6 Effective Ways on How to Stop Second-Guessing Yourself

Before I start talking about how to stop second-guessing yourself, I want to clarify what that means because many people confuse “not second-guessing” with “doing things without any thinking”.  

First of all, doubting everything, including your own thoughts, is a great source of developing your wisdom.  However, if you have already come up with your plan, you cannot doubt the validity of your plan and your ability every 5 minutes, only because emotions and fear kick in.  To be clear, my definition of “second-guess yourself” goes like this:

Second-guessing means doubting your plan and your ability too frequently and the cause of doubting is negative emotions. 

Second-guessing yourself will make your progress really slow or even make you prematurely ending a supposedly working plan.  The following is a list of very useful things that you can do or practice to stop yourself from second-guessing yourself.

1. Be Aware of the Negative Second-Guessing Thoughts

Eckhart Tolle, one of the best mindfulness teachers, often teaches people through his writings and speeches that our mind has an “observer” part and a “thinking” part.  When we can start observing our own thoughts, we would realize that we are not our thoughts.  The next time your “thinking mind” is telling you that you are not good enough to do this or that, be aware of that thought.  You should say to yourself, “My thinking mind is having a negative thought.  Let me evaluate rationally whether the thought is valid or not”.  If you are aware, you get a chance to stop the second-guessing.

2. Realize that the Best People Don’t Win All the Time and Appreciate Yourself for Trying Your Best

Does Michael Jordan, known as The GOAT or The Great of All Time as a basketball player, hit his shots all the time.  No, he hits less than half of his shots.  That’s right, he misses shots more than he hits shots.  So, should you second-guess yourself due to a previous failure?  No, the previous failure is a missed shot.  The attempt you are making now can be the made shot.  No one knows.  The only thing that is for sure is that you have no chance to win if you are making an attempt.  One of my favorite books is Nassim Taleb’s “Fooled by Randomness”.  In his book, Taleb expressed that life is full of randomness.  The problem is not that there is too much randomness.  The problem is that when we succeed, we think that we are smart.  When we fail, we think that we are dumb.  

3. Know the Game that You are Playing and Know the Odds for Winning the Game

This point can be viewed as an extension of the previous point.  To illustrate this point, let’s assume that you are founding a new startup.  It is famously known that 90% of startups fail.  Therefore, in theory, if you can found 10 startups in your lifetime, you would have one successful startup.   If you have just failed your first startup and think that you are a useless person, you really are not paying attention to the reality.  Having said that, there is a balance that you have to strived.  Just because you know that a startup has a 90% failure rate, it doesn’t mean that you don’t have to try your best to increase your odds.  

4. Know the Difference between Lead Goals and Lag Goals

If someone building a business asks me to give him or her a book that can help the business the most, the book would be “The 4 Disciplines of Execution”

by Chris McChesney, Sean Covey, and Jim Huling.  The book is simple, rational, and logical.  The most important lesson from the book is that we have to understand the difference between “lead goals” and “lag goals” and we should pay a lot more attention to “lead goals”.  An example of “lead goals” is to make 50 sales calls a day.  An example of “lag goals” is to have 10 clients signed up for your seminar.  The difference is the “lead goals” are something that you can control and “lag goals” are something that you cannot control.  “Lag goals” are something that happens if you design and execute the “lead goals” right.  

5. Realize that Will Power is a Limited Resource

Sometimes, second-guessing happens when you fail to execute something that you fail to execute something that you have planned.  For example, you have planned a diet to manage your weight but you couldn’t stop yourself from eating a cake when you walk around in a mall.  That’s when your emotional mind beats your logical mind and controls your action.  These are problems that most people have.  Rational people just approach the problem differently.  They are aware that will power is a limited resource.  There is no way for them to walk near these tasty cakes after an exhausting working day if they are having a diet.  They know that at a moment like this is when the willing power is at its lowest.   

6. Develop a Growth Mindset

One of the most important self-development books is Carol Dweck’s “Mindset: The New Psychology of Success”.  In her book, she mentioned that fixed-mindset people always think they are the smartest in the room.  Growth-mindset people don’t care about whether they are the smartest but rather try to learn from others and grow.  If we can adopt a growth mindset, we would understand that each failure we encounter is a way to learn and become better.  


If I can only point out one effective way to tackle second-guessing, I would say it’s “be aware of your thoughts”.  Another way of saying this would be to “develop mindfulness”.  Different ways of developing mindfulness include meditating, long walking, playing an instrument, etc.  Once, you are aware of your second-guessing thoughts, you have a chance to use different strategies to tackle the thoughts.  

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