Your Guide To A Winning Lifestyle

Why Winging It Will Help You Succeed



When you are trying to accomplish something or build towards a goal, it is easy to overthink and overplan things. Whether it’s getting the number of that cute girl who works the cash register at Panera Bread, or you’re trying to build a multi-million dollar business, at some point we all fall victim to paralysis by analysis. We simply spend too much time and effort trying to figure things out as opposed to actually getting them done.


If you have something you want to do, just do it.


Just wing it. It’s one of those things that is difficult at first, but in the long run it will serve you well. The main thing winging it helps you with is taking action and moving forward. A buddy of mine in the army told me that your plan will never survive first contact with the enemy. What this means is that something will inevitably go wrong, as do most things in life. It happens sometimes, but rarely does something every play out the exact way we expect it to.


Let experience be your guide.

And when things do work out, it is often in an area of expertise where we have extensive experience to rely on, and tough lessons learned from mistakes and failures. For example, let’s say that you want to become an above average chess player. Maybe not world champion or even professional level, but good enough to beat nearly anyone who crosses your path outside of a chess tournament.


If you want to get this good, how are you going to get there? If you are going the route of the overthinker then you will most likely buy a few good books about chess, read up on advice from the chess greats, watch some youtube videos, and do some chess exercises. This will help you, but at this point your knowledge is purely theoretical. It has not been tested, and even after all of the research and education you have given yourself, you are no closer to your goal. You haven’t even played a game of chess.


The path of the action taker is certainly more simple, but much tougher and laced with failure and tough lessons learned. The action taker may take a cursory glance at some educational materials, but the main thing that he is concerned with is getting experience and playing games. He knows that the more hours of playing time he has, the more experience he gets and the more different situations pop up in front of him. Playing 100 games brings considerably more experience and lessons learned than reading 100 chess books written by the all time greatest players of chess.


First, without the experience, you probably won’t be able to grasp most of the concepts these fantastic players were talking about. Second, you are putting yourself under pressure to win in actual games. Instead of reading about strategy or certain tactics, you are putting yourself in situations that, over time, build perseverance, creativity, commitment, courage, risk taking, and decision making.


These are things that are far more valuable to a chess player, or almost any other area in life, simply because these are things you cannot read about if you want to cultivate them, you have to flex these skills like a muscle and exercise them in order for them to develop.


Overplanning pulls you away from the present.

I talk a lot about staying in the present in my writings, and so does Wells,  and it’s for a good reason. Staying in the present not only helps you to appreciate life more and cultivate a sense of gratitude and abundance, but it also dissolves your sense of self. When you are in the moment, completely present, your focus leaves yourself and tunes into whatever is happening around you.


You may have had an experience, whether it was during a sporting event, competition, hanging with buddies, spending time with a cute girl, or an artistic endeavor, where time melts away and you are completely one with what you are doing. You lose track of time and get in the zone. It’s an absolutely amazing and inexplicable place to be. Awesome.


When you overplan or overthink and try to figure everything out before it happens, you are pulling your focus away from the moment, and instead focusing on something that does not exist. You are focusing on these dreams you have created, which are important, but in order to make your dreams come true you must first grab a hold of the present moment, become one with it, and steer it in the direction of your goals with your decisions and commitment.


When you are only trying to figure things out all the time, you are pulling your attention away from the moment, which not only degrades your performance and results, but also deprives you of your fullest capacity to enjoy and appreciate life.


Learn to embrace failure and live in the moment.



Winging it works. It helps you to stay in the present, and helps you to move forward at a much faster rate than trying to figure out things before they happen, because figuring it all out will never actually happen.


I will say this. Thinking, planning, and trying to figure things out are not bad things. They serve a purpose and help us to chart the course after a failure, and apply lessons from victories to new situations as well. These are important skills to develop, but they are not to be relied on as the only tools in your toolbox.


When they are combined skillfully with experience and action, you will learn from your past victories and failures, see past obstacles and the solutions you have found, and blast through familiar territory while less experienced people struggle where you once did. Take any endeavor, and the person with more experience will more often than not move more skillfully and confidently through challenges and obstacles simply because they have seen them and overcome them before.


Combine these two forces to create incredible productivity and achievement in your life, but if you are going to choose one, just wing it.



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