How To Become A Successful Risk Taker


Of all the skills in life to learn, I believe risk taking is the most important. Imagine how dull your life would be if you never took chances. Without taking risks, you might never have found that great hole in the wall restaurant, traveled the world or found the love of your life. Everything great in life requires a little bit of risk to make it happen.

For example, several years ago a friend asked me and about twenty other people to accompany him on a trip to Southeast Asia. Everyone eventually backed out except me. That trip became one of the defining moments of my life. And I did it because I was willing to take the risk to do it.

Becoming a risk taker seems to have a negative connotation to it. The word brings up images of danger, hazards and even loss. But no matter how dangerous the idea of risk taking is, there is an even greater danger of not taking risks. Risks are a key ingredient to living life to the fullest.

Fortunately, the skills of becoming a successful risk taker can be learned.

Get in the mindset

The first thing you need to do is make sure you’re looking at risk the right way. Think back to a time when you were socializing with a group of people and you told a joke you thought was really funny, but no one laughed at it. That joke is an example of a small social risk. Perhaps you were embarrassed or thought negatively about yourself, but really it doesn’t matter. Do any of those people remember your bad joke? Not at all.

I know it may seem strange to start off an article about how to become a successful risk taker by illustrating a failure. However, I am here to tell you there is no such thing as failure. There is only feedback. In the above example, the feedback you got was that the joke really wasn’t all that good. The only conclusion is to not tell the joke again and try something else.

That is how professional standup comedians work. They regularly introduce new comedic material to their act and gauge its reaction. If it doesn’t work, they get rid of it and try something else. Eventually their act is a series of carefully calibrated routines they have tested out over many attempts.

Entrepreneurs act very similarly. If you look into the history of many successful businesspeople you will find a long history of unsuccessful enterprises. Since all we see from the outside is success, it might be hard to realize all the setbacks they dealt with.

Start Small and then Go Big

The best way to become a successful risk taker is to start small. Try an exotic kind of food you’ve never eaten before, take a road trip somewhere, or just start talking to more people. Just get in the habit of saying yes to new things. Some things might not be as good as you expected, but you’ll be surprised how often you find something great.

Once you build up the habit of trying new things, you’ll want to experiment with some bigger risks. Plan a trip to another part of the world, join a new club, ask out that attractive person or take a class in cooking. And if you’re really up for it, you can start up your own business, take a year off to sail around the world or do something even more amazing.

If you keep at it, eventually you’ll get really good at taking risks. Your success rate will go up since you’ll have all this risk taking experience behind you.

Overcoming Your Fears

Risks by their very nature are risky and that can be a little frightening. This fear is natural, but can be a roadblock in things you want to do. When you understand how fears limit you then overcoming them is easier.

Fear just needs to be understood. That’s why starting small and working your way up to bigger things works. It gets in your head just how little there really is holding you back.

Also understand, sometimes fear can take another form in excuses. This appears when someone has an idea to do something, but something, one thing, is holding them back. They’ll often claim this one thing is “preventing” them from doing what they want to do.

Admittedly some circumstances (physical abilities and demographics for instance) can prevent you from doing what you want. However, in many cases the excuse is just a form of fear holding you back. Recognizing this will help you overcome this hurdle.

Risks vs. Gambling

I want to clear something up about risks though. One should never take on something that is too much for them to handle if it doesn’t work. One example would be to put all your money into a single insecure investment. That is gambling and is not advised.

The key difference between a risk and a gamble is the consequences. If the situation you’re taking would seriously set you back or even ruin you if it didn’t work out, that is a gamble. A risk is something that even if it doesn’t work, you’ll easily recover from it and be able to function normally afterwards. There is a fine line between the two, but if you carefully ease into risk taking, you’ll get a good instinct of where the line is for you.

Once you learn how to become a successful risk taker, you’ll be able to do anything you want to. Fear will still be there, but it won’t hold you back. Best of all, you’ll be living the life you want.

As Dale Carnegie once said, “Take a chance! All life is a chance. The man who goes the furthest is generally the one who is willing to do and dare.”