How To Be Successful

Compared to other areas of human expertise ‘success advice’ seems to be a relatively unhelpful body of knowledge which is surprising because being successful is something that we are all so interested in. In fact, my pet theory re: giving advice is that it is a just a socially acceptable way to show off and it is not really about genuinely helping others replicate their success but even that cynical perspective doesn’t explain why the advice that is offered (no matter what the true motives) doesn’t make replicating success much easier. There seem to be two explanations: the first is that people don’t really follow the advice or second they follow the advice but it’s not very useful. I’m not sure which is true, probably a combination of both. One thing I have been struck by is the number of successful people who advocate taking risks and following ones passions even though it is against what almost everyone I know does. The obvious explanation is that these successful people are suffering from sample selection bias where it worked out for them and so they have their perspectives skewed by this but I find this hard to believe given the large number of extremely smart people who have given this advice. I think part of the problem is that there are three fundamentally different ways to be successful in life and the belief systems and approaches that each require are extremely different, maybe even opposed.

  1. Competitive success
  2. Creative success
  3. Corporate success

I shall try and discuss each of the three types and suggest the type of thinking required to succeed at each.



  • Sports


  • Success is inherently zero-sum and defined as beating someone else.
  • Extreme power law in returns – Michael Jordan the greatest basketball player ever is worth $1bn, Lebron James the greatest player today is worth $300m, but the 500th best player in the world doesn’t even play in the NBA.
  • Success is largely a function of execution not creativity. Messi is a very creative player but he’s not doing anything fundamentally new on a football pitch.
  • Success = talent + hard work.


  • How to deal with failure/losing – being resilient etc.
  • Being very competitive – motivation is external i.e. beating someone else.
  • Importance of work ethic (over talent).
  • Need to develop self-confidence, self-belief.
  • Selflessness of putting the team ahead of the individual.



  • Startups, Music


  • Success is still zero-sum but rather than beating someone it’s about doing something completely new.
  • Similar extreme power law in returns – but harder to tell if on path to success. Einstein was a patents clerk, Airbnb’s Brian Chesky was heavily in debt and unemployed.
  • Success is largely a function of doing something radically new.
  • Success = basic competence + radically new insight


  • Courageous about risk-taking – dealing with lack of external signs of progress/success.
  • Need a passion/mission to motivate hard work.
  • You only need to be right once. The failures/experiments dont’ matter.
  • Okay to be weird/do weird things – it increases the probability do something new.



  • Education qualifications, corporate life


  • Much less extreme power law of returns but still very competitive. Larger number of successful people – e.g. 100,000 best lawyer in the world and you are still a very well-paid partner.
  • Success is about avoiding major negatives e.g. personality problems, bad qualifications, lack of work experience.
  • People should be well-rounded – smart, sociable, team work etc.
  • Success = education + work experience + soft skills – big problems

Advice/expertise (usually from parents)

  • Work hard so you can play hard outside work.
  • Play the game – office politics, how to win friends and influence people etc.
  • Don’t take any major risks/deviations from the standard path or risk losing the corporate route (you don’t want any gaps on your CV).
  • Grow up/be realistic/take responsibility.


The, albeit uncomfortable, conclusion of all this is I think that it is extremely difficult to pursue more than one type of success at a time. In fact, I might even go as far to argue that each person is only has a realistic chance (at most) of one type of success. If you really, want to become that Olympic gold medal winning gymnast you are not going to be able to study sufficiently to do well in school and maintain the insurance option of being a corporate success. Similarly, the very competitive people that do well in sports tend to not do well as founders because extremely competitive people tend to copy others and fail to do anything truly creative (just think about all the dismissive things that YC’s Paul Graham and Paypal’s Peter Thiel have said about extroverted, but low conviction MBAs). Similarly, the exact qualities that helped investor Michael Burry who has Asperger’s, a glass eye and refuses to communicate with anyone except via email see what others could not and successful short the sub-prime mortgage market would at the same time made it very difficult for him to succeed in a large bureaucratic organisation. I think this explains why there is such a large disconnect between the advice that someone like investor Vinod Khosla gives and most peoples’ Mum. It’s not that the advice is bad but that it’s just not relevant to the type of success that most people are trying to pursue.The scary implication of all this, of course, is that the path I have chosen/have had chosen for me is the ‘creative success’ route where the extreme power law in returns means a very high chance of failure.