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Why you aren’t “winning” and how to change it

If you feel like you’re not winning in life and want to make a change, this post is for you.

The state of “winning” or “not winning” in life is different for a lot of people. So this post is really for those that want “more”. Do you want to win MORE? 

Why do some people win more often than others? It’s a good question that I’ve pondered many times. I also wonder why some people win a lot and then lose in such a big way that it cancels out all of their winnings. This is one of the biggest problems with stock traders. I know day traders who have built up their accounts for 6-12 months and then in one emotional day of trading, blew up their entire account. 

Some people experience the opposite situation. They lose and lose and continue to experience losses and then *BAM* a big win that covers all of their losses. You could also lose your entire life and win in heaven. You could gain the world and lose your soul. 

The point is that winning is subjective. However, it is assumed that the majority of people can tell the difference between a lifestyle of winning versus a lifestyle of losing. Shaping this lifestyle is within most people’s control. 

So how does a person create a lifestyle of winning? 

My opinion is that the first step to winning is to define what winning looks like. 

What does winning look like to you? Once you define it, then you can work towards achieving it. 

Next, you have to determine when you will win. Winning is an event that happens on a timeline. 

I define winning in life as having

  1. Success hitting your health goals
  2. Success hitting your wealth goals
  3. A measurable level of happiness in meeting your other goals (lifestyle, destiny, etc.)

Winning is having measurable accomplishments. 

Without goals, you can’t win because you don’t know what a win is. 

A great level of health, wealth, and happiness is my idea of winning. It’s the classical idea, but my deviation is that similar to Christian hedonism, I believe ultimate happiness can only be found in being connected to God, which could look more like “losing” in the traditional sense. Depending on your goals. This post was difficult to write because of that doctrine. Ultimately, I believe most people want to have more health, wealth and happiness (however, you may define it personally based on your own goals and desires.)

So why do some people win more? 

When I win, I wonder if it is due to some characteristic, talent or secret knowledge I’ve obtained. Sometimes, I feel like it is simply “time and chance”, random and beautiful blessings that God has given me. However, I believe that to increase your rate of winning, you must have a few key ingredients, but none more than this…

The Motivation to Win

I have learned a few things about myself that I am proud of. I know I am ambitious, so I work towards achieving goals. Ambition is one of the reasons I am motivated. I’m willing to do what most people won’t and I’ve proven that to myself many times because of this motivation. This willingness to act or we can call it “motivation to take act” gives me the power to push forward and through challenges. Lastly, I have patience, which is also important because winning can take time. Patience helps you maintain motivation. 

Ask a guru how to win and they will say: 

  • Work Hard
  • Show Up
  • Work Smart
  • Build A Network
  • Innovate
  • Learn Sales
  • Etc. 

All of which are great ideas, however, without motivation, everything is impossible. 

So how can someone get motivated to win? 

The joy of winning is motivating, however for most people that I know who have mega success it is not the joy of winning or winning more that motivates them. When you make more than 100k per year, having more money does not really change much within your lifestyle. Your health can only be so good and we are all slowly dying so at some point, that motivation is usually seasonal. Personal happiness is very motivating, but the reality is that you don’t need much to be happy if you choose to be happy. So why are some people motivated to win and achieve all of their goals, dreams, and desires? 

Is it because they hate losing? 

I hate losing and can relate to this thought. I have strong goals because I hate the opposite of my goals. I grew up with “wants” and I was not satisfied with the level of wealth that we had. I didn’t like being dependent. I didn’t like having a choice made for me based on money, time, resources or knowledge. For me this felt like it took away a freedom that was not only attainable, but legal, moral and achievable. For example, not being able to have “healthier” food because it costs more, is a situation that is fixable. A million little reasons planted seeds of ambition within me. We were blessed growing up and were certainly not desperate. I was grateful for what I had, but I also felt that there was more. I felt like I could win more. 

I didn’t want to lose. 

So how do you win more? I answer this question by looking at the reverse…

How do I not lose? 

If you understand how people lose, then you can avoid the pitfalls and increase your chances of actually winning. Focusing on the positives of winning is great, but it’s the dips, barriers, and traps that cause people to lose. Unfortunately, these traps are not always apparent.

Health, wealth, and happiness are intertwined. For example, if you lose your sleep and it affects your health, most likely your wealth and happiness will be impacted as well. Therefore, you have to take each part seriously. 

Another thing to note is that the factors that affect whether you win or lose are similar. 

To win you must: 

Be in the right place, at the right time, with the potential and willingness to win. 

To lose you must: 

Be in the wrong place…

Or at the wrong time…

Or without the capacity to do what is required to win…

Or without the willingness to do what is necessary. 

Or you are at the wrong time or without the capacity or willingness to do what is required to win. 

One thing can cause you to lose. It’s one event that occurs at a specific place in time.

This is a bird’s eye view, but simply put, the factors are: 

  1. Place
  2. Time
  3. Capacity
  4. Motivation

None of which you can completely control, but you can work towards increasing your odds. 


This is a matter of positioning, which can be looked at from a macro or micro perspective. Where are you in the world geographically speaking? Most people in America have it pretty nice. 

Is it the best place in the World to find health, wealth and happiness? That is a topic for another day. The point is that it is far better than many places for opportunity to succeed. I’ve been to over 25 countries and have seen many different ways to win, geography isn’t everything, but it is extremely important. 

Now if you make your money in America and live in a country with lower cost of healthcare and lifestyle, then you might win more by simply moving. Especially if you have health concerns. 

One State in the USA, can be experiencing an economic crisis and another State can be enjoying a trend of growth. Geography matters. If you work in the oil and gas industry, you will probably have a higher chance of winning in the oil field vs some island. Unless of course, you can do your work from a computer and an island makes you happier. 

You don’t have to settle for where you live or what you have known. There are States where I have more allergies and States where I feel like I can live healthier or enjoy better friendships and that affects my happiness.

Apart from Geography, “Place” can mean where you are at within your career, what vehicle you are using to get where you want to go, and it can even mean where you are spending your time. If you are working from a home office with a ton of distractions and can’t get any traction, then it might be a good idea to move. 


This is extremely important. Most people suffer from a lack of time management or the proper prioritization of their time. If you don’t have time, then you don’t give yourself the ability to win. You also have to think about the time it takes to do what is necessary. This is also related to capacity, but it is important because estimating time is a key factor. Think of all the ways timing is impacting your ability to win and if timing is causing you to lose. 


I think this is the most misunderstood and underestimated factor to losing. Most people do not think that they lack the capacity to win. Capacity means that you have the ability. You have the time, capital, education, knowledge, motivation, understanding, wisdom, equipment, network, etc. Understanding what is needed is difficult. Some people have a great capacity and others don’t. Some people think college will give them capacity and others think books or youtube videos or courses, trade shows, conferences, clothing, nice watches, ability to take risks, etc., will give them the capacity to win. The truth is that no matter what you think. You are either right and will win or you are wrong and will lose. You can’t fully know what is required or if you have the capacity until you try. 

What if you just aren’t smart enough? No one wants to believe that and It might be true depending on your goals and ambition. 

I am under the opinion that most people are actually smart enough to achieve success. However, the level of success is definitely going to be a question of capacity. So to lift the capacity you can either learn everything you can, amass capital, mentors, and skill and then hope to have the capacity or you can take the shortcut and partner with someone that is already winning or has won in the way that you want to emulate. This is the best way to judge if you have “what it takes”. 

It is rarely one thing that you are lacking or one thing that will change everything for you. Most likely it is a lot of things that you will have to increase and develop over time. 


Lastly, we have the motivation to win. This seems easy, but it’s not just the willingness to do what is necessary only if “necessary” is easy. It is the willingness to do what is necessary when it means sacrificing everything. Giving up time, money, pleasure, and anything else that might keep you from winning. You need the motivation to increase your capacity and more importantly you need the motivation to try to increase your capacity and try to win, when winning is not guaranteed and trying means that you are risking comfort. This is something that is extremely rare, but entrepreneurship demands it.