I'm the opposite of your profession. I'm a pickpocket. I snatch watches.

Whenever I hear ruminations, like yours, about lost career opportunities, I am reminded of Malcolm Gladwell's 2008 best-seller, Outliers. My immediate reaction to your post is that while you may have squandered some opportunities, it is equally plausible that you made the most of those in your life's path. My reaction is based upon Gladwell's analysis of why some people find more career success than others. In a word, a key ingredient in success is actually happenstance of things beyond one's control, like birth month, birth year, geography and the like.

I gave the book to my eldest child when she was in college and I plan to urge my two younger kids to read it to prepare for their respective careers. I've excerpted sections of Wikipedia's description of the book below, in lieu of my own synopsis:

Excerpted from Wikipedia:
Outliers: The Story of Success is the third non-fiction book written by Malcolm Gladwell and published on November 18, 2008. In Outliers, Gladwell examines the factors that contribute to high levels of success. To support his thesis, he examines why the majority of Canadian ice hockey players are born in the first few months of the calendar year, how Microsoft co-founder Bill Gates achieved his extreme wealth, how The Beatles became one of the most successful musical acts in human history, how Joseph Flom built Skadden, Arps, Slate, Meagher & Flom into one of the most successful law firms in the world, how cultural differences play a large part in perceived intelligence and rational decision making, and how two people with exceptional intelligence, Christopher Langan and J. Robert Oppenheimer, end up with such vastly different fortunes.

While writing the book, Gladwell noted that "the biggest misconception about success is that we do it solely on our smarts, ambition, hustle and hard work." In Outliers, he hopes to show that there are a lot more variables involved in an individual's success than society cares to admit, and he wants people to "move away from the notion that everything that happens to a person is up to that person." Gladwell noted that, although there was little that could be done with regard to a person's fate, society can still impact the "man"-affected part of an individual's success.

The book begins with the observation that a disproportionate number of elite Canadian hockey players are born in the first few months of the calendar year. The reason is that since youth hockey leagues determine eligibility by calendar year, children born on January 1 play in the same league as those born on December 31 in the same year. Because children born earlier in the year are bigger and more mature than their younger competitors, and they are often identified as better athletes, this leads to extra coaching and a higher likelihood of being selected for elite hockey leagues. This phenomenon in which "the rich get richer and the poor get poorer" is dubbed "accumulative advantage" by Gladwell, while sociologist Robert K. Merton calls it "the Matthew Effect," named after a biblical verse in the Gospel of Matthew: "For unto everyone that hath shall be given, and he shall have abundance. But from him that hath not shall be taken away even that which he hath." Outliers asserts that success depends on the idiosyncrasies of the selection process used to identify talent just as much as it does on the athletes' natural abilities.

A common theme that appears throughout Outliers is the "10,000-Hour Rule", based on a study by Anders Ericsson. Gladwell claims that greatness requires enormous time, using the source of The Beatles' musical talents and Gates' computer savvy as examples. The Beatles performed live in Hamburg, Germany over 1,200 times from 1960 to 1964, amassing more than 10,000 hours of playing time, therefore meeting the 10,000-Hour Rule. Gladwell asserts that all of the time The Beatles spent performing shaped their talent, and quotes Beatles' biographer Philip Norman as saying, "So by the time they returned to England from Hamburg, Germany, 'they sounded like no one else. It was the making of them.'" Gates met the 10,000-Hour Rule when he gained access to a high school computer in 1968 at the age of 13, and spent 10,000 hours programming on it.