Lesson 2; The Philosophy of Freelancing

If you want to be a freelancer you have to think like one. The philosophy of freelancing is like this; you’re Humphrey Bogart (or Katharine Hepburn) pulling the African Queen through the mosquito-infested swamps and you have no idea how far or close you are from that open water that will free your ship and career. So each day you step back into the water, risking the parasites, hoping the next assignment will be your big break.

The key is to take advantage of your opportunities if and when they come. All you can do is increase the chances that one of these opportunities will knock on your door. The only way to do that is to network. Cultivate relationships. Join associations. Meet, date and sleep with as many people who can advance your career as possible. Be bi-sexual. Return calls. In other words, be open-minded and get involved.

For writers a good place to start is becoming a member of MediaBistro.com. Lessons, jobs, parties and much more. Illustrators can find similar at their local Graphic Artists Guild. Illustrators could also send postcards. Companies like Steve Langerman can help create mailing lists to suit your needs. (Enclosed is my last card. Pick an image which can be interpreted many different ways. This was about financial inertia…and once for aggressive portfolio investing…and later used for exploring import banking. I could use it for retirement plans in a pinch.)


And finally, for humorists and cartoonists, enrolling at Harvard and working on the Lampoon is the best way to get your foot in the door. Alternative, less painful, ways will be discussed in future posts.

Next Week – Lesson 3; Lying to Clients

Lesson 1

Enough about me. Let’s get to work. Beginner illustrators pick up your electronic pens, this is your first lesson.

1. Time is money. Exhibit A is an example of my style years ago. Stupid.


2006 © Bob Eckstein

2. Today my style is efficient and time saving. Notice that I render everyone’s face with a black dot. Pure and simple.



2006 © Bob Eckstein

3. Here I add emotion by making my protagonist pushing something. Whatever issue you are illustrating just have the figure push it, preferably left to right. Notice I don’t even have time to change the background colors.

That’s a lot for one day. More tomorrow.

What, Me Worry?

Everything in the world is right again. My publisher and editor, who I am pretty damn lucky to have, liked my suggestion of taking the parts they wanted cut and keeping them in. I’m happy with this solution. The size of the book, my editor has shared with me, will be changed from the cigarette box dimensions talked about at last week’s meeting to something like an adult reading size book the type buyers gravitate towards. But of course, that’s their decision. I’m behind them 100% whichever way we decide to market this book. Sounds like we’re a well-oiled book machine here. I kind of knew all this would work out and in the end we’d be on the same page. When you work in this business as long as I have, you have to exercise patience and understand it’s a process. My friends said tonight at dinner it looked like I lost a lot of weight and that I looked like hell. It felt good to eat again.

This morning I did my TV spot. I was sweating like Ernest Borgnine. It airs tomorrow in Pennsylvania (Channel 16 WNEP 6pm News) and soon on YouTube. A lot of people will see it – I won’t be one of them. If I see how stupid I look and sound I'll never agree to be on TV again.

The host Mike Stevens was a really nice guy and I have to make sure to send him a nice thank you. Here’s a picture of the full TV crew unloading all the cameras and equipment in my driveway.

I Feel Your Pain

Today a Florida judge ordered that cartoonist Jose Varela be held for mental exams being arrested for holding the Miami Herald newsroom hostage for three hours with a knife and fake machine gun. The disgruntled freelancer draws cartoons for the paper and demanded to meet with the head editor. As Chris Rock once joked, I don’t approve…but I understand.

And psychological tests for cartoonists is always a sound idea, anyway.

When we last left MY dilemma, my publisher was crushing my lifelong hopes and dreams. It’s Monday and I’ve received dozens of e-mails of support and advise regarding my predicament. This group also includes the principles in the story, who assure me everyone wants me to produce a book I’m happy with…as long as I’m happy producing a gift book in their vision. Everyone will be discussing this further later today. Meanwhile, time to clean up around here. Tomorrow morning a TV show is interviewing me in my house about my non-existent book and the enormous antique snowman collection I've amassed. Below is a small part of this display. I’m torn about to what to serve the crew. I’m thinking deli meats.

Illustrating My Favorite Team's Woes

Here’s the final. My parents told me they bought an extra copy for me when I see them. But no time to gloat. By tomorrow I have to come up with ideas for a group of financial stories and charts running in Money Adviser magazine and I have already exhausted all the metaphors to illustrate retirement saving or online shopping in the past couple of years. My motivation is the challenge to come up with something new each issue – I’m not getting paid for the execution of the illustration but for the ideas. The pay is little. It'll take four of these financial illustrations to make the same as I did drawing a crack on Eli Manning's helmet for the Times.

Meanwhile I need an idea for my TimeOut cartoon by late tomorrow. I just started working on it this morning while lying in bed finding the initiative to make an overdue bathroom stop. Something to do with Christmas…The Illustrated Guide to Christmas Ornaments…Christmas Ornaments for Atheists…I probably can’t come up with enough symbols of atheists…OK, Christmas Ornaments for Atheists and Racists, and I’ll do a Michael Richards ornament...not enough… Christmas Ornaments for Atheists, Racists & Dentists…OK, Christmas displays in department stores…ugh.

In a Curry

Walking through Columbus Circle I’m hitting anyone within a four foot circumference with either a Keihl’s bag or Restoration Hardware, starboard. I have done all my Christmas shopping in one of these two stores. I hope everyone likes moisturizers and hand-cranked flashlights.

I have been thinking about eating at the Whole Foods café all day and I reach under the sneeze guard and scoop up Indian rice and curried chicken when I hear bird calls. It’s my cell. The Times has a job but they need me to drop everything and send them sketches about the NY Giants falling apart by 9 pm. It’s already 6 pm. Only doctors and other freelancers at the Whole Foods café could possibly understand my predictament. But I have no choice–the Times are my highest paying client and I get a job from them, if I’m lucky, only once every two months. The holidays are the busiest time for illustrators because editors and art directors are scrambling to fill space in these usually half-baked issues. The publications expect the freelancers to work over the holidays and have a finish waiting the morning their return from their extended weekend.

In this case there's only one day before deadline. The job is a half page color illustration for a story not written yet. All they can tell me is that it’s about quarterback Eli Manning having problems. They have one suggestion for me; Humpty Dumpty except make the egg a Giant helmet. I tell them I’d happily do the job (and that I’m a big Giant, which is true) but not crazy about their Humpty Dumpty idea and promise to come up with something Op-Eddy. While straddling the bags on the A-train, I bounce ideas in my head starting with the football helmet as a prop. A trick to use when nothing great pops ups is to take two elements needed in the piece and distort the relationship between them. From this I have, considering the time crunch, an acceptable idea.


Once in my apartment I sketch two variations of this idea using a Wacom pad on my iMac. I have two monitors hooked up so that the palettes of Painter take up only one screen leaving me a clean slate in front of me. I e-mail the sketch by 8 pm with a note that I’ll pursue other ideas but first let me hear if this would work. Within an hour the art director e-mails back he’s happy and instructs me to proceed. By 10 pm I send a final. It’s only 240 dpi because it’s for a newspaper. I suck out all the Cyan, Magenta and Yellow from the black lines so it reproduces crisp (I wish someone would have shared this secret with me years ago). The next morning he replies he's good and we’re done. Only then does he mention money. I accept his offer and thank him for the job. The contract is e-mailed and I e-mail the invoice. From start to finish the whole process has been paperless.

Panic Mode

I look everywhere for my agent's cell phone number. Her office machine is telling me she will be out during the Thanksgiving holiday. I'm OK, we can wait until she returns. OK, under control, I found her cell number.

She's driving to Massachusetts with her boyfriend to have Thanksgiving with her family. I apolognize for the three frantic e-mails waiting for her when she returns and explain we can talk about this Monday...if she's already well on the road and it's too late to meet.

I start e-mailing my manuscript to family and friends who didn't even know I was writing a book asking anyone for advise. I relive the fateful meeting a dozen times. I analyze if should I return the first installment of the advance. Or do I start giving ultimatums to the editor and publisher? Do I suck it up and make a gift book, the best darn gift–book ever overlooked by the literary community?

I drive to my sister-in-laws where someone drops the turkey and spills oil starting a grease fire in the oven. This temporarily cheers me up.

The Beginning of the End

Today’s meeting with my publisher could not have gone worse. A total disaster. The meeting was set-up to hear what my new editor thought of my final manuscript and to meet the production department. I went into the meeting light on my feet–confident and smiling. 90 minutes later I felt like I was exiting a boxing ring, punch drunk with bad news. The last time I had such a drop in my stomach was twenty years ago when I was walking out of the Smithaven Mall out in Long Island right after being dumped the first time I was in love.

Like that fateful day at A & S department store, I was blindsided. Ideas of creating the perfect “gift-book” filled the conference room. And once I heard the book dimensions were to be 5” x 7” it pushed me over the edge–I don’t remember much said after that. The edits on the book included cutting 8,000 out of the 38,000 I turned in. At the time, I was thinking that’s almost half the book! What happened? She was such a sweet, innocent–looking editor. Why did I do to make her hate me so? The last time we meet I remember we had this great lunch.

I had spent five years writing and researching this book on snowmen and practically bankrupted myself. The others in the room were not in on the scam. I didn’t know I needed them. In 2001 I had enough of pleasing art directors, sending cold pitches to magazines, sketching a dozen cartoons for every one that passed snuff. The plan was to write books. Disappear for months at a time and find an agent and editor who are too busy to edit me heavily. The first book I started, a comedy about 18th century Arctic exploration, I quickly realized would not open any doors for me. That would have to be my second (or third) book. No, that first book would have to sell. Make my mark and then write books that nobody wants to read. So I walked into Barnes & Noble and imagined looking for a book I wanted to buy. It happened to be the holidays and all I saw at the front tables were cookbooks and spiritual crap. What about a holiday book for Jews? Atheists? I’m Catholic but even I’m sick to death of Santa Claus, which come to think of it, has nothing to do with Jesus. Then it hits me; The History of the Snowman. Since that moment I started quitting my regular gigs I took for granted and started buying snowmen from yard sales. Earlier this year I traveled through Europe to meet with historians who were gathering whatever information they could find for me about the first snowmen man made. The project has since cost me, easily, $50,000, about $6,000 on eBay alone.

This was to be my breakout laundry truck leaving the prison, me stowed away under a pile of smelly underwear clinging to the hopes of a book about snowmen. The moment when that art director suggested marketing my book for placement at the registers, (killing any chance of the book being reviewed, garnering respect, or triggering other book deals) that laundry truck pulled into another prison. My plan, I see now, was flawed.