Risk, as defined rather technically by Wikipedia, is “independent from the notions of value, and, as such, eventualities may have both beneficial and adverse consequences.” Phrased in a way that doesn’t leave you scratching your head, we could simply say that taking risks can either work in your favour or work against you.
Despite risks not always paying off, they’re often necessary. They enable us to grow and learn from our mistakes. We’re actually lucky that this is the case, seeing as we take quite a few risks throughout our lives.

As children, we try things like putting random objects in our mouth, climbing trees, and the more daring among us even attempt to ride our bicycle without using our hands. The latter either resulting in impressed friends or a trip to the local hospital. As adults, there are risks we face when buying a property, performing DIY or opting to make a serious career change.
Every day when we leave the comfort of our homes and venture into the outside world, there will be risks to face. Thankfully, we’re conditioned to avoid most of them so they’re rarely a threat. Risk roulette has nothing to do with these small risks - you know, the ones like eating spaghetti bolognaise with a white shirt on or wearing 6-inch heels to nightclubs that are surrounded by cobbled roads.
Instead, risk roulette is more about the ‘biggies.’ The risks we view as serious, all-encompassing, and life changing. More specifically, risk roulette is all about knowing when to take these risks.
There’s a big difference between risks that are just plain stupid and those that could go against you but feel necessary. An example of the first being like the time I had jumped into the deep-end of a swimming pool knowing full well I couldn’t swim. The second being similar to when I had quit my full-time job in order to pursue work on my internet business.
A couple of years ago, I had to play the risk roulette. I was 18 years old, had finished my first year of a two-year college course, and had a steady job in a clothes store. I had a great group of friends and from an outsider’s perspective, my life looked good.
Then I received a job offer.
The offer was to leave the UK and move to Cape Town (South Africa) to become the social media manager for some of the largest companies in the world. I had been writing on the topic of Internet marketing for a few years so had managed to build quite a name for myself, but was determined to finish college and go down the ‘conditioned path’ I had been expected to.
I laughed at the man who thought I was crazy enough to drop everything and move across the world. I thanked him for the consideration, and told him I would consider the offer the following year (after I had finished college) if it was still available.
Yet, within a few hours, I was already on the phone to my dad telling him I was leaving college, resigning from my job and moving to a country where I didn’t know one single person. My dad is fairly apathetic, so it was quite a surprise to hear him laughing down the phone. He honestly thought I was joking.
Once I had convinced him I was serious, he gave me his full support. I called the company who had offered me the job and told them about my change of heart. I said goodbye to my friends and family, I handed in my notice at work and I started preparing everything I would need for my move to South Africa.
Right now you’re probably wondering what changed my mind. Well, that’s simple: I knew when to place the bet.
If we knew the outcome of a risk was going to be fortunate then it wouldn’t be a risk;- it would just be an action or an event. In my situation, I had no idea whether I was making the right decision, but there was something about the circumstances that made me realise I had to grab the opportunity with both hands.
My Position
If you consider my position, things start to make a little sense:
- I had no interest in any of the college courses I was doing
- My long-term goal was to work for myself as an internet marketer
That’s it; that’s all that matters. It doesn’t matter that I had a job or that I was in college. Those two bullet-points above provide enough information to know that I needed to place the bet and take the risk.
Could I have waited until finishing college before I made my move? Sure. Would the job offer have still been available? Possibly.
This site is all about breaking out of the mould, doing something different, creating your own reality. I knew I should be going for what I want, I knew when to place the bet, simply because it felt right and it aligned with my internal compass. Some call this feeling gut-instinct, others call it intuition. Whatever you name it, you must learn to trust it and let it guide you in life.
The biggest risks aren’t career changes, buying properties, moving to another country or anything even remotely related. Do you know what the biggest risk you face in life is? The biggest risk of all is failing to go for the things you want in life because you’re afraid of the outcome.
That outcome may be judgments from others, the possibility of failure or the situation you end up in. Whatever it is, we’re usually afraid of it.
Instead of waiting for your life to be perfect or for your friends and family to be convinced about your decisions, follow your own path. And, just like in everyday life, this path will also present risks you must face along the way.
In order to know when to place the bet, you just need to ask yourself a simple question: “Does the opportunity align with my core desires.”
Core desires are not monetary – which, of course, you’ll know once you have them – they’re more about freedom, expression and doing what feels right at the very depths of your Being.
Remember: the biggest risk is not the ones you may face on your journey. The biggest risk is not going for what you want because you’re afraid of the outcome. As long as you know when to place the bet, you’ll have no regrets when you’re lying on your death bed.

Boy did this post resonate with me! Fear really is the greatest obstacle to living your dreams, and unfortunately the fear is often legitimate (fear of not being able to make enough money to support yourself or your family, etc). But your last line is one I often quote to myself and others: far worse than enduring fear while alive, it seems to me, is enduring regret as you approach the end of your life. I must always remind myself that my ability to predict what’s going to happen when I take risks is actually quite limited and things almost always turn out differently than I think they will (usually less bad). Thanks, Glen!
Great post, life is full of risks, understanding risk and what it means to you is part of understanding life. Like you I have taken several risks in my life most of which have paid off.
Recently I have taken a huge risk and am not sure if it is going to work out, however I am taking one day at a time and following my dream. Fear is something I have had to overcome on many occasions
All the best
Scott
Glenn your writing just keeps getting better and better. I actually had to save a quote from here in to my quote archive. I’ve only done that with one other blogger (Leo Babauta) Heres the link, to your quote on goodreads. I’m hoping other people will see it and go to look up the author.
http://www.goodreads.com/quotes/show/186645
Thanks JS!
Although you couldn’t have spelt my name any further away from what it really is
I’ll have to fix that.
The thing what I like most about that inner-compass or intuition is how it works to guide you to the best possible option even when you don’t know every single variable. As oppose to always listening to that risk-averse voice inside your mind that never seems to shut-up, intuition is more like a calm gentleman that usually speaks when you inquire. I guess it’s like the sayings says, “follow your heart” or simply “go with your gut”.
Great post Glen, awesome stuff.
This is an excellent post about taking risks. I’ve taken quite a few risks in my life, but not the good kinds. More and more I’m realizing that when taking a risk you have to ask yourself, “Does what I want come from a place of love?” For example, if I’m taking a risk because I love someone or something or a job or whatever, that’s probably a good risk to take and I’ll regret it if I don’t, but if I’m taking a risk because it seems dangerous or fun or un-boring, it’s probably not the right kind of risk. Life is meant for taking risks — just make sure they are the right ones!
Encouraging post, Glen.
Over the past year or so I’ve come to realize what you’re saying here. It’s one thing to think it or know it, and a completely different animal to act on it. Moving to Cape Town may not have been ‘risky’, but takes a lot of bravery many people don’t have. Props to you… live on, dude. I’m working on my end, trying to kick my butt into waking up.
¨The biggest risk is not going for what you want because you’re afraid of the outcome.¨
Thinking like this is very motivating. Seems that we`re taking a big risk either way, whether we do what we want or not, so we might as well go with our gut, I know it could save a lot of ¨what ifs¨ in the future.
PS: I love the picture
I really liked this post. It definitely connected to a situation that I’m going through right now. A year ago I took the giant risk of playing football which I had no experience with and I was also in the worst shape imaginable, with chubby cheeks and a big belly. Now that my freshman year of football is over and I have lost weight, I realized that I really didn’t wanna go through all of that again especially because I did not have a strong passion for football as some of my friends did. So I took a big risk again by deciding not to play while ultimately facing disapproval from my friends and family along with my coach. But I needed to do something because I was afraid of the bad outcomes in playing. I could have been a good lineman but an unhappy one that was there for the wrong reasons. Now I have to stick to my decisions and not look back
Hey Calvin,
Thanks for sharing your story. Definitely sounds like you went with your gut, so-to-speak.
Did you ‘replace’ the football with anything?
Kind of. I want to do winter track this year but my fall sport slot will be empty
I really enjoyed this post. I think as we get older we become really conditioned not to take risks or take chances. Yet, it’s the very thing that makes us grow. One of my friends says “the bigger the risk, the bigger the rewards.” Learning to detach from outcomes I think is another key to taking risks. You’ve learned some valuable lessons very early in your life before conditioning took over.
Awesome post Glen. This needs to be shared with more people. Getting out of your comfort zone may be scary, but what’s the point if you don’t live the life you want? Your life isn’t meant to be scared, it’s meant for living. Break out of your space and stand up to the plate. Challenge yourself and you will be rewarded.
Hey Glen
As others have commented..this is a great post for where I am right now too. I like this because as you say it was still a risk but you knew when to place the bet. I used to just dive into things and wonder why they didn’t turn out, but it’s being smart about it too
Jen
Great story Glen.
It is great to hear about people with the courage to do big things. It is too easy to follow all the other sheep, so that is what most people do.
I feel the biggest risk in life is not acting on your dreams now. Inaction is a guaranteed path to old age and eventual death, if you are lucky. If you are not lucky, you will get sick or be in an accident and die much earlier. There is no tomorrow. There is only now.
What you are doing now is exactly who you are as a person. Are you a TV watcher or are you engaged in living an excellent life?
You make some great points, Glen… It took a lot of courage to did what you did, and to face all the judgments you’d receive from everyone you DID know for making such a decision. I bet you couldn’t wait to get to Cape Town! heheh
It reminds me of when I quit MY job to pursue working online. I took quite a big pay cut at first, but my wife and I haven’t been happier since. Some looked at me strange, as if I was crazy, mostly because nobody I knew had any faith or knew much about making money online, or knew anyone who was successful at it–so I understand their response; however, it did take some courage to be able to let everyone know about my decision, and stand strong behind it.
Thanks again for the great post Glen, I like how you use your own personal stories and experiences to illustrate your points–very effective!
Well, I’m here going through a bit of a risk assessment muddle – a longtime friend of mine needs surgery and the best place for it turns out to be Bangalore, India; she really wanted me to accompany her and I really wanted to go. I can’t think right now, when I might get an opportunity to go to India again and know she needs someone she is comfortable with to accompany her. But because of personal-business reasons I feel I can’t / shouldn’t
I can’t help feeling like I’m losing an opportunity! But that I believe is because if I had the resources, India would be a place I’d want to visit for business – sourcing materials, not to mention culture! I’m betting on there being another time. Right now, my sensible self is saying it’s too much to take on…
It’s great when you’re able to see an opportunity for what it is and know when to place the bet as you did – this, I must admit is not one of those clear moments for me! I’ve said no, but I’m still holding on to a small thought that if circumstances change, my bet may change…not a good gambler right now!
Enjoyed your post as usual! And couldn’t help giggling a bit with you using ‘wearing 6inch heels to the nightclub’ as your illustration following on the subject of your previous post…I’m assuming it’s not you in those heels…:)
Excellent post, Glen. Your words really hit home, because I am at a crossroads right now of making different life decisions. It is too true that the real risk lies in simply making the move, and attempting the things that align with your core values. I love that question that you pose to see if this is the right risk to take. I’m writing that one down.
Hey Karen,
What decisions are you in the middle of?
I’m glad you could relate to the post
One of the books relating to the topic of risk / reward that I find myself referring to time and time again is EIGHT KEYS TO GREATNESS, by Gene Landrum. (Risk-taking is one of the eight “keys.”) Usually you can get a used copy of it online for, like $2 + s/h. It’s also available in Kindle format. While I don’t agree with everything Landrum states (and, oy, he could really use a proof reader / fact checker), it is worth reading if you are interested in unlocking your hidden potential. Be mighty!
Hey Bill,
Cheers for the book recommendation. Not really a fan of books with numbers as titles (don’t ask
) but I might give it a look.
Cheers,
Glen
Nice post, you really do have to pay a lot of attention to your thought process and your emotional state when making plans and decisions.
Without doing so you can to easily fall into the trap of particularly not doing something for the wrong reasons.
Yes Sir!
You are correct!
Take the plunge, full well knowing that the decision can lead to a bad result. Some things just feel like the right thing to do even though it seems counter intuitive, like you did with quitting your college and working on internet marketing.
There are so many nay-sayers in the world who will tell you you will not make it.
Keep going and then in a few years time see how the roles reverse, where you are living life the way you want it and those nay-sayers are working their 9-5 job for little money and they hate their job.
A bientot Glen!
What most people most realize when making choices is that – whatever they choose in ten years it probably wont matter anyway. This is a very liberating point of view and is one that i wish more people would use