How to take calculated risks without letting overthinking stop you.
Stop looking for the perfect choice.
The ability to take calculated risks is one of the most important skills you can learn.
Whether it is in: Your life. Your career. Your business.
There will always be important decisions with risks involved, making it essential to pick the best choice.
However, when faced with these types of decisions, it is easy to overthink. We obviously don’t want to be wrong, but there are so many variables to take into account that it can feel impossible to pick the right option.
And honestly, I struggled to take risks as well.
I would constantly weigh the possibilities, and could never make up my mind.
But after a while, I decided I had enough of it.
So I did some deep research and after weeks of trial and error, I was able to build a simple system to fix it.
What I am about to show you helped me take the correct risks while avoiding overthinking.
Let’s dive in right away.
Why we overthink when we take risks
To understand how to fix the problem (overthinking) we first have to understand why the problem even exists.
And the reason we often make the wrong decision or overthink a specific risk is because of the way our brain works.
Let me explain.
Our brain is affected by a concept known as Loss Aversion.
It wants to avoid losing at all costs, and that’s the problem.
When we are faced with a risk, there is always a possibility that we can lose.
So your brain starts overthinking:
“Should we try to build the business? No, we could waste our time and money. But if we do nothing, we could miss out on a lot of money. What if I build the business this way? But then this could happen, and then this, and that, and…”
You get the point.
It constantly tries to find a solution with 0 possibility of losing, which doesn’t exist.
To fix this, you have to force your brain to acknowledge that failure is a necessity and will not ruin your life.
Here’s how:
The 3-step strategy to take risks without overthinking:
The 2-questions framework.
The first step is to ask yourself 2 questions. These questions are made to ask your brain: “Whether you fail or lose, can you potentially get something out of this?”
We do this to force your brain to acknowledge that failure isn’t actually failure. It is like learning in a different way.
When buying a course, you exchange money for knowledge.
It’s the same thing with failure, but you are simply exchanging time with experience instead.
Here are the questions (we will use the answers in the next step):
Question 1:
“If this project fails, can I survive the loss, and will the lessons I learn make up for the failure?”
Assume you will fail. Don’t ask if you will fail; ask if you can afford to lose when it happens.
This tells you if the consequences can actually ruin your life, or if it simply a small inconvenience you can easily recover from.
And if you lose the time or money, but the data, experience, and skills you walk away with are equivalent to paying for a valuable real-world course, your downside is safe.
You aren’t actually losing; you are just paying for an education.
Question 2:
“If this actually works, does it create a meaningful advantage, teach me a valuable skill, or open a door I didn’t have yesterday?”
Not every risk needs to change your life overnight. It just needs to help you make progress.
If succeeding makes your tomorrow undeniably better than today, the potential gain is genuinely beneficial.
Now let’s use the answers:
The Decision Process to Take The Right Risk.
After you have answered those 2 questions, all you need to do is put the answers in this framework.
With it, your decision will instantly be made for you:
No / No (The Stupid Risk): If it will actually hurt you if you fail, and the potential gain is tiny: Walk away. Taking this risk would be useless (and kind of stupid)
Yes / No (The Procrastinator’s Trap): If you fail and you don’t actually lose anything, but the reward is meaningless: Don’t do it, you will just waste your time on something that can’t move you forward.
Yes / Yes (The Best Move): If you can learn something when you fail, and the best-case scenario helps you make progress: Do this immediately, you literally cannot go wrong with this choice.
No / Yes (The Particular Case): If the potential reward is huge, but when it fails, you lose something important: Don’t do it, you’d be better off doing something better, rather than take this 50/50 chance.
However.
For the Particular Case, if you feel that you have very strong odds of actually winning this (80%+ chances of success), you can take the shot.
But if you have to think about it for a while, do some long research, and make some calculations for it. Your odds are not good enough and you should be aiming for something else.
The Anti-Overthinking Hack: The 3-Second Rule.
Finally, if your brain unfortunately loves to overthink things, you must apply the 3-Second Rule to this entire filter process.
This rule is: If you have to think about the answer to either question mentioned above for more than 3 seconds, the answer is automatically NO.
If you have to debate whether the lesson is worth the failure or if succeeding actually moves you forward, it very likely doesn’t.
A true great move is obvious the exact second you look at it.
What you need to keep in mind
Overthinking comes from fear: Your brain hates losing and searches for an option without risk (that doesn’t actually exist).
Reframe your failures: Treat a failure like paying for a course: you are simply exchanging time or money for valuable knowledge.
Ask two simple questions: “Can I survive the loss and learn from it?” and “Does succeeding actually move me forward?”
Use the 3-Second Rule: If you have to hesitate on either question for more than three seconds, the answer is automatically no.
You don’t need a guarantee that everything will work out perfectly, and you definitely don’t need to spend weeks overthinking.
Once you know that a failure won’t ruin you and a success will push you forward, you are ready to make your move.
Stop trying to predict the future perfectly, and go take your shot.
You just learned one strategy.
But maximizing your progress requires an arsenal of them.
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This maps almost exactly to how I coach players who won't commit to a shot at the net. They see two options, third shot drop or drive, and they freeze because they're trying to guarantee the outcome instead of just picking based on whether they can live with the miss. The 3-second rule is basically what I tell students about a dink decision. If you're still thinking about it, you've already lost the point.
Charles, curious if you've ever applied this to something physical, like sports or fitness, where the "failure" is more immediate than a business decision.
This is a very interesting article. The concept that comes to mind after reading it is amor fati. Let's make mistakes, because only they give us real value. Taking action has no downside. Maybe we lose our nerves, maybe we lose money on an investment, maybe we lose friends, but in the long run we gain the lesson that comes from our mistakes. By not repeating them, we gain something that stays with us for life. We must experience small, medium, and even major failures, because they are what shape our growth, not academic studies or tens of thousands of dollars spent on education. What mistakes can you make there? What mistakes can you make that are different from your peers so that you can discover the value you'll one day be able to offer others and earn a living from?