Entrepreneurship – Page 2 – A millennial's musings

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.

Do we really need women role models?

I have never bought in to the radical feminism that is all around us. However, today, for the first time, I realised something: we do actually specifically need women role models – for a particular reason.

The way we learn seems to come from our ability to mimic. From Aristotle to Kurt Vonnegut, to the modern self-help industry, they all agree that we learn by modelling people. I think that toddlers learn to walk at least in part because they want to be like everyone else abound them. So it doesn’t matter to them how many times they fell on their a*s. Same thing with language. Monkey see – monkey do. That’s what learning is about. That’s why doctors in training shadow more experienced doctors. However, as is the case with toddlers, we learn just by being close to something – without necessarily having chosen to do so. It’s like walking into a room full of people who are laughing at something – it is hard to stop yourself from smiling, even though you have no reason to laugh and feel really awkward now! That’s why we become the average of the five people around us.

The clincher is in the fact that it is much easier to learn from someone who you can relate to more easily. When I heard Arianna Huffington speak about her career, it just made so much more sense to me than when I heard countless other men. It’s not that I didn’t learning anything from men – far from it. However, seeing women in business is life-affirming and whatever it is that my brain saw in this woman that I am not even aware of – I feel that it really made a difference. It added certainty. It’s not that I don’t get inspired by male role models, but there was this added “if she can do it – I can do it too.”