There was no worse fate as a kid than going to summer school. Worse than breaking your arm or being being sent to Siberia, which was a common expression back then along with the top two dangers being quicksand and eating watermelon pits. This new issue of The Bob is the summer school issue. I’ve been very lucky to have had some great mentors in my life. Some are friends, some were teachers. You know who you are and I want to thank you. (And I know some who told me to quit, are no longer with us or don’t subscribe.)
When I was in college, my creative writing course professor (who I see occasionally on my Facebook page) would, anonymously, read my short stories to the class. Reading my work at that time when I could not get my humor or cartoons into the college paper (and after striking out at my high school paper, as well) was tremendous validation and boost to my confidence. I don’t know if I would have continued without hearing the class laugh. Shortly after that class I was a regular contributor to New York Newsday, SPY magazine as well as a critic for a music publication, all while still being unable to break into The Prattler, Pratt Institute’s school paper.
I don’t want to name names and leave anyone out, but one I WILL name, because you can all benefit from him now, is Jacob Krueger. He changed the way I think and work, even influencing the way I teach, as his style is very captivating. His free Write Your Screenplay podcast explains principles that carry over into other disciplines that involve any storytelling. I highly recommend you listen to an episode and tell me what you think. I’m going to recommend for writers this recent one.
The next will discuss cartoons, and then humor writing. This one is on illustrating.
This is the last painting for my upcoming book on museums. I am going to share my thought process and the very start of the piece, focusing on a small detail––I can’t share the whole piece before it’s published but can tell you it has to do with the day comedian Bill Murray decided to end his life.
Based on the masterpiece The Song of the Lark, I found myself struggling with this piece from the start because I got hung up on being married to the reference. I had done a good job up until now of being as creative and loose as I thought I needed to be with the rest of the book but lost that momentum when I returned to the drawing board after an unexpected break. I had been exploring, successfully, how to reinterpret pieces in my own color scheme. I see this time and time again that extended breaks from working can result in a lack of confidence. Painting is all confidence. It’s decision making. Some days I know when something works or doesn’t and what decisions to make. When I’m working nonstop, my decision making is instinctive. The work has swagger. But most of the time, when I’m going from one genre to another, or I’m distracted which is often, I’m a hack. I tried everything to not let that happen with this book. After I finished the 180 illustrations, I placed them in order of success. The bottom portion of the list, I went back and redid.
Here’s the real painting, which is in The Art Institute of Chicago.
I start with rendering the farthest points, getting the sky even though I know I am way over saturated. That’s a bit of my style, to make it my own, pumping up the colors. But this piece is all about subtlety and mood, capturing the unique light of dawn. I really begin to appreciate how great this painting is when I see how far off my piece is (and got scared that this was going to be a complete failure. How could I possibly get that dark break of dawn with my style?). So now I’m arguing with myself how do I drastically change the piece and make it an homage instead of me aping it. And now I have no confidence and making bad decisions.
What if I executed the painting as a business woman on a train station. It’s a poetic premise that is flawed because my readership, for the most part, will not be familiar with the original and not see what I did.
I decide to then place the modern woman with a business bag, holding a cup of coffee in the museum observing the painting in the same pose. Like this mock-up I would have used for reference…
I return to a depressed state after deciding 1) this is too contrived, 2) I would be making this more about the museum goer and losing the focal point and 3) museums don’t let you drink coffee in the museum.
So how can I do this painting in my loose style and make it look good? I can’t. My usual palette kills the grace of the original. So I try to at least exaggerate the brush strokes (as seen below). I while pull out the punchy colors I usually use with reckless abandon and will have to just let the chips fall…I painted myself in a corner.
I am not trying to copy the few elements seen here (nor could I ever reach that level of painting) but do them in my own way, as I see them without it looking like a mistake. Left of the huts does not exist. I imagined the painting double the size in scope and made it a horizontal.
One can also argue that the original (above) is too drab for a book. I’m not doing paintings, I’m illustrating stories for a book––a different job description. This piece WILL get de-saturated when it gets converted from RGB to CMYK for printing prep so I do account for that.
There is always a lost of color during that process but the trade secret is use “assign profile” ADOBE RGB 1998 to retain vibrancy.
You can see I’m trying to get primitive in spots from the original and at the same time, as close as I can get to it. It has nothing to do with any illustration skills. It’s all confidence and decision making, which comes and goes for everyone.
Detail of the finish:
Ghosting has become an acceptable form of response now from clients. One has to email two or three times to get a response. If the person you are dealing with is in their thirties or younger, good luck. It’s just the way everyone handles business whether it be your mechanic or a boyfriend or girlfriend. I was interested in getting tennis lessons. I was once a very good player and I’d like to get my game back up to speed again. I found someone great who I took a few lessons from and was all excited by my progress. I emailed, txted (I intentionally dropped the e in attempt to sound younger) and left phone messages for a follow-up, but never heard from him again. I feel like a modern day break-up. Hopefully nothing bad happened. I have no idea. The same is true for a few jobs I’m working on. I’m totally in the dark. Got paid something up front but who knows. Years ago we had none of these new modes of communication and it was never this easy…and this seldom happened. Ol’ man Eckstein is now leaving the front porch.
Comment left for a podcast I appeared on:
“After listening to Molly’s podcast for a year, finally had to delete her podcast after her latest podcast with Bob Eckstein. Bobs new book says cats won’t answer when you call your cats name. This is SO false.”
You can meet me at the following upcoming events:
Writer’s Digest Conference (NYC) Aug. 17-20
Milford Readers & Writers Festival (Milford, PA) Sept. 22-24
Miami Book Fair (Miami) Nov. 12-19



Drumroll….this issue The Felix goes to Liana Finck.
This cartoon is actually ten years old but I just came across it again and it would work again if it appeared tomorrow. To see more of Liana’s work, books and events go to her website here. Her Substack newsletter is here.
I sell lots of fun T-shirts of my designs. The profit margin for both me and Tee Public is very small thanks to shipping costs. All the money goes to the US Postal Service. But it’s so much fun to have all these shirts available.
To order online at Bookshop, CLICK HERE.
And with that, this ends another issue of The Bob. I do appreciate anyone sharing the newsletter and helping me get the word out. And thank you for all the very nice feedback I’ve gotten from the newsletter so far, it’s greatly appreciated.
Dear Jules, thanks for he kind words and taking the time the respond! More soon. I’m on the subway and distracted by dangerous pole dancers who are about to give me a foot sandwich. Best, Bob
Aren’t people just real busy re: ghosting?!