Risk-Taking and Progress

Posted on Thursday, June 25, 2026
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by Robert B. Charles
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A close up of a risk management flow chart on a blackboard.

“Progressive” America teaches false lessons, does not understand the real meaning of “progress.” Happiness requires risk-taking. We might as well teach young people to learn hard work by reading about it, or how to read by complaining and blaming others.

Truth is sometimes hard to swallow, but here it is: Anything of value or affirming of a person requires risk-taking, a vision, and working toward it. The opposite is all fiction.

The thought swept me today, not because “Progressives” promise everything for nothing, then blame others when their promises are empty, and not because Progressives dismiss individual responsibility and risk-taking for dependence.

No, I just think we do a terrible job of selling the idea in – and value of – risk-taking. So, what is risk? How do we encourage young people to embrace positive, life-changing risks? How do we stop them from being duped by Progressives into lazy dependence?

First, we need to explain that risk involves possible success and possible failure, which means you need to work for success and be prepared for failure. Just that, mentally preparing for both possibilities, actually builds strength.

Then, we need to explain how positive risk works and give young people a chance to prove the value to themselves. We need to show how getting back up after a failure makes them stronger, because now you know you can do it, learn, recover, and succeed.

Next, we want to teach how to take positive risks with commitment, have a vision, and work. People need to test things, succeed, or confirm their ability to recover if they fail.

This concept – working hard, failing, recovering, then advancing – is resilience. In business, academics, and everything that is meaningful in life, including surviving as a POW, this is what counts: being able to fall and get back up, resilience.

Next, we need to reteach that courage is required to start, a willingness to take risks, followed by full-on commitment, no break, resilience when we fail, and learning to succeed.

When you think about it, that is what self-reliance versus government-dependence is all about –openness to risk-taking. Progressives want dependence for votes; others do not.

Everyone else just wants a chance to take a risk and succeed, less government, more opportunity to try, make a living, put money away, succeed – or fail and be resilient.

That is America. That is also life. That is how anyone who succeeds does it: by facing adversity, sometimes benefitting from what adversity offers, overcoming it, and winning.

Knowing this, we have to re-teach what amounts to common sense, what has made America what it is, what brings real happiness, the courage to take risks, the ability to recover when we fail, and the sense of achievement that flows from learning resilience.

The British prime minister who inspired victory in WWII, Winston Churchill, was asked to define success. “Success is the process of going from failure to failure without loss of enthusiasm.” Elsewhere, he wrote: “Success is not final, failure is not fatal: it is the courage to continue that counts.” There it is, in two quotes, risk-taking until success.

In that spirit, Aristotle once wrote: “Courage is the first of human qualities because it is the quality which guarantees the others.” He, too, knew about resilience and risk-taking.  

So, what about now? What about restarting the risk-taking engine? Getting younger people to understand that the best things take time, work, and involve risk-taking – but produce the strongest character, the highest level of prosperity, only route to happiness.

In many ways, the real mission is about getting people off the couch, into training and then jobs, teaching skills, opening doors, and getting people familiar again with risk-taking.

In another sense, this is about history – the history of the nation and humanity – which has only ever advanced or shown “progress” by risk-taking. Nothing comes for free.

Bottom line: Risk-taking is the only way to advance. Sometimes – as Reagan reminded us after the Challenger accident, gains require loss. Risks are taken, losses sustained, we learn, and go forward. But that is the only real definition of “progress.”

As Reagan said that fateful day, 40 years ago: “The future doesn’t belong to the faint-hearted; it belongs to the brave.” Once again, we must teach it.

Robert Charles is a former Assistant Secretary of State under Colin Powell, former Reagan and Bush 41 White House staffer, Maine attorney, ten-year naval intelligence officer (USNR), and 25-year businessman. He wrote “Narcotics and Terrorism” (2003), “Eagles and Evergreens” (North Country Press, 2018), and “Cherish America: Stories of Courage, Character, and Kindness” (Tower Publishing, 2024). He is the National Spokesman for AMAC. Today, he is running to be Maine’s next Governor (please visit BobbyforMaine.com to learn more)!

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