How To Become A Better Risk Taker

The Uncomfortable Truth About Risk and How To Overcome It

Matt Russell
Oct 10, 2019 · 10 min read

et’s face it, nobody likes taking risks. Why would they? Risks leave you feeling vulnerable and uncertain about how things will turn out. They seem unwise, reckless and sometimes, downright scary.

But the reality is, just about everything worth doing in life requires risk.

Think about the last time you applied for a job or promotion. Did you know how it was going to work out? Or the last time you asked him or her out on a date? Were you certain they would say yes? The question is not “Do you know how it will work out?”; but rather, “Are you willing to go for it anyway?” in spite of the risk.

“If you decide that you’re going to do only the things you know are going to work, you’re going to leave a lot of opportunity on the table.”

— Jeff Bezos (Founder of Amazon)

I know this is easier to said than done, but read further and I will show you proven methods used by Steve Jobs, Jeff Bezos, Amelia Earhart, and other extraordinary people that helped them overcome risk during pivotal times in their lives.

The Uncomfortable Truth About Risk

The uncomfortable truth about risk is that your goals are inextricably linked to uncertainty. If you are ever going to achieve them you must decide to pursue them anyway, despite the risk involved.

The sad part is, most people never get there. They get caught in “analysis paralysis” and never take action.

They keep trying to reduce the risk in their mind, thinking…“Do I ask her?” or “Do I mention I’m interested in that opportunity” or “Do I quit my job and do that thing I always wanted to do?”

Whatever the situation, they fail to realize the solution is not in analyzing risk, but in accepting it.

You Can’t Connect The Dots Looking Forward

Steve Jobs, Founder of Apple, emphasized this point during a commencement speech he gave at Stanford University. He said, “you can’t connect the dots looking forward; you can only connect them looking backward.” These weren’t just words to him either, they were a mantra for his life.

He had no advantage over you or me when he founded Apple. He was a young man in his 20’s with little experience, no college degree, and almost no money in the bank. Yet, there was a great difference between him and most of us.

I bet you know what it is too… Yep, you guessed it. He didn’t get stuck analyzing what he wanted to do to the point of inaction, but rather, accepted the risk involved and decided to pursue what mattered to him anyway.

He didn’t wait for a future time when he was more “experienced” or had more “credentials,” nor did he wait until he had large amounts of money in the bank or investors lined up. No, he didn’t do any of that. Instead, he had a firm conviction in what was important to him and poured his whole self into pursuing it.

We have to be careful not to analyze ourselves into a corner — sometimes just taking action is the answer.

When is the last time you believed in something so much you were willing to risk everything to pursue it? This is the essence of life. Don’t fall into the trap of thinking there will always be another opportunity; you don’t know what the future holds, this may be your only opportunity.

Time Will Pass By Whether You Like It Or Not

Steve Jobs was keenly aware of the temporalness of his life. He knew opportunities were fleeting and moments were precious. There is a quote he heard as a teenager that had a profound effect on him. It says:

“Live every day as if it’s going to be your last, and one day, you’ll be right.”

— Malachy McCourt

In response Jobs says, “all external expectations, all pride, all fear of embarrassment or failure… just fall away in the face of death, leaving only what is truly important” He says further “remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”

Jeff Bezos, Founder of Amazon, wrestled with this same thing when deciding whether or not to leave his high paying job on Wall Street to start what would later become Amazon.

Bezos says what finally convinced him to take the risk was a simple question. He asked himself, “If I don’t do this, at the end of my life will I regret having never tried?”

That was enough to shift Bezos thinking from “Why?” to “Why not?”. It gave him the spark he needed to stop analyzing all the reasons why he shouldn’t take action and start asking why not?

Anyone who has ever accomplished anything worthwhile in their life also had to wrestle with this.

Consider Those Who Have Gone Before You

Not everyone wants to be a world-changer, but everyone wants to change their world. Whether that is becoming a better parent, spouse, or friend; that is pursuing a hobby or activity you love; or, that is just becoming the best version of yourself; whatever it is, you have to make some sort of change in your life to get there.

The following people overcame risks and accomplished extraordinary things. They favoured “action” over “analysis” and began asking “why not” instead of merely “why.” Whether you want to accomplish something extraordinary or just extraordinary to you, be encouraged by those who have gone before you.

Jeff Bezos, Founder of Amazon, would have never started the largest internet company in the world if he had not first quit his high paying Wall Street job.

Colonial Sanders, Founder of KFC, would have never created one of the most successful food franchises in history if he didn’t challenge the conventional wisdom of the “right age” to start a business — beginning to sell chicken from a streetside restaurant at 65.

Martin Luther King, Civil-Rights Leader, would not have transformed the way people thought about racial discrimination and segregation in America if he didn’t have the courage to share his dream in the face of adversity.

Amelia Earhart, Aviation Pioneer, would not have been the first female to fly solo across the Atlantic and pave the way for future women in science and aviation if she didn’t follow her passion and dare to challenge the status quo.

Your goals are not only possible, they are within reach. All you have to do is decide to take the next step and you will be on your way to making them a reality.

Three Questions To Help You Take Action

While studying the lives of the extraordinary people above I noticed a common theme. In order for them to take action, they first had to reconcile within themselves an answer to the following three questions.

Question 1: Do I absolutely believe in this?

Taking risks is always worth it when you genuinely believe in your pursuit. This conviction is what will carry you through the hardships and make the victories all the more rewarding.

During the early years of Apple, things were rough. Sales were down and Steve Jobs was actually booted out of the company. If Jobs didn’t absolutely believe in his cause he could have (and probably would have) called it quits. However, at his core, Steve Jobs had a mission to revolutionize the way people interacted with technology.

This belief was bigger than his circumstances and inspired him not to sit around feeling sorry for himself; instead, he founded a digital film company called Pixar. This is the film company that later made Toy Story (the first digitally animated film) and I don’t have to tell you this, you already know it was a huge success.

As a result, Apple (still flailing) brought Jobs back into the company and that changed everything. With Jobs back at the helm, Apple applied that same innovative spirit to its products and literally transformed the way people interacted with technology — making his belief a reality.

I am a huge fan of this quote from Theodore Roosevelt and I think it fits well here. For anyone looking to set out on a cause you deeply believe in, consider these words:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” — Theodore Roosevelt

Question 2: If I never do this, will I always regret it?

They say at the end of your life you will seldom regret the things you did; rather, you will often regret the things you didn’t. Approach life with a deep sense of conviction for what you believe and when you have an opportunity to pursue something that matters to you, go for it. Don’t get stuck in “analysis paralysis.” You will never have all the answers, nor can you compensate for all the risks. All you can do is decide to take action in spite of them, and if you are driven by what you truly believe, it will always be the right choice.

In a 2001 Interview, Jeff Bezos recounts the moment he decided to start Amazon. He says he went to his boss at his high paying job on Wall Street and told him “you know I am going to go do this crazy thing and start this company selling books online.” His boss told him “let’s go for a walk.”

Then they spent the next two hours in Central Park where Bezos told him his idea and why he believed in it. His boss then told him “you know, this actually sounds like a really good idea to me, but it sounds like it would be a better idea for someone who didn’t already have a good job.”

Jeff Bezos then recounts the next 48 hours where he mulled over the decision to quit his job and participate in the internet which he genuinely believed was going to be a big deal.

He thought, what kind of framework should I use to make this really important decision. Then, he says being a nerd, he came up with a “regret minimization framework.” To do this, Bezos projected himself forward to the age of 80 and said, looking back at his life from age 80 how would he feel about this decision. He knew he wouldn’t regret participating in the internet, he also knew he wouldn’t regret trying and failing; however, he absolutely would regret having never tried. He knew that would haunt him every day.

He says this made his decision incredibly easy and as a result, he quit his job that summer to start Amazon. Over two decades and over 200 billion dollars later, it still appears he made the right choice.

Although the future is uncertain and success is never guaranteed, if you take action you will never have to look back at the end of your life with regret — wondering how something might have turned out. You will know that you were in the “arena” giving your all toward a worthy pursuit, which is hard for anyone to have regrets about.

I’d rather regret doing something than not doing something.

— James Hetfield

Question 3: Can I see the next step?

You can seldom see the whole picture, but you can usually see the next step. The greatest pitfall of analysis is it never ends. You can continuously think of a thousand reasons why something will fail or why the timing isn’t just right, but if you shift your thinking from “Why?” to “Why not?” it changes your paradigm.

Instead of trying to understand and dissect all the steps from beginning to end, you just see the next step — the obvious one right in front of you. This distils all your analysis down into a single question. “Why not take the next step?”

Then, after you’ve taken it (and likely succeded) another step will appear. It is sort of like Indiana Jones’ Leap of Faith in The Last Crusade.

Amelia Earhart loved flying, but she had a bigger mission at heart. She believed that women had a place in science (which wasn’t a commonly held view at the turn of the 20th Century) and she used aviation as her platform to share that message. This was articulated in her speech A Woman’s Place In Science, delivered in 1935.

She didn’t analyze all the reasons why she would never be able to convince the masses of her view, nor did she mull over what people would think, she just saw an obvious next step in front of her and she took it.

This step was to jump in the most extraordinary scientific invention at the time, the Airplane, and attempt to do everything a man could do in it (and even more).

Her plan wasn’t elaborate, it was simple. She observed the obvious next step, and after she accomplished it, she took another “next step.” This is what drove her to attempt to fly around the world — no man had done it yet.

She wanted to pave a way for future women in science and she knew that if she could be the first pilot to circumnavigate the world in an aeroplane, this would give her a bigger platform to share her message. It would also provide her with an indisputable case that women can make great contributions to the field of science.

Although her attempt to fly around the world was unsuccessful, her message that women have a place in science was — all because she decided to act on what she deeply believed in, one step at a time.

Keep your eyes on the goal, and just keep taking the next step towards completing it. If you aren’t sure which way to do something, do it both ways and see which works better. Never look down to test the ground before taking your next step; only he who keeps his eye fixed on the far horizon will find the right road.

— John Carmack

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Matt Russell

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Personal Development Writer — Just a Man On a Journey to Pursue What Matters in Life.

The Startup

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