Bill Watterson on the Real World

Written by Sean Murphy. Posted in 4 Finding your Niche, Founder Story, skmurphy

Excerpts with commentary on Bill Watterson’s 1990 Kenyon College address: “Some Thoughts on the Real World By One Who Glimpsed it and Fled.”

Some Thoughts on the Real World
By One Who Glimpsed it and Fled

Bill Watterson addressed the graduating class of Kenyon College in May 1990. He was at the midpoint of his decade long career drawing Calvin and Hobbes. His talk was candid and reflected the fierce commitment to his art that caused him to forego millions–if not tens of millions–of dollars in licensing revenue and to step away from the strip five years later while it was still hugely popular.

There is a lot of food for thought here for entrepreneurs to consider the real purpose and mission of their business. Who are you serving and why.

The quality and frequency of your thoughts determine your livelihood

“My job is essentially to come up with 365 ideas a year.

If you ever want to find out just how uninteresting you really are, get a job where the quality and frequency of your thoughts determine your livelihood. I’ve found that the only way I can keep writing every day, year after year, is to let my mind wander into new territories. To do that, I’ve had to cultivate a kind of mental playfulness.

We’re not really taught how to recreate constructively. We need to do more than find diversions; we need to restore and expand ourselves. Our idea of relaxing is all too often to plop down in front of the television set and let its pandering idiocy liquefy our brains.

Shutting off the thought process is not rejuvenating; the mind is like a car battery–it recharges by running.”

Bill Watterson in his May 20, 1990 graduation address at Kenyon College

When I read this passage I realized I had not considered drawing cartoon to be knowledge work, but clearly it is. Entrepreneur is clearly another calling that requires creative problem solving ability on a daily basis. Cultivating your mental playfulness to enhance your creativity is a key insight entrepreneurs must act on. If you are watching television to “re-charge” you are making a serious mistake.

Its a magical world...let's go exploring

Letting your mind play is the best way to solve problems

“Letting your mind play is the best way to solve problems.

For me, it’s been liberating to put myself in the mind of a fictitious six year-old each day, and rediscover my own curiosity. I’ve been amazed at how one ideas leads to others if I allow my mind to play and wander.  […]

A playful mind is inquisitive, and learning is fun. If you indulge your natural curiosity and retain a sense of fun in new experience, I think you’ll find it functions as a sort of shock absorber for the bumpy road ahead.”

Bill Watterson in his May 20, 1990 graduation address at Kenyon College

Looking at most challenges as an adventure and summoning your curious inner six-year-old are two perspectives worth cultivating. Curiosity does not get enough credit as a valuable trait for entrepreneurs.

Watching my career explode on the launchpad caused some soul searching

“When I was sitting where you are, I was one of the lucky few who had a cushy job waiting for me. I’d drawn political cartoons for the Collegian for four years, and the Cincinnati Post had hired me as an editorial cartoonist. […]

As it turned out, my editor instantly regretted his decision to hire me. By the end of the summer, I’d been given notice; by the beginning of winter, I was in an unemployment line; and by the end of my first year away from Kenyon, I was broke and living with my parents again. You can imagine how upset my dad was when he learned that Kenyon doesn’t give refunds.

Watching my career explode on the launchpad caused some soul searching.”

Bill Watterson in his May 20, 1990 graduation address at Kenyon College

Watching your first startup explode on the launchpad is painful, as is watching your second and third startups explode during take-off or low orbit. All are valuable real world crises to learn from. Even a  startup that launched well will see you operating beyond your founding assumptions within four to seven years. I think the key is smaller and more frequent explosions that are well constrained–“safe to fail” or “small bets”–as well as a deep understanding of your moral compass and long term goals.

It’s worth recognizing that there is no such thing as an overnight success

“I tell you all this because it’s worth recognizing that there is no such thing as an overnight success. You will do well to cultivate the resources in yourself that bring you happiness outside of success or failure. The truth is, most of us discover where we are headed when we arrive. At that time, we turn around and say, yes, this is obviously where I was going all along. It’s a good idea to try to enjoy the scenery on the detours, because you’ll probably take a few.”
Bill Watterson in his May 20, 1990 graduation address at Kenyon College

Most of the time the opportunity for “overnight success” is sold by folks who are interested in making a profit on your dreams without actually fulfilling them. I have to catch myself when I think that I am “one more step” away from success: I am on a lifetime journey toward excellence.

I found that what I was chasing wasn’t what I caught

“I still haven’t drawn the strip as long as it took me to get the job. To endure five years of rejection to get a job requires either a faith in oneself that borders on delusion, or a love of the work. I loved the work.

Drawing comic strips for five years without pay drove home the point that the fun of cartooning wasn’t in the money; it was in the work. This turned out to be an important realization when my break finally came.

Like many people, I found that what I was chasing wasn’t what I caught. I’ve wanted to be a cartoonist since I was old enough to read cartoons, and I never really thought about cartoons as being a business.”
Bill Watterson in his May 20, 1990 graduation address at Kenyon College

Don’t take a job with a company that has very different values. Don’t do business with people who are shortsighted, greedy, or otherwise unpleasant. Don’t take investment  from people you don’t want to take input and direction from. If you cannot connect the dots between what you are doing and what you want to be doing, do something else that is in closer alignment. In the real world we all have to work for someone, for many people, pick managers and customers and business partners who respect your values.

An enviable career is one thing, being a happy person is another

“You will find your own ethical dilemmas in all parts of your lives, both personal and professional. We all have different desires and needs, but if we don’t discover what we want from ourselves and what we stand for, we will live passively and unfulfilled. Sooner or later, we are all asked to compromise ourselves and the things we care about. We define ourselves by our actions. With each decision, we tell ourselves and the world who we are. Think about what you want out of this life, and recognize that there are many kinds of success. But having an enviable career is one thing, and being a happy person is another.”
Bill Watterson in his May 20, 1990 graduation address at Kenyon College

The intelligent pursuit of happiness requires finding personal fulfillment in your work.

 “To pursue the happiness within our reach, we do best to pour ourselves into faith, family, community and meaningful work.”
Arthur C. Brooks “A Formula for Happiness

Creating a life that reflects your values
and satisfies your soul is a rare achievement

“Creating a life that reflects your values and satisfies your soul is a rare achievement. In a culture that relentlessly promotes avarice and excess as the good life, a person happy doing his own work is usually considered an eccentric, if not a subversive. Ambition is only understood if it’s to rise to the top of some imaginary ladder of success.

To invent your own life’s meaning is not easy, but it’s still allowed, and I think you’ll be happier for the trouble.”
Bill Watterson in his speech to Kenyon College graduates 1990

This reminds me of Thomas Szasz observation, “People often say that this or that person has not yet found himself. But the self is not something one finds, it is something one creates.” As with most design challenges, the key is removing self-imposed constraints on the solution that are not intrinsic to the problem and exploring the possibilities this now enables for you.

“Creative leaps are discontinuities, qualitative changes. They involve three steps: identification of self-imposed constraints (assumptions); removing them; exploring the consequences of their removal. That is why there is always an element of surprise when we are exposed to creative work–it always embodies the denial of something we have taken for granted, usually unconsciously.”
Russell Ackoff in “The Democratic Corporation” (page 99)

Zen Pencils’ Bill Watterson: A Cartoonist’s Advice is a one page on-line comic that explored this last excerpt.

Where to Find Watterson’s “Real World” Talk

Related Blog Posts

Note: Calvin and Hobbes is available on-line at The cartoon “Its a magical world…let’s go exploring.” is the final one published–so far. All of the books remain in print and are listed at

Trackback from your site.

Comments (6)

Leave a comment

Quick Links

Bootstrappers Breakfast Link Startup Stages Clients In the News Upcoming Events Office Hours Button Newsletter SignUp