laugh at my naiveté, I also celebrate the girl that saw so much possibility in her future. And I ask to please, please have more of that in my present.


* I did actually create, though it’s not up anymore. The part I neglected to consider? Hungover people do not blog.
** To be fair, I still have that addiction.

Whatchu think?

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