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?”

Great Reads: Flow

Flow: The Psychology of Optimal Experience

This book by Mihaly Csikszentmihalyi started an entirely new field of research, and defined many terms that you’ve probably heard, but perhaps don’t fully understand.

Most of us would choose play time over work time, and that’s often the wrong choice if we value our happiness… facing challenges well matched to our skills gives us the opportunities to learn and grow that are essential to happiness. When we choose leisure activities that are essentially passive we lose these opportunities for growth and happiness.

If you aren’t fully satisfied in any facet of your life (and especially in your work) you need to read this book.

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?”