Entrepreneurship – Page 2 – A millennial's musings

Time, Socrates and Taleb

N.N. Taleb has to be one of my favourite thinkers of our time. He has taken uncertainty – the root of all evil to so many people – and mathematically explained why it’s not such a bad things at all. In fact, in certain circumstances, we can benefit from uncertainty by being what he calls antifragile. WordPress just underlined this word in red, which is disappointing. It’s a concept that should spread widely.

He sometimes posts one liners on Facebook that then generate a lot of discussion. His most recent:

“The tragedy of our time is the monoculture of ideas: all ‘thinkers’ are forced to believe the same bullshit.”

Not that I am trying to meta-prove him wrong, but I disagree. It’s not the tragedy of our time. It has almost certainly always been that way. Ever since I first heard Socrates talking about youth, I’ve been highly sceptical of any remarks that proclaim that our time is somehow unique. Arguably one of the most powerful minds of all times said:

“The children now love luxury. They have bad manners, contempt for authority; they show disrespect for elders and love chatter in place of exercise.”

It’s quite fascinating really. You’d swear he was talking about the kids now – with their latest iPads. However, he said this sometime during 5th century BC.

It would be too sweeping a statement to say that nothing ever changes, but it’s fair to say that human nature remains fairly constant – which is what Taleb’s comment is addressing. I don’t think that that’s a pedantic reason to disagree with him. I think we’re so prone to see ourselves as unique and special that we forget to learn from history.

UPDATE: So I left a brief comment to this effect on Taleb’s post; my first time to do so. And then – he replied! He replied to only 2 comments of over a hundred (the other one exposed him as a Russian spy), so I feel a bit like the sensei at the top of the mountain talked back. His comment was: Globalisation. That’s an interesting take on it. On top of globalisation, there is also the internet – so the monoculture gets even stronger. I guess there is an interesting point arising out of this discussion: our propensity for herd mentality is made even worse by the internet.

It’s difficult to meaningfully stand out when the way to get heard is through the network effect.

Confessions of a career-switching millennial

I seem to never be able to shake the feeling that I am not doing what I should be doing. I always try to look for the lead domino – the most important thing I should be doing. I haven’t reached that extreme where I am stopped by perfectionism. I am aware of this trait and cognitively, I understand that done is better than perfect.

However, even when I am doing things – I nearly always feel that the part of my brain that is meta-analysing: is this really what I should be doing? What is the opportunity cost? What am I missing out on by being here? Obviously, when part of my RAM is taken up like this, I am less functional. In addition, it is quite the saboteur: it kills motivation.

I am also very familiar with how it is possible to get nowhere fast. Execute brilliantly, get a brilliant result – but not the right result. It’s like not being quite sure where you are sailing to, working hard to get to a good place, arriving at a beautiful tropical island only to realise that you’re allergic to everything on it.

I’ve always envied the people who didn’t struggle with this. However, at this point I realise that many of them oversimplified their problems. Engaging with uncertainty – including the uncertainty of one’s own mind is optional. A lot of the people who have this seemingly inalienable clarity simply ran away from uncertainty and are blissfully ignorant in their cocoon.

In a sense, I’ve experienced this clarity myself – I’ve always known where I wanted to live and that I want certain people around. These things always appeared kind of black and white to me – of course, I oversimplified. However, there’s a significant difference here: you can generally move quite easily. You can build new relationships relatively quickly too. And the thing that you dedicate your life to – that has a big lead time on it. It is also subject to a compounding effect. People who spend long periods of time doing something specific almost inevitably become exceptional at it. This also kind of means that if you don’t commit to one thing – you will never be quite good at anything. It’s a scary thought for any millennial.

As a millennial, I have already switched a couple of very different jobs – being a doctor, working in management consulting, a start-up, diverse small business projects – and I often do many of these things at the same time. The reason for switching was never a failure of any sort. What was it?

I think part of the reason is a kind of insatiable curiosity about real life. With formal education now taking not all out 20 years – and in my case it was very intense formal education, I have a feeling like there is so much out there I haven’t seen. I feel compelled to try things. Perhaps, I only have this insight due to the education I’ve received. I’m not quite sure.

Another reason was the feeling that something is missing. It always feels like I should have more ownership – and to be really able to put all my weight behind a project. Perhaps that’s why it feels like there has to be the one thing that I will do.

Things aren’t as I expected: being a doctor is quite different to how most people imagine it to be. What makes an office job good or bad also came as a complete surprise. Entrepreneurship isn’t something I considered remotely interesting, in fact I hadn’t considered it full stop when I was younger – it wasn’t quite as glamourised back then. Again – it turned out completely different to how I imagined it. As I keep learning that the only way to figure whether I will like doing something is to try it -how can I resist wanting to try it? This approach is congruent with the way traditional advertising doesn’t work with millennials: we have learnt not to trust what we’re told – at least in certain circumstances – and instead we rely on social proof, the next best thing after trying it yourself.

I think a lot of people prefer the comfort of certainty to the dangers of this journey – hence they stick with the thing they know. Why is it though that things aren’t as I expected? I doubt I am the only one. There seem to be a lot of informational asymmetries and a huge amount of erroneous preconceptions when it comes to younger people deciding what they will do. I know this because I am in touch with many of them in my education project. I wish we could dispel the myths that surround certain activities. At the same time, I know it’s impossible for a variety of real world reasons.

I guess we live in an age where the barriers of moving between careers are low enough so that those who want to brave those seas can do so, but high enough that we can’t quite see what we are getting into – so the only way to find out remains through experimentation.

UPDATE: Literally, minutes after posting this, I randomly ended up on LinkedIn – where I saw a chap I remembered from school change career. He’s one of the most intelligent people I know. He just went from M&A lawyer in a top firm to an iOs developer – also in a top firm. I think I know what’s on his mind.

The dangers of laser-like focus

Passion and focus are spoken about all the time. “You have to be passionate about what you’re doing, or it’s not right for you.” All the heroes of our time – mostly in tech – are known for their relentless focus on their passion. It probably culminates in the now near-mythological figure that is Steve Jobs.

I am highly distractible, but when it came to something I consider important – I’ve always been the kind of person who locks on – and that’s it. A certain degree of fanaticism was involved in many of the projects I pursued. When I was a medical student, the rest of the world didn’t exist outside of medicine. When I did HIIT, I really did it – stars in my eyes and all. Even this – I said I would blog every day.

In my experience, it’s a double edged sword. Focus is always avoiding the completeness of the present moment. We trade awareness for a hope of a better future. It’s still puzzling to me how one can be purely mindful and make plans, but our culture certainly tells us to make lots of them – and don’t forget the assorted to-do lists to go with it.

Even forgetting about mindfulness, focus is dangerous: focus on the wrong thing – and it’s a real problem. I’ve obsessed about the things that most girls obsess about: boys, weight, nice things. I am in my 20s, so it’s quite forgivable. Still, having the kind of personality that locks onto things, it’s tough to get out of a focus-rut once you are in it. It’s not OCD, but the word tormenting seems appropriate. My only medicine for this has been mindfulness – or a rude awakening from the real world. I much prefer the former.

For those of us who are super-focused, or those reading all of this advice to be laser-focused and wishing that they could be like that, remember that it comes at a price.

Knowing what to want

It’s always been difficult for me to choose what it was I wanted to “do with my life”. The main reason for this is that conventional low-risk options promoted to school students are all meh. It is hard to choose between broccoli and cabbage when you’re really after ice cream.

What is it to want something? In the XXI century pop culture sense, it is to be excited about something. Stoics talked a lot about wanting – as one of the most important things. They didn’t give much direction as to how to choose what you want. However, having a direction is life is key according to them. Buddhism seems to focus on the present and away for the need for certainty that is a prerequisite for goals.

It seems that the most successful people choose one thing that they won’t give up. Some call it passion, but it’s not really possible to actually be consistently passionate about something. For most people, it is a way of feeling special and having a sense of belonging – I am a painter. Rather than being something to work at, now it is a romanticised notion. Furthermore, a lot of people live in limbo of not having found their passion yet. This presupposes that it has been decided for you. Not feeling in control or having responsibility for your so called passion is a sure way to fail. Lastly, it’s a great excuse to never starting to do anything. If you commit to something, you can fail – people would rather not try and avoid the possibility of failure. What drives people to keep going is why they’re doing it. However, it’s not enough.

We want to do things we are good at. Small wins and a sensation of progress is what keeps us going. Hence, it makes sense to do things that we are good at. Of course, the more you do something, the better you get at it – but it always makes sense to play to your strengths.

Even if you are fantastic at something, however, it makes sense to make life easier for yourself by making yourself different. Getting to be the best in the world at one particular skill is awfully hard. The chances of success are very small. However, you can be in the top 1% in the world by working hard at it. Is this enough? It is – when you combine it with something else. It is much easier to be the best in the world in something super niche. You may not be the best physicist or the best economist, but you may be the best at applying the computational methods used in physics to economics models.

The secret is that there is no secret

We already know everything we need to know. Yes, there is some useful knowledge out there. Knowing that cutting down on carbs will help us to get leaner is a little bit of revelation, but for most of, our grandmothers probably told us to eat more vegetables – all the way back before we knew what carbs were even.

If it had been down to information, anyone with a smartphone would have a six pack and cruise around on a yacht.

It all comes down to awareness. Awareness of what you’re doing at each given moment. The choices we make in real time are the closest thing to this coveted secret. Small things add up – the small decision we make consistently shape who we are. What we do on our lunch break matters. Do you read a book? Go to the gym? Check Facebook? Does it explain a lot about where you are now? If you’ve ever lived in a place with a harsh snowy winter and a roasting summer, you’ll know that the landscape goes from frosty white with metre deep snow to vibrant green in about six weeks. Small things add up.

For most of us, it means taking more responsibility. Letting go of our egos. Working harder – at the important things. Having discipline. Failing and bouncing back – time after time.

The importance of self-awareness

I often think of The Great Gatsby. While everything in it has been said before, it seems like a particularly easy-to-understand piece on human nature – not least because it seems to be reflective of what our society looks like almost 100 years on. Gatsby was great because he was motivated by love and incredibly focused and resourceful in his quest. There were also many reasons why he wasn’t great: he lied about his origin, he lied about his name, he was a criminal, he had no problem seducing a married woman with a child… Most of all he got carried away from reality. He didn’t see Daisy for who she really was even though it should have been obvious. He suffered from infatuation, limerence and obsession.

There’s an interesting dichotomy that arises from obsession. On the one hand, it is a way to get motivated like nothing else. I was recently listening to an interview with Travis Kalanick, the CEO and co-founder of Uber, who talked about how he chose his idea. He said he was in love with the idea of Uber. He also said that after you fall in love with your idea the hard part is to adjust it to the world so that it is exactly the best it can be. It seemed that all great entrepreneurs develop their businesses for some kind of personal reason. Mark Zuckerberg said that Facebook was something he would have wanted to use for himself. He seems fascinated with how people have huge areas of the cortex dedicated to deciphering the meaning of facial expressions, seemingly minor detail. The kind of motivation that’s required to spend every waking hour you’re not doing coursework in one of the top universities working on social websites means intense interest. Whether it is obsession or not, it’s close to it. Our culture seems to value obsession. In fact, the word has connotations of real dedication and martyrdom. There are gyms called Crossfit Obsession. A “normal” person couldn’t have the level of dedication that these entrepreneurs have, or a particular variety within the men and women of Crossfit – we’ve all met them. A healthcare professional would surely class them as having traits of OCPD, or find a way in which their activity is a form of escapism.

However, all great entrepreneurs are sufficiently in touch with reality so as to know how to adapt. This brings me to the second part – obsession needs to be balanced with reality. For anyone who knows the feeling, they know that this is much easier said than done. When one tries to reflect on reality, it is easy to slip into denial. Alternatively, it can be easy to see the flaws, decide that you obsession is silly and give up on it. It is much harder to see the flaws and incorporate this information meaningfully into your quest.

This idea of either idealising or damning your quest first came to me when I was dealing with patients who had emotionally unstable personality disorder as a doctor. People with EUPD tend to undergo something called splitting: something/someone is either perfect, or they aren’t worth thinking about at all. In fact, this is characteristic of many personality disorders. For example, people with narcissistic traits are very quick to decide that someone’s opinion is worthless if they don’t like something about this person.

How is it that some people are able to benefit from the momentum of obsession, but not dragged down by the unhelpful ignoring or reality or give up on their idea at the first sign of imperfection?

Are these great entrepreneurs necessarily all free from toxic personality traits? Not at all. It must be possible, however, to be sufficiently self-aware so as to let those parts of your personality that you need the most at a given moment to fully express themselves. After all, all these personality traits that we regard as vulnerable – and put them down as traits of personality disorders – evolved for a reason. They made sense in a context. They are only called abnormal because they stopped being adaptive when the environment changed, but the person who developed them lacks the self-awareness required to acknowledge that they are using legacy software – never mind adjust again. So it’s not like there’s just one personality type, not one strategy that will carry you through, but like Darwin said – it is the most adaptable that makes it through. Adaptability is completely a function of self-awareness.

So, how could we hook up with some of that self-awareness? My hypothesis is, as always, by paying attention to it. It is surprising how commonly people are unable to describe how they feel. How do you feel right now? Is it easy for you to answer? In normal life – and in psychiatry – I’ve met pretty high functioning people who are unable to answer that question. Really and truly, they look at you like you are an alien, look away and after about 10 seconds they say, I don’t really know. It’s obviously a spectrum and it’s not uncommon. Some of these people will try and assess how they should feel, making cognitive judgements about their circumstances. It’s called alexithymia. I think this is the first step. Ask the question – how does it feel? Putting words on it is a good place to start. Tackling physical sensations first could be an even better idea. When you notice that you are hungry – how does it feel? Is there a pain in your abdomen? Where? What kind of pain? Is it a cramp or a dull ache? Is there some nausea that comes with it? Does your abdomen feel warm or cold? Essentially, it is a form of mindfulness. With some practice it will be easier to put words on your feelings, or your inner state. It’s not a case of needing to soul-search. It’s not cognitive, it’s all about feelings. Whether we like it or not, emotions play a decisive role in our behaviour – they give rise to our behaviour, that’s what the word means. I think that mindfulness has the potential to increase self-awareness like no other instrument at our disposal. Mindfulness is known to increase empathy. Self-awareness is no less important. People who lack empathy are probably lacking insight into their own feelings to begin with. It may even make sense to think of self-awareness as a form of inner empathy.

If there was one thing that I think would advance someone’s personal development by leaps and bounds – it would be self-awareness. It doesn’t matter that you aren’t the strongest, the tallest, the smartest – or whatever, but if you able to be sufficiently self-aware so as to surround yourself with the right people – you can compensate for those weaknesses – and focus on your strengths.

Addicted to headphones

As soothers are to toddlers, headphones are to anyone who has given up their soother. As someone who’s trying to incorporate as much mindfulness as possible into my life, I was wondering why listening to music is so addictive. Anytime I leave the house I get a little rush – mmm, headphone time! The gym is great for listening to music too. Weights seem lighter and the treadmill moves in slow motion to David Guetta.

Having learnt about the rush on dopamine that’s associated with anticipation and how it makes our daydreams addictive, I’ve become intrigues as to what behaviours of mine are affected by this. I think my craving for the bass to drop is the same.

It all began when I started exercising. As well as being phenomenally good for me, it has turned into an exercise in escapism. When I hear my favourite tracks, my mind always wonders to the good times I had with my friends and all those associated daydreams. Essentially, listening to music has become an augmented day dream for me.

It seemed near impossible to leave my phone behind as I went for my evening walk. It genuinely felt like saying goodbye at the airport as your best friend is leaving for Australia (that would be a remote location relative to me!) I did. And it was a very nice walk. I noticed the shops that I passed by, I noticed some cool constellation – still no idea what it is – and I even helped someone with directions. Most of all, however, I was able to think more clearly.

My yearning for the headphones is a case of classical conditioning. Once the music is on, my thoughts are off to a nice place – away from here. They go in a circle and never reach anything. This time – walking without headphones was different – I was more aware of what was around me – and in my own head. I came home and wrote some interesting notes down about a question that had been bothering me before hand. All of these occurred while I was walking – in relative silence.

I would argue that it is good to give up the headphones once in a while. Maybe even most of the time. Listening to music is different for different people, but for me it is a way to run away from my current state into a safe place. It’s necessary sometimes, but most of us probably overdo it.

Should we avoid losing?

Freud is famous for all kinds of weird reasons. I believe it is more of a reflection on society than it is on Freud. He got some stuff right and some stuff wrong. One of the things that he managed to articulate incredibly well is this simple concept: we are driven by wanting pleasure and avoiding pain. In this simple equation, avoiding pain is much more important. In other words, we will forego pleasure in order to avoid pain. I remember learning that lesson when I was 7: I am sure I’ve done a lot to learn it through my own mistakes, but what got really etched into my brain was my cat’s behaviour. My lovely cat, she was probably about 5 months old then, got on top of the kitchen counter while no one was looking. I may have been an accomplice in her trespassing. She speedily made her way to the divine smelling milk that was getting heated up on the hob. As she put her pus into the pan, she must have burnt herself off the edge of the pot. She jumped right down with a loud meow. She didn’t get seriously hurt. What fascinated me though is that she never went near the hob again. Ever. Even if I put her regular cat food bowl on the switched off cold hob. She would just proudly sit there and wait for me to put it back where it belongs. My cat made a decision – and it was final. Avoiding pain is key.

If you come to associate something with pain, you will probably fear it to some extent. So the question is: should you be afraid of losing and associate it with pain? On the one hand, it means that you will avoid losing. Is that the bottom line though? Winning isn’t the same as never losing.

I don’t know whether losing in some shape or form is part of the obstacle course. Maybe you can just get through a life of poetry in motion without ever losing. I don’t think I can think of any examples of it though. It is important to remember that the people we think of when we think of success generally have some control of what is put out in the world about them. So we are looking at a highlight reel. However, considering some really famous actors, politicians and business people – it is easy to think of things that were outright flops. Cringy films, awkward public statements, bad investments, a personal life that could be on Jeremy Kyle – it all seems part of everyone’s journey.

As somebody who has a clear sense of agency and whatever control that humans can have over their own lives, I envisage life as a series of option trees. Every time there is a fork in the road – that’s when life is shaped. Moments of choice are what shapes that part of our lives that we can control. However, I have been making the assumption that if I make the right choices, I will never experience losing. Hence, losing equals bad choice – my bad choice. I am starting to question that assumption.

It is important to take a step back and consider what we call losing. What do we call failure? Is failing simply falling short of our expectations? In that case, for anybody who likes philosophy and mindfulness, it is immediately obvious that losing happens in our heads – not in real life. Expectations are great, but a dose of humility can be a real treat when we get so carried away so as to believe that we are owed our preferences at all times.

Not to sugar coat it – because it is true – but losses now can mean large gains later. While that’s a metaphor for our experience, it is quite literally a description of an investment: debit now for credit later. To continue with the investment analogy what really matters is how you compound it. Does a loss mean new learning and information that adds to your overall game or does it mean debilitating poison that stops you from carrying on? It is clear that the latter option is better. So maybe being afraid of losing in and of itself is damaging. I don’t know for certain that losing is unavoidable. A consultant psychiatrist I used to work with and revere used to use this metaphor: if you want to box, prepare to get punched.

It’s not easy though, to find a balance. If you focus too much on being OK with losing, you will get too comfortable with low standards. This seems to logically make sense. There’s an interesting analogy I would like to draw. I have discussed the Stoic attitude to death in this article. Essentially, not fearing death is one of the most liberating things that a person can do. This goes against all logic: surely, if you stop fearing death you are more likely to die? Yes and no. It seems that literal life-or-death situations are thankfully exceedingly rare for most people. Unless you actively seek out dangerous situations, you are unlikely to die prematurely because you adopt this belief. However, you are more likely to take small risks – as now, they are framed in this bigger perspective and seem not that huge at all. So could it be that by de-vilifying failure, it is possible to make better decisions rather than worse ones?

If you focus too much on always winning, losing becomes too scary to deal with. I don’t think it is better to assume that losing is inevitable than to assume it is possible to avoid it. Assuming anything is always risky business though necessary to simplify things. Sometimes we will lose because the timing isn’t right, sometimes it will be completely beyond our control – but we have to keep our eyes on that part of it that is within our control. I think the key is to not think of losing as detracting from your final wins – that are surely ahead of us. Winning is a long game and losing is just a lesson that refines our approach and let’s us know how to do better next time. Failure is a form of constructive criticism or a reflection of conditions beyond our control. Should we be afraid of failure? All in all, I think it is too high a price to pay as it constricts our ability to get to the big wins. Should we avoid losing? I don’t even know if that’s completely necessary. It’s not the actual end result. If you make a P&L statement analogy, high costs don’t mean no profit.

In medical ethics, they often talk about an act of commission and acts of omission. In other words, to act and to not act are equally consequential. In the medical context it is something like this: you cannot euthanise a person by actively injecting potassium chloride in their veins, but you can allow someone to die by choosing to not instigate active treatment (in most parts of the world). In our culture, we have come to see failure as a negative consequence of an act of commission. Doing something outside of what is prescribed is an act of commission, meaning it takes more deliberation and implies more responsibility. It is much more likely to cause strong emotions if it doesn’t go right than ending up with the same result from doing nothing. So what about acts of omission? The definition of failure has to allow for acts of omission. I think failing to invest in something worthwhile or to tell someone you love them is as bad as investing with poor returns or being rejected. However, if we only concentrate on avoiding losing, we are bound to miss out.

Moving from Freud to Frankl, it’s important to consider the meaning of failure. I think the visceral fear of failure comes from the meaning people have been conditioned to attach to failure: you are failing because you aren’t good enough. I mean you may as well take a gun and shoot your sense of self. What is enough? Enough is completely in our heads. Maybe you are failing because you aren’t that good yet. It’s describing the same facts, but the way it makes you feel is completely different. A much better question to ask would be: how can I use this? Looking at failure from more than one angle instead of fixating on a bunch of assumptions is going to help. If you can make use of it, then there’s nothing to be afraid of.

Our brains are somehow wired to move towards the thing we think about the most. Those who survive car accidents tell how they could only think about the thing that they crashed into – rather than thinking of the gap that they may have been able to drive through safely. Budgeting for the downside is good, but once a decision is made, it has to be a fleeting thought at the back of your mind. You can’t focus on avoiding failure and expect success. Even in those forms of financial investments where avoiding losses is the foundation of all success, the game is to put yourself in situations where losses are least likely – rather than trying to predict them, e.g. in trading. In venture capital, it’s the opposite – you only need one smashing success. While we can’t be completely unaware of our surroundings, the focus has to simply be on winning.

I think it is time to start letting go of the fear of losing because that way we’re risking missing out on something really great. Losing requires humility to accept our own mistakes non-judgementally and use them. Only this way, we have a chance of winning in the long term.