What I learned from getting everything I wanted.

Written by
Christopher Collins
Read time
12 Minute Read
Published on
January 29, 2021

Introduction

"I want the money, money and the cars/ Cars and the clothes/ The ho's/ I suppose. I just wanna be, I just wanna be successful."
"And it's like, it's almost like it made me feel like it may not be right what I want, you know? [...] But at the end of the day, I just want to be successful. So that's what the record meant to me."

Drake, speaking to MTV News in 2009, is referring here to that sense of cognitive dissonance we'll all feel at points in our lives. These tipping points, usually brought about by a change in circumstances or a memento mori, are times we become aware of the unimportance of our thirst for material success. 

For many of us, we can objectively see the hollowness of Drake's lyrics but subjectively step on that hedonic treadmill day after day, year after year, until it's too late. I have also enjoyed that treadmill. 

You see, at the ripe old age of 30, I've accomplished much of what I wanted when Drake first released 'Successful' back in 2009 on the So Far Gone mixtape. Unusual for a person of my age, I know, but try not to look at the swan jealously. Always remember the frantic paddling that is going on below the surface. 

In the hit song, Drake, Lil Wayne and Trey Songz confer on the merits of fame and fortune. What's interesting to me now, in hindsight, is that they also candidly opined on the compensation to your actual values one has to pay for these aspirations. The line "I suppose" indicates doubt, and I know this doubt all too well. 

The allure of success they rapped about was evident to a young guy like me. I too wanted so badly to be successful that I sacrificed my twenties to attain affluence. I worked incredibly long hours, gave up anything I considered non-essential and studied diligently to become someone extraordinary. 

Unfortunately, being extraordinary is quite challenging, and I am most likely right in the middle of the bell curve; As average as they come. When you achieve some material success, you understand that this is not where you'll find your sense of completion. You also understand the pain and imbalance Drake's success metrics can cause us. 

I've burned the candle at both ends for seven years. I learned some lessons along the way, and I want to share them. 

But first, a preamble. 

Despite what I am about to tell you if offered the opportunity to travel back in time to my 23-year-old self and give him some advice, I'd say, "knock yourself out!". 

Even though I now don't measure success in the way I once did, I wouldn't mention the dreadful sense of fear, the depression, the anxiety, the anger, the resentment and the tears that wreaked havoc on me in the pursuit of material accomplishment. 

I wouldn't bother mentioning the five years of psychotherapy I needed to survive. I certainly won't tell myself that I'll eventually surpass my monetary and lifestyle goals and still felt unequivocally morose. 

No. None of that would get through to me at 23 because I was acquisitive and terrified of not providing for myself or my future family unless I was 'the man'. You know 'the man', right?

I wanted that Emerson sense of Self-Reliance. I did not seek outside myself as prescribed, and now live to tell these tales of wanton disregard for my health, be it mental or physical. 

Thankfully for you, I also have some life lessons to share that may encourage you to enjoy the process and the fruits of your labour a little more that I did. They might even dissuade you from wanting the money, cars and women in the first place. 

With all of that in mind, here goes. 

Lesson One: You Are The Sum Of Your Actions.

I used to set New Year's resolutions and tell everyone who'd listen. I thought this would ensure accountability. 

In 2016 the resolution was to "Do more, say less" which I proudly posted on my monitor. I learned late in 2015 that if a goal is closely related to my identity, prematurely sharing that goal can make me feel like I've achieved my aim. Sharing my goals meant that my level of effort was often inversely proportionate to the number of people I told. 

Ambitions in the identity category would be something like, "I want to become an investor," which was mine. They're the "who we want to be" kind of aspirations we are all told to have. 

The research suggests that if someone recognises our identity-related behavioural intention, this gives us a premature sense of possessing the aspired-to identity. 

In reality, this meant I was continually telling people what I was striving for but wasn't undergoing the necessary steps to achieve the goal. I am now frighteningly aware of my ignorance when trying to become something and keep my big mouth shut until I get there. 

My suggestion to you is to keep a journal. Write out what it is you wish to achieve, or have seen someone else accomplish. Below this, try to reverse engineer the achievement of this goal by creating a checklist of steps you need to take. 

Tell nobody and speak about your goal only when someone notices the steps you are taking. This validation by a peer is proof that you are doing the work. Let your actions speak. 

Lesson Two: The Principle of Priority. 

For a long time, my life consisted of long working days punctuated by nights spent frustrated that I didn't get enough done. I'm a list person. I have a list for everything and have always found a sense of achievement in completing my list. 

I didn't understand how much of my self-worth was dictated by my productivity level as a younger guy. The more I juggled and the busier I was, the more important I felt. Everywhere I looked "hustle" was being preached, and I stood in the pulpit spreading the word of Silicon Valley. 

Elon Musk was telling me to sleep at the office. Mark Zuckerberg was expounding on the merits of moving fast and breaking things. Warren Buffet advised that focus and diligence were his most important attributes. 

What chance did I stand? These men were the paragons of business culture. 

Yet, my lists persistently became longer as our business grew. I developed a level of conceit only seen in young entrepreneurs with nascent businesses - that notion of "no one can do this task as well as me so I should do it myself". A longer list just meant more reasons to self-lacerate at day's end. 

I wasn't moving fast enough. Or maybe I was moving too fast in the wrong direction?

In the Bhagavad Gita attachment is defined as the root of all suffering. My identity was slowly becoming morphed into something that now saddens me—people who represent their lives by the participation trophies they have earned and their productivity. We become attached to our work as if it defines who we are. 

I had to learn detachment from my work to control my mind and develop a new sense of self-worth. This detachment made my attitude to work more calculated and far less emotional, but allowed me the clarity of thought to prioritise. 

The detachment then allowed me to differentiate between was urgent and what was necessary. This discernment is an essential life skill. 

"The Principle of Priority . . . states (a) you must know the difference between what is urgent and what is important, and (b) you must do what's important first." 

Steven Pressfield was on to something here. 

In life, as in work, you will be faced with many seemingly urgent tasks. I learned from my ill-placed respect for the hustle-culture heroes that busyness is a fool's game. Nothing in your work is ever as critical as it seems. 

In defining what is important over what is urgent, I ask myself a simple question. "Will you remember this seemingly urgent thing on your death-bed?". If the answer is no, it's chucked off my list favouring that which I deem essential. 

Lesson Three: Vanity Hears Nothing But Praise

The concept of ego is tricky. Many contemplatives have tackled this idea of our sense of self. Essentially it comes down to this: The ego is our self-image. It is the identity we craft to preserve our sense of significance, the understanding of our importance and our place in the world. 

The ego is our paper armour. It is our self-centred ambitions and the petulant child inside all of us. It is vanity. 

Our ego also creates the intellectual vice of surety. Epictetus says "you can't learn if you think you already know" and this was something that took me many years to internalise. Listening to my critics and embracing the objectivity my peers could provide me was an uphill battle. 

Honestly, I'm still climbing up that hill. All that I have changed in my life is that I have become aware of my frailty and understand that it usually begets failure when I am confident I am right. 

I now seek out contradictory opinions and solicit feedback rather than shying away from it. There is an equation I like to follow when making decisions or creating something new. It goes like this:

Take Action -> Solicit Feedback -> Filter what people say -> Form new conclusions -> Take New Action -> Repeat. 

When going through this process early on, I would hear praise and think "great, no need for further feedback. I am on the right track". This reaction to praise is a rookie mistake. This low-level conceit is the ego manifesting again. 

Instead, think "If three out of five people offer positive feedback, great! There are now two pieces of feedback I can use for improvement." This thought process is not easy and requires a level of humility that is very challenging to achieve. 

Take the small wins, but walk the tight rope between self-esteem and ego as carefully as you can. Do not be afraid to be contrarian, but understand that contrarianism requires humility as well as confidence. 

Lesson Four: Connection Fosters Joy

Idealism, consumerism and romanticism are addictions. Add cocaine and an excellent salary to that concoction, and you've got what most young people would consider modern life. We all know it, but few admit their addictions because they are socially acceptable. 

Chasing the proverbial golden goose is what many of us spend our lives doing, but few of us pay head to La Fontaine's words that "Greed loses all by striving all to gain". We often lose what we have and need to reach for what we don't have and don't need. 

Loneliness is pervasive in modern-day western societies, yet paradoxically, we are more connected than ever through social media. Johann Hari makes the point in his book 'Lost Connections: Why You're Depressed and How to Find Hope' that social media is to genuine connection what pornography is to sex; a poor substitute. 

What happens when you aspire to something grandiose but unimportant like money or status only to achieve it prematurely? If you are fortunate enough to recognise you have reached the desired destination in the first place, it's a jolting experience. At least, anecdotally that is how I felt on the back of a mental breakdown in early 2020. 

I referred earlier in the article to sacrifice and compensation. You see, life all boils down to opportunity cost. Opportunity is the value of the next best alternative whenever you make a decision. Choosing to eat at Five Guys means you can't head to Sprout & Co. for a salad. The second-order trade here is tastier food over health. 

Choosing my career as my priority meant I traded:

  • Quality connections with loved ones for shallow business relationships.
  • Connection to nature and travel for time spent at the office. 
  • Connection to the present for financial projections. 
  • Connection to more meaningful work for wealth accretion. 
  • Time spent on hobbies for time spent on my career. 

Hari referred to "junk values" as these vein pursuits we allocate our time to. They replace what truly matters to us. In hindsight, they led me to loneliness, more severe depressive episodes and constant low-level anxiety. 

I don't often hear my favourite Hip-Hop artist wax lyrical about the connection they have with their mom, but that's just what I value nowadays. I have learned the power of gratitude for what we have and genuinely love over what we want. 

I also developed the opinion that many of my aspirations for ostentatious wealth and worldly success were a sickness of sorts. A perversion of the mind that many of us have. I always wished and worked for what I didn't have. I sacrificed health for the achievement of arbitrary goals. 

You can avoid these mistakes, and here's why:

If you can recognise that connections are worth more than money early on in your life, you can determine how much money, power or status is enough. Knowing what enough means for you (and it will be completely subjective) will allow you to slow down. 

Leaving university and knowing that you want to be financially independent by 35 means you can quantify what "independent" means. Knowing you want to amass one million subscribers on YouTube by 30 means you can plan accordingly. 

Yes, you will lose the strength of your connections to loved ones for a period while you give everything to your ambition, but they are aware of your timeline and can see the end. However materialistic they may be, some of us have to pursue our goals to learn we don't want what we so badly wish for at this moment. 

There is one caveat to this manner of thinking. You must listen to your loved ones when they remind you that you have met your original ambition. You won't admit it to yourself, and you'll begin to lie to yourself. You'll rationalise another project. You'll justify another hundred thousand subscribers. 

Self-deception and denial are all part of the process. If you can build in what traders call a limit order, you can accept the inevitable denial you will experience in the face of bigger and better opportunities. A limit order is an instruction to trade if the market price reaches a specified level more favourable than the current price.

While society screams "more" your limit order will remind you that you have defined what "enough" is. In your case, your limit order will be your loved ones or your close friends arguing with you about the gradual shift in your objectives. This mission-creep is an inevitable truth of entrepreneurship. 

Tell your goal to those closest to you, how long it will take and what you are sacrificing quality connection for. Ask for a reminder you when you've reached your specific objective and tell these people that you will likely try to convince them that you must keep going.  

This one lifehack might save you from making many of the mistakes I made. 

Conclusion

The muffled interlude before Drake's third verse is supposedly wise counsel.

"Alright well, um, alright. We... we'll fuckin' figure it out. You know what you—you know what you're doin' with it, you know, makin' it to the top. All the way to the top. Yeah, you do it for the money, and not the honey, you know what I'm sayin'? You know what I'm sayin'?"

I believed that doing it for the money was essential to society, and following the teachings of Adam Smith, Milton Friedman and Friedrich Hayek, I was doing the right thing. Self-interest put food on more tables than my own. 

This "do it for the money" doctrine is the Western way of life at the collective level. We're all capitalists in some way or another. Money talks, and we listen. Some of us refuse to admit our part in this culture and dissent on Twitter (founded by a capitalist) using our €1,000 phone (created by a capitalist). Can you sense the sarcasm in my words here?

I felt that missing dinners with friends and working weekends was the path to financial freedom, and it was. It just made me lonely, aggravated my depression and warped my sense of self. I became what I needed to be to meet society's KPIs. 

I know now that I will reflect on my twenties as a necessary time for trial and error; For adversity and tumult. 

I can't phrase this better than Jim Carey did in his Commencement Address at the 2014 MUM Graduation so I'll quote him. 

"I've often said that I wish people could realise all their dreams and wealth and fame, so that they could see that it's not where they're gonna find their sense of completion."

I hope the lessons I have shared will help you through your twenties. Whatever path you choose to take, they're exciting and terrifying for the same reason; You're young!

I'll leave with you the advice I would tell myself at 23, "knock yourself out!". Exhaust yourself so you may realise what you have to give up to be truly extraordinary. There is nothing wrong with the contentments of mediocrity. Mediocrity is working out just fine for me. 

Do you still want to make those trades? Will you recognise what truly matters to you in time as I did? 

The answer to that, dear readers, is up to you. Hopefully, you will read my words and introspect instead of following Drake's "wise words from a decent man".