27 Simple Tactics You Can Use Today to Become an Intrepid Risk-Taker

Problem: We’re pre-conditioned to avoid risk even though we deal with it on a regular basis. As a result, we do poorly when forced to make a risky decision because we’re totally unprepared.

Solution: If we engineer small risks in our lives on a daily basis, we can become better equipped to deal with bigger problems as they arise.


I love taking risks. Smart ones, that is. I love to strategize and attempt to out hustle the people who tell me my ideas are crazy and won’t work. I like the feeling I get when something goes right, and I can see that I had a hand in making it so. I’ve even slowly learned to enjoy the feeling when something goes wrong and appreciate the new perspective it gives me about life.

I wasn’t always like this. In fact, it’s a fairly recent development over only the last three years or so.

Why are we normally so uncomfortable taking risks? Probably for the simple fact that we don’t know what will happen if we do. Why does that worry us? Because we usually default to assuming the worst case scenario will come true.

The Decision Computation

The human mind doesn’t like unknowns. Since it’s constantly running and processing, it can’t work with them. They screw up the system. So what does your mind do when it comes to an unknown? It makes up an answer. Where experience lacks, the brain glosses right over it and fills it in with it’s own answer for “What happens next?”

For most of us, that’s a problem because this part of the equation is controlled by our amygdale—the Lizard Brain.  When the brain comes to an unknown variable in the decision computation, it makes up a value—the worst one it can imagine—and plugs it in as if it were reality and goes on about its business.

This is the end of the line. Without even realizing it, we take a worthwhile endeavor and send it to the back of our mind, labeling it “too risky” without even realizing that the process we used to judge it was inherently flawed. The equation contained the wrong numbers and it was rigged to fail us before we even got started.

The solution, then, is to trick your brain into plugging the right numbers into the decision computation. One of the easiest ways to get started is to simply ask “What if everything goes right?” rather than the usual opposite. You’ll ask yourself the second question anyway; you have no control over it. You do have control over the first question, and the more you ask it, the more you tip the odds of following through with your idea in your favor.

Think of your brain as a big lottery machine filled with losing numbers (like most real lottery machines). Every time you think a negative thought, another losing number gets thrown in the mix. Every time you think a positive thought and ask yourself, “What if this went right?” a winning number gets thrown in the mix.

The game is rigged against you, but you have the power to turn the odds around.

The Education Barrier

It’s one thing to know how to do something, but quite another to actually do it. How do you get yourself to buy into your new knowledge and act on it? How do you overcome the dread of knowing about all the losing numbers in the lottery machine, but still take on the task of outnumbering them with new, winning ones?

The answer to that question, for me, has been self-education and experimentation—picking something uncomfortable, and then finding a way to test it in a way where success shows a good proof of concept, but failure isn’t catastrophic—mixed with intense study and observation of people and ideas that have already worked.

Slowly but surely, this builds my confidence to a level that allows me to take on bigger and better risks. Over time, the decision computation becomes rigged in my favor.

Just getting started is the hardest part, but that’s easily remedied with one simple question of self-reflection that’s really hard to face:

If I died tomorrow, would I be satisfied with how I lived my life?

Take a few seconds (or minutes) right now and really ask yourself that. There’s no way to run away from a question like that. Even if you try to lie to yourself, you’ll know the truth.

If you can honestly answer “yes” to that question, then feel free to stop reading now and get back to whatever you were doing.

If, on the other hand, the answer isn’t so clear, then perhaps its time to start working on your mind and rigging that decision computation in your favor. Maybe it’s time to start working towards getting comfortable taking risks.

This is urgent. Current overall life expectancy is 67.2 years. How many do you have left?

27 Simple Tactics You Can Use Today to Become an Intrepid Risk-Taker

Here are 27 tactics you can use right now to build your confidence and get comfortable taking a risk. The more you do and the more frequently you do them, the better you’ll feel about taking a chance. Start with just one. There are lots of options here, but don’t move on to a new tactic until you’ve completed one.

You can bookmark this list to come back to each time you need something new, or print it out and use it as a checklist. Whatever you do, just get started.

Tactic #1: Call a stranger from the phone book. (5 minutes)

Did you know it wasn’t that long ago that talking to strangers on the phone was a daily occurrence? You used to have to call the operator just to get patched through to who you wanted to talk to, and half the time you ended up being connected to the wrong person.

Now that the system is perfect, you never have to talk to anyone you don’t want to, but… do you want to do that? What if you dug a phone book out of a recycling bin, flipped to a random page, and dialed a number? What if someone answered? What if you told them why you called and asked to talk for a minute?

What’s the worst that would happen? Dial tone, that’s what. But your confidence will get a booster shot.

Tactic #2: Ask someone on a date. (15 minutes)

For some reason, we hold rejection as one of the most terrible things that could ever happen to us, but what if you looked at it as an incredible opportunity instead? What if you embraced the idea of rejection therapy?

Rejection is like most things in life, the more we get of it, the less we care about it. S/he said no? Great, we’re on our way to making the daily quota! Who’s next?

How many dates have you ask for today?

Tactic #3: State your unfiltered opinion. (1 minute)

Years of political correctness and charm school have beaten it into our heads that we ought not ever say a thing that might offend someone else. I don’t think the intention was to squash any semblance of a unique opinion, but that’s more or less what it’s done. Yes, it’s our job to raise the level of discourse, but not at the expense of individual thought.

The next time you have something important to say, but you’re not sure how it’ll be received, say it anyway. This one comes with consequences, but the temporary pain up front is more than worth the piece of mind that comes with knowing you never have to betray yourself again.

What do you feel strongly about?

Tactic #4: Speak up when you see something wrong. (1 minute)

There are things that are technically wrong, and things that are just plain and simple wrong. If you want to keep your nose out of that first category, be my guest, but never let your own discomfort stop you from standing up for what’s right in the face of what isn’t.

Start small. See someone littering? Call them on it. Did that guy down the street just kick his dog? Make a scene. Standing up for what’s right is called “integrity.” You must have it.

What injustice can you stand up to today?

Tactic #5: Take a last minute trip to somewhere you’ve never been. (Variable)

Before you travel, the world feels big and scary. After you travel, it still feels big, but the scary part goes away. That’s what we’re after.

Travel is fatal to xenophobia, and the more places you go, the more you start to realize we’re all the same no matter how different we look or behave. Booking a last minute flight to somewhere strange is also a great exercise in learning to make decisions quickly and deal with the consequences. Your trip won’t be a relaxing vacation, but you’ll come home with more than some chintzy souvenir.

Where will the cheapest airfare take you today?

Tactic #6: Try to speak a foreign language with a native speaker. (60 minutes)

You don’t have to go far to do this. If you live in any city with more than about 500,000 people, you ought to be able to find a community that natively speaks something other than English.

Find a translation dictionary online (here’s a good one), learn 10 useful phrases like “Where’s the bathroom?,” “I’ll have a veggie burrito,” or “Your dog just pooped on my shoe” and go make a conversation.

Do this once a week and you’ll learn a new language, get comfortable with frustrating conversation, and probably end up playing checkers once a week at the local community hall with all your new friends.

What language communities exist where you are?

Tactic #7: Ask for something you don’t think you could get. (10 minutes)

This is another take on the rejection therapy game. Being told “no” is one of the greatest, most liberating feelings ever because it means that you actually asked, got an answer, and can now focus your energy elsewhere rather than worry about the answer you might get if you ever got the nerve to ask.

It’s easy to implement, too. Just think of something you could ask someone else for that would be meaningful to you. The only requirement is that you have to believe they’ll say no. You rarely get what you don’t ask for in life, so best to make too many requests than too few.

If you need help getting started, just ask me for something. I’ll probably say no, but that’s kind of the point, isn’t it?

Tactic #8: Give an impromptu public speech. (15 minutes)

I’m not sure when we decided that speaking in public was almost as scary as snakes, but it doesn’t really change how ridiculous that is. To tell the truth, I don’t think that anyone is afraid of the public as much as they’re afraid that their own ideas are no good.

And what better way to test them than with an impromptu public speech. Hey, if that nutjob that stands in front of your office building preaching scripture 16 hours a day can do it, can’t you?

Go to the other side of the street, stand on a curb, and tell the world something important. Most people won’t listen. But what if a few do?

What do you have to tell the world? Where can you tell it?

Tactic #9: Write down your biggest goal and take one step towards it. (60 minutes)

Dreams are not the same as goals. Dreams are something you fantasize about, and goals are something you actually work towards.

Take thirty seconds (your first impression is probably right), and write down the biggest dream you have. What would you love to accomplish? Now, what can you do in the next five minutes, without relying on anyone else, to take one step towards it and turn it into a goal?

Your first step is the most courageous. Each one after that gets easier and easier.

What can you take one step towards today?

Tactic #10: Show your art in public. (90 minutes)

The art we create, whether it’s a painting, a piece of music, a poem, or something else entirely, is really personal and the common instinct is to hide and protect it. If you put it on display, it could be criticized or misunderstood.

If you keep it to yourself, that will never happen. Of course, it’ll never be recognized or praised, either. In fact, it may not even be art at all because the purpose of art is to change how people think about something. If no one sees it, no one is changed.

What creation of yours can you put on display? Where can you show it?

Tactic #11: Try something you’ve never done before. (Variable)

I firmly believe this ought to be a mandatory action for every one every single day, but until I’m the supreme ruler of the world (vote for Tyler in 2020!) let’s just focus on the two of us, shall we?

Here’s the deal, I promise to try something I’ve never done before—no matter how small—every single day of my life and tell you about it right here. You’ve got it a bit easier because you don’t have to tell anyone. You just have to do it.

What sounds interesting? How can you get started today?

Tactic #12: Take on a physical challenge you’re unable to complete. (10 minutes, several times a week)

Last year I did something called the 100 Pushup Challenge. I don’t particularly care about pushups or how big my arms are; I did it because I thought I couldn’t. Interestingly, about two weeks in, I’d changed my mind. Nine weeks after that, I did 100 pushups. How about that?

It’s pretty amazing how far your idea of “possible” can expand once you start something. You don’t need to be able to see the finish line. You don’t even need to believe, at first, that you can finish at all.  Believing that you can just get started is enough. You’ll figure out the rest as you go.

What’s your “100 Pushup” challenge?

Tactic #13: Negotiate over something. (30 minutes)

Haggling, negotiating, bargaining—whatever you want to call it—is only uncomfortable because you’re doing it wrong. A good negotiation feels great, and the results are almost always worth it.

To get what you want, you have to ask for it. In this case, ask for more than you want, then be reasonable and negotiate down to just slightly more than you want. This is a skill that will serve you well your entire life.

Who’s got something you want? What’s your opening offer?

Tactic #14: Publicly state your biggest goal. (1 minute)

If you have trouble holding yourself accountable for the things you want to do, the best solution I know is to make the whole world your overbearing boss. Go out on a limb and tell people what you want to do and why you want to do it. Some will call you crazy, some will brush you off, but some will encourage you and check-in on your progress.

Publicly stating my own biggest goals has spurred me to pursue them much faster than I ever would have without the accountability, and it only takes getting over that first moment of fear to do it.

What’s your biggest secret desire? Who can you tell it to?

Tactic #15: Make a piece of art and try to sell it. (240 minutes)

Art is personal, it’s intimate, and it’s highly meaningful to the person who creates it. That’s why trying to sell it can be one of the most challenging tasks you ever take on.  If you can get comfortable doing it, though, you’ll have sidestepped one of the biggest hurdles any creative person ever faces—standing up for the value of your work.

A good way to avoid the discomfort that comes with this type of exercise is to research what people are willing to pay for work like yours and set the price that way rather than attaching the price to your own idea of what it should be. That’s a good way to price anything, actually.

What can you create today? How much will people pay for it?

Tactic #16: Talk to a stranger on the street. (2 minutes)

How many times a day do you silently stand in line at the grocery store, post office, bus stop, etc. and never so much as acknowledge the people around you? Maybe you give a slight head nod or brief smile and go on about your business.

What if the next time, instead, you looked that person right in the eye and said “Hi, my name is ______________. Nice to meet you.” Maybe you’d get a brief hello or nothing at all. Or, maybe you’d get an interesting conversation. It’s a crapshoot, really, but what’s the worst that could happen? Why not take five seconds to try it?

How can you break the ice today?

Tactic #17: Tell someone you appreciate them. (3 minutes)

Maybe I’m the only one with this problem, but I have a hard time expressing my gratitude to other people, especially if it’s directed at them. There’s something about an exchange like that just makes me uncomfortable, like I won’t be able to communicate it clearly. Of course, that’s why I made a commitment to myself to do it more often—at least once a day.

Showing your appreciation for someone is a powerful act that strengthens any relationship, but it’s not always the most comfortable thing to do. Make a commitment to yourself to do it on regular basis and see how much confidence you gain and how many people you affect.

Who’s done something great today? How can you let them know you noticed?

Tactic #18: Give more than you can afford to charity. (10 minutes)

I’m becoming more and more a believer in the idea that the generous have more to give. Charity is not just for the rich; everyone has something to give. Try taking it a step further and making it hurt a little bit the next time you give.

Giving away more than I think I can afford always makes me nervous in the moment. Writing that check or clicking that “submit” button gets my heart pounding a little bit, but I’ve never once regretted it.

Who’s worthy of your support? How can you go the extra mile for them?

Tactic #19: Give away something that’s special to you. (10 minutes)

It hurts to give up something special, but it’s not so bad if the result is gaining something even better. It’s really funny how we become attached to material things, and breaking that bond is a big step towards learning to take risks. When you don’t fear losing something you don’t need, many more things become possible.

What do you treasure, and who would treasure it even more than you?

Tactic #20: Talk to a homeless person. (10 minutes)

Every single one of us comes from the same place. On some level, we all want the same things for ourselves, whether we’re royalty or living in a refrigerator box behind the Seven-Eleven. The system we’ve built makes it easy to stay within our own little socio-economic circle, but there aren’t really any rewards for doing so, just comfort, which is really no reward at all.

The next time you see someone down on their luck, try striking up a conversation. They’ve been cast off by the rest of society, but that doesn’t mean you have to ignore them. Look at every conversation you have as an opportunity to learn something new.

How can you go outside your circle and strike up a conversation today?

Tactic #21: Make a decision based entirely on your gut feeling. (0 minutes)

If you’re the type who overanalyzes every decision—a malady I readily admit to—try making one with no analysis at all. Instead, decide entirely on your instinct. It doesn’t have to be a big decision, at least not yet.

The thing is, your first impression of an idea is usually right—not always, then it wouldn’t be a risk—but usually. At least 90% of the times I overanalyze something, I end up coming to the same conclusion I did when I first conceived it. Try it out for yourself.

What have you been debating about for too long? What feels right?

Tactic #22: Learn about a religion you don’t believe in. (180 minutes)

In certain strategic situations, cultivating ignorance can be a good thing. When it comes to understanding your fellow man, it isn’t. Religion can do good things for people, but where it’s patently flawed is that it typically prescribes one righteous path and all those that go another are damned. This idea becomes so ingrained in your identity that learning about a competing belief becomes threatening to your own—a forbidden fruit, so to speak.

But people of the world believe different things for different reasons and knowledge is never the enemy, testing your beliefs is never harmful, and understanding competing views can never hurt you. Perhaps they’ll strengthen your resolve in your own.

What belief system scares you the most? What would you like to learn about it?

Tactic #23: Admit your greatest inadequacy to yourself. (5 minutes)

Our weaknesses are what we spend the vast amount of our time and energy running away from in life. Trying to hide them and shy away from addressing them is an exhausting battle, but it’s one we fight every day because we don’t want anyone to know we’re not perfect.

But no one is perfect; you already knew that. So why do you have to be? Admitting your own inadequacies to yourself and even embracing them is terrifying at first, but then it’s liberating because they no longer have power over you. Your energy is now free to work on something more productive.

Here, I’ll start: I’m awful at maintaining relationships.

Your turn. What’s your biggest weakness?

Tactic #24: Admit your greatest strength to yourself. (5 minutes)

On the other hand, admitting and accepting your greatest strength can be just as scary because, well, what if it’s not what you want it to be?

The bigger risk, of course, is a life spent trying to squeeze into a shoe that doesn’t fit. Once you accept that you’re great at something, even if it’s not what you think you want to be great at, you can move onto the next step, which is using that strength in a way that suits you. The possibilities are practically endless once you get real with yourself.

What do you excel at, even if you don’t enjoy it?

Tactic #25: Start a business. (24 hours)

Do yourself a favor and forget everything you’ve learned growing up about how risky it is to start a business. It’s only a big risk if you do it wrong. There are so many tools and opportunities these days to start a meaningful, risk-free business that it almost doesn’t make sense not to.

Identify one skill you have that others ask you for help with, and then start charging for it. Focus on the essential and avoid every single cost that doesn’t directly translate into more money in your pocket. You’ll have a thriving side gig before you know it. And once you’ve created something like that, almost any risk will start looking like child’s play.

What strength do you have that others would pay for?

Tactic #26: Do something you’re unqualified for. (Variable)

In his book, The Four-Hour Work Week, Tem Ferriss revealed something that I think all of us know, but never admit to ourselves: It’s easier to win something really big than something mediocre because there’s less competition.

Most people are happy (or very unhappy) to set goals for themselves that fit right within the range of what they think they’re capable of. Since most people are average, most people set average goals. Therefore, there’s an incredible amount of competition to be recognized for something mediocre.

On the flip side, hardly anyone takes on the really big, audacious goals, so those that do are rewarded handsomely for it.

What feels too big for you to achieve? How are you going to get started today?

Tactic #27: Start a project you don’t think you can finish. (Variable)

When I started Riskology.co, I had a terrible track record for starting and stopping projects. At the beginning, I thought this would be another project I’d abandon as well. Now, I’m pretty happy that I let myself take that chance and start anyway.

When it comes to doing something really big, you won’t be able to see the finish line from the start, even if you know where it is. Never stop yourself from trying something new just because you’ve failed before because what’s another failure, right? Just another notch on the belt. But what if it turned into something great?

What have you been meaning to start? What if it didn’t matter how long it took to finish?

Feel free to add your own tactic to the list in the comments section.


This article was inspired by Adam Baker of Man vs. Debt and Corbett Barr of Think Traffic. Pay them a visit; it’ll be worth your time.

Image by: toettoet