When was the last time someone called you prudent? Probably never.

Prudence doesn’t exactly scream charisma or dynamism. It’s not a trait you slap on a résumé or a word that trends on LinkedIn. (And thanks to its similarity to the word “prude,” it also probably isn’t an adjective that made anybody cool in high school.) But I firmly believe: prudence is one of the most attractive and necessary qualities any entrepreneur can have.

(Re)defining prudence

Merriam-Webster tells us that prudence is the ability to govern and discipline oneself by the use of reason; shrewdness in the management of affairs; the skill of good judgment in the use of resources; and circumspection as to danger or risk.

Sounds like something to aspire towards to me. Let’s check one other big old book for a definition.

Proverbs 22:3: “The prudent see danger and take refuge, but the simple keep going and pay the penalty.”

Proverbs 12:16: “Fools show their annoyance at once, but the prudent overlook an insult.”

Proverbs 14:8: “The wisdom of the prudent is to give thought to their ways, but the folly of fools is deception.”

In practice, prudence is about self-discipline, foresight and good judgment, emotional intelligence, and the courage to pause before taking action. Think of prudence as the leadership lens that zooms out—seeing not just the immediate opportunities but also the potential pitfalls, not just the current situation but the market, the possibilities, the end game. Prudence doesn’t mean avoiding risks. It means taking smart, deliberate risks that align with your values, vision, and long-term goals.

Prudence isn’t boring—it’s brave.

Prudence in action: taking big swings

As an entrepreneur, there will come a moment when you need to make a decision that will shape your company’s future—a “big swing.” Whether it’s pivoting your business model, launching a groundbreaking initiative, or entering a new market, these decisions often come with uncertainty and fear.

I led an e-learning company for 10 years. For the first four, we were a custom shop. Everything was personalized, branded, and storied for the client. Then we took a big swing: we would become an off-the-shelf (generic content) provider first, then add custom when needed.

It was a decision that went against everything we had created up to that point. Process, people, messaging, philosophy—all had to change. What if we missed? What if people weren’t on board? How would it affect our current customer base? Revenue? Cash flow? It was an idea we chewed on for six long months.

But prudence, paired with boldness, guided the transition. By evaluating market trends, gathering team input, and weighing the potential outcomes over time, we made the jump. It paid off, and we were set up for the next five years of growth.

Big swings aren’t reckless leaps; they’re the culmination of prudent planning, deep discernment, and calculated courage.

Tools for prudence: a discernment framework

To lead with prudence, leaders can use frameworks to guide decision-making and avoid emotional impulsivity. One such model is Suzy Welch’s 10-10-10:

1. Immediate Impact (10 minutes/hours): What are the short-term consequences of this decision?
2. Mid-Term Impact (10 days/months): How will this decision play out in the medium term?
3. Long-Term Impact (10 years): When the dust settles, will this decision still align with your values and vision?

Layer on a “values multiplier” to ensure your choice reflects not just a single moment’s needs but a sustainable, mission-driven path forward. Is this decision in line with your values? You’ll know by how you answer this question: Would you make this decision 10 times? 100 times? 1,000 times?

Prudence is a virtue—and a practice

There’s a reason prudence is one of the seven virtues. When you exercise prudence, you shield your people from unnecessary risk and love your neighbor well. It forces you to slow down, seek guidance, and trust in the right timing over our own urgency.

Prudence can transform your entrepreneur journey from reactive to proactive. So, the next time you face a crossroads, don’t just take a leap of faith—take a leap, with prudence. See danger and take refuge, but also take risks with wisdom. It’s not only the right thing to do; it’s the kind of leadership that leaves a lasting impact.

Prudence isn’t flashy, but it’s the backbone of great leadership. It’s the wisdom to plan well, lead well, and trust well. In a world that glorifies speed and decisiveness, prudence is the underrated trait that sets great leaders apart.

Prudence might not make headlines, but it will make you the kind of leader people want to follow. And yes, that makes it downright sexy.