How baseball can help you choose a path in life

Are you a contact hitter, or are you a slugger?

In the game of baseball, a hitter is either a "contact hitter" or a "slugger":

The contact hitters are on-base percentage guys. They just want to strike out as little as possible and 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 regular job-type-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.

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. I've often joined small teams as the first technical architect, which for me is the same thing. I'm all-in on asymmetry, swinging for the fences. As an entrepreneur, 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.

Should I go get a job? Or should I do a startup?

Sometimes people who are just getting started in life ask me what they should do. "Should I go get a job? Or should I start a business?". I tell them this baseball story, and then I tell them to go get a job because it's hard to be a slugger, and there are way fewer successful sluggers than contact hitters.

Anyway, the people who are really born to be entrepreneurs won't listen to me because they're called to be entrepreneurs. They can't not start a company! And that's a necessary component for success. In other words, if you're asking me (or yourself) this question, then you should probably opt for a job, live below your means, and invest the rest.

And, aside from difficulty and success percentage, there's another reason to take a job over starting a business:
- Once you start a job you specialize in something and you can become more employable over time.
- Once you start business-building, you become a generalist and mostly-unemployable in the professional world. (I know, I tried and failed to get hired at both Google and Facebook immediately after building and selling a multi-million user app company.)

Those skills echo into the rest of your 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.