Cultivate Enterprise to Take Initiative and Seize Opportunity

We can put ourselves in situations or environments where we are more likely to encounter opportunity. We can teach ourselves to better recognize and evaluate opportunity. If we want to seize and exploit an opportunity, however, we must take initiative. We must act.

A bias toward action, the willingness to do something different or difficult, the eagerness to embrace a bold undertaking – these are the hallmarks of the enterprising person.

Some people are more naturally enterprising than others, to be sure. They are inherently driven, ambitious, self-starting go-getters. Others need to look a little harder to find their motivation.

No matter. Regardless of where we fall on the action orientation continuum, we can cultivate the quality of enterprise. We can develop specific tendencies that will move us to act when action is needed.

12 Ways to Reframe Setbacks as Opportunities

Speaking at the convocation of the United Negro College Fund in Indianapolis in 1959, John F. Kennedy said, “When written in Chinese, the word ‘crisis’ is composed of two characters – one represents danger, and one represents opportunity.”

From a purely linguistic perspective, Kennedy was wrong about what those particular Chinese characters actually represent.

JFK wasn’t the first to make this mistake, and many others have made it since. The trope has been repeated by journalists, bloggers, motivational speakers, and politicians for decades.

Managing the Motivation Gap between Aspirations and Expectations

We all have aspirations. We may aim high, low, or somewhere in between, but we all have some hope of achieving something. Our desires may not always be well formed or clearly stated goals, but we have them.

We also have expectations regarding our ability to achieve our desires. Expectations, like aspirations, range from low to high.

Advice about how high we should set our expectations varies, too.

“High expectations,” said Walmart founder Sam Walton, “are the key to everything.”

Use Your Beginner’s Mind to Open Your Prepared Mind

In 1973, 27-year-old Vernon Hill decided to start a bank. He launched a single, nine-employee branch on a highway in southern New Jersey. Vernon didn’t call it a “bank” or a “branch,” though. He called it a “store.”

Although he had worked afternoons at a bank while an undergrad at Penn’s Wharton School, Hill’s professional experience was primarily in real estate and fast-food retail. He scouted and developed sites for chains such as McDonald’s, CVS, and Jiffy Lube, and had an ownership stake in dozens of Burger King restaurants.

As a relatively inexperienced newcomer to the world of banking, though, Hill was able to cast aside many of the preconceptions people had about how banking ought to be done.

Don’t Let Myers-Briggs Limit Your Opportunities

When she was 14, a girl in Chautauqua County, New York began keeping the company of a 21-year-old local hoodlum named Johnny. He was the son of a reputed gangster, indulged in liquor and gambling, and sometimes carried a gun. He also had a steady income and access to several cars, which no doubt impressed his young romantic interest.

Partly to encourage her interest in show business, but probably mostly to separate her from Johnny, the girl’s mother sent her to a prestigious school of theatre and dance 400 miles away in Manhattan.

Unlike the school’s star pupil of the time, Bette Davis, the girl did not thrive. For most of her time at the school she felt frightened, intimidated, and humiliated.

Scroll to Top