"The biggest risk is not taking any risk. In a world that's changing really quickly, the only strategy that is guaranteed to fail is not taking risks."

Mark Zuckerberg

In this post, we’re going to talk about something that sounds negative but is actually the key to unlock pretty much EVERYTHING you want in life.

Think about the earlier quote from Mark Zuckerberg:

“The biggest risk is not taking any risk. In a world that's changing really quickly, the only strategy that is guaranteed to fail is not taking risks.”

Unfortunately, the word ‘risk’ has a negative connotation associated with it.

But when we talk about risk, let’s give a few examples of what we’re NOT talking about:

These four scenarios are far more common than you think! And I bet you can probably think of a few scenarios of your own.

The misconception with risk is that it’s something undertaken that is dangerous. Yet, a better definition of risk is: “An opportunity that can significantly enhance your situation, while carrying a possibility of failure.”

But, let’s face it, pretty much ANYTHING we do in our pursuit of growth and self-mastery carries the risk of failure in the short-term. However, it shouldn’t be tainted with the same brush of what are generally just ‘bad decisions,’ like the four scenarios we mentioned earlier.

There’s a huge difference between risk in the sense that we’re talking about here, and bad decisions that are made by people every day who will sadly have to struggle with the consequences. And generally, the people who make bad decisions have made a habit out of it so it keeps happening.

The main thing that stops people from getting out of their comfort zone is this closely linked component of risk which is a ‘fear of failure.’ So let’s quickly explore the concept of failure and risk in more detail.

1. Failure:

Contrary to popular belief, failure should not be viewed as so terrifying that is causes inaction. It’s the pursuit of failure that has created the most dominant and wealthiest companies in the history of civilization—embracing innovation, pushing society forward, and raising standards of living for people around the world.

In fact, Amazon founder Jeff Bezos once revealed his own experience with failure: “I’ve made billions of failures at Amazon. Literally.” That’s coming from arguably the most effective business leader of all time who, from his own garage, built an online bookstore that became the world’s most valuable company. Not book company. The world’s most valuable company, in any industry.

On the condition that you learn from the failure and rise once more, your ability to seek it out is one of the greatest assets you can have. This is where having a growth mindset is essential.

2. Risk:

Again contrary to popular belief, risk carries significant upside and its probability of failure can be mitigated. For any situation, you can maximize the potential upside while minimizing the downside, such as through your own due diligence (or employing the services of someone who is a specialist in that field), or seeking counsel from a mentor or mastermind.

Think about when SEAL Team 6 came knocking for Osama bin Laden in the middle of the night. It was a huge risk, but they spent months preparing—years, in fact, if you factor in the CIA’s involvement—so they could maximize their potential upside while minimizing the downside. Even with all the planning, they still lost a helicopter on the mission, but the carefully planned risk eliminated the most dangerous terrorist in the world.

If you’re faced with a decision and you can’t identify any upside (or it’s only minuscule), it’s a bad decision—not a risk! If you want to be successful in life and business, you need to put your heart, wallet, and time on the line every now and then for what you believe is the greater good.


In a letter to shareholders, Jeff Bezos once wrote, “I believe we are the best place in the world to fail (we have plenty of practice!).”

And the episode quote from Facebook founder and CEO Mark Zuckerberg notes that “The biggest risk is not taking any risk.” In 2007, at age 23, Zuckerberg became the world's youngest self-made billionaire, so it’s worth listening to what he has to say about success. Those who don’t take any risk are the ones who perennially make bad decisions in their own lives, like keeping all their money in the bank because they believe it’s the best strategy for long-term wealth creation.

Both Bezos and Zuckerberg are acutely aware that every failure increases their chance of hitting a home run, as Amazon and Facebook have done with numerous innovations that propelled them from risky startups to two of the most valuable companies in the history of civilization.

In alignment with the modern-day tech moguls, Think and Grow Rich author Napoleon Hill said, “Those who will not take a chance seldom have one thrust upon them.”

Anytime I get the urge to stay in my comfort zone, I read that quote and it lights a fire right under me.

Now that we properly understand risk, let’s flip the script on those four earlier scenarios to illustrate what might be a better course of action and more appropriate use of risk:

Scenario 1.

Bad decision:
Dating someone who is toxic and destructive to your life because you believe you can change them.

Calculated risk:
Spending more time with someone who you sense a deep connection with and allow each of you to explore those feelings. If you bring out the best in each other, and your time together forms the seedlings of love—you will have to put your heart on the line as you commit to each other (perhaps the biggest risk of all)—but it might just be the best partnership you ever form.

Scenario 2.

Bad decision:
Starting a business without doing your due diligence because you think you already know it all.

Calculated risk:
Identifying a problem faced by many that you can solve through starting a new product / service. You seek the counsel of both a business mentor and a mastermind of your peers to help figure out what you don’t know about the industry and its potential complexities. Your business has no assurance of success, but you’re strengthened from collective wisdom and launch a business that could make all of your dreams come true, while helping many people in the process.

Scenario 3.

Bad decision:
Maxing out your credit cards because you believe the law of attraction will look after you.

Calculated risk:
You retain 15% from every paycheck and invest it, via dollar cost averaging, into a fund that tracks the index and enables you to harness the power of compound interest. While the media outlets try to rattle you with reports of “catastrophic meltdowns” in global markets, you stay the course because of your goals and professional advice.

Scenario 4.

Bad decision:
Not focusing on your fitness because you might get hurt.

Calculated risk:
You’re time-poor and stressed from work, so you decide that yoga might be the best form of exercise. You have never done a class before, but you ignore your ego and go at your own pace until you feel confident progressing to the more technical movements. There is the risk you fall flat on your face, but a few months later, it might just be the very activity that restores balance to all areas of your life and allows you to make new and healthy friendships.

ALL of these amended scenarios carry a possibility of failure, but without the risk there is no reward. You’ve gotta risk it to get the biscuit.

To finish, let’s dive into a passage from Napoleon Hill:

“Success always involves risk. You must take a chance by investing your time, money, and effort. It pays to be thoughtful and deliberate in your analyses of opportunities, but don’t let timidity hold you back.

Because you have worked hard to develop those things you must risk, it is natural for you to place a high value on them. But what good are they if you do not put them to use? You will recognize opportunity only to the extent that you are willing to consider risking your time, money, and effort.

Being confident gives you the courage to face risk and act when opportunity arises. No one on earth is going to force success upon you; you will find it only to the degree that you actively seek it out.”


Until next time,

Onwards and upwards always,
James Whittaker

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