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Everything Your Know About Freedom is Wrong

Updated: Jul 16



For many, freedom is the absence of responsibilities and obligations- the chance to do whatever you want, to pursue a passive lifestyle of limited exertion and physical effort. It is lying on an exotic beach sipping a colorful cocktail.


What if I told you that everything you think you know about freedom is wrong.


I quit my high-paying corporate job at the end of February 2020, eleven days before the World Health Organization declared COVID-19 a pandemic. I was working in Mexico City and decided to return to my native South Africa and retire in the beautiful city of Cape Town. I was 48 and looking forward to putting my feet up after hustling for 25 years in the banking and technology sectors. The last 10 years of my career had been spent in a global financial, software, data, and media company covering Mexico, Central America, and Colombia.


Then the pandemic hit, my 18 year marriage imploded, and by the end of December 2020, both my ex-wife and my 18-year-old daughter returned to Mexico City. I rejoiced at the prospect of being completely free. I could dedicate 24 hours a day to doing whatever I wanted. I was accountable and answerable to no one. I could surf all day, play golf every day, watch Netflix all day, leave the toilet seat down, live like a slob, eat whatever I wanted and no one would complain. I could date multiple women on a casual basis – I was living in a male paradise.

I am now 12 months into my hedonistic life of freedom, and let me share what I have discovered. This has been the loneliest, saddest and depressing year of my life. The single biggest thing I discovered is that freedom is NOT the absence of responsibilities, and discipline, and routine. In fact, it is the exact opposite.


Freedom is actively pursuing responsibilities, disciple, and routine. It is the process of turning yourself from a slave into a master. Freedom, and happiness, is the process of finding the chains that control you, that make you anxious and depressed and then working on dismantling those chains. Notice how I said “dismantling” and not “breaking out”. Liberation is a process – not an event. This is not like busting out of Alcatraz. It is more like the French Revolution which took more than a decade. It is a long and agonizing process of self-observation, and self-correction, and control.


So what does it mean to be the Master? Let us start off by explaining what being a master DOES NOT mean. It does not being an insensitive, mean, and miserable dickhead. I am a fan of Steve Jobs. I admire his determination and resilience (he was fired from his own company), his vision, and his attention to detail. However, I am mortified by the number of people that celebrate and emulate Steve Job’s management style. He treated people like shit – he was not kind and in my opinion that made for an unpleasant environment. He was a ruthless dictator making all the decisions himself. This showed a lack of trust in his employees. This made him unpopular with his team. Maybe, when you are endowed with that level of genius and vision, you can afford to be a dickhead. It appeared to have worked for Apple. In 2018, it became the first-ever company to reach a market capitalization of $1 trillion. But maybe Apple would not have reached this valuation in 2018 had Steve Jobs not been such a manipulative asshole.


Jobs was not a master manager – he was a great leader but I do not believe that he was able to fully optimize the talents of his employees. Had he been a substantially kinder human being (which he could easily have been without compromising on his unique vision and indefatigable work ethic), I believe that Apple would have been far more successful. When Steve Jobs died in October of 2011, Apple stock was trading at around $14. Ten years later, Apple stock was trading at $160. Do yourself a favor and have a look at the Apple price chart on Google Finance. The exponential growth in the price has been experienced since he passed away. I understand that he laid the foundation for the future success of the company, but a large part of that growth has come in the last 5 years, where Apple stock has risen from $28 to $160. You cannot ignore Tim Cook’s more humane, inclusive, and nurturing management style in understanding this 5X performance in the past 5 years.


One of the most damning misconceptions is that kind people are weak and insipid. The Dalai Lama said, “compassion and tolerance are not a sign of weakness, but a sign of strength”. I am a finance guy, and I tend to think in terms of return on investment, and kindness has the best return on investment in the world. What is the cost of being kind to someone? What does it cost you to volunteer at a homeless shelter, pick up garbage on the beach, let someone go in front of you in line, offer up a compliment to a stranger? Absolutely nothing. What is the value of this kindness? In many cases, it is priceless.


Being a master does not mean being tight assed and ungenerous. Ebenezer Scrooge was not a master. He was a slave to his own avarice and was miserable and depressed. The biggest problem that many people face is that they don’t understand who they are. The first step to freedom is becoming a master in self-awareness.

You hear this often – you need to know who you are. Your first reaction may be, how is it possible to not know who you are? I ask many people who they are and they tell me what they do, or what their interests are, or where they are from. Not knowing who you are does not mean you are unsure about the nature of your biography. Self-worth is at the essence of self-awareness. How much are you worth – people quickly equate worth with money. We hear in the financial press that Jeff Bezos is worth $200 billion. But this is not about money – it is about your inherent and intrinsic worth.


If you do not know what you are worth as a person, there are two things that you cannot handle. You cannot handle praise, and you cannot handle criticism. More importantly, you cannot love and you cannot be loved. That is very fucked up because you have no idea what you deserve. You are in constant need of external validation.


How do we seek this validation? Online dating apps are commonplace. When a bunch of people like you on Tinder – based on a few photographs, a BIO, and a handful of interests, you suddenly feel attractive, desirable, and strangely happier. Other social media such as Instagram, Twitter, and TikTok are other places where we look for the validation of the desirability of our lives and existence.


Fortunately, or unfortunately, depending on how you were raised, knowing who you are is the fruit of having been known by someone else from the start of your existence – most commonly your mother and father. If you grew up in an environment of positive reinforcement where your needs were met unconditionally and you were valued regardless of how often you threw a tantrum, then you are golden.


The general rule is that unloving parents generate self-hating children. When a baby looks up at their parents from the cot, it does so with total innocence and tries to charm the parents into loving them. It is this power to attract the love that is at the core of their survival. Kids adore these giants and are in awe of what they can do. At this point, there is no innate desire for the child to question the authority of their parents – that will come later in life. For now, they are very sensitive to how well they are performing in getting their parents on their side.


If they feel loved, they can focus on the more pressing business of learning how to lift up their heads, eat solid foods, and how to walk. If love is in a more restrictive supply, the picture becomes a little more complicated. Some parents are not charmed by parenthood – they leave the babies to scream, there may be violence and there may be hysteria. The child knows they are in grave danger and if the situation is not corrected soon, they will be abandoned on a hillside to die.


The natural reaction of the child is to double down and make more of an effort to ingratiate themselves with their caregivers. When we look at this through the lens of an adult, we come to the conclusion that the child starts to blame and resent the caregiver because they have not yet developed that outwardly critical way of thinking. Instead, they look inwards and blame themselves. They internalize the blame and this does a great job in nuking their self-worth. But all is not lost if you were not blessed with loving and affirming parents. A skilled therapist can do a good job of mirroring your true worth and validating you.


Here is the goal, guys. For you to be free, you need to be able to trust yourself, feel more whole and not have this insatiable need for validation and affirmation. If you need external affirmation to feel good about yourself, you are a slave to other people. You are addicted to them. You are a junkie and other people are your dealer. Your dependence on them is unhealthy – and these people do not have your best interest in mind. If you stop performing (paying for the drugs), they will threaten to take away their affirmation (they withhold their product from you) – and then you will find yourself in a deep and dark hole.


Let us do something practical. Make a list of people whose opinions matter to you in order of importance. To be truly free, no one's opinion should matter to you. You should not care what other people think of you – the only important thing is what you think of yourself.


It is natural to care about what other people think of you – especially if you are in a relationship with them. You want to be in their good books – you want to be liked because you are afraid of being cut off, and be alone and starved of intimacy.


If you want to be the best version of yourself, I can almost guarantee that you fear other people's opinions. Why is it that people are terrified of doing presentations, or asking questions in a large public audience? You are worried about social disapproval. Let me tell you something that should quickly help you get over your fear of social disapproval. Most strangers/mild acquaintances generally do not give a fuck about you. They are so wrapped in their own internal struggles and miserable lives that they don’t have time to dwell on the horrible presentation you gave last month, or the massive zit you had on your nose last week, or the stupid comment you made to them at the water cooler yesterday.


Parents on the other hand are trickier because they are not “just anyone”. It has been calculated that the average child will spend 25,000 hours in the presence of their parents. Parents can do a great deal of good in affirming and strengthening their kids, but they can also do a great deal of harm, and this harm does not come to an end once you leave the house. Not only do they leave deep scars subconsciously, but you will likely continue to seek their affirmation until the day they pass away. This means their opinions of you will have a high weight on your self-awareness for the majority of your life.


I understand this is counterintuitive, but you need to liberate yourself from the opinions of your parents. Parents have perfected the art of making their kids feel like shit – why do you wear your hair like that, why don’t you come and visit more often, that girlfriend of yourself is a tramp, why don’t you get a better job? I am not saying you should disown your parents – I am saying you should work hard at divorcing the opinions your parents have about you. They are also carrying lots of hurt and baggage, and often the words they speak over your life are not framed objectively or with your best interest in mind.

Here are four things you cannot achieve unless you have self-awareness.

a) Sustained Happiness

If you are not self-aware, your opinion about yourself is out of your control – it is in the hands of third parties who do not necessarily have your best interests at heart. If you are on social media, anyone with an internet connection and a smartphone can send you a shitty DM saying you are stupid or ugly, and it will throw you into the toilet for the rest of the day. A friend reads your message on Whatsapp but doesn’t reply for a couple of days and you wonder what you did wrong. This is a miserable existence and one in which you are enslaved by the affirmation – or lack thereof – of others. You may find yourself in a lapse of days or weeks where everything is running smoothly and you feel affirmed. Your life is a ship that has found a favorable current, but the ship has no rudder – so when the current switches (your partner says you are a useless piece of shit and they wished they had never met you), you have no control over your new direction. Notice how your happiness was short-lived and not sustained.


b) Healthy Human Connections

Humans are designed to live in tribes, communities, and societies. We were not supposed to live in isolation and we thrive on healthy human connections. In these connections, people will let us down and at times they will even reject us. Your friends might overlook you and not invite you on a fishing trip, or the local neighborhood watch might forget to ask your opinion on a pressing security matter. This rejection can be digested in one of two ways. If you have low self-esteem, you will personalize this. You will come to the quick conclusion that you are the reason for this oversight or rejection. It may be due to something you did, said, or generally because you believe you are a piece of shit unworthy of the attention of the offending parties. If you have high self esteem, you do not give a fuck.


c) Cope with Rejection

The sooner you understand this truth about life the better – people are judgmental and they will reject you. The most important thing is how you handle this rejection. What is the single most feared word in the world? No. We are terrified of asking for something because we will be mortified if the answer is NO. It is not that NO is so scary, but it is the feeling that is associated with this word that makes us cringe. The problem is that most people, when they hear the word NO, hear something else. They are hearing: “You are a piece of shit, you are repulsive, you do not deserve to be alive, you are a waste of space and the world”. It is no wonder that we are reluctant to ask.

As with most things in life, it is worthwhile taking a step back in an attempt to get some context and perspective. One thing we can say with the utmost certainty is that it is obvious that people are not saying this to us. We are OK and we do deserve to exist so how do we explain the NO. It is actually quite simple – it is nothing personal. At that exact point in time when the question was asked, it so happens that we did not fit into that person's plans. There are a lot of things that we would give people if they only asked – money, time, affection, but we are not aware of their plans. We cannot read their minds. There is an asymmetry of information, so instead of jumping to extreme conclusions, we should either brush off the rejection or request more information.


d) Healthy Long Term Relationships

If you don’t love yourself, it means that you never experienced unconditional love as a child. You do not believe you are enough. So when you get into a relationship, you find it a challenge to accept the love that is being offered unless you have earned it. Depending on your level of self-loathing, you may never feel worthy of love and therefore seek out people who treat you how you feel you deserve to be treated – or in this case, mistreated.


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