In This Article
Learn how to take smart, calculated risks. Science-backed tips for decision-making under uncertainty and building your risk tolerance.
Gymnast Simone Biles knows how to take calculated risks.
In one case, that meant adding a never before landed “triple-double” to her winning routine at the U.S. national gymnastics championships. In another, it meant choosing to withdraw from the Tokyo Olympics after experiencing a mental block that put her physical safety in jeopardy.
Notice what those two decisions have in common. Neither was reckless and neither was timid. Each was a chance taken after weighing the upside against the very real downside.
That’s the skill we’re after here. And the good news? It’s completely learnable.
So how do you decide when a leap is worth it? And how do you build the nerve to take it when the outcome is genuinely unknown? Will this blow up in my face? Keep reading, because that’s exactly what the rest of this guide is for.
What Is Calculated Risk-Taking?
A calculated risk means choosing to pursue a goal whose outcome isn’t certain, but where you’ve weighed the likelihood of success against the potential downside and the odds look good.
Here’s what that actually involves:
- Thinking through the possible outcomes
- Sizing up both the upside and the cost of being wrong
- Getting a feel for how likely each one is before you commit
Any real risk-taking means leaving your comfort zone, which opens the door to bigger wins and bigger losses at the same time. Those uncomfortable stretches are also where a lot of your growth lives. Once you understand the rewards and the dangers, it gets much easier to move forward even when you can’t see the whole road.
A Risk Isn’t the Same as a Calculated Risk
A risk is anything with an uncertain or potentially harmful outcome. Risks are often unpredictable and the fallout, good or bad, can range from trivial to severe.
A calculated risk is a subcategory with more homework behind it: preparation, analysis and a deliberate effort to shrink the downside and grow the upside.
Say you’re weighing two job offers for the same gig washing windows on New York skyscrapers. One pays above-average wages but provides only the minimum safety gear. The other pays less but has invested in top-of-the-line equipment for every employee.
Both carry the same baseline danger of dangling off a high-rise. One adds financial risk, the other adds physical risk. So which do you choose?
That answer depends on factors that are different for every person. And figuring out your own answer is exactly what calculated risk-taking trains you to do.
Risk vs. Uncertainty: Why the Difference Matters
Here’s a distinction that quietly changes how you make big calls. Some situations come with knowable odds. A fair coin lands heads half the time. An insurance company can price your policy from actuarial tables. Economists call that risk: the probabilities are estimable, so you can run the math.
But most of life’s biggest decisions don’t work that way. Should you switch careers? Launch the business? Move across the country for someone? Nobody has a reliable probability for those. That’s uncertainty, a concept the economist Frank Knight made famous back in 1921 in Risk, Uncertainty and Profit1. As an MIT explainer2 puts it, the odds in these situations are unknown, unstable or not even well-defined.
So why does this matter for you? Because in genuinely uncertain situations, a precise-looking calculation can fool you. Think of it like a fortune cookie wearing a lab coat: running elaborate numbers on a future nobody can forecast creates an illusion of certainty. The figures look exact, but that precision is borrowed from data you don’t actually have.
So the move here? Stop pretending you can calculate your way to a safe answer. Instead, use judgment, think through a few plausible futures and, where you can, run a small test before betting big. Calculated risk-taking is less about nailing the odds and more about preparing for a range of outcomes you can live with.
Factors That Affect Risk-Taking
Research has linked a number of factors to how much risk a person is comfortable with. Knowing your own defaults helps you spot when you’re avoiding a smart risk out of habit rather than logic.
- Age: Generally, younger people are more risk tolerant than older people, though your appetite shifts unevenly across different areas of life. One study found that tolerance for financial risk3 drops sharply in older age, while tolerance for recreational risk falls more steeply between youth and middle age.
- Gender: That same research found gender plays a role too. Other work suggests4 men tend to apply for a job when they meet about 60% of the qualifications, while women often wait until they meet 100%. Interestingly, the reasons women gave leaned less toward doubting their ability to do the job and more toward not wanting to put themselves through a process they expected to lose.
- Personality: The book The Introvert Advantage describes how sensitivity to dopamine, the brain’s “feel-good” chemical, tends to differ between introverts and extroverts. Extroverts often chase that hit through stimulating, riskier activities, while introverts can feel overstimulated by the same situations and gravitate toward quieter ones. There’s also a personality trait psychologists call sensation seeking, defined as the pull toward novel, intense experiences and a willingness to take risks to get them5. High sensation seekers don’t just take more risks, they actually perceive the same activities as less risky than other people do.
- Culture: The norms around you shape what feels normal to risk. For example, CEOs from cultures6 that lean more risk-averse are less likely to make high-risk business moves.
- Personal history: Your past experiences quietly set your baseline. If you were a gymnast in college and now coach kids, you’ll happily attempt a cartwheel. Try one for the first time in a decade, land badly and throw out your back, and your tolerance for tumbling will plummet.
How Fear and Your Brain Shape Risk
Fear is the emotional response to a threat, real or perceived. It’s what kept our ancestors alive when a saber-tooth cat appeared on the ridge.
These days the threats are usually social rejection, the fear of failing or the discomfort of the unknown. Your emotional brain7 treats all of those as danger, and things like context, distraction and what you’ve learned from others tune how loud that alarm gets. Meanwhile your slower “thinking” brain can step in and remind you that you’re not actually in danger.
Here’s a quirk of human wiring worth knowing before you make any big call: a loss tends to sting more than an equal-sized gain feels good. The classic research on how people decide under risk, the work behind prospect theory8, found that we judge outcomes as gains or losses against wherever we’re starting from, and we weight the losses more heavily.
A quick honesty note, because you may have heard losses described as hurting “twice as much” as gains. The newer evidence is more modest. A large 19-country replication9 confirmed the broad patterns hold, but the effect is smaller than the original headline and depends a lot on how the choice is framed. So treat it as a real tilt in your wiring rather than an iron law. You’re generally more sensitive to what you might lose, which can keep you frozen in place even when the smart move is to act.
There’s a second emotional shortcut at play. People often judge how risky something is by how they feel about it, what researchers call the affect heuristic10. When you like an option, you tend to see it as low-risk and high-reward. When you dread it, the risks loom larger and the rewards shrink. That gut read leans on you even harder when you’re rushed, which is exactly when it pays to slow down.
So here’s the takeaway. You can’t delete fear, and honestly, you wouldn’t want to. But naming these biases as you feel them takes some of the steam out of the emotional resistance to a calculated risk.
11 Tips For How To Take Risks (The Smart Way)
Have A Support Team
Nobody takes a leap well while white-knuckling it alone. Whether you’re leading a business, running a house full of rambunctious kids or steering your own life solo, the right kind of support is what makes risk-taking feel doable.
- Emotional support: Risk-taking is stressful by design, because uncertainty and the chance of failure come baked in. A few supportive people in your corner give you somewhere to process the nerves, talk through your fears and steady yourself before you decide.
- Practical support: Some forms of risk-taking include making decisions in areas that you’re unfamiliar with. Bringing in outside expertise lets you gain advice on opportunities and untapped resources you may not have considered. You can also identify potential risks and how to mitigate them. Over time, you will likely gain enough understanding in some areas that you no longer need some forms of practical support.
- For example, if you decide to start your own company because you’re very good at editing YouTube videos, you may find that you need to draw up contracts for your clients. You could do vast amounts of research to become well-versed in contract law, or you may find it more valuable and economical to hire a lawyer to draw up several templates you can use.
- Accountability: Answering to someone else for your goals makes you far more likely to follow through, and the effect is strongest when you schedule a specific time to check in instead of making a vague promise.
- Diverse perspectives: Having a support team can provide other perspectives. You can make more informed decisions by hearing different opinions and asking for alternative solutions to the challenges you are facing.
Try This: Make a list of five people you trust to help you make decisions. You might email or call them and say, “I’ve been thinking about making some decisions in my life that are out of my comfort zone. I’d like to have a few people I know I can trust to bounce new ideas off of as I’m figuring this out. Can I reach out to you when I need some help?”
Reframe Definitions of Success and Failure
Success is being able to accomplish an aim or purpose. In society today, we usually identify success in terms of producing something tangible or measurable. Failure, on the other hand, is anything besides success.
Here’s the big problem with that: if success is one narrow target, then everything else gets dumped into the failure bucket. That’s a lot of territory. But by reframing how you use “success” and “failure,” you can create definitions that give you more chances to win and a far kinder view of the flops.
One option is to be more careful about what you are defining as a successful outcome. For example, let’s say you’ve never run a marathon and doing so is your new goal. If your definition of success is finishing the race, but you’ve never run more than a mile, “success” is a long way off.
If you reframe your goal to be “I’ll go running four times a week, and add one song to my playlist each day to lengthen the time of my run,” You’ve now set yourself up to have success four times a week instead of once in a few months, while still pursuing a long-term goal of a marathon.
If you audition for a lead role in a musical but are cast as a supporting character, is that a failure? Do you pack up, go home and never audition again? Well, that depends on your definition of success and failure.
Think about how these different definitions depend on your situation and affect your mindset:
- A successful audition is getting a lead role
- A successful audition is getting a role
- A successful audition is remembering all my lines and music
- A successful audition is doing my best performance yet of my monologue and solo
- A successful audition is getting up on stage for the first time in my life
If success is achieving something, failure is, by definition, everything else. That covers a lot of territory.
What if a failure, instead of meaning “didn’t succeed,” could be read as a “First Attempt In Learning”?
“Failure is not the opposite of success. It’s a stepping stone to success.”
That reframe comes from Arianna Huffington, who co-founded The Huffington Post and credits the line to her mother11. It’s a clean example of widening what “failure” gets to mean.
Try This: Think of something in your past you considered a failure. How could you reframe it as a stepping stone to success? For example, maybe you didn’t get a job you were hoping for, but that rejection motivated you to rewrite your resume to reflect better your skills, which got you a different job in the future.
Start Small
If the idea of taking risks makes your brain warp and melt over the sheer vastness of it all, take a deep breath. If this is you, you’re not alone. You can start small.
Think of risk tolerance like a muscle. Building your comfort takes time, consistency and an appropriate load for your current abilities. Nobody walks into the gym on day one and deadlifts a car. Atomic Habits recommends developing habits by simplifying the goal to a task that can be completed in two minutes or less.
For example, if you want to start running more, begin by just putting on your running shoes every day.
Here are some ideas of low-stakes activities you can consider to build tolerance for risk and the skills needed to make calculated decisions.
- Try a new hobby
- Travel to a new place
- Ask for feedback from someone you trust
- Go out to dinner at a new restaurant
- Start a conversation with a stranger
- Start a side project of something you’re considering doing full-time
- Speak up in your next office meeting
- Talk about what you want to do or achieve
- Journal about what holds you back
- Visualize what you want in great detail
- Pick a mantra to recite daily focused on growth and taking chances
- Make it a time-limited bucket list
For more ideas, take a look at Want to Change Your Life? Use These 13 Science-Backed Tips
Try This: Write down three low-stakes activities you want to try and give yourself a deadline to try them.
Define Your Goal
Now it’s time to take on a more substantial risk. Hopefully, at this point, you have some wins under your belt, either by redefining what you consider a win or increasing the number of new things you’ve tried.
With this experience, evaluate the opportunities in your life. To quote Alice in Wonderland:
Alice: Would you tell me, please, which way I ought to go from here?
The Cheshire Cat: That depends a good deal on where you want to get to.
Alice: I don’t much care where.
The Cheshire Cat: Then it doesn’t much matter which way you go.
Knowing where you want to end up is what tells you which steps will get you there. It applies to your career, your relationships, your social life and your health.
When Jeff Bezos was deciding whether to leave a comfortable Wall Street job to start Amazon, he leaned on what he called a regret-minimization framework. As he described it in a 2001 interview, “I wanted to project myself forward to age 80” and look back having minimized the number of regrets, knowing the thing he’d most regret was never having tried.
That instinct has a name in the research. Psychologists who study anticipated regret12 find that we often choose the option that protects us from future self-blame rather than the one with the best odds on paper. That can push you to play it too safe or, like Bezos, to take the leap.
So here’s the question worth sitting with: which version of me will I regret more, the one who tried or the one who didn’t? Whichever answer you can’t live with, that’s your tell.
Try This: Write down a goal you want to achieve. For example, you may want to run your own company. Is it a side gig you do in off hours or a full business with dozens of employees? List out some of the decisions you’re likely to face as you pursue this goal, especially ones that involve risk.
Get The Facts
Now that you know where you want to end up, it’s time to figure out how to get there! Remember, the difference between a risk and a calculated risk comes down to understanding your odds of success and making choices that shrink the downside and grow the upside.
So gather as much information as you can in a reasonable amount of time. Say you’re deciding whether to keep renting an apartment or invest in a home. You might weigh:
- Price (upfront, mortgage, insurance, etc.)
- Location (distance from work, school, church, gym, etc.)
- How long you plan to stay
- Upfront costs
- Flexibility in design and remodeling
- Maintenance responsibilities
- Taxes
- Importance of home equity
Decisions about changing careers, moving locations and pursuing education all have their own list of factors that need to be considered.
In business decisions involving potential investors, having a clear understanding of the finances and production numbers is crucial for success. In a “Shark Tank” study, we found that entrepreneurs who were clear about numbers and reasonable with equity split were about twice as likely to succeed—only 32% of ‘yes’ deals had math problems, compared to 64% of ‘no’ deals.
Pro Tip — Run a premortem: Before you commit, imagine it’s a year from now and the risk blew up in your face. Then write down every reason it failed. Working backward from an imagined failure surfaces blind spots that a hopeful forward plan tends to skip, so you can shore them up before they sink you.
Try This: For a risk you’re considering, write down every question you can think of, then start researching to see how many you can answer. If you want to start investing, pull the historical data on at least three funds you’re weighing. A simple spreadsheet keeps your answers in one place.
Consider Your Resources
Having a clear understanding of your resources can be the difference between a wild risk and a calculated risk. These can include time, money, support, education, talents, energy and physical assets.
For example, imagine you’re a manager of a team that is constantly overwhelmed by work demands and you are at your physical and emotional limit. Let’s take stock of your available resources:
- You may have coworkers or direct reports who have the time but lack the education to take over some of your work.
- You may see if there is enough work to justify hiring a new employee.
- Maybe there is an up-and-coming employee who is well suited to be promoted into an assistant manager role.
- You may have resources at HR to help train employees on improving time management skills to improve efficiency in the office.
- You also have all the education and training you’ve developed from your time working in this role. Those skills could be transferable to another role in the company or another company that is a better fit for your career goals and work-life balance.
For some of us, it’s easy to start listing resources and options and then tumble down a rabbit hole of endless possibilities. If that’s you, set a timer, get the big rocks on paper first and trust your gut to fill in the rest.
Try This: Think of a time you had to make a decision that had some risk to it. Write down what resources you ended up using, and also consider what other resources you had available to you at the time. You may find you had more resources and options than you realized.
Make Your Pro/Con Lists
A pro/con list can be a valuable resource for organizing all the information you’ve collected. Being able to see options side by side allows you to compare and contrast while also making it easier to identify what priorities are most important for you. It will also allow you to see patterns that might not have been apparent earlier.
You’re a college student trying to decide between two internships. After you’ve researched your options, these are your lists:
Internship A:
| Pros | Cons |
|---|---|
| Paid | Not in my area of interest |
| On-Campus: will be around friends | Housing costs for the summer |
| Regular hours | |
| Potential for job next fall |
Internship B:
| Pros | Cons |
|---|---|
| In line with potential career | Unpaid |
| Summer with family | Long commute |
| No housing costs | Have to make new friends |
| Name recognition for resume | Have to move to another state |
Which internship is better? Well, that depends on your values. If you’re someone who puts a higher value on stability, internship A seems like a good fit. If family and new experiences are higher priorities for you, internship B would probably be better.
In most cases, it’s a matter of two good options with different opportunities and outcomes. The hard part is not knowing what those outcomes might be.
Try This: Create a pro/con list for something on your mind. It could be as simple as eating in vs. going out to dinner. The more you do it, the better you’ll get at analyzing the tougher decisions using pros and cons.
Embrace A Growth Mindset
Learning from every experience, the wins and the flops alike, is one of the most reliable ways to sharpen your decision-making. A growth mindset13 is simply the belief that your abilities can be developed rather than being fixed at birth.
People who hold that belief tend to chase new ways to succeed instead of protecting an image, and large studies find that mindset interventions can increase challenge-seeking and persistence14, especially for people who are struggling or feel out of place.
One honest caveat, because the research is clear about it: those effects are real but modest, and a growth mindset alone won’t do the heavy work. It pays off most when your environment actually rewards effort and treats a smart flop as part of the process rather than a black mark.
Imagine for a moment you saw risk-taking purely as a chance to try something new and learn. The possibility of things going sideways wouldn’t be a failure, just an experiment to run and review. How would that change the way you size up your next risk?
Taken too far, of course, that mindset could talk you into ignoring real consequences. But paired with the rest of these steps, treating a risk as a chance to learn is a powerful way to keep creating new experiences.
Try This: Roleplay with a trusted friend or family member as though you have already taken the calculated risk you’re considering, and achieved your goal. Perhaps it’s asking for a raise or asking someone out on a date. How did future you grow and develop in order to accomplish the goal or take the risk?
Give Yourself Time
Once you’ve collected your information and come to your decision, give yourself permission to take a step back and mull it over.
Research suggests15 that even a brief pause on a snap decision can give the brain a moment to sort the useful information from the noise.
For bigger, messier decisions, taking a few minutes or sleeping on it does the same job at a larger scale.
On “Shark Tank,“ the sharks often pressure entrepreneurs to decide on the spot and warn them against stepping out of the room to think. The data pushes back. Our research found that of the ‘yes’ deals, 17% of the entrepreneurs stepped out of the tank, while only 5% of the ‘no’ deals did. Buying yourself a moment to think isn’t the deal-killer it gets made out to be.
If you’re already risk averse, this can easily turn from a helpful tip to a dangerous pitfall, so if you’re more likely to end up procrastinating rather than considering thoughtfully, give yourself a time limit to ponder your options.
Try This: Pick a decision that needs to be made, such as where to vacation. After gathering your information and making a list, write down your decision. Set it aside: at least 30 minutes for a small decision, but no more than 12 hours. At the end of that time, read what you wrote and if you still agree, consider the decision finalized.
Lead By Example
Employers, managers and leaders affect attitudes toward risk-taking in work environments. A leader who talks about and encourages smart risk-taking but rarely pursues calculated risks is sending mixed messages.
The co-founder of Netflix has talked about how one of his earlier companies leaned hard on process to keep people from making mistakes. His line about where that leads: “if you dummy-proof the process, you only get dummies to work there.” Over time, Netflix built its culture around open communication, transparent information sharing and an environment where smart people are encouraged to disagree out loud and take risks.
The key is to build an environment that models smart risk-taking and makes room for smart failures and honest best attempts. Remember, a risk that doesn’t pan out is often just a first attempt in learning. Real success tends to arrive only after a few strategic tries.
Encouraging and rewarding smart failures and best attempts will show employees that calculated risks are valuable and important. But there is a difference between smart failures (a calculated risk with a less-than-positive outcome) and mistakes (misguided or wrong attempts). As a leader, be able to identify and discuss the difference with your employees.
Try This: Offer a reward (such as lunch or a gift card) to an employee who took a calculated risk that didn’t succeed on the first attempt.
Think of the Benefits
It’s human nature to fixate on the scary parts. But once you can take calculated risks, the payoff is genuinely BIG.
Benefits of risk-taking include:
- New opportunities for growth and experiences
- New skills and personal development
- Changing internal dialog from “I’ve never taken risks” to “I can take risks because I’ve done it before and learned from the experience”
- Increased self-confidence, self-esteem and resilience
- Improved decision-making for repeated practice
- Developing greater innovation and creativity
- Potential for higher rewards in goals, financial gain and personal satisfaction
- Overcoming fear, building inner strength and better managing future adversity
Frequently Asked Questions About Taking Risks
What is a calculated risk?
A calculated risk is one you take after weighing the likely outcomes and the odds of success or failure, rather than acting on impulse. It carries a higher level of preparation and analysis meant to limit the downside and maximize the upside.
How do you become more comfortable taking risks?
Treat risk tolerance like a muscle and build it gradually. Start with low-stakes risks (try a new hobby, speak up in a meeting, talk to a stranger), reframe failure as a learning step, and lean on a support team for encouragement and perspective.
How do you decide whether to take a risk?
Define what success looks like, gather the facts, take stock of your resources and make a pros/cons list. Then give yourself a set amount of time to sit with the decision so your brain can sort the important factors from the noise before you commit.
What's the difference between risk and uncertainty?
With risk, the odds are knowable, like a coin flip or an insurance table, so you can do the math. With uncertainty, the probabilities are unknown or unstable, which is true of most big life decisions like career changes or starting a business. In uncertain situations, judgment, small tests and planning for a range of outcomes beat a precise-looking calculation you can’t actually trust.
Why is taking risks important?
Calculated risks open the door to growth that staying in your comfort zone can’t. They build new skills, confidence and resilience, sharpen your decision-making and create opportunities for bigger rewards in your goals, finances and personal life.
Taking calculated risks is a skill, and like any skill, it grows with practice. You won’t get it perfect, and that’s okay.
So here’s your path forward:
- Gather a support team and redefine how you view success and failure
- Exercise your risk tolerance by starting small
- Prepare for bigger opportunities by defining your goal, collecting information, weighing your resources and making pro/con lists
- Embrace a growth mindset and give yourself time to mull the decision over
And if you’re a leader, show calculated risk-taking by example and reward smart attempts however they land, always keeping the short and long-term payoffs in view.
Six months from now, you could be the person who took the leap instead of the one still wondering. Ready to feel steadier the next time you pitch a bold idea? Check out How to Be More Confident: 11 Scientific Strategies For More Confidence.