Luck Be a Lady: Becoming a More Decisive Leader

Kate Carney
3 min readJan 6, 2022

Being a great leader means being decisive.

Sure, making quality decisions is important but making no decision is a decision and, often, a crappy one (unless you get lucky).

Being decisive means making decisions earlier, faster, with greater conviction, consistently, in the face of ambiguity, incomplete information and in unfamiliar domains. Sounds like startup life.

To be successful founders need to be decisive. They need to move with speed, experiment early and often, embrace failure, and navigate ambiguity. Communicate with conviction to instill confidence and create a committed team that will execute on their decisions.

Today, I want to look at the role of luck, risk, and regret in being decisive. Sure, I can tell you to set deadlines, limit your options, and avoid the perfectionism trap, but first you have to learn to love luck, risk and throw regret out the window.

Are You Feeling Lucky?

In her book, Thinking in Bets, Annie Duke tells us that the quality of our life (think business success) = the quality of our decisions + luck.

She says life is a game of poker, it involves luck, uncertainty, risk and, on occasion, deception.

Most of us don’t want to accept that luck factor. We want there to be a high correlation between the quality of our decisions and the outcome. We want control. So, we get stuck in the gathering information stage, scenario planning and modeling, seeking feedback, and weighing the options.

If, as leaders, you get comfortable with the existence of uncertainty and accept there is an element you can’t control, can’t see, it frees you up to be more decisive. You become unstuck.

In fact, many people tend to think of luck as a positive. They think of luck as making a crappy decision and getting a great result. So, go ahead and embrace luck.

Is Risk the Same as Luck?

On the flipside, we often think of risk as the potential for loss. Making a solid decision and getting bad outcome.

A colleague recently shared with me something Cynthia Rowley said at a conference in October:

If there isn’t a 50/50 chance that something will be epic or ruin my career, then why bother?

I love that. She embraces risk, or better yet, is fueled by risk. She is looking at the odds, measuring the risk, and the riskier the better. Unlike luck, risk is something we can quantify, measure, and identify (leaving aside the black swan event).

She clearly knows what she is willing to bet and, therefore, to lose. She’s playing big.

Being decisive means accepting loss. Defining what you are willing to lose. As founders scale their businesses, the stakes get higher, the dollars involved multiple and the number of people relying on you grows.

Studies show that humans suffer from loss aversion. Daniel Kahneman found that the fear of losing $100 is more intense for people than the hope of gaining $150.

My guess is founders are fueled more by the upside potential for wealth creation and in making change, improving lives, and being of service.

They jump into a world of uncertainty and risk headfirst and, as they scale, the stakes get higher, the bets bigger. They are going for epic.

Regret Nothing!

When I heard the Cynthia Rowley comment, it reminded of something Lauren Maillian, a fearless marketer, investor, advisor, and entrepreneur, said about approaching risky opportunities:

“Will I regret it if I fail?

In her book, Annie Duke, explains that regret is one of the most intense emotions and, therefore, would be more instructive if it occurred before the decision. Sounds like a mind trick to me.

How will you feel if you get a negative outcome? Can you come to terms with it before you make the decision? Will you regret it if your worse fear comes true? I think it is hard to have those “intense” emotions without living the actual outcome but it’s a good question. Similar to asking what are you willing to lose?

We rarely regret the decisions we make, rather, we regret the outcomes. If we get lucky with a bad decision, no regrets. We all have decisions that fall in that bucket!!

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Kate Carney

I help women entrepreneurs scale businesses. I am a business consultant and legal advisor.