When I Grow Up: Reflections on Turning 35

When I Grow Up

As a ten year old, I spent my days watching the heroic feats of Charles Barkley as part of the 1993 Phoenix Suns and then attempting to mimic his heroics on my backyard basketball hoop. When people asked me what I wanted to be when I grew up, I said that I wanted to play in the NBA. Eventually, my lack of height, frequently mistaken for a lack of talent, crashed my hoop dream party.

And so, I needed a new answer to the question “what do you wanna do with your life?”. We’re first asked to seriously ponder this question at age seventeen, a good eight years before our prefrontal cortex — our brain’s rational decision maker — is fully online, and before we have any legitimate life or work experience.

Fortunately, the entire notion of a job for life — or even a career for life — is no longer relevant. This is good news not only for 17 year olds, but for 27, 37, 47 and 57 year olds, most of whom either still don’t know what they want to do with their lives, have never truly pondered the question or have convinced themselves that they’re happy where they are (more on rationalising bad decisions later).

Having recently turned 35 and reflected on this question, not just in the context of career but in the context of who I am today, it became apparent to me that who we are, what we want, where we’re going is never going to be definitive, especially not in a fast changing, technology driven world in which we should resign ourselves to being lots of things. My reflections lead me contemplate what I’ve learned, what I believe to be more true than other things, what I’ve changed my mind about, and some of life’s more existential questions such as meaning and love.

Having read at least 200 non-fiction books on myriad topics all geared towards personal development and growth, having interviewed over a hundred thought leaders on my podcast and spoken with hundreds more in less formal settings, having experienced countless things across numerous countries and various contexts and having developed businesses from the ground up I’ve learned some things that I believe to be true.

It was challenging to write this, because effectively there’s lots I’ve learned across myriad disciplines, but what I’ve attempted to do in this post is to summarise some of my key learnings, the key all encompassing learnings that one can apply to anything.

Socrates once said that the unexamined life is not worth living so I hope that you can take some value out of my own self-examination, especially if you’re in your mid-thirties.

Note: I should stress that this is not supposed to be a literary masterpiece by any stretch. Rather, it is a collection of life’s lessons that I pieced together on a wintery Sunday afternoon at home in Melbourne, more for my own consolidation of learning than anything else.

1 — Life is not Linear

35 is a peculiar age. It’s between the relative freedom of your twenties, and the social expectancy of your forties, by which time you should have stability in your career and finances, be happily married with children, a pooch and a white picket fence… or so the narrative goes.

We’re told that our mid-thirties are a transient period. This statement supposes continuous linear growth. However, notwithstanding some medical breakthroughs, today’s human population will be gone in 120 years time. It’s not like there is gold at the end of the rainbow — the rainbow a metaphor for our lives. If our ultimate purpose is to reproduce and to contribute to our planet and our race, then this is something we do throughout life, not towards the end. In fact, we do less of this as we reach our twilight years.

Furthermore, the person I am today bears almost no resemblance to who I was 10 years ago as my worldview, attitude, behaviour, life post, experiences and even physical being is concerned.

Instead of linear, why not just see life as an event? If you zoom out far enough and look at our lives on a 100,000 year timeline, that’s all it is. An event, or, a series of lots of small events, each representative of who we are at that point of time.

Life is more bar chart than line curve.

What we think life is like
What it’s really like

Having earned multiple degrees, worked for huge brands like EY, KPMG and Macquarie Bank, founded a funded web startup and an innovation consultancy, hosted a popular podcast, become a published author, traveled the world extensively and racked up a number of investments, some might say that I’ve carved out what amounts to a successful 35 year old’s existence.

It’s all relative though. If i compare myself to say, Michael Jordan, Elon Musk or Friedrich Nietzsche at 35, then my meagre achievements aren’t worth mentioning. But one thing I’ve learned that is fundamental creating the mental space to be your best is to not compare yourself.

2 — Don’t Compare Yourself

Three rules I follow:

  1. Instead of comparing yourself to others, compare yourself with who you were yesterday.
  2. Look at how far you’ve come, not just how far you have to go.
  3. If you do compare yourself, don’t forget to compare yourself to everybody who’s eating your dust too, not just those who are supposedly ahead of you.

We are our own harshest judges.

In a world of social media it’s easy to find people who are ‘better’ than you at something but that doesn’t mean that they are better than you ateverything. Legendary talk show host Larry King has conducted more than 30,000 interviews in his career and as far as interviews go, he is the king in more than just name. But what of his personal life? King has been married eight times to seven women, effectively making the same mistake twice. He has opened up about being ‘not very good’ about a lot of things, among them baking. “I don’t know a thing about baking”. So if you’re handy with the cookie dough, you’ve already got one over Mr King.

Whoever you’re comparing yourself with, realise that you’re probably not seeing their whole and the one attribute that you are comparing yourself to probably doesn’t account for the countless attributes that you are not only better than them at, but that they would love to see more of in themselves.

Elon Musk is revered by many, including me, as the modern day Nikola Tesla, however he has struggled with what often comes across as social awkwardness, multiple marriages and overly critical press and shareholders. So he too has his flaws.

3 — There is no ‘meaning of life’

We grow up thinking we humans are the centre of the universe, that we’re in one way or another sacred. The world has been spinning for several billion years. Homo sapiens, in our current form, have been around for 150,000 years — that’s 0.0037% of earth’s existence. Humans were absolutely nowhere to be seen for 99.9963% of the time that Earth has been spinning.

Furthermore, despite what Plato and Aristotle taught, Earth is not the centre of the universe. It’s a tiny speck in an ever expanding universe in which there are more stars than grains of sand on our beaches.

We — and all of the made up stories we tell ourselves to make sense of the world and give it meaning — are insignificant. We just happen to have developed some semblance of intelligence that supports communication, reason and storytelling, stories that ultimately led us to believe that life has some great meaning. Short of reproduction and contributing to our race and planet, our lives don’t have any genuine meaning, other than the meaning we personally prescribe to it.

The meaning or underlying purpose we prescribe to our lives, in line with the notion that life is one large series of events, is transient.

Once you concede that we are ultimately insignificant, you can get out of your head and in the spirit of Oscar Wylde, stop taking life too seriously.

4 — Purpose is Transient

What drives me as a 35 year old compared with my younger self is shifting. I used to be driven mostly by money, power and status. Today it is freedom, fulfillment, learning, growth and love that I seek. For me, I spent my late twenties jostling for position in the management consulting world, seeking more money, power and status.

Why? Because for the most part I wanted women, lots of them; probably to satisfy my ego and quell childhood insecurities. The thing about lots of women is that it doesn’t bring you sustainable happiness or contentment. You end up with fleeting moments of gratification and almost immediately thereafter end up back in square one. Worse still, the longer you play that game, the longer you shut out the opportunity for a committed relationship that serves more than just your ego and your genitals.

5 — We Know Less Than We Think

It wasn’t until the 15th Century that Copernicus discovered that the Earth actually revolves around the Sun. Up until that point and for almost two millennia, we believed in the Ptolemaic view that the opposite held true.

The more I know, the more I know that I know nothing

I used to read something in a book, take it on face value and preach it vehemently to anybody that would listen. I would foolishly take things personally if people didn’t agree. Nowadays, having encountered countless contradictory, ‘science-backed’ positions in my time, I find myself on the opposite end of that spectrum. I question many things. I ask questions like “was this evidence skewed to support a pre-existing position?’ or “how might this data be presented differently to tell a completely different story?”

For example, New Zealand went undefeated in the World Cup of 2010. Based on this fact alone, one might conclude that they held aloft the trophy gloriously come the final day of the tournament. Dig a little deeper and you’ll find that they drew all of their games and bowed out of the tournament in the very first round.

There’s usually at least one, if not numerous contradictory arguments for any position one holds across almost any discipline. And when it comes to science and peer reviewed academic journals, there’s no shortage of confirmation bias at play or insufficient evidence, ‘dirty’ data or otherwise misinterpreted data being used to form judgments. There’s various other factors influencing the legitimacy of peer reviewed journals, large corporate lobby interests and cognitive biases being just two more of them.

How many ‘black swan’ events does one need before we question the merits of peer reviewed journals? We can only make decisions based on the evidence we can see, not the plethora of evidence we can’t.

What I Know To Be True

I don’t know anything to be absolutely true (see what I said before on absolutes). The unashamed certainty of my twenties and perhaps even my early thirties is gone. The more I’ve learned, the more I realise just how little i know about most things and how wrong I can actually be and have been. As human beings we can only know so much about the vast ever-changing world in which we live and of the multitude of variables that can influence whether something is true or not.

I now look for evidence for and against a position to move closer to truth, the ‘most right’ truth based on the evidence I’ve collected. And because of that, today I subscribe to the ‘strong opinions, weakly held’ philosophy. There are probably countless black swans in the universe that contradict our version of truth.

6 — Tolerance

Today I am more tolerant because I subscribe to many of the ethos that underpin determinism; all events, including moral choices, are completely determined by previously existing causes. We are ultimately the result of our environment, genetics, past experience, upbringing, cultural factors and biological evolution, among other things. We don’t have complete authority over our thoughts (just try to control the next thought that comes into your brain) or our behaviour.

As a result, I’m more tolerant of others with different views. As Abraham Lincoln was thought to have said, “don’t criticize them; they are just what we would be under similar circumstances.”

7 — Age ≠ Wisdom

I don’t conflate old age with wisdom, especially not in western societies. Just because someone is older than you it doesn’t mean they know more than you. Most people go through the motions, never questioning anything of significance, and become a product of social construct, an automaton of sorts. They end up doing a whole bunch of things without ever contemplating why they did it in the first place, short of satisfying some desire to satisfy convention or some primal urge.

I’ve learned that the slightest bit of reason, curiosity and emotional intelligence puts you at an advantage over many people operating on autopilot. Life experience can only teach you so much. If you actually take the time to read and take ownership over your learning then you will be at an advantage over someone much older than you who has only ever relied on life experience, particularly if that life experience has been constrained to a narrow existence.

Conversely, just because someone is younger than you it doesn’t mean that they know less than you. It might actually mean that they know more, at least about certain topics. Having not played chess in years, I recently came head to head with my 14 year old nephew who had been playing the game at school. He wiped the floor with me with some basic fundamentals that he later shared. The moral of this story? People all have different experiences and by working together, we can go much further than we can on our own.

At its core, you can learn something from everyone.

How wise are well, really?

We think we’re wise, but that’s just an age thing and relative to current human lifespans. Today we think that the elderly are wise — an 80 year old is wise. When people lived to 40 did they think 35 year olds carried with them grand wisdom? If we lived a healthy and adventurous life to 500 and looked back on what we knew at 35 would we think we were wise then?

8 — Beware of Absolutes

I’ve learned to watch out for people who talk in absolutes like ‘all X are Y’ such as “everybody who voted for Trump is a nazi”. Things are rarely, if ever, black and white and neatly demarcated and people who speak in such absolute terms generally haven’t thought critically about said topic and are more often than not just being lazy.

Echoing this point, I’ve learned to watch out for people who are absolutely certain of themselves. I have more faith in people who say they are 70% confident with a decision because they’ve done their homework but are unsure about some variables that may influence the outcome of their decision versus someone who says they are 110% confident just because.

On this point:

  • People who show off tend to have low emotional intelligence and self esteem because they’re showing off to derive validation from outside themselves.
  • People who talk too much and don’t listen usually don’t have anything of value to say.

9 — Rationalising is a Blessing and a Curse

We’re great at rationalising which can be both a blessing and a curse; a curse because we might rationalise bad decisions and habits, and a blessing because by truly committing to a rationalised decision — such as our choice of romantic partner — we’re less likely to experience regret and have wandering hands as a result. However, the benefits of rationalising when it comes to decisions such as a life partner, a place of abode, an otherwise expensive purchase or vacation spot only works when you truly commit to your decision in good times and in bad.

This aligns with what psychologist Barry Schwartz puts forward; the case that there are two types of people in the world — maximisers and satisficers. Satisficers tend to settle for the good enough option whilst maximisers look for the best possible option. Schwartz says that while maximisers tend to make what on paper is the better decision more often, they are generally unhappier than satisficers because their decisions are usually laced with regret and a grass is greener complex. As a lifelong maximiser, I’ve learned that there is a relative freedom and mental clarity that comes with diligent satisficing.

10 — Cheerleader versus Quarterback

When it comes to romantic relationships, you might have the ideal mate in mind, the proverbial Quarterback who is intellectually gifted, emotionally intelligent, smoking hot, fit and active, doesn’t smoke, runs their own company, contributes to philanthropic causes, is wordly, a voracious reader, a wiz in the kitchen, a slayer in bed, speaks three languages and is embracing of different cultures (note: this is not my ideal woman, I swear!)

As an entrepreneur with a predisposition towards taking risks and maximising outcomes, I’ve always searched for the proverbial Quarterback. And while I have enjoyed the single life, I am at a period of my life where I long for more stability, for something deeper and more authentic. But the proverbial Quarterback doesn’t exist because once you find them, like anything of value, you normalise their positive attributes, your dopamine receptors get blunted to the initial highs associated with finding them, and you start to notice all of the subjectively negative characteristics you didn’t when you were still wearing dopamine-laced rose colored glasses.

We’re wired to notice what’s different, whats negative. No matter who you end up with, you will likely find yourself having to work really damn hard to keep the relationship afloat and to not question why you got together in the first place.

I’ve learned to stop chasing what doesn’t exist, and instead search for and become a Cheerleader — respectively, somebody who can support my goals and somebody whose goals I can support.

We evolved from tribes where we knew no more than maybe 50 or 100 people. We derived everything we needed from the tribe. In today’s Hollywood driven western society, we expect to find that magical unicorn from whose teets (not literally) we can suck out everything we seek, which, is totally unrealistic.

Your partner doesn’t necessarily need to have all of the attributes of a Quarterback because we still derive all of our needs from our tribe, our social network. Expecting everything from one person is a recipe for eternal disappointment.

11 — On Relationships

Radical transparency or open, clear and timely communication is key to doing away with most of the bullshit problems, arguments and passive aggressiveness that plagues most romantic relationships.

Showing vulnerability helps us to build better relationships, whether that be in a personal or professional arena.

Without values alignment, you’re ultimately facing an uphill battle and can only make it work if you change the other person which is never a good position to be operating from.

As with happiness, clear expectations about what the other person wants, does or believes is key; if one of you doesn’t want kids, perhaps it’s best to discuss this earlier in the relationship instead of on your honeymoon.

If you marry a rockstar, then you can’t complain about the new tattoo, the Harley, the being away from home for extended periods and being in the studio late at night. That’s what you signed up to.

12 — Happiness = Reality — Expectations

Unhappiness, which can be an enduring state due to blunted dopamine receptors, is oftentimes a result of a gap between what we expect and what we get in reality, usually in the absence of what we appreciate.

This is why motivational gurus like Tony Robbins suggest replacing expectation with appreciation. This is why I keep a journal in which I write down three things I was grateful for that day, each night before I go to bed. It’s hard to feel like a victim when you are wired to all of the positives you have in your life.

13 — Judge Less

I used to judge people hundreds of times a day as I passed them in the street; for their smoking, their smartphone addiction, their putting on makeup on the train, their weight, their speaking loud in public spaces and so on. It didn’t serve any purpose other than to make me grumpy and bitter because resentment is like swallowing poison, hoping it will hurt the other person.

A little more than two years ago I embarked on a 21 day challenge to judge less. And since then I’ve worked hard to train that muscle and to not default to judging people based on what I perceive to be lapses in judgment on their own part.

I’ve come to realise that what people do is all part of a bigger plan. For example, I might jump to conclusions judging someone watching some cheeky reality television on their phone as they make their way to work on the train. But perhaps they have a high pressure life and that train ride is the only time they get to unwind. That girl putting makeup on on the train, perhaps she was kept up all night by her crying baby and ran out of time to do something as non-consequential as put her proverbial face on in the morning? You never know what people have got going on in their lives. Leave them be. Focus on yourself.

14 — I am NOT Perfect

While it’s easy to pick flaws in other people, they could just as easily find flaws in you. Someone might judge the fact that sometimes I turn up to the office straight after a morning gym session in active wear which I’ll continue to wear all day if I’ve got no face to face meetings on (other days I could be in ripped jeans and an old Guns n Roses t-shirt!). People might object to my having a beer at 4pm on a Friday, how I struggle to do away with my lifelong tendency to bite my nails, how I’ve struggled to commit to any one romantic partner and no doubt hurt a lot of people along the way, or how I spend a lot of time on my own reading and writing. On the physical side, I’m an average height and have a Eastern European schnoz.

They could find many surface level flaws that aren’t representative of the whole to discredit your entire being.

Often, when we judge people it’s a reflection of something we see (or don’t see) in ourselves. If I’m judging someone for speaking loudly in public, maybe it’s because I tend to be soft spoken, shy away from being loud in public places and perhaps see something in them that I wish I saw more of in myself?

15 — Compassion for Others

We are all trying to make sense of things. We all have our weaknesses. It is easy for me to judge people for not wanting to go to the gym but there’s lots that I should be doing that every fibre in my body tells me not to, and sometimes I give in to that voice.

As such, be compassionate for others. We are all in this thing called life together and we are all trying to make sense of it in our own way. Some of us are more proactive than others but that’s no reason to judge. We all suffer and struggle with its many questions, with its nauseating highs and debilitating lows.

Forgive people for as Stoic philosopher Seneca said, “they do wrong through ignorance, not intent”.

16 — We are Wired for Negative

Biological evolution wired us to notice threats and negative elements in our environment. As such, we overemphasise negatives and underemphasis positives. We notice negative events faster and hold on to them much longer than positive ones.

Being more cognizant of this will help us to notice the many positives in our lives and not be consumed by the negatives and become one of those people who always laments that the world is going to hell, even though on paper, insofar as education, healthcare, homicide rates and other macroeconomic indicators are concerned, we are living in the best times ever.

17 — On Getting Married

Many of my friends are getting married and having kids and I couldn’t be happier for them! Does that however put them ahead of me? There is a supposition in their being ‘ahead’ of me that getting married and having kids is an achievement. Remember, there is no ahead in a life that is a series of events. Yet, many people get married and have kids for all the wrong reasons — and this is manifest in divorce rates which eclipse the 50% mark in most western societies. Social expectation, your parents’ wishes, your age — these are all not great reasons to get married.

Any single person in their thirties who has been to a friend’s wedding and sat at the ‘singles table’ might feel a little inadequate. While you’re questioning yourself, refer to what I said about comparing yourself earlier and consider all the other things that make you awesome, things that required more than a marriage registrant.

And when it comes to tying the knot, heed what Roman philosopher king Marcus Aurelius said; “nothing should be done without purpose”.

18 — Beware of Instant Gratification

I’ve learned to look out for instant gratification, partly thanks to Tim Urban’s Wait But Why blog, which helped me crystallise something I sort of already knew by way of a delightful little monkey he calls the Instant Gratification Monkey — always looking to do the easiest thing in any circumstance. The problem with instant gratification is that while it feels good in the moment it usually compromises our longer term goals.

Questions to ponder:

  • Who do you want to be in a year?
  • Who do you want to be in five years?
  • What actions do you need to take to become that person?

Do you want to lose five kilograms? Then giving in to instant gratification and devouring that bag of Doritos in your cupboard isn’t going to serve your goals.

We’re wired to react instead of respond and we’re wired for fight or flight responses. But instead of jumping to conclusions and being at the mercy of your reptile brain, when it comes to big decisions it pays to pause, wait a few seconds, minutes or hours, breathe, think, and then and only then, act.

19 — Beware of your Ego

Just as us humans aren’t sacred, we, as individuals, aren’t the centre of the universe. Everybody isn’t looking at us and looking to judge our every move. The truth is nobody cares. And if they did? You shouldn’t care.

It’s easy to behave in self-limiting ways based on a flawed belief of how people see us. The reality is that we are who we think we are, and we can show up as whoever we choose to show up as on any given day, at least insofar as how we choose to carry ourselves and behave is concerned — it’s all a choice.

20 — Holistic Thinking

Having grown up in an ethnic Eastern European household, I was taught to think that for some reason or another, that Macedonians were superior to all the rest. Of course, I know now that this is far from the truth but I also know that it’s not just the Macedonian community that does this but all ethnic communities. And this notion of ‘us’ and ‘them’ extends beyond nations to groups of any persuasion. Wherever you can find something in common you can align with someone — whether that be on gender, the area you grew up, the school you went to, the music you listen to and so on.

Symbols and buckets might help us make sense of the world and neatly categorise things so our brains can compute, but it doesn’t necessarily make them right, and our tendency to align with people based on variables that are in common is one we should watch closely.

Interestingly, when it comes to art or reproduction, it’s usually the coming together of different ideas and of different ethnicities respectively that has the best results.

21 — There is More That Unites Us Than Divides Us

Instead of buckets, look at the whole. When you look under the sheets, you realise that have more in common than others than not. For example, communities in the west have the following in common with the far east.

  • Marriage
  • Education
  • Language
  • Spiritual Beliefs
  • A love of beer
  • A love of sex
  • A desire for community
  • A desire for psychological safety

Yet for some reason, human beings have separated into groups and waged bloody wars over trivial matters like who gets to pass out bread in Church.

22 — Happiness is Fleeting

We are all seeking happiness, but happiness isn’t some blissful undying end state, it is a fleeting feeling that is based on dopamine being released in the brain, which at any time, is finite, and short lived. Instead of seeking happiness, we should be seeking meaning, growth and contentment.Otherwise we will only ever be disappointed at how fleeting happiness is and always be reaching for something we’ll never obtain.

If we have meaning in our lives then we are willing to suffer, to ride the lows, because we are working towards something greater. Like I said earlier, I don’t believe that life has some all-encompassing meaning that binds us all, but that we seek our own personal meaning, a meaning that is transient, and so long as we believe in that meaning, then we will be able to persist through life’s struggles.

23 — The Arrival Fallacy

And if we meet said expectations, are we happy then?

No, I’ve learned enough about psychology to know about the arrival fallacy — or what you might know better ‘shifting goalposts’. We think acquiring X will make us happy, until we acquire it and the initial shine wears off. Then we want X2. Then we acquire that and think, “boy, if I could only get to X3, then I’ll be happy”.

Again, this comes back to normalising, a concept I introduced earlier. If you spend your whole life working hard to become a professional athlete and then you make it, it doesn’t take long — maybe a few weeks — before you begin to normalise that lifestyle and find other things to concentrate on such as making the starting lineup, winning the MVP award, taking home the championship ring, appearing on the cover of Sports Illustrated, doing an endorsement deal with an apparel company and so on. Where does it end?

In short, we are wired for growth and for progress. Accept that but enjoy the journey. Acknowledge where you are today and how far you’ve come, otherwise you will always be in a state of “not there yet” or “not good enough”. Just appreciate that there is no end game and that life is an ongoing journey of learning and discovery scattered through a series of events.

This is why I ask myself the following question often: what do i have that if it was stripped of work hard to regain?

Everything changes. Nothing is permanent. Enjoy the ride.

24 — Reconcile Contentment with Ambition

I have often struggled with this question of reconciling calm, clarity and contentment with drive and ambition. Until one day it hit me as clear as day; I can think better and perform better if I have inner peace, mental clarity and acceptance of what is, instead of being in a perennial state of inadequacy, anxiety and angst.

25 — Nice Guys Don’t Finish Last, Non-Assertive Guys Do

I used to think that nice guys finish last, then I realised that it was just non-assertive guys who finish last. Some of the most successful people I’ve met are authentically nice, but they are assertive. Nobody likes a dick.

26 — What People Say, Think and Do Aren’t Always the Same

People might say and do things that don’t reflect their true beliefs because either they’re lazy, they’re trying to cultivate an identity, they want to be accepted or be part of a group and so on. This shows up on the modern world under the guise of ‘preference falsification’ and in a sales context, the counterfeit yes — when someone says yes because they don’t want to face the discomfort of letting you down when ultimately they mean no and you’re not likely to hear from them after your sales call.

27 — It’s Much Easier to Destroy than to Create

28 — You Can’t Please Everyone so Don’t Try

If you try to be something to everyone, you end up being nothing to everyone. Instead, polarise. Don’t stick to the middle — you’ll only fall into the crowd. You won’t be memorable. To be memorable, to be remarkable, you need to stand out. Only by being polarising and being okay with being hated by some, can you create the conditions to be loved by others.

The thrash metal band Slayer has one of the most devoted followings in all of music but 99% of people on this planet would dare not put on one of their records. But Slayer doesn’t need the 99%. They’ve done well for over three decades now appealing to the 1% of hardcore metalheads who love their aggressive music.

29 — Time is Precious

I’m way more conscious of how I spend my time now than ever before. I only say yes to the shit I really wanna do like starting my 35th birthday with a 6am surf at Bondi Beach as opposed to saying yes to every speaking opportunity that comes up. Furthermore, as I spend more time on my business, on writing and on podcasting, I value the time I have to spend with friends and family more and try to make this time special rather than look at my smartphone the whole time I’m visiting mum.

30 — Success, Hard Things, Habit and Environment

Motivation, willpower, discipline — they’re all finite. But once you make that thing a habit, it’s much harder not to do it, and you’re not wasting precious cognitive load and generating anxiety in the anticipation of doing said hard thing.

Four steps to cultivating habits for success:

Step 1: If you want success, you need to do the hard things.

Step 2: To do the hard things, cultivate habits.

Step 3: To cultivate habits, create an environment that makes habit forming easier.

Step 4: Do the hard things.

31 — Influences

I’m a lot more conscious of who I surround myself with nowadays. My twenties were full of alcohol-fueled parties and the friends who served me then don’t necessarily serve me now. This also extends to the types of content I consume, be it blogs, podcasts, books, film and other forms of entertainment.

32 — Health and Fitness

Further evidence that our beliefs are always changing, I’ve changed my mind about lots in the health and fitness domains.

For example:

Old view

  • Eat six times a day
  • Eat breakfast without fail
  • Avoid fat
  • Eat within 30 minutes of finishing a workout

New view

  • Eat twice a day and have a few snacks
  • Skip breakfast and fast for 14 hours a day
  • Consume about 50% of your calories from good fats
  • Don’t eat for 2 hours after a workout

33 — Decision Making

Your intuition + credible other people’s intuition + data = better decisions.

However, in order for that intuition to be effective, you need to collect a lot of dots by way of learning and experiencing many things. After all, intuition is simply pattern recognition and patterns can only be recognised when you’ve seen them before.

Intuition can only take you so far though which is why you should use data to support decision making. But always be aware of whether you have enough data, whether the data is clean and whether it is being interpreted correctly. Be data-informed, not data-driven.

34 — Too Much of a Good Thing

Just because something is good for you, too much of it can actually be detrimental and even debilitating. I wrote an entire article on this called The Inverted U which you can check out here.

35 — Reality Is

Reality is ultimately what you pay attention to. At any given moment there are tens of thousands of bits in your immediate environment but you are only honing in on several hundred. Therefore, your reality and the reality of someone standing in the same room could be completely different.

With that…

36 — Nobody Knows WTF is going on!

Joe Rogan once said that “we’re all kids who got old and nobody knows what the fuck is going on”. In 500 years, will the human race (if it hasn’t destroyed itself) look back on us and laugh at our sophisticated ways as we do looking back on the witch burnings of the Renaissance? Probably. There’s so much we don’t know about our own world, let alone the ever expanding universe.

I change my mind about things regularly. Experts on my podcast contradict each other.

Experts are rarely that. If you’re an expert at a narrowly defined field chances are you’re not seeing the whole picture. I am wary of anyone who considers himself an expert — they usually stopped learning long ago.

People only have very small domains they know about. A preeminent professor in artificial intelligence might not know how to catch a fish or tend to a flesh wound.

We are really good at doing very few things, so much so that if we were left to our own devices to catch and cook our food, find clean water, keep our roads clean, build, heat and light shelter, design clothing and so on most of us would probably be dead in weeks.

One existential thing I’ve learned is that the collective stability of the world is supported by our daily rituals that keep us sane — exercise, sleep, long walks, alcohol, binge eating, medication, meditation, sex and so on. Deprive people of all of these things for a prolonged period of time and just see what happens.

37 — Daily rituals and habits that serve me

  • Long walks and hikes in nature and even in urban landscapes
  • Exercise
  • Meditation
  • Fasting
  • Cold exposure
  • Sex
  • Conversation
  • Philosophy
  • Healthy food
  • Books
  • Writing and creating
  • Music
  • Coffee

38 — Regret, Discomfort and Premortems

I learned long ago that rejection (or failure) is better than regret.

I learned that in order to grow, you need to get out of your comfort zone.

I learned that you either win or your learn.

So with that, whenever I am posed with a challenge, rather than shy away from it, I remind myself that failure and learning is better than regret, and I dive in.

I ask myself the following questions, somewhat inspired by Tim Ferriss and Marcus Aurelius:

  • What’s the the worst possible outcome and can I live with it?
  • How might I mitigate against a negative outcome?
  • How quickly can I bounce back from a negative outcome?

I seek contentment from within by trying to live a virtuous, principle-centred life, not from outside of myself — which is not in my control. External validation means you’ll live someone else’s life.

I I can foster contentment and self-esteem from within, then I am free of the pain that comes from rejection by others. I can always bring myself back to peace and calm by reminding myself of the certain virtues and character attributes I hold dear and that, as cliche as it sounds, I am enough.

On regret: Regret eats you up. Instead, feel it, learn from it and move on.

39 — We Never Truly Arrive

On being virtuous, it’s a lifelong endeavour, not a state you reach. We never truly arrive — we never truly reach complete enlightenment — if we do we have probably checked out of society and are ‘ohming’ away on a hilltop by an ashram somewhere. Rather, it is a daily practice to try and be our best, to try and live up to virtues we hold dear and importantly, to forgive yourself when you have a less than virtuous day.

40 — Watch Out For Bullshit Narratives

“Because everyone else is doing it.”

It’s easy to become institutionalised based on the peer groups at your organisation, your social circles and so on. Don’t. Once you identify with an institution, you stop identifying with your own goals, because the goals of the institution and yours rarely align, as much as said institution might like to tell you so. One way to avoid doing so is to associate with different groups of people and consume different types of content. Get out of your bubble.

41 — You Can Teach an Old Dog New Tricks

While 35 might not necessarily be ‘old dog’ territory, I think you only stop learning once your will to learn subsides. Since turning 30, I’ve learned how to build a seven-figure business, I’ve learned about online marketing and growth hacking, about venture capital, I’ve learned how to rock climb, skateboard, ride a motorbike, I’ve dabbled in standup comedy and I’ve learned how to speak comfortably in front of audiences of several hundred people. I’ve learned how to write books, podcast and even taught myself some basic Portuguese which served me well whilst I was in Brazil for the 2014 World Cup - “Muito bom!”

42 — Will I Remember This in Five Years?

In the absence of doing, there is nothing. For a lot of us that equals boredom and hurt. We often do things to distract ourselves so we don’t have to feel hurt. So we may as well make the doing worth it by questioning the underlying why behind what we’re doing.

A great litmus test on deciding whether to say yes to something, or no to something, is “will I remember this in 5 years?”. The more often you finding yourself saying ‘yes’ to this question the more fulfilling and rewarding experience of life you will have.

It’s easy to default to going home after a day at the office, sitting in front of TV and watching Netflix. It’s comfortable. But comfortable isn’t memorable. Unless you’re reading, comfortable often doesn’t support growth.

43 — Beware of False Idols

So many entrepreneurs talk about crushing it and about hustling. But what’s the point? What will you say on your deathbed? What is your endgame? How do you measure success? How do you measure happiness and contentment? How do you measure a life well lived? What kind of life are these entrepreneurs leading you towards?

Just because other people derive their total sense of self worth and identity from crushing it in business and use their newfound fame to preach their misguided philosophies, it doesn’t mean you should blindly follow their lead!

You can be happy without the 16 hour days. Your business can be successful. You just need to learn to focus on value creation and how to work effectively. What’s the point of success if you’ve never got free time to enjoy it, if you’re stuck behind a laptop all the time or if you haven’t cultivated any true friendships?

True joy in life comes from living a principle-centred life where you live a balanced life — where you don’t neglect community, health and adventure, not one that is heavily invested in a solitary pursuit, which if taken away from you, leaves you debilitated.

44 — Anxiety

I’ve had a tendency to get anxious in the anticipation of doing things; interviewing a big name on my podcast, giving a keynote in front of hundreds of people, going for an early morning surf, jumping out of a plane — and in all of these cases the anxiety completely subsided as soon as the said event kicked off. It’s all in our heads. As Mark Twain is thought to have said, “I Am an Old Man and Have Known a Great Many Troubles, But Most of Them Never Happened”.

A little bit of nerves can be a good thing, as it can wire us to prepare and to do the work — but too much is unhealthy and is often miscalculated and leaves us living our lives under a dark cloud.

45 — Just Let Go to Support Creativity

Don’t overthink or criticise yourself as you create. While I was writing this I just wrote. I had 5,000 words and about 500 of them were typed incorrectly as I madly got the ideas down on the page as opposed to focusing too much on structure, stories, spelling and grammar. I corrected course in subsequent edits.

If I had criticised myself as I went, I’d spend hours on each paragraph. The same goes for life. Just get out there and do things, correcting course as you go. If you criticise yourself too much — if you put forward a thousands reasons why you can’t do something (you can always find them if you look), then you’ll never do anything. You’ll never be anything.

46 — It’s NEVER the right time.

No matter what you’re contemplating, it’s never the ‘right time’ to do it. You will always have a reason not to do it — kids, mortgage, vacations, your job…so just do it anyway (see above).

47 — Be Present.

Don’t dwell in the past. Don’t dwell in the future. Just be here. Now.

48 — Breathe

Three deep breaths can work wonders for your mental state.

49 — Joy of Missing Out (JOMO)

I used to, and still occasionally do, suffer from FOMO (fear of missing out). As soon as the sun shines, I feel the desire to go out and do ‘stuff’. But I realise that is simply my desire for instant gratification kicking in and that to do great things, sometimes, we need to sacrifice. If I listened to every urge to go out and do stuff, I’d never get anything done! Also, I take joy in the quieter moments in what is a pretty demanding life, when i can simply read, write, go for a long, watch a documentary on Netflix or just sit still and just be.

50 — Be Interesting, Don’t Seek Interesting Things

I’ve made several ‘third life crisis’ purchases. A Telsa Model-S, a Hyosung cruiser motorcycle and a custom beach throwback bicycle. However, I’ve learned that possessions are okay, so long as they bring you lasting value, so long as they’re not just a form of retail therapy that leaves you basking in their glow for all of one hour and wondering why you made said purchase by the time you got home.

Today, I am happier and calmer with less. I used to buy lots of junk — mostly clothes. I recently cleaned my house of possessions — disposing of about half of what I owned and about ¾ of my clothes. I felt an instant rush of inner peace that I still enjoy every time I walk through my front door.

On the odd occasion that I find myself in a shopping mall or at a retail strip browsing what’s on offer, I realise very quickly “I don’t need any of this crap”. This comes back to deriving a sense of self from within, not from any external piece of material with a label on it.

Two virtues that I hold dear now:

  1. Not to seek relief in material possessions, places, work, drugs, experiences or sex
  2. To do the work, even when you don’t feel like it

51 — It’s all a Choice (sort of.)

How we feel at any given moment is a choice, a byproduct of our judgments. It is your choice to keep a cheerful demeanour. The power to do so is within you. I know that this is at odds with determinism, but if you’ve been given the power to think in this empowered way, then exercise it — use it or lose it.

“Remove the judgment ‘I am hurt’, and the hurt is removed” — Marcus Aurelius

52- Values Alignment

Whether you’re looking to build a cohesive startup team, or a sustainable, mutually beneficial relationship with a significant other, nothing goes further than values alignment. Otherwise, you’re effectively playing tug of war and wondering why you can’t take forward strides.

53 — There is No Growth Without Discomfort

54 — Take a Long View to See Clearly

To better understand how things work today and where the world might go, don’t take a short view based on your experience of life, instead take a long view and zoom out. It’s hard to see new technologies like blockchain disrupt the incumbent and all powerful banking system until you zoom out and look at how so many once indomitable structures and institutions were toppled by change.

55 — Becoming Bulletproof… it’s okay to be Human.

Cognitive therapies, smart drugs, nootropics, beast mode, #fitspo, #hustle…you name it, there’s trillions of dollars out there wrapped up in the industry of crushing it. Not only that, but there’s so much narrative out there about being strong, crushing it, not letting yourself succumb to negative emotions, being a rock. But….we are not rocks.

We are human beings. And it’s okay to be a human being. It’s okay to not be bothered some days and lie on the couch. It’s okay to sleep in now and then. It’s okay to have the burger with a side of fries sometimes. It’s okay to feel down and to cry. It’s okay to take the odd day off. We are not robots. We all have our vices.

Even Jocko Willink sleeps in past 4:38am occasionally. Listen to your body more. It usually holds the answers.

56 — You are NOT What You Do

Don’t identify too closely with what you do. Doing so will make it harder to change, as the world outside you warrants, or as your own intrinsic meaning shifts. You are more than just the title on your business card and you should open yourself up to exploring different paths as part of life’s many series of events. This, again, ties in to living a balanced, principle-centred life, to cultivate your identity rather than seek it out from just your work.

Closing Remarks

While this list is by no means conclusive and doesn’t even delve into some of the more profounds things I’ve learned about managing my energy and productivity, I wanted to hone in on some of the more existential things in life.

I could probably add to this list tomorrow, but I think at 8,200 words and counting I’ll call it.

Will this list look the same at 40? Probably not. I’ll be a new person then.