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.

Jen’s Zens: Jen on What Life Is

“Life is being tagged in things you don’t want to be tagged in.” – Jen

Jen’s Zens: Jen speaks on the ambiguity of emotions

“I’m, like, tired.”

Thumbnail image for Life Lesson: Give Up the “Shoulds”

Life Lesson: Give Up the “Shoulds”

I’ve been in therapy for two years and some change. I went to therapy because I was sick of giving myself grief — grief over not being successful enough, not blogging enough, not exercising enough. The list went on and on. I am, and always have been a perfectionist, you see. A favorite bit of […]

Jen’s Zens: Jen on trusting intuition

“You are the only one who knows when beer o’clock is.” – Jen Heller

Jen’s Zens: Jen on Living in the Now

“If you died tomorrow, wouldn’t you want to have a good beer today?” – the ever wise Jen

Jen’s Zens: Jen Speaks on Universal Suffering

“No one likes being broken up with.”

Thumbnail image for Two Thoughts on Downton Abbey’s Season Three Premiere

Two Thoughts on Downton Abbey’s Season Three Premiere

1. “Have you swallowed a dictionary??” I laughed out loud. And then again. I paused the show, and said to Will…”Isn’t that hilarious??” He didn’t think it was so funny. He knew the truth: Mrs. Patmore was using a phrase commonly used in Victorian England around the turn of the century. “Swallowing a ‘dic’”, or “swallowing […]

Thumbnail image for 5 Most Embarrassing Moments of 2012

5 Most Embarrassing Moments of 2012

5. Turning a Fun Social Reunion Totally Awkward It was the Sunday before Christmas. I was out shopping with Julia and doing what I do best: visiting local businesses, saying hello and giving them some money. I love supporting indie businesses! I particularly wanted to visit a colleague’s shop. I hadn’t seen her new shop […]

Latest From 12-year-old Jen

Seventh grade. No boyfriend. Regrettably. Daydreaming of Olympic stardom. Also regrettably.

More mortifying tales of pre-pubescent Jen

Latest Blah Blah Blog

There's more where these come from...

Stuff I love

  • Green Tree Recycled TP

    With 96 (!) rolls, these are a great value. And they come in a big box you could potentially use as a fort later!

    That hits the spot! →
  • John Hughes Movies

    Masterpieces of teenage comedy! We’ll pretend the Home Alone sequels didn’t happen.

    Me want this! →
  • Cat Carrier

    This is necessary whenever it comes to moving the Guster around town. He proceeds to soil it.

    I must have it →
  • Green Heritage Toilet Paper

    One of the softer eco-friendly options available. Buy bulk and have toilet paper forever!

    Yes, please... →
  • Veronica Mars

    This teen spends her free time solving mysteries!  

    Sign me up for this! →
  • Saved by the Bell

    Zack, Jessie, and Screech teach us what to expect from high school!

    Get Saved! →
  • 30 Rock

    The wacky antics of Liz Lemon and her crew

    Get rocked now! →
  • Pretty in Pink

    Great John Hughes movie, great 80s soundtrack

    Buy the movie or album! →
  • Green Forest 100% Recycled TP

    The highest post-consumer content of any recycled toilet paper! Also, it’s soft & absorbent.

    I'm ready to wipe green! →
  • The Babysitters Club

    The babysitters weren’t scared. They had a club.

    I want to go to there →
  • Days of Our Lives

    TV’s longest-running daytime soap! It will never be cancelled!

    Load up on Days stuff! →
  • My So-Called Life

    The tortured life of Angela Chase. Be still my heart.

    I want to go to there. →
  • Are You There God? It's Me, Margaret. by Judy Blume

    So raw.  So true.  So pubescent.

    Buy Now →
  • Singing Machine Karaoke Machine

    A high-tech karaoke machine for home use. It lets you see your performance!

    Don't hesitate -- buy it now! →
  • Husqvarna Chainsaws

    Husqvarna sets the standard for world-class chainsaw mayhem!

    Let 'er rip! →
  • Kick-Ass Websites & Blogs

    We make those over at Artsy Geek. It’s our specialty.

    Go on.... →
  • OXO Shower Caddy

    So great I just had to make a video about it.

    Buy Now → Learn Why I LOVE IT!
  • Heavy Silverware

    Feel the weight of the fork in your hand. None of that flimsy-ass Target shit.

    Here here! →
  • Tom Waits

    Sweet nothings and gruff ballads I could listen to all day. Not to mention that sex appeal.  Mee–ow.

    Buy Now →
  • Dreamhost Web Hosting

    Worker owned cooperative…and they’re green.

    Register A Domain Name! →

Thank you for coming by. It’s good to see you.

  • This field is for validation purposes and should be left unchanged.