Michael Shaw has a love/hate relationship with drawing.

On the one hand, Shaw, an advertising copywriter by day and cartoonist by night, has a permanent callus on his left index finger from more than 40 years of habitual doodling.

On the other hand, he really just doesn't enjoy it that much.

Yet, Shaw, now 52, just can't stop churning out cartoons.

"I guess I like the fine line between self-amuse and self-abuse," he says.

Fortunately for Shaw, flagellation sells. To date, Shaw has sold dozens and dozens of cartoons to publications around the country and around the world, including more than 100 to America's No. 1 destination for magazine cartoonists: The New Yorker.

Shaw started cartooning at 10 years old, inventing characters and making comic books with his twin brother, Patrick. One of his early creations was a take on the Fantastic Four – "The Tranquil Four," says Shaw. "Four guys who didn't like to do anything. I only made a few cartoons with them," he adds.

Cartoons have been something of an obsession for Shaw ever since. He published cartoons in his high school newspaper. He had a regular strip in his college paper. He made his first sale to a Greek magazine, The Athenian, in the early '80s while he was teaching English in Athens. After Greece, Shaw taught in St. Louis and sold cartoons to a magazine there.

"I was selling to local magazines wherever I was living," he says.

It goes on. He later went to the University of Missouri for his Master's in Journalism, where he wrote his thesis on – what else? – cartoons. Shaw was even able to use his cartoon skills to sell himself into a job as a catalog copywriter in Cincinnati.

"The hiring manager was into it," Shaw says. "The cartoon shadow is never far away."

But The New Yorker was always the top prize. Shaw had submitted cartoons to the magazine in the '90s, but never took it very seriously. But in 2000, Shaw set his sights on The New Yorker – nothing else would do.

He began submitting 10 cartoons every single week. After six months, he received a large packet back.

"I thought it was my 'Welcome to The New Yorker' kit," he says. Instead, he found every cartoon he had submitted to them with a note that he should include his own return postage.

Not discouraged, he kept sending in his cartoons. A year later, Shaw entered 25 of his cartoons in a contest for the historic Algonquin Hotel. One of his cartoons was selected as a winner: a drawing of a closed hotel room door with a sign on the knob that said, "Already Disturbed."

Again, Shaw thought, "I've made it! This is it!" Shaw won a trip to New York, a stay at the Algonquin Hotel and a celebration of New Yorker cartoons at the Algonquin's equally historic Oak Room featuring noted cartoonists including Roz Chast and Bob Mankoff, cartoon editor of The New Yorker.

But his winning cartoon was never published, and his dream of being in The New Yorker was as of yet unachieved. So he just kept at it with his 10 cartoons a week.

"My wife thought I was crazy," says Shaw.

But crazy paid off – after three years of steadily submitting cartoons to the magazine, The New Yorker purchased one: a drawing of an inmate in a jail cell reading a book titled, "Chicken Soup for the Criminally Insane."

Shaw's subsequent success with The New Yorker has little to do with his actual drawings; in fact, he's received comments back from the magazine such as "Draw better," and "This desk looks like it's made of cheese."

Mankoff has remarked on Shaw: "There are good, good cartoonists and there are good, bad cartoonists. Michael is a good, bad cartoonist."

Meaning that while Shaw can't draw, he's got the gag line down pat.

"The idea comes first, then the drawing," Shaw says. He quotes Mankoff: "It's not the ink. It's the think."

To that end, Shaw's drawings are very deadpan. He doesn't add big noses or bulging eyes. He doesn't want his cartoons to look funny – he wants them to be funny.

Take, for example, one he recently sold to The New Yorker: four people around a table in a restaurant, an older couple and a younger couple. The drawing itself shows very little. It's the caption that holds the joke: "My, this Cabernet pairs well with your parents and the four martinis I had at the bar."

Currently, Shaw is splitting his time between Milwaukee, where he works as a copywriter at Kohl's corporate headquarters, and Cincinnati, where his family lives – his wife, Jennifer, and children, Hannah, 16, and Liam, 12. "I'm living a bi-lifestyle," he says. "Only it's a bi-state lifestyle."

One would think that his weekly Milwaukee-to-Ohio-and-back commute would provide ample time for musing over ideas, but he says he does surprisingly little cartoon thinking on the road.

"It's hard to draw while driving," he says. "It's almost harder than texting."

Besides, Shaw's ideas don't come from trying to think of ideas. He lets inspiration come to him, and it comes from everywhere – from a coworker's off-hand comment, from something overheard in line at the coffee shop, from something he saw on the news.

"I steal a lot of ideas," he says.

He continues to submit 10 cartoons a week to The New Yorker – including, on occasion, a re-submission of his contest-winning "Already Disturbed" cartoon, which has yet to be published. He sells one cartoon a month on average, and though he is hesitant to reveal how much he is paid per cartoon, he does say that The New Yorker is the best-paying publication in the cartooning industry.

But it's not about the money, Shaw says. "When you consider the number of submissions, plus the amount of time spent coming up with ideas, plus drawing roughs, actually submitting, then creating finished cartoons, it comes to about $2.75 and hour."

There's no end in sight for this compulsive cartoonist; cartoons are just a part of his life.

"I like that cartoons are quick, easy and accessible," says Shaw. "You can present complex issues instantly. It's like a peanut for your brain. You eat it, you're done."

And the faster, the better, according to Shaw's cartooning credo: "Tragedy plus time equals comedy. But who has time anymore?"