Upside vs. Downside

Think about the next plan you have, at work, in business, at school, even personally, and analyze it as upside opportunity vs. downside risk. Downside risk asks “What’s the WORST that can happen?” If your action failed completely, what’s the most you would lose? How much time, money, respect, etc. would you give up? Upside […]


What do standardized testing in schools, bureaucracy in health care, and the inflexible application of laws have in common? They are all thoughtless. Not thoughtless because nobody put intellectual effort into creating these structures. Thoughtless because they give us excuses to avoid using our brains. We stop thinking because it’s seen as safe, and the […]

The iterative Loop unrolled

Let’s break down the Loop a bit more and flesh out some details. Before starting, you’ll want to establish some long-term goals. Answer the question “What would my life/business/career look like if everything was going the way I wanted it to?” Often a way to do this would be to envision a typical day for […]


A major tool of the entrepreneur mindset is approaching your life, your education, your career, and your business as a series of loops Not the treadmillish, Sisyphan, “Groundhog Day” self-repeating kind of loop, but a style of iteration that allows you to explore opportunities, solve problems, and tackle big goals in a manner that reduces […]

Entrepreneurs learn for a living

When I talk to people about entrepreneurism, people who haven’t had experience often expect the conversation to focus on business plans and investors, on marketing and advertising. While those will be important at various times, the real work of the entrepreneur is learning. Entrepreneurs learn through doing. More generally, the essence of the entrepreneurial process […]

Introducing the Creative Iteration blog

“Entrepreneur” has historically referred to a risk-taking creator of businesses. However, over the last several years, the term has started to be applied to people who share the characteristics of entrepreneurial businesspeople. These include: acting rather than talking or planning solving problems through creativity as well as perseverance believing that the world and people are […]