Lessons from The Retired Artist (The Adventures of Tom Sawyer)

Tom Sawyer, the famous mischievous child returns home after a scuffle with a new boy in the neighborhood. He was punished by his caretaker, Aunt Polly,  and given the arduous chore of painting the fence. Tom gathered the equipment and reluctantly went to carry out his task.

He painted for a while under the hot sun, paused for a moment, and examined how much work he had left – there was a lot of more unpainted fence than there was painted fence, and upon realizing this, Tom fell into a state of melancholy. He didn’t want to go on, but he had no choice. He didn’t want to get punished with more work by his aunt.

As other children walked by, Tom gets an idea. He offered to fetch a bucket of water to one boy if he agreed to paint the fence, that failed. He then offered some money, that failed too – the other boy was in a rush to fetch the bucket of water, and he too was afraid of punishment.

He thought about paying other children, but then realized he didn’t have enough money to buy more than a few minutes of freedom.

Then suddenly, he gets a brilliant idea.

When Tom was first painting the fence, he meditated on the idea of child labor, and he realized a surprising fact – other children seem to enjoy doing their boring chores. He noticed that instead of complaining or getting discouraged, they carried out their tasks with glee. This psychological fact inspired him.

Tom continued to paint, but this time, he did so slowly. And every once in a while, he paused, took a step back, and examined his work the way an artist would. He seemed to be immersed in his task truly enjoying every moment. As this was happening, another boy named Ben approaches. Ben was entertaining himself, enacting a scene where he was sailing a boat, and despite his loud and excited tones, Tom didn’t seem to notice – he was so engaged in his work.

Ben approached Tom and this conversation took place.

“Hello, old chap, you got to work, hey?”

Tom wheeled suddenly and said:

“Why, it’s you, Ben! I warn’t noticing.”

“Say—I’m going in a-swimming, I am. Don’t you wish you could? But of course you’d druther work—wouldn’t you? Course you would!”

Tom contemplated the boy a bit, and said:

“What do you call work?”

“Why, ain’t that work?”

Tom resumed his whitewashing, and answered carelessly:

“Well, maybe it is, and maybe it ain’t. All I know, is, it suits Tom Sawyer.”

“Oh come, now, you don’t mean to let on that you like it?”

The brush continued to move.

“Like it? Well, I don’t see why I oughtn’t to like it. Does a boy get a chance to whitewash a fence every day?”

This inspired a change of attitude in Ben, who was suddenly intrigued.

Ben stopped nibbling his apple. Tom swept his brush daintily back and forth—stepped back to note the effect—added a touch here and there—criticised the effect again—Ben watching every move and getting more and more interested, more and more absorbed.

Tom then explained to him how this job was given only to him, because he had the skill and conscientiousness to see it out successfully. He demonstrated how engaged he was in his task.

This enticed Ben too much, now he wanted to have a go and asked Tom if he could, arguing that if he was in Tom’s position, he would be act charitably. But Tom didn’t let him, saying that his aunt wouldn’t allow anyone else paint the fence, and that he couldn’t risk giving the job because it was too difficult to get it right. At this point, Ben loses his patience, begging Tom to give him the brush, and even offering an apple that Tom had his eye on. Tom agreed.

Tom gave up the brush with reluctance in his face, but alacrity in his heart. And while the late steamer Big Missouri worked and sweated in the sun, the retired artist sat on a barrel in the shade close by, dangled his legs, munched his apple, and planned the slaughter of more innocents. There was no lack of material; boys happened along every little while; they came to jeer, but remained to whitewash. By the time Ben was fagged out, Tom had traded the next chance to Billy Fisher for a kite, in good repair; and when he played out, Johnny Miller bought in for a dead rat and a string to swing it with—and so on, and so on, hour after hour. And when the middle of the afternoon came, from being a poor poverty-stricken boy in the morning, Tom was literally rolling in wealth.

It’s hard not to smile when you read the words “the retired artist sat on a barrel in the shade close by.” It’s a perfect archetypal image of the trickster and it has been recreated so many times in pop culture. Despite the simplicity of this tale, there are many lessons to be gleaned.

Willingness to Experiment

Tom didn’t have to try new things. He could have just stuck to the task and slogged through the drudgery the way any other boy in his position would. But Tom refused to surrender to fate, he constantly tried new things, from bribing to offering to exchange chores – he even offered to show the first boy he saw his wounded toe – but none of this worked. His initial attempts were futile. But left with the choice of drudgery, or willingness to experiment, Tom went with the latter.

Rich Skill Set

The talented persuader must have many tricks up their sleeve. It is not enough to be relentless, there are other talents that must be put to use. Tom had the creativity to come up with the plan and several other plans, he had the acting chops to fool his victim, and the patience of a master negotiator to make Ben enthusiastically fall for his trap.


Tom understood that perception was everything. And this works on two levels. He first saw the children willing carry out their boring chores with happy looks on their faces, perhaps realizing that he didn’t feel bad for them because they seemed to having a good time. This was the seed to his imaginative plot. If he could make it seem that he was having fun, other children wouldn’t pity him, they’d want to be him!

Tom said to himself that it was not such a hollow world, after all. He had discovered a great law of human action, without knowing it—namely, that in order to make a man or a boy covet a thing, it is only necessary to make the thing difficult to attain. If he had been a great and wise philosopher, like the writer of this book, he would now have comprehended that Work consists of whatever a body is obliged to do, and that Play consists of whatever a body is not obliged to do. And this would help him to understand why constructing artificial flowers or performing on a tread-mill is work, while rolling ten-pins or climbing Mont Blanc is only amusement. There are wealthy gentlemen in England who drive four-horse passenger-coaches twenty or thirty miles on a daily line, in the summer, because the privilege costs them considerable money; but if they were offered wages for the service, that would turn it into work and then they would resign.

Deception Scales 

There are many universal psychological tendencies. These commonalities make it possible for manipulators to succeed – whether through marketing, seduction, or persuasion. People generally fall into the same traps because they have the same thought patterns. If you can figure out how to trigger the right thought pattern, you win. Tom fools Ben and manages to make many other kids his victim by using the same trick. Deception scales.


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