top of page

When Is It Ok To Take Risk? - Art Of War Strategy

  • Writer: by J. Khoo @ Mr Art of War
    by J. Khoo @ Mr Art of War
  • Jan 1
  • 6 min read

Updated: 2 days ago

Is It Ok To Take Risk? - Art Of War Strategy

In life, we will face challenges and also opportunities.


But it may comes with risk of success or failure.


The question is, should you take the risk? Or should I just let the opportunity pass?



When is it okay to take risk in life, work or business?


My answer is, it is OK to take risk if you have a strategy.


Let's explore the psychology of risk and the solution to minimize risk through,



This is the most famous Art Of War book that was written 2500 years ago for kings and generals, by Sun Tzu. It is sec/retly used by leaders and CEOs today.


Most of the time when people have conversations about taking risks, the discussion frequently focuses on a common concern: What if I fail?


This question shows the deep worry a lot of people feel when they have to step out of their comfort zones.


Having fear is human nature and it is OK!


It is good to have fear. Fear keeps you alert and makes you cautious of every decision you make. It makes you question every single move and observation.


Having no fear can sometimes be seen as reckless and making decisions based on chances. Lets discuss...



The Risks of Business and Personal Ventures


Business Risk:


For example, when you're an entrepreneur diving into a new business project or starting a new company, you need more than just money—you're also putting in a lot of time and personal effort.


If things don't work out, it's not just about losing money; it can also hurt your professional reputation and shake your confidence.



Personal Risk:


When it comes to personal risk, people might decide to try out a new career, move to a different city, or invest in personal growth opportunities, all of which come with their own uncertainties and potential outcomes.


For instance, moving to a new city for a job can open up a lot of opportunities but might also leave you feeling isolated and facing the challenge of making new friends.


Likewise, putting time and money into education or training can boost your skills but doesn't always guarantee a payoff.


The fear of failing in these personal adventures can make you hesitant to step out of your comfort zone, which can ultimately hold back your personal growth and fulfillment.


The Balance of Risk and Reward


The decision to take risks is a balance between risk and reward in business and personal life. It can be tricky, but it’s key to making smart choices that fit with your long-term goals.

How then do you balance risk and rewards? Let's look at calculated risk and being reckless.



Calculated Risk-Taking vs. Reckless Behavior: Understanding the Difference


However, it is crucial to distinguish between calculated risk-taking and reckless behavior.


A person who takes risks thoughtfully and with awareness of the potential outcomes is fundamentally different from someone who acts recklessly.


A calculated risk-taker understands the implications of their actions, weighs the pros and cons, and is genuinely concerned about the possibility of loss.


A risk-taker has a mindset focused on minimizing negative consequences while maximizing the potential for success.

In contrast,


A reckless individual disregards the potential dangers, acting impulsively and often making decisions based solely on chance rather than strategic thinking.

Is it OK to take risk? - Sun Tzu Art of War Strategy.

Managing Your Risk Strategically: Insights from Sun Tzu's The Art of War


It is Ok to take risk. However, it is essential to examine what risk means within the framework of The Art of War, a 2500 years old military treatise by Sun Tzu.


The Art of War book highlights how crucial it is to have a solid strategy, be prepared, and smartly weigh risks if you want to win.


Here is Sun Tzu's famous quote,


Know yourself and know your enemy, and you will not worry about the results of a hundred battles.

Sun Tzu suggests that knowing your own strengths and weaknesses, as well as your opponent's, helps you make smart choices that can give you an edge.


Being good at sizing up risks is key for anyone aiming to succeed in life, work, or business.


It means gathering the right info, thinking through different scenarios, and considering both the short-term and long-term effects.


Taking a strategic approach to assessing risks helps you make smart decisions that balance moving forward with being careful.


Basically, being able to handle risks wisely is a sign of good leadership and successful entrepreneurship.


The most wisest advice by Sun Tzu on taking risk is, one must always measure their risk and look at options to solve it.


Here is Sun Tzu's wisest qoute on what you should do when you are taking risk,


The general who makes many calculations in his temple wins the battle. The general who makes few calculations beforehand loses the battle. Many calculations must be done to lead to victory, and few calculations lead to defeat. Looking at this I can foresee you will likely win or lose.

Sun Tzu in his Art Of War book, he tells the readers of his book to be aware that all battles comes with risk. Risk of losing soldiers and great amount of money to fight a battle.


He urges us to perform additional calculations to reduce risk.


He then also said,


In the Art of War, the first thing to do is Measurement, the second is Calculations, the third is Quantification, the forth is Comparison, and the fifth is Possibility of Victory.

After doing all your calculations you must come out with a few options and lastly look at the probability of success. This is The Art Of War strategy on mitigating risk.




The benefits of taking risk in the Art Of War perspective.


1. Taking risk teaches you to think bigger -


Engaging in risk-taking encourages you to expand your horizons and embrace a broader perspective on opportunities.


Those who play it safe in life or business often confine themselves to a narrow path, hesitant to venture beyond their comfort zones, thereby missing out on the vast potential that lies just outside their familiar territory.


Sometimes, great opportunities come with low risks, but the fear of failing or the unknown stops many people from exploring them.


By keeping an open mind, you can find tons of possibilities and come up with creative solutions and ideas that you might not have noticed before.


This change in how you see things not only helps you grow personally but also encourages a vibe of exploration and innovation.



2. Taking risk can improve your strategic skills -


Taking risks means you have to think things through, plan, and come up with strategies.


When you're dealing with unpredictable situations, you need to look at everything from different perspectives, weighing the good against the bad. This kind of evaluation really sharpens your strategic thinking skills because it involves a deep dive into all the data, resources, and possible outcomes.


On the flip side, avoiding risks can make you complacent, with little motivation to think outside the box or get creative.


By regularly stepping out of your comfort zone and taking smart risks, you can really boost your ability to come up with strategies that are not only effective but also flexible enough to handle changes.



3. Taking risks builds your confidence -


Taking risks and succeeding can really boost your self-confidence.


Every time you dive into something new and tackle challenges, you gain experiences that strengthen your belief in yourself.


This growing confidence isn’t just about personal wins; it also affects how you see your role in different areas, whether at work or in personal projects.


As you become more confident, you’re more likely to take on new challenges, push your ideas, and go after bigger goals.


This self-confidence not only improves your own performance but also has a positive impact on those around you, creating an atmosphere where taking risks is viewed as a way to grow and succeed.



4. Taking risk makes you a great leader -


Good leadership is all about being confident and wise, and you get there by being willing to take some risks.


People naturally follow leaders who are decisive and have a clear vision, because it builds trust and gets everyone motivated.


A top-notch leader not only takes smart risks themselves but also encourages their team to tackle challenges and check out new possibilities.


This approach creates a vibe of innovation and toughness within your group, helping everyone aim for bigger goals.


As a leader, when you show your are not afraid to take risks, you can inspire their team with purpose and drive, pushing for shared success and a joint effort to beat any challenges.


In the end, leading with confidence and smart thinking is what sets great leaders apart.



It is Ok to take risk. You need a strategy.


It is perfectly ok to have fear. What you need is courage and a strategy


Your answer is found in the Art Of War.


In The Art Of War, Sun Tzu says,


To fight and conquer in all your battles is not supreme excellence; Supreme excellence is to subdue the enemy without fighting.

Fighting and conquering takes a lot of hard work, energy, and resources. There are better ways to win your battle. 


MrArtOfWar.com teaches you the strategy to win in life, career, and business.


Is It Ok To Take Risk? - Art Of War Strategy

bottom of page