Timothy Dexter was an incredibly eccentric person and businessman. He was also incredibly lucky.

Born in Massachusetts on January 22, 1747, Dexter had neither schooling nor money. He began life as a farm laborer alongside his father before becoming an apprentice to a Boston leather dresser at 16.

Five years later, Dexter completed his apprenticeship and moved to Newburyport, where he had his first stroke of luck. There, he met and married a wealthy young widow and purchased a large mansion using her money.

Dexter quickly became unpopular amongst his neighbors, who saw him as an ill-educated and unrefined man that married into money. Undeterred, he set out to increase his fortune by purchasing a number of large ships and launching an international trade business. When his neighbors heard the news, they purposely gave him bad business advice in the hopes that he would lose his fortune and move away.

A Stroke of Good Fortune, And Then Some

At the end of the American Revolutionary War, Continental (U.S.) dollars had depreciated severely and people were itching to get rid of them. Dexter wagered that America would survive as a nation and purchased vast amounts of Continental bills. His risky move paid off and the U.S. made good on the money, making Dexter extremely wealthy.

A neighbor jokingly gave him the idea of selling warming pans, used to heat beds in the winter, to the West Indies, which had hot weather year-round. Dexter had the last laugh, however, when the pans sold out. The captain of his ship sold them off as ladles for the booming molasses industry instead.

Next, a rival trader told Dexter to ship coal to Newcastle, which was already supplied from the large coal mine there. When he arrived with his shipment though, the mine was on strike, allowing Dexter to mark up his coal prices. He continued to make seemingly strange yet profitable business choices, such as shipping stray cats to the Caribbean as a solution to rat infestation.

Dexter notably faked his own death simply to see how people would respond. He also decorated his Newburyport estate with 40 statues depicting great American characters, along with a statue of himself. Underneath, the inscription read: “I am the first in the East, the first in the West, and the greatest philosopher in the Western World.”

So was Timothy Dexter a lucky person? Was his good fortune a series of coincidences? Or was he less foolish than his peers believed?

The Winning Personality of Lucky People

Richard Wiseman has been studying how luck plays a role in our lives. He wanted to see how chance opportunities come about and their impact on people’s lives. He began by examining the difference between self-professed lucky and unlucky people.

Wiseman found that lucky people score significantly higher on extroversion. They smile twice as often and engage in more eye contact. Their sociability, Wiseman explains, helps them increase their likelihood of a lucky opportunity because they meet more people, connect better, and maintain relationships.

Unlucky people, on the other hand, scored twice as high on neuroticism. To see how anxiety affected people, subjects were asked to watch a moving dot in the center of a computer screen, as large dots unexpectedly flashed at the edges of the screen. Almost all participants noticed these dots.

To increase anxiousness, the experiment was repeated with another group, who were offered a financial award to focus on the center dot. More than a third missed the large dots on the edge of the screen that popped up.

While anxiety helps us focus on a task, it also blinds us to other opportunities. As a result, unlucky people miss out on prospects because they’re too busy worrying about one thing. They develop tunnel vision in their career, missing viable job opportunities. Or, they might talk to a few select people at a social gathering, and then lose out on meeting other interesting people.

Lucky people, on the other hand, are open to new experiences. They’re more willing to talk to new people, travel to new places, and try new things.

Dexter was no exception. Despite his illiteracy, Dexter decided to make his mark by publishing a memoir. After completing his book, A Pickle for the Knowing Ones, he stood by the road and handed them out for free. His book became extremely popular, if not for the content, then for its oddity.

A second edition was to be printed, except this time his editor asked him to use punctuation. In classic Dexter style, he included a full page of punctuation marks at the end, telling readers to “peper and solt it as they plese.” Several more editions were printed to meet public demand.

A Lucky Attitude Towards Life

Wiseman conducted another experiment. This time, he gave people a newspaper and asked them to count the number of photographs inside. Unlucky people took about two minutes to count the photographs. Lucky people took seconds.

On the second page, there was a large message that read: “Stop counting. There are 43 photographs in this newspaper.” Unlucky people tended to miss the message, while lucky people spotted it right away. The self-professed lucky people were simply more observant.

Dexter had become adept at finding good opportunities by asking around about commodities. On one occasion, he travelled to Boston and purchased so many whale bones that he ended up monopolizing the market. He charged his own prices for the material that later turned into corsets, collar stays, and numerous other products.

Dexter later wrote: “I found I was very lucky in spekkelation. Spekkelators swarmed me like hell houns.”

Lucky people are also optimistic. They have positive expectations, which lead to self-fulfilling prophecies. Even if things take a turn for the worse, they can spot the good in a situation. Unlucky people might see the same situation and only point out the negatives.

Not only do positive expectations help people become happier, but they can also help make the most of difficult situations. To sell an abundance of wholesale bibles in the West Indies, Dexter sent a notice that every family needed one or else they would go to hell. This approach, though less than ethical, netted him thousands in profit.

One of the best examples of positivity, though, comes from Stephen Hawking. He once said, “I was lucky to have chosen to work in theoretical physics, because that was one of the few areas in which my condition would not be a serious handicap.” Stephen Hawking has helped us understand our universe better and serves as a role model for people with disabilities.

How to Increase Your Luck

To see if unlucky people could turn their luck around, Wiseman enrolled his participants in his “luck school”, where he put people through a series of exercises to increase their luck. The results were astonishing.

After one month of enrolment, 80 percent of people reported themselves as happier, more satisfied with their lives, and most importantly, luckier. The lucky ones became luckier, and the unlucky turned lucky. They had been taught how to spot good opportunities, have a positive outlook, and to make better decisions.

Take Carolyn, a 34-year-old care assistant who had described herself as unlucky. She had previously injured herself in numerous accidents, was unable to pass her driving test after three years, and felt like she could never meet the right person. After she finished her luck training, she became more social, passed her driving test, and wasn’t accident-prone anymore.

To increase your luck, you can practice what the “luck school” participants did:

Keep an open mind (and pair of eyes). Worrying about obtaining a goal endlessly can unknowingly close you off to other possibilities. Having an open attitude and looking around for new opportunities can open you up to lucky chances.

Worrying about obtaining a goal endlessly can unknowingly close you off to other possibilities. Having an open attitude and looking around for new opportunities can open you up to lucky chances. Look on the positive side. Focusing only on the negatives dampens your spirits and future expectations. When you go from complaining about scraping your knee to being grateful that it wasn’t any worse, it becomes easier to try new things.

Focusing only on the negatives dampens your spirits and future expectations. When you go from complaining about scraping your knee to being grateful that it wasn’t any worse, it becomes easier to try new things. Do something out of the ordinary this week. Routines can lead to ruts, whether it’s talking to the same people, eating the same food, or doing the same type of work. Stepping outside your boundary increases the likelihood of a lucky break.

You Can Be Lucky, Too

Many often attribute other people’s fortunes to good luck, while their own misfortunes are the result of bad luck.

It’s true that some people are born with advantages, or events happen to us that are outside our control. You might try for years to break into the entertainment industry, while someone else simply walks outside and gets scouted for a modeling contract. Flukes happen.

But they don’t happen all the time.

You see, Dexter opened up as many chances for himself as possible. He wrote dozens of letters to the local government for a position in public office. He observed what his prominent neighbors were doing and emulated their actions. He sailed far and wide in his shipping vessel, talking to merchants and selling his wares.

As much as Dexter enjoyed his luck, he worked endlessly to find good opportunities. Are you opening yourself to chance?