I got into a discussion on Twitter that subsequently led to some interesting comments about the benefits of hindsight and how strategy and success can look so deliberate once we’re on the successful end of things.

It got me thinking about the benefits of hindsight in telling a story, our education system and reporting of business success in the media.

Hindsight is a great thing for story writing because the beginning and the end are known.  To repeat something that I tweeted in the discussion, “Most of school you’re taught to assess facts and write an answer to the known. Life and business requires adaptation to the unknown.“.  That is the whole point.  Writing about something after it has happened means the story is necessarily biased towards the known outcome.  In short, it makes it look like things were more known or more planned than they actually were.

This got me thinking about school, and how school can better prepare people for uncertainty they’ll face in the real world.  You see, for most fields, knowledge of the knowns is all that is required.  I certainly wouldn’t want my doctor to try a new and unproven approach to surgery in place of a proven one.  However, particularly in business, or the attainment of most goals, what is more important is the ability to respond to external stimuli and react accordingly.  Not necessarily with one correct answer but with the best answer at the time, or perhaps many different answers.

So how to teach this in school?  I realised that we need to understand where similar principles already exist.  In my opinion, two of those areas are sport and music – particularly jazz or just jamming.  And what lessons can we learn from these two skills.  It’s just that, they are skills that are practiced.  If a mistake is made, you are penalised (a fat rejection in basketball or stuffing up your solo in music).  However, you know next time what to avoid and how to be better.

Where were we.  Yes.  Entrepreneurship, startups, business men, business women, business teenagers.  We often read their stories with interest on Techcrunch, Mashable, TED, Business Week, Fast Company and gang.  However, as we discussed in the aforementioned Twitter converstation, their stories often make them seem like super-people when it comes to achievement.  But that is only because of the benefit of hindsight.  You see, anybody can be an entrepreneur, it just takes an idea, constant practice and some luck.

P.S. If you’re already a successful entrepreneur, or you’re planning to be one, do me a favour and write a daily diary of you work towards your goal.  It will make for more interesting reading when you’re finally featured on Mashable.