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 I was asked by a friend of mine to accompany him on a trip to Southeast Asia.  He asked about twenty people to go with him.  Everyone eventually backed out except me.  That trip became one of the defining moments of my life.  Why did I do it and so many others back out?  Because I am a risk taker.

Becoming a risk taker seems to have a negative connotation to it.  The word brings up images of danger, hazards or 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 stand up 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.”

Do you have stories of risks you’ve taken?  Or do you have anything you’ve always wanted to do, but have something holding you back?

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  1. Everyone looks at me like I’ m a crazy person when I tell them the stories of what I’ve done/what I do. Even running a marathon makes people raise their eyebrows. People really just get comfortable in their own space doing the same thing every day. That’s why I do the list-to force myself out of my comfort zone. Here’s to taking risks!

    • Jessica, I agree. Some people just don’t break out of their comfort zones when they get into them. I can tell you push yourself though. Keep at it and you’ll continue to have even more of those crazy stories.

  2. I think you have a wonderful and interesting blog here, it’s different from other blogs I read. Keep writing about your crazy stories, it’s a big motivation!:D

  3. great blog man! its addicting. Great info for us travel freaks out there!

  4. Thanks for the comment Steve. Will check back here shortly when it isn’t 3.13am…hehe, keen to have a read about your mixed drinks article.

  5. Also, you should definately make it to Oktoberfest at some point… I was so excited about it once I’d been, I considered it “the one thing everyone must do at some point in their life”. Well, I liked it so much I’m going again this year, I’ll be there for the opening weekend too!

    • Oh yeah, Oktoberfest is something I want to do. I haven’t had a chance to do it yet, but it looks like I would have a great time there.

  6. Here’s to having two hole in the wall restaurants before the age of 24 and going back to school at 30 to become an archaeologist. mmm, what next. lol

  7. I feel like in American society doing anything out of the ‘normal’ track is seen as risky. Not buying a house by age 30. Not getting married soon enough. Getting married too young. Having kids too young / too late. Going back to college at a later age or not going at all. Whatever is not the trajectory is seen as an unreasonable ‘gamble.’

    • I agree with you. There does seem to be pressure to do what is expected or normal. Anyone who takes their own path is seen as taking a gamble. That’s why I think that being a successful risk taker is so important. It’s the difference between a normal life and an extraordinary one.

  8. hey thanks alot Steve….what ever you wrote sir…its wonderful…..i like to take risks but people start laughing on me sir….i dnt know why they laugh on me sir…….i love to do different things everyday…..i am a kool guy…:)
    godblesss every1…

  9. well i have seen many publications but i have liked this one.
    i’m one person that doesnot like to go out of the things that i call reasonable.
    i have a lot of fear, i’m almost 30 and i have never dated even any girl in my life because i’m scared.
    but i want to change all that and start living my life.
    i know if i start doing this, i’m going to a amaze many people and that is what i want to do now.

    • Richard, I’m glad you liked my post. The best thing you can do is change your life to get it where you want it to be. Don’t let fear hold you back. You’ll never be able to get rid of fear completely, but you can learn to control it. Figure out where you want to go in life and keep going towards that goal.

  10. I left a ten year career to travel. Some people think I’m crazy but there will be a job if I come back, it may not be the one I want right away but we’re so lucky in North America, there is always a way you can make money even if it means working fast food. People in other countries don’t have the same luck.

    • I think you’re crazy too, but in a good way. You’re right that you can go back to something after you’re done traveling. It probably won’t be what you left, but all that traveling would be worth it.

  11. the blog was really interesting, I hope for a big change in my life .

  12. The blog is spot on, not just for being successful, but for living a meaningful life. Risk does not just mean doing things that will benefit you. Looking back at our parents and previous generations, risks did not just result in new business. Sometimes it resulted in nothing more than stronger families, better children, and friends. Taking a vacation you cannot afford so your children can experience something new, engaging in activities with your children, and leaving work early for family night are all risky behaviors. The risks are economical, personal, and career. In my opinion personal risks can lead to growth and success both personally and professionally. I leave this response after becoming a Boy Scout leader with no Scouting or outdoor experience, spending more money than we could afford to take the dream vacation going on a photo camping safari in Africa, and asking the hard questions at work.

    • Hey John, there are a lot of different types of risks. Economic, personal and career ones. Sometimes they pay off and other times they don’t. But how often does growth happen until you take a chance or two? I remember a time when I was extremely shy. Just talking to someone new was scary, but I took that social risk and started meeting people. As a result, my life got better. And it all started with taking a risk.

  13. Barry Longden says:

    One great fear for many is looking like a fool and some people do foolhardy stunts rather than risk losing face in front of their friends. I believe we all take risks of a kind in life and everyone holds back from doing certain things out of fear. Often we choose what scares US the least out of two actions.

    • That’s the way I used to be. I used to care whether I looked stupid in front of other people, but eventually I got over it. You have to risk looking stupid and try not to care when it happens – otherwise you might hold yourself back too much from doing what you want to do.

  14. Hey Steve,
    I’m currently in a conundrum in my life. I want to take risks, one it particular is that I want to move overseas and try like in the UK (I live in New Zealand), but several fears, or fears manifesting themselves as excuses are stopping me. I’m considering just a month long holiday to the UK first, provided my work will give me one, but this will use up all my money and I’d probably get a lot more from just flat out moving, and trying to find work there.

    Would you recommend baby steps and going for a holiday – or should I make the leap and move?

    If this isn’t the place for questions no worries. It was on my mind and your article connected with me somewhat

    • That’s a tough choice. Since I don’t know what the job market looks like over there, I couldn’t make a guess as to how likely it would be to find a job. I went through something similar though. I moved to a major city far away from my home town without finding work first. I trusted in myself that I would find something eventually. Well, it didn’t take long (two days in fact). Of course, back then I had a lot of money saved up to last six months or so without work.


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