Taking Risks In Life: Why You Should + How To Do It Right

Disclosure: this page may contain affiliate links to select partners. We receive a commission should you choose to make a purchase after clicking on them. Read our affiliate disclosure.

Do you ever look back at your life and wish that you had made a different decision or taken another path?

When reflecting on these times, can you remember why you chose one direction over another?

Most people will answer that they were afraid to choose the riskier option because of what could have happened if they did. As such, they chose the easier, safer, or more certain option because they knew it carried less chance of embarrassment or failure.

That said, most people end up deeply regretting the chances they didn’t take, rather than being haunted by the temporary discomfort of embarrassment or rejection. In fact, one of the top deathbed regrets that people have is that they didn’t take more risks in life.

So, what does risk-taking look like? Why is it important? And what is the best approach to taking them?

Speak to an accredited and experienced therapist to help you take more and greater risks in life if this is something you struggle to do. You may want to try speaking to one via BetterHelp.com for quality care at its most convenient.

What does it mean to take risks?

The basic definition of taking a risk is going ahead and doing something even though you know the consequences might be less than awesome. For example, asking someone out on a date is taking a risk because they might turn you down and that would hurt you emotionally.

Similarly, going skydiving is risky because your parachute might not open and you could end up splattered in a field amongst terrified and contemptuous cattle.

Some situations are riskier than others (as mentioned above) and are even labeled as such. There are also lower-risk endeavors that aren’t quite as daunting.

Low-risk financial investments, for example, are considered a sure thing. You might not get as much of a monetary return on your investment, but it’s unlikely that you’ll lose much money, if any at all. In contrast, high-risk investments often offer the possibility of a massive return… but there’s just as much of a chance that you’ll lose the shirt off your back.

Essentially, to take a risk means doing something, anything, in which the outcome is uncertain.

Why is it important to take risks?

It’s said that nothing is certain in life other than death and taxes, which means that every single thing we do requires some measure of risk.

People are very keen to “stay safe” these days, but there is no such thing as real safety. To live an authentic, fulfilled life requires one to throw themselves off proverbial cliffs on the daily and discover whether they’ll sink or soar.

Risk is something we need to do in order to experience the life we’ve been blessed with. Below are just some of the reasons why it’s so important to take risks on a regular basis.

How can you get to know who you are if you don’t try different things?

I recently came across a blog post in which someone was talking about their “safe foods.” This person wasn’t neurodivergent, nor did they suffer from any kind of food allergies. Instead, they stuck to foods they knew and were comfortable with because they were “afraid” of what other foods might taste like.

They thought that things like coffee, Thai food, and samosas smelled amazing, but they were just too damned scared to try them.

Look at some of your favorite foods and ask yourself how sad it would be if you had to go through life without ever having tried them. After all, you obviously weren’t born loving fettuccine carbonara or burritos. You had to risk a potentially unpleasant sensation in your mouth in order to determine whether they were good or not. But how sad would your life be without the amazing foods that you adore?

All of life is like this.

Every single thing you like was new to you once and, therefore, had a risk associated with trying it. You slowly become the person you were destined to be by stepping out of your comfort zone again and again.

You’ll never know unless you try.

I’ve known people who have fallen into deep pits of depression because they haven’t gotten the job they wanted, nor gotten together with a lover they were aching for, simply because they were too afraid of rejection or failure. They’ve literally spent decades lamenting “the one that got away,” except that person or job opportunity didn’t “get away,” they weren’t even attempted.

I once asked a friend of mine why he never bothered going after a girl he was completely in love with, and he told me that he wouldn’t have been able to deal with it if she had rejected him.

There have been so many situations in which people have been into each other, but since neither of them took the initiative to let the other know, those chances for connection were squandered.

Yes, it may hurt for a while if the person you desire doesn’t reciprocate that affection, but it would be so much worse to find out 40 years later that the person you loved actually felt the same but didn’t think you were interested because you didn’t take that leap of faith.

The biggest contributing factor to people not doing things is fear. In particular, it’s fear of the unknown and all the “what if” anxieties associated with it. Most people talk themselves out of doing things because they’re more hung up on the potential negative aspects than the positive ones.

Here’s an example: let’s say you really want to get into martial arts, but you have a lot of fear associated with it. Maybe you have a bit of social anxiety or you’re scared about how much it’s going to hurt when you get hit at the dojo. As a result, you’ll find reasons to talk yourself out of it.

The people there are going to be too aggro. You don’t want to have to deal with other people’s sweat, and so on. In fact, you’re better off without that mess!

In reality, this isn’t the case at all. In fact, at a good dojo, you will undoubtedly get your fair share of bumps, strikes, and the wind knocked out of you… but that’s exactly the kind of physical and emotional conditioning you’d need to fare well in a street fight.

Everything will suck at the beginning, because both your muscles and your mind will be unused to that particular kind of training and exercise. The movements will feel clunky and unfamiliar, and you may get hurt a bit before you learn how to block properly. But that’s okay. That’s what your teacher is for and that’s why you have the opportunity to practice with others.

The teacher will push you hard, but they’ll also take good care of you. The people you spar with aren’t specifically out to hurt you. They’re practicing their technique, as are you! Besides, getting hurt because you didn’t block their strikes is a great way to improve your defensive techniques, right?

You’ll develop invaluable coping mechanisms.

Have you ever wondered why certain friends of yours don’t seem to be plagued with anxiety or self-doubt? Instead, they tend to approach and deal with situations with confidence and self-assurance.

That isn’t because they’re secretly deities walking around in human costumes. Rather, it’s because they’ve exposed themselves to countless difficult situations and learned to cope with the outcomes accordingly.

I’ve seen people refuse to read books that they know they’d love just in case they see a word or phrase that “triggers” them and makes them uncomfortable. Rather than exposing themselves to it enough times that it stops bothering them, they’ll run away and hide from it, thus making themselves even more sensitive to it in the future.

Risks allow us to build up resistances and grow thicker skin. Life is going to throw difficulty at all of us, so it’s a good idea to learn how to cope.

For example, whenever someone travels, there’s a risk that their luggage will be lost. It’s frustrating when that happens, but it’s not the end of the world. You learn to pack essentials into your carry-on and make do until the airport returns the luggage to you. And if that doesn’t happen, you can pick up a few replacement items to get you through.

After you’ve learned once that you can handle such a situation, it will be less likely to cause you anxiety in the future.

You know you can handle it, so why worry?

Being expansive is far more rewarding than being contractive.

When we’re afraid or hesitant, we contract into ourselves. This is where we get the description of someone “shrinking” in fear. In contrast, when we’re courageous, we expand. We literally open our hearts and minds to the potential of greatness.

There is no life without risk.

If you use a car to go shopping for groceries this week, you risk being T-boned in an intersection by a drunk driver. Do you plan on showering sometime soon, despite the risk of slipping and breaking your neck? How about eating? With every bite, you risk choking to death or having a new allergic reaction to something.

Get the idea? Absolutely every single thing you do involves risk of some sort. There’s no avoiding it, and there’s always the possibility of failure or devastation around any corner.

Many people are wracked with anxiety about the possibility of failure, so they hold themselves back from countless things that could bring them joy or success just in case things don’t work out. They don’t want to risk embarrassment, disappointment, or potential failure.

The thing is, the only way you are guaranteed to fail is if you don’t try at all.

Besides, there’s no success without failure. When we misstep at something, we try again until we get it right, and we learn an extraordinary amount in the process. Furthermore, I don’t know about you, but I’d rather risk and fail miserably than spend forever wondering what might have been if I’d actually had the courage to try.

How to take calculated risks.

The best way to deal with risk-taking is to approach it from a methodological standpoint. Sure, we’ve all done risky things at the spur of the moment, but most risks we take in life will be calculated ones we’ve considered carefully over time.

1. Do your research.

Quite simply, understand as much about what you’re about to do as you possibly can before actually doing it. The reason for this is because the light of knowledge generally dispels the shadow of fear. When you have answers and information at your disposal, you’ll feel a lot less anxiety about potential missteps. Uncertainty can never been completely overcome, but it can be minimized.

A great example would be trying rock climbing. Throwing yourself into outdoor rock climbing without any practice would be extremely high risk; however, a lower, calculated risk would be to learn all you can before you do it.

Go to an indoor climbing gym and take lessons from professional climbers. This would include learning how to tie climbing ropes properly, how to use carabiners, what type of clothing and shoes are best to wear, and what to do if x, y, or z goes wrong so you know what to do in case of an accident or unforeseen adversity.

Build up hand, wrist, and leg strength with weights and elastic bands. Practice climbing in the beginner area, and work your way up (literally). This will take time, but give it a few months and you’ll be strong and confident enough to do an outdoor climb with the help of seasoned professionals.

You’ll have an incredible time while gaining confidence in your own abilities. In fact, that confidence will spill out into other areas of your life, so the next time you feel anxiety or trepidation about a situation, you’ll remember how you overcame your worries and managed to climb a literal mountain. If you can do that, imagine what else you can achieve!

2. Determine whether the benefits outweigh the potential downsides.

Chances are you weigh the pros and cons of various risks on the regular. For example, you know how delicious that gutbuster 3000 burrito is going to be as it tantalizes your taste buds and makes you purr in gustatory delight, but how are you going to feel in a few hours? Will that abdominal trainwreck be worth the momentary deliciousness?

Do this same pro/con weighing for every risk you’re thinking of taking. Write down all the good points that you think will be associated with this endeavor, as well as all the potential downsides that may occur.

Then, if you find that the good points outweigh the bad, consider proceeding. If, however, the “this is going to end really badly” list is several times longer than the benefits package, you may want to reconsider it.

Or, if you’re like me, you might try it anyway just to see what happens and deal with the consequences as they unfold.

3. Consider all the potential outcomes.

Whenever you’re planning something—be it a home renovation project or a trip—it’s important to try to anticipate all potential difficulties. By doing so, you can determine how to deal with these eventualities and create contingency plans for all of them.

As you can imagine, a great approach when considering doing potentially stupid things is to anticipate anything and everything that could go wrong, and then envision how you’d deal with them.

I recently watched some videos of professional snowboarders who travel the world, bravely boarding down the Rockies and lower Andes in Patagonia. These guys throw themselves down slopes that could kill them if an unexpected avalanche happened, and each one of them has suffered fractures, dislocations, and concussions. They all know that each trip could potentially be their last, but you know what? They do it all over and over again anyway.

They would rather risk getting severely hurt than give up the closest sensation to flying that they’ll ever have.

4. Do the small stuff first.

This expands upon what we said about practicing bit by bit before taking on something big. It’s swimming in the shallow end of a pool while wearing water wings instead of diving off a boat into the ocean.

Just like climbing the beginner wall at the gym, you can start with low-risk/high-return ventures that can help to build up your self-confidence.

Start lifting 10lbs and doing repeated reps at the gym instead of throwing your back out lifting 100lbs. Cook a simple breakfast dish and expand your culinary repertoire one ingredient at a time, instead of risking defeat (and a potential nervous breakdown) trying to cook an entire holiday dinner for the first time.

As you grow more confident in your abilities, you’ll naturally be able to handle larger and more demanding potentialities. Additionally—and this is massive—your self-confidence will be bolstered enough that a small setback will simply be an obstacle to overcome, rather than a crushing defeat.

5. Psych yourself up.

In addition to learning all you can about the thing that you’re getting ready to risk doing, be sure to psych yourself up for it in the most positive way possible. Create a music playlist that gets you going or maybe have a uniform of some type (like a lucky Iron Maiden T-shirt) that you can wear to put yourself in the right mindset.

Focus on bringing as much positive energy to this as possible, even if you’re trembling deep down.

Some people even find that a dose of liquid courage (like a shot of whiskey) can help to boost their confidence and courage just enough to get past their fearful hesitation.

6. Feel the fear and do it anyway.

Courage isn’t the absence of fear: it’s getting on with things even though you’re shaking in your boots. You may feel scared or anxious as you’re about to do the risky thing, but you’ll feel immensely relieved after you’ve done it.

Even if it doesn’t go the way you’ve planned, you can feel a huge amount of pride and satisfaction in the fact that you didn’t let your own worries or potential failure stop you from pursuing something (or someone) you wanted.

So, it’s not a case of learning how to be fearless, but rather forging a healthier relationship with fear.

7. If it doesn’t work out, regroup and try again.

If you don’t get the job that you really wanted, it’s okay to feel disappointed. The key is not to allow yourself to fall into a pit of despair. Instead, ask the hiring team if they could give you some insights as to why you didn’t get the position.

If they tell you about shortcomings they found (e.g., problems with your resume, certain behaviors during the interview process), then you can take steps to improve them. This way, you’ll be better prepared for the next job that you apply for.

Alternatively, if they tell you that you did everything right, but the other person was just a tiny bit more qualified, then you know there isn’t a problem with you at all; you just need a bit more experience.

Similarly, if you take a risk and ask someone out, and they tell you that they’re not interested, try not to be completely crushed by it. We all have our perceptions of what people are like, but that doesn’t mean that’s who they really are. Furthermore, we don’t know what’s going on in their heads. If someone says they’re not interested, it’s unlikely that there’s anything wrong with you personally, it’s just not a great match.

See this as a blessing rather than a defeat. You two might have gotten together and had a seriously unpleasant time, only to end things on a sour note. Instead, you’ve had practice approaching someone, and you survived them turning you down!

So now you can approach a person who’s likely better suited to you and know that if they decline as well, you’ll survive that too. Best of all, when you connect with a person who’s right for you, it’ll be that much sweeter.

See this as learning to fail with grace. Kindness, courage, composure, faith, and unrelenting will can get you through the most trying of situations. You’ll learn from each and every one of them and become a better, brighter version of yourself as a result.

How to find the courage to take your chances in life:

Taking risks can be intimidating, but it’s also immensely fulfilling. Additionally, it’s likely that you already have more courage than you give yourself credit for—it’s merely been hiding behind shields of social expectations and ingrained self-doubt.

Here are a few things you can do to help you find the courage to take your chances.

Let go of fear.

As we talked about earlier, the main thing that holds people back from living their best life is fear. It’s all in your mind, and has no real power over you unless you grant it some. When you feel fear rising up, ask yourself if you know what you’re feeling is real and true. If it isn’t, then why are you afraid of it?

Seek things out for yourself, rather than taking another person’s word for it.

How often have you heard people say that they’re afraid of doing something because someone they know had a bad experience? Quite often, things that intimidate us are terrifying until we learn the truth of them. Then, the weight of the situation dissipates like mist.

Whatever it is, look into it and get practical know-how and experience. For example, many teens are terrified by the idea of driving, but it quickly becomes second nature once they’ve been behind the wheel a few times.

Try to avoid overanalyzing.

Many people hold themselves back from doing things they really want to do because they “what if?” themselves into paralysis. Think about all the things you’ve ever experienced, and ask yourself whether any of them have ever unfolded exactly the way you dreamed of.

We can never see all ends, so it’s a good idea to flow with things rather than trying to analyze and anticipate every possibility.

Immerse yourself in media that inspires you.

Listen to music that uplifts you and makes you want to look to the sky and roar. Ignore or avoid media that fills you with anxiety or lowers your self-esteem. Furthermore, don’t waste your time getting into battles with trolls online. Refocus that energy into endeavors that inspire and energize you.

Choose inspiring heroes.

This expands upon the media exposure mentioned above. If the heroes in a film or TV series you’re watching spend the entire time awkwardly flailing, stumbling, and apologizing, then find other, better heroes!

Watch or read things where the characters are brave, resourceful, and skilled rather than bumbling, hesitant, and crippled by anxiety. More Aragorn or Katniss Everdeen, less Sheldon Cooper or Willow Rosenberg.

Be true to yourself.

We now live in an era where being strong, brave, and assertive is looked down upon, while those who are timid and apologetic are lauded as role models. You can be courteous, gentle, and kind and still be very brave and fierce.

Love and courage are expansive forces, and they are also rather contagious. When people see others standing up and fighting for what’s right and true, that inspires them to get over their own fears and do the same.

Ask yourself what kind of life you want to live.

A person who risks nothing may avoid temporary discomfort or disappointment, but they’ll be guaranteed to experience an exceptional amount of regret. They’ll simply plod safely through life without any thrills, elation, or amazing stories to tell about the time they nearly broke themselves in half doing that incredible thing that was the highlight of the decade.

What kind of a life would that be? If we don’t seize opportunities that are offered to us, we deny ourselves the chance to live fully. To do this one must take risks, upset the boat, and be prepared to argue and fight if need be in order to live authentically and to defend that which is ours.

Many people tamp down their true natures so as to fit in better with those around them, but that takes its toll. If you’ve been holding back from doing the things you really love, or being yourself around others because they find you “too intense” or “too much,” then consider changing your social circle. Having to be less than what you are to make others more comfortable wears down one’s spirit over time.

That isn’t a recommendation to immediately cast aside all your friends and family members and go cliff diving without any practice, of course. The middle road is often the best option here.

Weigh your pros and cons as mentioned, take those calculated risks, and don’t be put off if things don’t go the way you want them to. Honestly, 99 times out of 100, things unfold as they should rather than how we might want or expect them to go. Furthermore, they usually end up being far better than we expected.

I’ll tell you this right now: I’ve taken a lot (and I mean A LOT) of risks in my life, and I wouldn’t be who or where I am now without them. Some had disastrous results, and I’d be lying if I said that I haven’t experienced more than my fair share of physical injuries as well as heartbreak. But each experience—even the awful ones—was a learning experience that I would never have had anywhere else.

Each of these experiences taught me incredible lessons, for which I couldn’t be more grateful. I have great memories and stories to tell, and I treasure the people I have in my life, all of whom I would never have known had I not thrown myself off the proverbial cliff. It all goes to show that taking risks can lead to joy and fulfilment that you never thought possible. You just have to have the courage to try.

“What if I fail?”
“Oh darling, but what if you fly?”

Still not sure how to go about taking risks because some part of you is holding you back? Talking to someone can really help you to handle whatever life throws at you. It’s a great way to get your thoughts and your worries out of your head so you can work through them.

Speak to a therapist about it. Why? Because they are trained to help people in situations like yours. They can help you to identify and understand the things that hold you back so that you can become more comfortable taking a risk now and then.

BetterHelp.com is a website where you can connect with a therapist via phone, video, or instant message.

While you may try to work through this yourself, it may be a bigger issue than self-help can address. And if it is affecting your mental well-being, relationships, or life in general, it is a significant thing that needs to be resolved.

Too many people who are afraid of risk try to muddle through and do their best to overcome it, but they often never really get to grips with. If it’s at all possible in your circumstances, therapy is 100% the best way forward.

Here’s that link again if you’d like to learn more about the service BetterHelp.com provide and the process of getting started.

About The Author

Finn Robinson has spent the past few decades travelling the globe and honing his skills in bodywork, holistic health, and environmental stewardship. In his role as a personal trainer and fitness coach, he’s acted as an informal counselor to clients and friends alike, drawing upon his own life experience as well as his studies in both Eastern and Western philosophies. For him, every day is an opportunity to be of service to others in the hope of sowing seeds for a better world.