Building Your Risk-Taking Muscles

Lots of people urge you to take risks, dream big, work for yourself… what exactly are they encouraging you to do?

Anyone can take entrepreneurial risks, in almost any situation. You don’t need to start a business, quit your job, or totally reorient your life.

When military officers advocate for change from within one of the world’s largest bureaucracies, photographers refuse to shoot a job the way that a client says they want it done, or pilots propose new operating rules that upset the establishment… we take entrepreneurial action.

How can we develop our entrepreneurial risk taking muscle while we keep our day jobs?

There are a multitude of small risks that we can take every day, without betting our jobs or our family’s security. Every time we do, our risk-taking muscles get a little stronger…

Not everyone will decide to take big risks, and that’s ok. You should find a role that’s right for you… and building your risk taking muscles can help no matter what you choose to do.

How do you approach risk? Are you exercising your risk taking muscles, or letting them atrophy?

Start with Why? Continue with Why Not?

I’m going to build on the work of Simon Sinek… Simon suggests that we “start with why” and use this focus to drive our decision making. This is great advice, but incomplete.

When we have a sense of our why, the next best question to ask is “Why not?”

  • Why not start this business?
  • Why not write that novel?
  • Why not travel to a place my parents think is scary?
  • Why not volunteer my weekends to a cause I believe in?

Continue reading “Start with Why? Continue with Why Not?”

What do you Optimize For?

Once a year, I spend a weekend with my “tribe” at the World Domination Summit in Portland Oregon. There are any number of reasons I keep coming back… including exposure to ideas that force me to reconsider my life and priorities.

In 2015 it wasn’t until the closing speaker that an idea seized my mind and wouldn’t let go. Derek Sivers told us about how he sold his company, and donated most of the proceeds. He told us it was an easy decision, because he “always defaults to freedom…” whenever faced with a decision, freedom is what he optimizes his life for.

I’d never considered my priorities in quite that way, so I asked myself… if I had to pick only one thing as the most important, what would it be? Continue reading “What do you Optimize For?”

You’re the sort of person we’re looking for…

I didn’t get involved with disaster relief to improve my customer service skills, but…

In a job interview with Amazon I was asked: “We pride ourselves on customer service. Can you tell me about a time when you exemplified customer service?”

My response: “Absolutely. Let me tell you about an experience I had as a volunteer with the Red Cross in New York City, on a disaster relief call in the South Bronx, by myself at 1 am with a family who had just seen their house destroyed.” Continue reading “You’re the sort of person we’re looking for…”