How Entrepreneurs Take Calculated Risks That Actually Pay Off

The greatest risk you run is not taking any. Without risk, an entrepreneur is likely to become stagnant, complacent, and never meet their potential to be successful and fulfilled.

When you think of calculated risk, what comes to mind?




Keep in mind – calculating can never eliminate risk entirely, nor will it guarantee success in the long run. But there’s no denying some of the biggest risks taken in business have resulted in the greatest achievements.

In this article, we feature tips from local entrepreneurs and how they’ve redefined calculated risks to scale their enterprises and enjoy the entrepreneurial journey. These tips may change how you approach risk, make you more proactive than reactive, and eliminate your fear of failure.

Fail Successfully

Failure. Seemingly the biggest fear of every entrepreneur. No matter how long you’ve been in business, startups, and other pursuits–fear of failure manages to lurk in the minds of even the most successful business people who have been doing this for decades.

Take it from these Fortunate Failures.

But the thing with failure is that it’s inevitable. Even just accepting that point is going to propel you beyond your competitors who run from it. Because when it catches up to them, it’s game over.

To fail successfully, on whatever scale the failure occurs, is to learn, grow, and above all– try again. Not just from a motivational perspective but an analytical one. Specifically, where did you go wrong? In fine detail, rewrite the process, note all factors that didn’t add up to your desired outcome. Dissecting and learning from your failures will be your greatest asset when calculating risks.

To fail successfully means you are able to:

  1. Uncover unknown weaknesses
  2. Dare you to evolve
  3. Reset your focus
  4. Cultivate a support system
  5. Can even make you more credible

Failure provides an opportunity to practice prudent reassessments, develops versatile thinking, builds courage, and forges greatness. Messing up completely (sometimes several times) is a critical stepping stone toward business success.

Trust Yourself

Great leaders do what they believe in, and nothing less.

Under perfect conditions, good business would consist of decisions that are either black or white–cut and dry. But the real world presents a shade of grey where infinite possibilities exist. You can’t discover the possibilities of your heart without believing they’re possible and taking the plunge.

Your risks as an entrepreneur are yours to take and the results are yours to manage. The more in touch you are with your long-term goals and exactly what success looks like to you, the easier it will be to trust your decision-making process. But my no means should you ever allow fear to prevent you from making a decision that in every other way feels and appears to be the right one.

Some business moves will require much deliberation and calculating, but some risks require you to go with your gut.

The “Go All In” Myth

Entrepreneurs, especially new ones, tend to operate on the notion of all or nothing and believe the only way to achieve great success is to go all in.

Entrepreneur Michael Kehoe shares his philosophy on calculated risk for business leaders. He encourages new entrepreneurs to reserve taking bigger risks for later in their journey and if possible, maybe avoid them all together after enough experience is gained.

“In truth, the real way to success is to be very calculated, taking small risks that build up to something bigger.” Kehoe promotes the power of learning from small failures in order to prevent them on a larger scale. Building a business is a steady series of small risks and the agility to capitalize on the ones that achieve the greatest outcome.

“In truth, the real way to success is to be very calculated, taking small risks that build up to something bigger."

Test Your Ideas

Redefining fear, failure, trusting in yourself business baby steps makes an immeasurable difference in how you calculate risk and make decisions . But they are incomplete without a contingency plan.

Before executing a risky mover, creatively plan as many potential results the risk may yield. Can you handle the worst possible outcome? Are you prepared if you achieve the best outcome? This kind of preparation can be time-consuming but significantly reduces anxiety surrounding the risk, builds courage in leaders, and offers several backup plans.

There’s no denying that taking chances in business can cost you money, your name, and potentially even your dreams. But if you want to disrupt your market, tap into your unlimited potential, and be an innovative leader– take as many calculated risks as you can get your hands on or someone else will.

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