Expose yourself to as much randomness as possible.

I've always loved to write, and I kept a diary of what I thought about my business, being an entrepreneur and other things of interest to me.

It got a little stressful in my first two years of high school, trying to make conference calls with investors in between classes, but I definitely learned a lot of important time-management lessons.

Taking on short term risk can involve switching jobs, joining new groups / associations in the area, launching a personal blog, running an experiment within your existing job. These are some practical ways to inject volatility into your life, and thus some risk.

I'm just the smallest dot in a big map of human history.

Sometimes Plan B can have the same desired outcome, but a different path for getting there.

Expose yourself to as much as possible. Attend conferences no one else is attending. Read books no one else is reading. Talk to people no one else is talking to.