How to Be Cool – This Is How You Develop an Unstifled Personality

Being cool.


What an incredibly desirable skill. Or is it an attribute? Maybe it is a mindset or a talent.


To be honest, I have no idea. Being cool was, is and will always be by default something very difficult to define.


It is one of those human traits that you find quite easy to identify but at the same time it is so difficult to describe precisely.


I remember back in my high school days, when being cool was actually the cornerstone of one’s popularity, I struggled a lot identifying the main ingredients that comprised the idea of coolness.


Sometimes I was cool, sometimes I tried too hard to be cool and sometimes I wasn’t cool at all.


Nobody really taught me how to be cool and in my attempt to exhibit a behavior I didn’t quite understand, I usually got lost in the translation of the behavior itself.


While growing up, however, the way I acquired knowledge and the way I understood things changed dramatically. I realized that the easiest way to identify the essence of coolness is to find people who are perceived as cool and study their behaviors.


And that’s what I did. I studied rockstars, I studied actors, I studied many famous people who were supposed to have internalized the idea of coolness.


The problem was that when you try to compare your reality to the reality of a rockstar, your reference point is kind of distorted.


I couldn’t really connect with what they were projecting because their world was totally different than mine.


It is easy to be cool when you are famous and many people know you and admire you.


When nobody knows you, however, things are somewhat different.


So, I decided to focus my attention to people who were closer to my reality. Back in the days when I was constantly trying to improve my social skills, my main source of information was various Dating/Self Development coaches.


One of them was Brad Branson who eventually became one of my favorites.


Yeap, that’s Brad


There was something about this guy that differentiated him a lot from other coaches. When most of other instructors were trying too hard to impress and were also projecting a more distant vibe, Brad was managing to communicate an unstifled personality that was kind of epitomizing the idea of coolness.


And in my eyes that was very important.


Although I never got to know him in person, I learned a lot from Brad.


I learned that success in your dating life can have a huge impact in your future professional success. I learned that self-esteem really comes from within and that constantly seeking external validation will only get you so far. But most importantly I managed to somehow copy parts of his behavior and communication style that helped me develop a more unstifled character.


And that’s why I thought it would be nice to contact him and see if he could share parts of his personal journey with us in order to make the idea of coolness a bit more attainable for everyone.


Brad was really happy to talk to me and he provided some really insightful answers to some really challenging questions of mine.


Check them out:


Can you tell us a bit about yourself and at what point of your life you are at the moment?


It was almost seven years ago when I decided to start my journey into self-development. Back then I was helping guys improve their dating skills and build confidence so they can go up to girls and make the conversation work well and eventually turn rejections into opportunities.


From understanding social dynamics and having to dive into the self-development world, I tried to internalize all those concepts and eventually become a better coach.


A huge understanding of what I know today comes from the fact that I traveled a lot and that I managed to interact with different cultures and comprehend the commonalities of humans around the world.


Eventually, I kind of applied that skillset to the rest of my life and I came to understand that happiness is not just going out, meeting girls, and being indulged into all kinds of debauchery.


Happiness is more like having the ability to figure out every aspect of your life.


And I managed to do that by being able to apply the path of mastery that I had through success with women to areas like business, networking, goal setting and things that can actually help you become a well-rounded individual.


I totally agree and I think that you are doing a great job communicating your new philosophy. Apart from that however I feel that you are a really cool guy. Not in a try-hard kind of  way. But more like in an authentic and sincere way. How did you get to that point? Were you always like that or did you have to go through some personality changes to reach that stage?


Before we go there I would like to try and give my own definition of cool. What does it actually mean to be cool? To be honest I am not sure if I have the perfect answer but if I had to summarize it in one sentence it would be the ability of a person to offer pure value to others.


Value can be offered in many ways but the most typical example is when people can offer value to the vibe, like being able to increase the fun of an interaction so that others can enjoy their company.


That said, however, offering value to the vibe presupposes that you don’t expect anything in return. You don’t really need a reaction from others and you don’t seek external validation in order to keep adding value.


What I have I identified through all these years of coaching, is that the problem with most guys is that they are stuck in their high-school reality where they were not part of the cool kids.


With most people as much as I teach them, and as much success they might have, they still have this insecurity during their interactions and they constantly try to prove themselves.


They think that if they keep hooking up with girls and becoming better with women, they will finally become part of the cool kids.


I like to call this phenomenon “the glass ceiling” because for some people no matter how much they invest in themselves, there will always be a glass ceiling above them that doesn’t allow them to break through their problem and feel comfortable in their own skin.


The only way to break through this “glass ceiling” is to embrace a complete freedom of outcome in order to cultivate the required self-esteem to the point where you don’t need external feedback anymore in order to evaluate your self-worth.


And if you ask me why do most people fail to break through this glass ceiling, I would say because they are afraid to dive deep enough to face their past and things that have happened that keep them imprisoned in this “not so cool” reality.


It’s funny that you mention that because a lot of the stuff we cover in our articles are based on identifying ways to break free of your inner child and develop your adult self. From your standpoint, what are the most effective ways for a person to motivate himself to start working towards this direction?


I think that one of the big challenges people have, as I mentioned before, is the independence of the outcome and external feedback.


The thing is that in order to build a belief you need feedback. So you have this old belief and you filter everything through it and all your experiences are reinforcing that belief.


It requires a very strong combination of emotional intelligence and self-esteem for the individual to try and dispose this old belief and adopt a new and more refined set of beliefs.


Emotional intelligence gives you control and helps you take responsibility for your life, including your past. This way you embrace bad situations in a more responsible way and you consider them feedback rather than failure.


Self-esteem helps you take control of your awareness and where you focus your awareness. Every decision you make and every behavior you exhibit, can either increase self-esteem or decrease it.


It is like opening the fridge and facing a decision between drinking a can of Coca-Cola or a bottle of water. Becoming aware of your decision at the moment and choosing the water, inevitable helps you increase your self-esteem because you are aware of the benefits of your choice.


Most people unfortunately act in the moment without even thinking about the outcome of their actions, and this lack of awareness obviously leads to a huge decrease in their self-esteem.


In my opinion that is the main factor that differentiates the cool people from the not so cool ones.


It is more like having the ability to realize that when you feel that you are not cool it is because you have this low sense of self-worth and that you need to start taking control of your perception of the past, and your perception of what is going to happen in the future.


This process is called self-efficacy and it translates to behaviors like:


  • If I decide to go and talk to a girl, how likely is that her reaction is going to be positive?
  • If I decide to start a business how do I know if it is going to be successful?

Most people fail miserably in that and obviously cannot get into the core of self-esteem.


I couldn’t agree more. Self-efficacy is a huge factor when it comes getting over outdated beliefs and growing as a person. I believe that with the areas that we covered so far we start to get a good feel of what it means to be cool. Based on your experience what are the main sticking points of guys when they try to develop the areas you mentioned?


I already touched on this point but I want to mention it again because I think it is extremely important. Become the person that offers value. Most men struggle a lot in realizing this part and eventually it becomes their main sticking point.


Let’s get one thing straight: if you try to be cool it presupposes that you aren’t.


If you try to impress and you feel that you don’t have enough value internally, this will show.


Part of what you should do to attack it head on is to go and become somebody that offers other people value. Create a lot of different relationships with people and see what it means to offer value in different areas of life.


For instance I have many friends that are extremely successful and I don’t even consider myself worthy of being friends with these people. Luckily enough I managed to offer value to them by helping them with their dating life and this helped me be cool around them.


So my advice would be to become good at something people like and offer value to them through that area. This can be anything from becoming really good at business, music, social skills or even gym.


The more value you can offer to others through the areas you are good at, the more this will help you build self-esteem and become cooler as a person.


Another sticking point I have identified is what I call the “Wallflower effect,” where you actually turn into a spectator during social situations. For example when you are in settings where everybody is outgoing and excited, you are just a little bit in your head and instead of joining in you are just a spectator and what happens is that you get more into your head.


I used to be like that and the way I tackled it was that I pushed myself out of my comfort zone but in small steps. So I became a little bit more outgoing, a little bit more talkative and a little bit louder and expressive.


This is so powerful because your environment can perceive even a small change positively and when the feedback you get is good, it automatically boosts your self-esteem.


And again, as we mentioned before, feedback shouldn’t be a point of reference for your change. What matters the most is the fact that you take control of the situation you don’t like and also to take small but concise steps towards the direction you want.


What you just said is so important. People don’t realize the importance of small steps when embarking on a new endeavor. It is the idea of breaking down a complicating system into its parts and then working on each part that ultimately helps you grow. It has been a great discussion so far and I really believe that everything you covered is extremely valuable for all of us. Now that I mentioned the word valuable, I wanted to wrap up the interview with your opinion on the idea of value because most of the areas we cover in our blog aim towards improving your value as a man both internally and externally. So, what do you think is the most important mental shift a man can experience in order to realize his value and through that epitomize the idea of coolness and experience it in its entire spectrum?


First off, the concept of value is quite an individualistic process.


So, value for me might be a completely different think than it might mean to you.


Everybody has a different definition of what that would mean to them.


For me at the moment is what I like to call “the man operating system” and it has to do with how you develop that clarity and confidence to know that everything you do is the right thing for you.


And value eventually comes down to finding a way to discover your values and making sure that everything you do aligns with those values.


This might sound complicated but it is actually quite simple if you think about it.


It translates to having a concrete idea of where you want to be in life and deciding to start heading towards that way.


This concept is so powerful that for me it holds the secret to why negative emotions are created and how we can eventually deal with them.


Negative emotions are more or less internal conflicts that arise from beliefs and situations that attempt to derail you from your way towards your values.


The more you invest in yourself and the more you make sure that everything you do aligns with your values, the more fulfilled and positive your life will be.


Most people, however, find it extremely difficult to comprehend this concept and usually what happens is that they suck at identifying the right values. They fall into the trap of social conditioning and pick “values” like money or being successful with women.


And the reason behind this is that those people lack a very important ingredient we mentioned before – self-awareness. They have no idea why they are doing what they are doing and most importantly why they value what they value.


For instance I am a big advocate of the so-called “virtual lifestyle” where you get to work online and for yourself. This lifestyle is becoming quite popular lately but people tend to misinterpret the reason why this lifestyle can be beneficial. Mostly people will tell you that they want to do it because they don’t want to work so hard or that they don’t want to have a boss. The reality is that working for yourself is way more difficult than working for others and yes having a boss doesn’t really feel good, but not all bosses are the same.


A more mature approach to this lifestyle would be: “I want to experience the virtual lifestyle because it will give me the chance to work from wherever I want and this way I can travel the world and meet new cultures and become a more open-minded individual.”


Getting super-precise on what specifically you value and the purpose behind those things allows you to first understand the idea of value and eventually internalize it and become a man of value.


So if I had to somehow define the mental shift that an individual must experience in order to become a man of value, is thinking for yourself.


This is ultimately what allows you to experience life in your own terms, respect the values of others and also identify people who share the same values.


In closing


It’s been a great conversation and I would like to personally thank Brad for sharing his amazing insight. I truly believe that coolness has somehow become a more tangible area after discussing all these and his advice can definitely help us further our concepts and evolve our thinking.


Brad has also read “30 Challenges-30 Days-Zero Excuses” and he recommends it as a great handbook for enhancing your social skills and mastering your social intelligence in your quest for a cooler personality.


Also, if you enjoyed this interview and would like to receive similar ones to your personal inbox don’t forget to subscribe to our email list. It’s free, educational and awe-inspiring.


Adrian Iliopoulos

I am the founder and main contributor at "The Quintessential Mind" - A unique personal blog that offers a holistic approach to self-development. I am striving to create high-quality content by investing in a reality-based form of self-help, informed by a deep understanding of psychology, philosophy and my own personal experiences and social adventures.
Adrian Iliopoulos