Every day, we roll the dice on a series of small risks.
We throw money into micro-investing apps when there’s every chance of losing it all when the next global disaster strikes.
We get into elevators when there’s no guarantee we won’t get stuck on level 3 with that gym rat who’s allergic to deodorant.
We get behind the wheel of a 4000-pound metal machine and hurtle down the road at 70 miles an hour. Heck, we even climb into cars of complete strangers, crossing our fingers that they’re not Uber-talkative.
We happily do all these things without giving them a second thought.
Because, if everyone else does them — they must be safe, right? Most days, we readily put our trust in machines, systems, and other people.
But when was the last time you took a bet on yourself?
That is, made a big and scary decision, and backed your own ability to figure it out if it all goes to sh*t.
Whether you’re finally starting that side hustle, moving across the world to your dream city, or asking out that cute stranger… it’s scary to take a leap into the unknown.
We tend to jump straight to the worst-case scenario when contemplating taking those potentially life-changing risks.
“What if my crush turns me down and blasts me for my cringe pick-up line in a viral TikTok?”
“What if my business completely flops and I end up $30,000 in debt and living in my mom’s basement?”
“What if NYC turns out to be more like I Am Legend than your favorite episode of Friends!?”
These fantasies might sound crazy, but they appear for a reason. Our brains crave certainty and constantly search for patterns. We’re not well equipped to deal well with ambiguity. It’s safe and cozy in our comfort zone— and that’s exactly where our brains want us to stay.
But, exciting, life-changing things seldom happen in our comfort zone.
Look at any person living an extraordinary life and you can almost guarantee their rise to success started by taking a risk — even a small one.
Why it’s important to take risks
Risk is all about taking a leap into the unknown and venturing into uncharted territory. Sure, there are adrenaline junkies who skydive from buildings and bungee jump from helicopters for the pure thrill of it. But, for the rest of us mere mortals, some risks are worth taking for one simple reason: What’s on the other side is better than our current reality.
That applies to creative risks, too. Many of your favorite products, songs, films, and art simply wouldn’t exist if the creator didn’t say to themselves, “Ah f*ck it, let’s just see what happens.” That includes the device you’re probably reading this on.
If you met Steve Jobs in 1985, you might have assumed that his risk-taking ways led to his downfall.
At the time, his innovations at Apple were groundbreaking but financially unsuccessful. Creating the first-ever computer with a graphical user interface wasn’t enough to prevent him from getting fired from his own company.
What would you have done in Jobs’ position? Maybe you would have counted your losses and thrown in the towel? That wasn’t his style. Shortly after getting ousted from Apple, he invested $12 million of his own money to start a new company called NeXT.
And guess what? That company flopped too.
But things soon came full circle. Without Jobs, Apple became stuck in what economists call the “Innovator’s Dilemma” — instead of investing in new technologies that disrupt industries, they simply sustained the status quo (i.e. they played it safe).
Steve Jobs’ leadership, vision for emerging technologies, and ability to stomach massive risks eventually paid off. After some lengthy negotiations, Apple welcomed his return to the company. The icing on the cake? They purchased NeXt for $429 million.
This kind of risk-taking is now a big part of Steve Job’s legacy at Apple. Through his early failures, Jobs became a master at taking the right risks.
The fact is: if you want to change the status quo — in art, business, or your life — you gotta risk it for the biscuit.
But, if you’re not accustomed to putting yourself or your work on the line this can feel like putting your nervous system in a blender.
So, if life has felt monotonous lately, and you’re ready to get out of a rut, here’s how to get comfortable with being uncomfortable.
How to get more comfortable with taking risks
Determine your risk tolerance
Much like coffee orders and credit scores, not everyone has the same risk tolerance.
There are a plethora of different factors that determine how comfortable you are with taking risks; from your personality and age to your upbringing and past experiences. Some people are also wired to be more impulsive than others (for example, people with ADHD).
Of course, you can increase your risk tolerance over time by slowly building up your exposure. But it can be helpful to get an idea of your baseline threshold, so you know where you’re starting from.
If you’ve ever had a 401(k) plan or other investment, you’ve probably filled out a risk tolerance questionnaire. Asking yourself similar questions can help you get a gauge on how comfortable you are with taking risks in life in general.
Generally, risk tolerance consists of two key dimensions: Risk capacity and risk appetite.
Risk capacity refers to how much risk you can afford to take on. Some questions to ask yourself here include:
- How long can I comfortably pursue this goal, while seeing absolutely no return?
- What is the worst-case scenario if I take this risk and things don’t work out?
- If the worst-case scenario happens, how quickly can I get back on my feet?
Meanwhile, risk appetite refers to how much risk you’re willing to take on to achieve your goals. Ask yourself these questions:
- What am I prepared to sacrifice in order to achieve my goals?
- Would I still be willing to take this risk if there was only a 50% chance that things would go my way?
- What about if there was only a 10% chance? Would I still be willing to try?
But can these hypothetical questions about risk actually help us make decisions in the real world?
In a study from the American Economic Review, individuals participated in both low-stake and high-stake lotteries. Some people were asked to play with real money, while others played hypothetically. In both real and hypothetical scenarios, most participants chose the less risky path.
So, considering these questions should give you a pretty good idea of whether you need to push the envelope a little more.
Think big, start small
The research on risk-taking shows that overall, we’re a pretty risk-averse society. There is, however, one notable exception: Entrepreneurs.
These innovators are a rare breed, who not only embrace taking risks, but actively seek them out.
In a study from the Cambridge Innovation Center (CIC), researchers found that entrepreneurs showed the greatest tolerance for risk. They also showed the greatest self-efficacy, internal locus of control, and capacity for innovation, compared to non-founder CEOs and employees.
Richard Branson is the quintessential example of the daredevil entrepreneur. Not only does he take big (calculated) risks in business, but he’s notorious for publicity stunts like jumping off buildings, racing powerboats, and chartering hot-air balloons.
But you don’t have to partake in death-defying acts to channel your inner entrepreneur.
One interesting finding from the CIC study showed that entrepreneurs have the greatest tolerance for risk, even when it came to small bets in a prize lottery.
If you want to take risks like an entrepreneur, it’s best to start small:
- Invest $50 into a micro-investing app instead of YOLOing your entire paycheck into crypto
- Post a painting on Instagram instead of moving to a cabin in the woods to become a reclusive artist
- And maybe strike up a few conversations with strangers on the street before nominate yourself to give a talk in front of hundreds of people
Prepare for the worst
The reality is, most of us don’t deal with life-or-death stakes on a regular basis. Often, we’re just putting ourselves or our work out there, or spending more money than we’re comfortable with.
What’s the worst-case outcome in these scenarios?
Usually, it’s something like: Failure, judgment (from others, or ourselves), or negative criticism. But you’re probably not going to actually die if something doesn’t work out.
Make no mistake, it can feel terrifying, but, in this day and age, most of us have the resources, safety net and support system to deal with potential or perceived rejection if that happens. We can bounce back.
So, it can be helpful to consider: “What is the absolute worst that can happen if I take this risk?” And to practice getting comfortable with that reality.
Entrepreneur and self-proclaimed “human guinea pig” Tim Ferris, runs an experiment every month called “fear setting.” This exercise is inspired by the words of Stoic philosopher Seneca:
“Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: ‘Is this the condition that I feared?’”-Seneca
The idea is to define the worst-case outcome in your scenario. And then to actively immerse yourself in that situation.
Say you’re worried about your business idea failing, and ending up with no money. You might practice living off $10 a day by eating simple and affordable foods. Hell, if you’re up for it, you could even pitch a tent in the woods to cut yourself from the comforts you’re used to.
Often, you’ll find that the “worst” is actually pretty tolerable.
Now, you don’t necessarily have to adopt a lifestyle of voluntary homelessness to do the fear-setting exercise. Sometimes, just envisioning the worst-case scenario is enough to make you realize that the risk isn’t as bad as you think.
Have a safety net
You might have heard the expression “Leap, and the net will appear.” And that might be true in some situations. But, do you really want to find out the hard way, by face planting straight into the ground?
Forgoing a backup plan can sometimes breed a certain type of resourceful hustle where you have to make it work. But, desperation can also lead us to make crappy decisions and do things we’ll later regret (like selling our mint-condition foil Charizard).
Having a safety net or a Plan B doesn’t make you a coward. It makes you strategic, and allows you to make better decisions knowing you have something to fall back on.
Maybe your safety net means saving up six months of living expenses before you quit your job to go full-time in your business? Or, making sure you have a crash pad in your hometown to return to, before selling all your possessions and moving to another city?
Having a safety net will allow you to take risks and make decisions with confidence and clarity.
Calculate the risks vs rewards
Even the most fearless entrepreneurs don’t take crazy risks just for the thrill of it. Usually, they take the leap after deep analysis to see if the possible benefits outweigh the potential risks.
Successful entrepreneurs take calculated risks — and so should you.
If you’re considering a risky gamble, try running a cost-benefit analysis first. Tim Ferris’ “Fear Setting” process comes in handy here, too. He recommends not only considering the pros and cons of taking the risk, but also the potential cost of inaction.
So, say you’re thinking about quitting your job to start your own business. You might draw up your cost/benefit analysis into four quadrants, that look like this:
The cost of inaction:
- Staying in a job I hate
- Only two weeks of vacation each year
- No work/life balance
- Setting a poor example for my kids
- I’ll always wonder “What if?”
The benefits of inaction:
- I get to stay in a job I’m comfortable with
- Nobody will judge me if I stay
The cost of action:
- It’ll take time and energy
- I might go into debt
- I’ll lose my health benefits
The benefits of action:
- Much higher earning potential (in the long run)
- I’ll get to work on something I’m passionate about
- I’ll get to work on my own terms
- I can make a bigger impact in the world and my place in it
In this scenario, it’s pretty clear that the potential benefits outweigh the perceived risks for this particular individual. So, if they’ve put their safety net in place and they have all the information they need to make a calculated decision, it makes sense for them to take the leap.
Create a prototype
There’s a lot we can learn about calculated risk-taking from the world of design thinking. Otherwise known as human-centered design, this is an iterative process used to facilitate creativity and innovation.
It takes a hands-on, 5-step approach to tackling real human problems:
The “prototype” step is of particular importance for us here.
Designers don’t build perfectly polished products or services and release them into the world, hoping that someone will buy them. They create an MVP (minimal viable product) — a low-fi and often fairly crude representation of their potential solution. Then they test their prototype with a real sample of customers as they seek feedback, iterate, and test some more.
One of the best things about this approach is that it reframes failure.
At this stage, failure isn’t something to be feared or avoided. It’s almost the goal.
Designers are purposely trying to break their prototypes, because in doing so they get closer to the final, best version of the product. You can’t find out what’s working until you determine what’s not.
You can use the same approach to get more comfortable with taking risks in your everyday life. Rather than looking at the first step in your plan as a finished product, think of it as a prototype.
Perhaps your goal is to quit your job and work full-time as a musician.
Your first prototype might be to tour with a band you love as a roadie, and volunteer to jump in on stage to support from time to time (hey, it worked for Tupac!). If that doesn’t get you where you want to be, you might iterate by releasing some of your own music on Spotify, to help people take you seriously, and show the band what you can do.
If perceived failure is your worst-care scenario, the prototyping mindset can help you take that fear off the table. Because once failure becomes a part of the process, it won’t be as scary as it used to be.
No risk, no reward
A life without risk is a safe one, but it’s also a boring one. It’s a life without innovation, novelty and growth. In other words, all the things that add meaning to our existence, and allow us to build a legacy.
And when you really think about it — you’re already taking risks everyday. You regularly put your faith into forces outside of your control. And you’re still here.
So, you may as well direct some of those gambles into the safest investment you’ll ever make — your own happiness.
It’s not always going to be easy — in fact, it’ll probably be terrifying. But taking small steps outside your comfort zone more often can normalize the discomfort and broaden your horizons to possibilities you never imagined before you took the leap.
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