Baseball and your career

This miki turned into an article:

This is a story of the difference between somebody who goes to work at a normal job-type-job every day for a career, invests into their 401K, and takes 2-weeks of vacation per year, versus somebody who starts small companies hoping they turn into larger companies and eventually result in an exit and a financial windfall.

At a young age, I made the decision to NOT invest in my 401K plan, and instead spend that money on programming books and web servers in order to pursue tech startups.

In baseball, a hitter is usually either an on-base percentage guy, or a slugger.

The on-base percentage guys just want to get on base as often as possible. They want a good batting average and if they end up with more singles than anybody else they have a great career.

The sluggers want to hit home runs. They care less about the batting percentage and more about the number of home runs. Sometimes they end up with doubles and triples, which is fine, but it’s the home runs they crave.

In a professional life, the on-base percentage people are those who get a degree, go to work at a job every day, invest in their 401K, live below their means and put the rest in the stock market. As long as they just keep getting on base, they’re going to have a fabulous career and retire on schedule.

The sluggers are entrepreneurs who try to build a company and make a big lump sum exit. They live at (or above) their means, never invest in anything except their own business (usually because they don’t have the money), rarely take a vacation without their laptop as well. It’s a risky strategy and many entrepreneurs never hit a home run, but those who do only need ONE in order to be financially secure for the rest of their life.

Just like in baseball, it is difficult to switch from an on-base percentage guy to a slugger, or vice versa. They are different mindsets and skill sets. If possible, it’s best to choose your path early on and stick with it. The commonly held notion that young people are more likely to be successful at building a big company is bullshit. As an entrepreneur, I know that I improve with age, and I KNOW that as long as I keep getting up to hit, I’ll be just fine.

As an entrepreneur, and a technologist, leader, and communicator, I am constantly getting better as I get older. I occasionally hit doubles and a triple, but it’s the home run I crave. Whether I’m founding the company, or the first technical architect, it’s the same thing - I’m invested in the asymmetry of the opportunity. Swinging for the fences.