5 Risk-Taking Tips for Naturally Cautious People
Cautious people can become excellent risk-takers.
Rebecca is 39. She's managed to get through life with no trips to the emergency room or insurance claims resulting from accidents. She's never sent a spicy text to the wrong person. Her goals are usually very sensible and measured. She loves this about her nature.
However, lately she's wanted to challenge herself. She decides to practice taking more calculated, well-thought-out risks. She particularly wants to concentrate on risks where the only downside is that what she tries might not work out. She'd still like to maintain her streak of no ER visits.
Many people set goals to be more self-disciplined and have better habits. Fewer people set goals to take more calculated risks. If you're looking for a new way to develop yourself (and round out your cautiousness), try this guide.
How to Take Sensible Calculated Risks
1. Look for Asymmetric Risks
A classic asymmetric risk is one where the downside is no payoff rather than harm or loss. For example, asking a question. If the answer isn't productive, you might waste a few minutes but you could gain something important.
Asymmetric risks have little downside but lots of potential upside (or vice versa, but avoid that kind!).
People fear rejection in this scenario. Even if you make a request and get ignored or denied, that might not sting as much as you anticipate, or lose face. A story: a month or so ago, someone I'd only interacted with twice asked me to write a reference for them. It was inappropriate and I ignored the email, but I quite admired the person for asking.
When I try something small and it doesn't work, I expect to feel frustrated but, in reality, I'm often quite proud of myself for trying.
Asymmetric risks give you a lot of headroom for risks that don't work out. Even with a lot of duds and just a few hits, risk-taking is still valuable overall.
2. Understand That Risk Taking Is an Evolving Process
Risk-taking isn't just about one experience. Each time you take a risk, you gain knowledge and skill. Each time you don't take a risk, you gain nothing.
Good calculated risk takers have built this ability over time. Then, they transfer it to new circumstances.
Consider creative risk-taking. Dud ideas often lead you to a good idea. Imagine you're following a pathway marked by candy wrappers, but not all contain candy. You follow the wrappers because the ones that don't contain candy take you to ones that do.
Calculated risk-taking often works like this. Things you try that don't work point you to a better idea, one that you wouldn't have had just by sitting around.
3. Combine Your Other Skills With Calculated Risk Taking
A concept I talk about in my book, Stress-Free Productivity, is that each of us is uniquely positioned to achieve some things others aren't. We have a unique Venn diagram of skills, experiences, personality, and perspectives.
Many different skills can contribute to being good at calculated risk-taking. There is a very long tail of strengths that can be helpful. For example, I'm good at filing away tidbits of information. I tend to have good instincts for what might be useful in the future, even if why, how, or when isn't clear at the time.
I've made this point a lot: the long tail of your strengths is very important. Don't only think about your top three personal strengths. Think of your top 30, at least. Using these is one pathway to creative, calculated risk-taking.
4. Scale Up What Works
Taking small risks cautiously makes sense when you don't know if something will work. When it does work, you may instinctively want to stick with your pattern of only small actions.
Timid risk takers have an instinct to not push their luck or quit while they're ahead. Sometimes the bigger block isn't the initial calculated risk, it's continuing. For example:
- You host a small gathering for three friends, and it goes well, but a year goes by and you haven't done it again or tried it with more people.
- You obtain one item you need through an alternative to buying it new, but stop there. You don't try it with any other purchases.
- You ask to break a small rule once and your request is granted, but you don't do that in any other scenarios.
- You try an Airbnb once, but go back to chain hotels because you're not sure if others will be as good as the first one.
5. Be Open to a Different Payoff Than You Expected
A risk that doesn't pay off in the expected way might still pay off.
For example:
- The answer to a specific question is no, but the request reopens communication with someone you might've otherwise lost touch with. Further conversations are fruitful.
- A calculated risk works but isn't as fulfilling as you hoped. You realize a better way to approach it.
- Something you try out for the purpose of saving time or money doesn't save time or money at all, but has a surprise benefit. Maybe when picking up an item you purchased from Facebook Marketplace, you discover a great park in a neighborhood you've never visited.
We need good self-reflection skills to notice unexpected benefits and make the cause-and-effect links between risk-taking and these diverse outcomes.
Select an Appealing Risk-Taking Experiment
Rebecca decides to experiment with taking risks in a few ways. She tries some unfamiliar technology to see if it can help her manage a complex process better. She decides to take a cruise for her next vacation even though she's not sure if she'll like it. And she chats more with a guy at the gym, even though she's worried he might misinterpret her friendliness as flirting and that could become awkward.
What types of risk-taking might interest you? Notice where you feel a slight pull and start building that competency.
If this article benefited you, I'd love to hear how. You can email [email protected].