Success Can Be Risky Business

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Risky business may not be suited for all but many of the strides I’ve made in business and in life were due to risk.


Yes success is risky business, I’ve known this forever. Call it risky, call it courage or naivete’, it’s reaching for the stars to grow and achieve success.

When I was 5 years old I climbed a bookcase to retrieve my little sister’s doll and, upon reaching the top of the stand, swung my leg into the glass doors accidentally gashing my knee; an emergency room visit followed, glass was removed, and 10 stitches left the scar I still have.

At 14 I hitchhiked regularly with my friends just for thrills. It was an adventure – life was an adventure – and I couldn’t wait to have one adventure after another. At 17 I went on a cross-country trip by myself from Miami to California and had another wild adventure that my protective Colombian parents never found out about.

Reflections on risk

Leaving home

As I was leaving home at 19 to take on my undergraduate studies my father said to me, “I worry about you, sweetheart.” I turned my head and paused in the doorway of the home I’d be leaving behind, probably forever, and answered awkwardly, “Why, dad?” I could tell he was holding back tears when he responded, “Because you like to take too many risks.” He was right.

About a month later I almost drowned when I jumped into the ocean from a giant boat to snorkel not knowing what I was doing. Three days before I had joined the SCUBA club on campus because that’s where all the cute boys were. Never mind that I’d never learned how to swim. Angels saved me that day.


As I got older my risky behaviors took on a more calculated demeanor. Yet, following a second divorce, and in the middle of a major recession at the tail end of 9/11, I resigned from a Fortune 500 management role – a 6-figure income, 5 weeks vacation and benefits galore – to start my own business. With two teenagers in tow and no financial support, I decided that my happiness deserved every ounce of risk that I could endure. 13 years later my company is still thriving; I have made it through the ups and downs of owning a small business.

It has not been easy. But anything less than bliss was never an option for me.


So when the question is asked, “Are risk-takers born that way?”

My tendency is to say “YES!” However, throughout the years I have learned that risk-taking may be easier if you are “born that way” but anyone can learn how take more risks or how to be a better, more effective risk-taker.

I mean, come on, we all know that without risk there is no reward, or that where there is low risk, there is low reward.

We have been programmed to believe that to gain success we have to take gambles. We must risk safety and security in order to reach for the stars and obtain our dreams. This may or may not be true but to the degree that we believe it is, we will continue to reap small gains with little pain, while those that stick their necks out obtain the rewards many of us only dream about.

Well, I’m here to tell you that you can obtain all your dreams by taking the smallest risks, even if and especially if you were not born a risk-taker.

I have figured out that all you need is a little courage – the courage to take seemingly scary actions, to say yes when you’re not 100% sure, to know when to jump in and ask questions later, to “go for it” when others are not supportive, and the courage to be invincible in the face of self-doubt.


One of my favorite literary heroes said,

“Whatever you do, you need courage.

Whatever course you decide upon, there is always someone to tell you that you are wrong. There are always difficulties arising that tempt you to believe your critics are right.

To map out a course of action and follow it to an end requires some of the same courage that a soldier needs. Peace has its victories, but it takes brave men and women to win them.” – Ralph Waldo Emerson 

One dictionary defines courage as “the ability to face danger, difficulty, uncertainty or pain without being overcome by fear or being deflected by a chosen course of action.”

Addressing fear

For me it means to be scared and then do that thing anyway.

Fear tends to rule over us but we can rule over fear by “observing” it as something outside of us instead of a condition that is upon us. If you could take fear, imagine it sitting in the palm of your hand, then put it in your pocket, take it with you, own it, even love it, you could then separate yourself from it and it would not have power over you.

Next page- What is courage?


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