Calculated Courage: How to make risky decisions!


What if our professional courage looked a lot like the courage described by Atticus Finch in To Kill a Mockingbird, when he describes courage as-

“when you know you’re licked before you begin but you begin anyway and you see it through no matter what.”

This quote rocks us every time we see it. And, we are reminded that two things are true:

  1. Courage looks a lot like a calculated start, despite the circumstances.
  2. Our convictions are more important than the uncertainty of whether we may already be “licked.”

It’s the uncertainty that usually derails us, mainly because following our beliefs, pursuing a dream or tackling a big project, can feel like jumping off a cliff. We can feel like we’ve landed squarely in the wilderness. And, we are there with all the other blaring cliches that say – we are on our own, it’s risky, and success is unknown.

We may do our best to hedge our bets and estimate odds, but most successful business leaders will tell you that there is a point when taking a risk is a pivotal act of courage, not a gamble. It is often when our convictions about what’s right or what’s best supersede.

Fortunately, author of How to Win Friends and Influence People, Dale Carnegie encourages us that,

“most of us have far more courage than we ever dreamed we possessed.”

And in business, courageous decisions are rarely uninformed risks. An article from the Harvard Business Review describes it like this:

“In business, courageous action is really a special kind of calculated risk taking. People who become good leaders have a greater than average willingness to make bold moves, but they strengthen their chances of success—and avoid career suicide—through careful deliberation and preparation.” (Kathleen Reardon)

So if we are going to see our project through, to be calculated in our courageousness and mindful of the fact that we have more courage than we think, what could a courageous decision making process look like?


Here is a great ordered list of tips from Small Biz Trends:

  1. Do lots of Research
  2. Anticipate Mistakes
  3. Set checkpoints and goals
  4. Be willing and ready to pivot
  5. Learn to love the word “No”
  6. Jump…
  7. Outline a plan B (our Omni team addition)

Ultimately, courage takes planning, practice and a healthy dose of persistence, especially if our Plan B becomes Plan A. But, it’s much harder to regret the courageous choice, than it is to regret the missed opportunity, or worse: regret for not standing for what we believe.

So, whatever 2018 resolution is staring you down, muster the courage, do the research and jump.




Courage, The Defining Characteristic of Great Leaders

Courage As a Skill

How Entrepreneurs Can Take Calculated Risks

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