Risk-taking is scary for most of us because there is always the potential for loss. We’ve been taught to be careful and avoid taking any unnecessary risks. Instead, we are cautioned to play it safe and just take baby steps toward our dreams.
While this approach does tend to feel safer there are also some serious downsides. For one, you can’t build momentum by holding yourself back. In fact, the longer we hold back, the harder it is to keep moving forward. Without forward momentum inertia kicks in until our progress comes to a screeching halt.
The risk factor
Have you ever noticed that most successful people have one thing in common? Nine times out of ten there was some degree of risk involved in their success. In one way or another, those “successful people” usually feel like they needed to take a chance in order to succeed.
Believe it or not, risk is not such a terrible thing if you view it from the right perspective. Most people look at it from the perspective of what they stand to lose if it doesn’t work out. But we also need to ask “what do I stand to gain if it DOES work out?”
Is it worth the risk?
Here’s a simple process to determine which risks might be worth taking. Use the following six criteria to analyze the situation BEFORE you jump in and make a final decision.
1) What do you stand to gain? With any risk, you’ll want to first look at the potential benefits. Make a list of what you stand to gain from moving forward and include as many details as possible. Consider every possible positive benefit you stand to receive. Make sure to consider the financial, emotional and physical upside. What’s the best case scenario?
2) What are the possible negative consequences? Along with the positive benefits, there are always a few possible negative consequences. That’s why they call it RISK. Make another list of these, again thinking about all the possible things that could go wrong, and what would happen if they did. Could you handle it? What’s the worst case scenario?
3) Balance, balance, balance. Now, compare the two lists and see which one has the strongest likelihood of coming to fruition. Would the gains be worth the risk? Would you be able to handle the negative consequences if they did happen? Are there any options for a middle ground decision that would minimize the risk without derailing the momentum? Should you break it into phases so you have an exit strategy, or should you just go for it with all you’ve got?
4) How realistic are your fears? Take another look at your list of negative consequences and ask yourself how likely they are to happen. The majority of the time you’ll probably find that your fears don’t have much real substance – they’re just fears. Evaluate each possibility carefully and determine whether it’s a real threat or an expression of some unrelated fear.
5) Go with your gut. After carefully weighing the pros and cons, you should have a solid sense of whether you should take the risk now, or lay a little more groundwork first. There is no shame in deciding to hold back if you feel you can’t handle the negative consequences right now! Remember, you can always re-evaluate the same risk at a later time to see if conditions are more favorable.
6) Now ask yourself – Why? What is your motive for considering this course of action? Is it in harmony with what you know to be right, or is it possible that greed or selfishness might be influencing you? Understanding your own motives will help you get very clear about what you should do. Always move toward the greater good.
Get yourself primed for action
By getting into the habit of evaluating risks in this way, you will empower yourself with the confidence to push through hesitation and move steadily toward a successful outcome. In the long run, confidence and determination will be a huge factor. If you are going to take a risk, getting your mindset right first will maximize your chances for success. That brings us to…
7) Don’t hold anything back! If you decide to go for it, give it your best shot. The first six points were the pre-action phase. Once you launch into action avoid the temptation to second guess your decision. Doing so will only undermine your progress. You’re already in the game, so now it’s time to focus on making things happen.
How are you at assessing risk?
Do you think that risk and success go together?
The lines are open!











{ 37 comments… read them below or add one }
Hi Jonathan,
Risk taking is a tough one for me to figure out. Like a lot of folks I’m pretty good at seeing someone else’s issues in a clear light, but for myself, this one is a mystery.
I am a confident and enthusiastic risk-taker in most areas of my life. I can uproot in a heartbeat and live in a totally different cultural environment, I thrive on adventures into nature where physical danger is a real possibility, I have always ventured into the unknown and loved every uncertain minute of it because the rewards are so great. My natural senses of curiosity, wonder, and awe, drive me forward into risk. And this risk-taking aspect of my nature is “the juice” of my life.
Where I am not good at handling risk though, is in areas that surround merging my personal interests with business. For some reason, I seem to hold back in this area. Instead of enthusiastically relishing the thought of taking a leap into an envisioned adventure, I find myself hesitating and diverting my attention from opportunities.
More self understanding and self empowerment is needed in this area of my life.
Thanks for the reminder to deal with this
John
John Rocheleau – Zen-Moments´s last amazing blog post ..Nature’s Cure for the Blues
Hi John, it’s exceptional how clearly you see yourself in differing situations. This level of self awareness is such a powerful gift. Your only challenge then is just to decide if you want to work on certain areas or not.
Think what an advantage that is over those who can’t accurately analyze there own responses to varying circumstances. John, I found your whole comment inspiring because you really see yourself.
Something I LOVED about John’s comment was his honest self assessment. I found it very moving.
Dear Jonathan, This a wonderful list, another one of those that young people should be given in school. Or at least “I” could have used it in school.
As an adult I try to look at as many of the points you’ve raised here as I can, and then act accordingly. Before making tough choices, I also go into them with this frame of mind: if I keep my eyes open along the way, everything is a fantastic lesson. I am here to learn, and to experience Life. And to do that I have to…..experience it!
When I was really young, I often held myself back because I wanted ALL the answers before I did anything. I wanted to know the outcome, the repercussions. I wanted a “sure thing”, which is often not the case. As a result I became totally immobilized. In fact so immobilized that I never followed ANY impulses.
Finally one day I decided I couldn’t live like that anymore. I looked at all the people around me and suddenly saw the mistakes they had made or were making, all the inappropriate things they said to others or me, and it hit me, “I can’t do or be any worse than them. So why not join the human race.” LOL!! So I did.
I am not perfect, nor have I lived a perfect life. I’ve made mistakes, done things I wouldn’t do again or would do differently, and so on. However, it’s been one heck of a ride. For me it was key to not become immobilized by fear. So much is lost when we let fear hold us hostage.
Thank you dear Jonathan!
I enjoyed this post.
Hugs,
Robin
Hi Robin, even when we scrutinize the potential risk/reward situation as carefully as possible, there are never any guarantees. And I don’t really think that’s even the point for those of us who love the journey.
I think the most practical application for all this is (for me anyway) the chance to fortify my confidence and gain some focus and clarity. I usually go for it regardless of the risks involved (unless it just plain ridicules). But the greater the risk the more focus and centered I want to be going in. I actually like risk.
I am SO like you. LOL!! I too thrive on risk, and yet I’ve been told by very close friends that even though I take more risks than anyone they know, that I have deeply rooted common sense. And I think it’s true. It’s a good mix, especially if one has a tendency to like risk.
I was just telling someone today that I refuse to let fear define me. We were talking about fear. I told her that if I sense I might fear something I HAVE to check it out and head right toward it, until I understand it and it no longer defines me.
I also love this line of yours: “I think the most practical application for all this is (for me anyway) the chance to fortify my confidence and gain some focus and clarity” YES!! I agree!
I really relate to the clarity/focus part….excellent!
It’s interesting to me that fear plays such a prevalent role in so many lives. Granted, this can happen for any number of reasons and I am not saying that it’s a fault or shortcoming of any kind. But for me personally it is a feeling that rarely enters the picture. I love helping people break free from the grip of fear because they always change in such remarkable ways once those shackles are loosened.
PS Your image of a hang glider is gorgeous. Is it you? Looks like it’s out here in my country, NM, AZ??
No, it wasn’t me. This is actually an older style hang glider than the souped up competition machines I used to fly. I chose it for the overall composition, thought it was breathtaking. Looks like the four corners area north of you, don’t you think?
Wow! I’d love to see a photo sometime of the type of machine you’re talking about. Does it have a name so I could google it. I love seeing things like that. I have to tell you honestly while I’m here; when I opened this post and I saw that photo up there, a great hunger arose in me to try hang gliding. I would need to be more fit, which I am working on (not for that reason, just because I am following your lead for the “most fit by 60 I’ve ever been” – at least trying
). And whether I ever hang glide or not, I just had to tell you about that intense feeling that rose so suddenly in me, out of nowhere. And I so admire you that you had the courage to jump off the cliff. So many many stories in you.
I flew a Seedwings Sensor 510. Remember, this was in the early ‘80 and the curved wingtips and 85% double airfoil were cutting edge. This was the fasted competition glider of it’s day and the choice of many of the top pilots. By the way, I never jumped off a cliff, I flew!
I should probably write some articles about those days. I remember flying the Owens Valley in ‘84. It was 100 degrees on launch (about 5000 feet above sea level) and we were wearing snowmobile suits because at 18,000 feet altitude (where we were going) things got pretty cold.
Jonathan,
My favorite quote, which is also one of the first quotes we were forced to memorize at the Naval Academy, is:
“He who does not risk, cannot win.” John Paul Jones
The goal of course is to take rational risks.
My project management background has taught me to mentally assess the probability of failure and the potential impact of failure when thinking about risk.
As long as we have an idea of what we want, and what may result from our risk taking, we should not fear failure. Having done so will make us better even in the face of failure. (And failure is only feedback, anyway).
Chris
Chris Akins´s last amazing blog post ..Free Deep Relaxation Meditation MP3
Hi Chris, what a balanced comment. I like your attitude about failure. In reality it’s all just feedback, success, failure, or something in between. Sometimes the reward of failure is greater than that of success.
Jonathan,
This is such “spot on” advice!! And…it’s something that hold a lot of meaning to me, personally. Sometimes those perceived fears can (and do) hold us back from what is possible. I know I’ve been there. And…I know there are still moments where doubt starts to creep in. So, reading this…GREAT stuff for me to absorb!!
Lance´s last amazing blog post ..The Moment
Hi Lance, hey, you faced your fear of swimming in the ocean. That was pretty awesome. It’s funny because you are so open and transparent that it’s hard to imagine that fear ever holds you back. I mean how many guys are brave enough to wear a pink wig on twitter for several weeks?
LOLOL!! re the pink wig (I’ve seen it) and. I agree with you Jonathan. I also like how you said, Lance is transparent. Yes, and that is one of his great strengths.
This resonated with me. I’ve been nudging around ideas for a blog post titled “Living on a Plateau.” I’ve lost 30 lbs since late spring, 50 overall, and, though I’m pushing exercise and healthy eating just as hard, my progress has slowed to a crawl. I know I’m still doing the same good things. My body is catching up. Muscle weighs more than fat.
Commitment to success was easier with faster, flashier results. Now, without momentum, I am living on dedication, long term and strong. Lack of strength is not as taxing when there is momentum.
Strength is an everyday maintenance sort of skill. If your step seven is deciding to go for it and making things happen, step eight is acknowledging strength for the long haul. My goal was change. My destination is optimum-for-me health. The patience of knowing my strength is how I am in the here and now.
I hope this makes sense to someone but me!
Hi Elizabeth, way to change your body, that’s just excellent. One of the dangers in striving for a goal is that we keep raising the bar so we never totally reach our goal. When that happens we are pursuing an ideal instead of a goal (I’m not saying that is what you are doing). It can be really encouraging to compare our progress to where we started rather than where we are going. When we look are where we are and see how much progress we have made it can be very motivating.
Imagine that you are climbing a very steep mountain. Your attention is fixed on the summit, but it’s a rough climb, you’re tired and your progress seems slow. If you stop and look back, all of a sudden you are amazed by how high you really are. Perspective is everything.
Jonathan, I appreciate this advice because I can see-saw between being overly cautious and being impetuous. This is such a clearly thought-out step-by-step “risk assessment” process that will definitely be useful to me.
All the points are useful, but the last point of examining your motivation is profound as well as your advice to always move toward the greater good. As always, thank you from my heart.
Sandra Lee´s last amazing blog post ..Expert advice on writing faster blog posts
Hi Sandra, I have learned that acting out of harmony with ones true sense of what is right often leads to self-sabotaging behavior. We always want to double check and make sure that we are not working a cross purposes. When we act in ways that create inner harmony our chances for success go way up.
Oh Jonathan, this post really resonated with me. What you have described is what I call a “why and why not list.” The method you have here works! Thinking of what you have to gain is influential, even if you think of what you may gain if you fail! Weighing the pros and cons of any decision is beneficial to us.
My husband, Mark, utilized this expressed method to make a major life change. He had worked for one company for 15 years, and struggled for 5 of those years with the idea of moving on to something new.
Using the method is challenging, and it requires a lot of considerations to conclude your thoughts on each aspect. Many of the things in both columns have why and why not list unique to them.
Anyone who uses this method has a hunger to make a change. It takes determination to do what you are presenting here. Even writing the initial list is an immense risk (it feels that way). The list is the first step to confidence and meeting your needs to what you want.
BRAVO my friend…this is exceptional advice!
Sandra Hendricks´s last amazing blog post ..The Difference In Troubleshooting and Figuring Things Out
Hi Sandra, what an insightful statement: “Anyone who uses this method has a hunger to make a change.” That is so true! When we feel that hunger it can be easy to charge in without being prepared. Writing the pros and cons down makes it so much easier to evaluate almost any decision, but is especially important with those big decisions.
Jonathan: I thought this was a great article and the tips you gave on evaluating risk were really helpful. I totally agree with you that we have to take some risks from time to time if we are going to achieve what we want, but we do need to make certain we are taking the right risks. I think the approach you described was great because it really allows you to evaluate things in a rational way. I know that so many times, my evaluation is more ad-hoc and probably not as disciplined as it should be. I am going to put your steps to work though the next time because I think they will allow me to look at the risk holistically and make a good decision. Thanks for sharing your insights.
Hi Sibyl, truth is I take a lot of risks because I enjoy the excitement and the challenge. But I also avoid being impetuous. I like to have a good idea of what I am getting into, especially when risk is involved. Let me know how this works out for you!
I used to go with the “put it all on black” approach to risk taking. I thought that any action was better than no action at all. At least I was doing something. Over time with natural maturity I have learned that not all risks are meant to be taken but they are first to be calculated to determine if the good outweighs the bad. I am so grateful for this post because it give me some excellent tips to add to my personal goody bag of self development. Thanks again Jonathan!
Frank´s last amazing blog post ..You’re Happiness is a Priceless Gift
Hi Frank, you made a really good point when you said: “Over time with natural maturity I have learned…..” That’s is really how most things work because experience is an EXCELLENT teacher if we a paying attention.
One of the really cool things is that we can accelerate that process by learning from other peoples experiences. This is one of the keys to faster personal development. We should all have a “personal goody bag of self development.”
In my opinion, success is not defined by your position in a company or how much you’re earning. Success is about being happy. I quit my job a few months ago to be a full-time mom. My company offered me promotion and flexible schedule just so I wouldn’t quit. I turned the offer down because I know already know what I needed to do. Happiness is about doing your own thing no matter what others say. =)
Hi Kirstine and welcome to Advanced Life Skills. I absolutely agree that “Success is about being happy.” And sometimes there is a degree of risk involved in moving toward happiness. That’s true in relationships, careers, and many other areas of life.
Thanks Jonathan.
Btw, great site.
Hi Jonathan. My way of assessing risks is pretty similar. However, I also like to draw up solutions to the things that could go wrong. I also consider my level of confidence. If I’m not believing in myself enough to take the risk then I wait. If there’s anything I’ve learned, it is that I’m more likely to fall on my face if I’m not in a pure positive mindset.
Nea | Self Improvement Saga´s last amazing blog post ..Do You Love and Value Yourself Unconditionally
What a great lesson to share with us Nea. “If I’m not believing in myself enough to take the risk then I wait. If there’s anything I’ve learned, it is that I’m more likely to fall on my face if I’m not in a pure positive mindset.” Excellent!
Thanks for a fabulous, thought-provoking article, Jonathan. I particularly love your line: “Always move toward the greater good.” Well, that and the comments about Lance’s pink wig

Naomi Estment´s last amazing blog post ..African Elephant on the Charge!
Hi Naomi, and welcome to Advanced Life Skills. Those are some awesome photos on your site. In you bio you mentioned Norwegian Forest Cats and being a cat lover (into flamepoints) I had to google them for a closer look. Beautiful.
Anyway, it’s nice to have you here!
There is always some degree of uncertainty in any choice. Allowing risk to manage our life is the same as allowing some bully to manipulate our behavior. Good points Jonathan…
Marko — Calm Growth´s last amazing blog post ..Achieve Tranquility of Mind- Important Things To Consider
What a great analogy Marko. Risk certainly can become a bully, but only if we allow it. Thanks!
Hello Jonathan.
So happy to visit your site.
Oh yes, risk and reward do go together. I suppose the risk has to have a bit of wisdom in it, but then the main drivers as you say are confidence and determination: and seeing as clearly as possible where you are going.
There’s been a big change in my attitude just recently. For a long time I just wanted to find more meaning in life.
Now I want to dare to open my heart to the material abundance that I once scorned…
motto of the British SAS I believe is “who dares wins.”
Look forward to visiting here again.
Every good wish.
Greetings Christopher, this was such an revealing statement: “There’s been a big change in my attitude just recently. For a long time I just wanted to find more meaning in life. Now I want to dare to open my heart to the material abundance that I once scorned…”
When we come full circle in our search for meaning this often happens. At first we see a distinction between different areas of life. But then we realize that abundance is an all encompassing state. So we open our hearts and allow it all in, which is completely different than just seeking material gain.
Thanks so much for sharing that with us!
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