How to maximise success through asymmetric bets

We live under the illusion of control.

We believe that we design our lives, we design our companies, we design culture, and we design human civilisation itself.  The way we do this, according to the belief, is that we analyse the situation, make a plan, and then execute it – and in doing so create the reality we desire.

Now for some simple things, this is true. Decorating our living room say, or building a road from point A to point B. I don’t wish to imply that nothing is deliberately designed. However such designable things represent simple “closed” systems – where we have sufficient mastery of all the variables as to narrow the gap between our intentions and the result. But when it comes to chaotic “open” systems, where there are more variables than we can grasp, and their relationship is more complex than we can compute, this gap widens – and we are incapable as a species of controlling their outcomes.

The examples I listed above – what we might call “the important stuff” – are precisely such systems.

As long-time readers will know, I’ve written a lot about this idea when it comes to businesses. About being prepared for your initial hypothesis to be wrong, and then “discovering” what you have actually created with your brand so you can fall into line behind it.

But when you think about this, couldn’t you apply the exact same principle to – say – your career?

How many of you followed precisely the path you envisaged at the outset?  And if you’ve achieved some success, how much of that was down to a brilliantly executed plan, and how much was down to isolated serendipitous moments?  The person you met at that event you almost didn’t go to; the book you picked up on a whim one Tuesday; the tweet you fired off without thinking about it?

Even for those careers that have a pre-ordained “on rails” path, which begins at university, like medicine, for instance, there are still infinite variables along the way which have a profound effect on the ultimate outcome.

Our illusion of control in such fields might better be described as a delusion: one that gives us all sorts of headaches as our best-laid plans fail to bear fruit, and we rail against the “unfairness” of those “less smart” than ourselves having opportunities seemingly fall into their laps whilst ours remain empty.

In this piece then I want to address a technique that enables us to maximise our chances of success in the face of this chaos.  Not a way of choosing our ideal outcome – which is impossible – but rather of making it more likely that we arrive somewhere we find agreeable; whether for ourselves, our families, our businesses, or our communities.

That technique is the liberal use of asymmetric bets.

The core idea of asymmetric bets is of course pretty simple, and I don’t want to teach you to suck eggs here.  It just means:

Acts where the potential payoff is massively higher than the cost of the act.

The investor Naval Ravikant gave some good examples of asymmetric bets on a personal level (you can imagine business equivalents), which included:

  • Investing in start-ups
  • Starting a business
  • Creating a book, podcast, or video
  • Going on lots of dates
  • Going to a cocktail party
  • Moving to a big city
  • Reading a classic book

Naturally, the cost of these actions varies wildly – investing in a startup will cost thousands, whilst reading a classic book is effectively free – but in each case, the potential payback far outweighs the investment you’ve put in.

So far this is all pretty obvious; but what is not so obvious is the realisation that the more you “overload” your life with such bets, the more likely you are to end up somewhere exciting.  If you do any one of these things just once, the overwhelming likelihood is that nothing will come from it, and you’ll think “well that was a waste of time”.  However if you do a wide variety of such things daily, you will gradually start to see returns as the wins start to unpredictably trickle through.

Another way of articulating the same idea is to think about it as simply opening yourself up to opportunity, and giving yourself “optionality”.  We’ve all heard the phrase “you make your own luck”, well that’s basically what this is.  The person who goes to 1,000 cocktail parties will almost certainly generate more opportunities than the one who goes to 5.  They won’t have been “lucky” however – not really – instead they were just living in a manner that invited options; options to which they simply need to say “yes” or “no”.

Asymmetric bets then are not so much individual things, but rather a way of life.  A habit and a mindset which bears unexpected fruit – and the opposite of the more conventional mindset which focuses itself narrowly on the cultivation of “expected fruit”.

Now it’s important to recognise here that unfortunately, the power of asymmetric bets doesn’t tend to accrue with different people very unevenly. A basic example of this is that an extrovert will probably expose themselves to this more than an introvert. This says absolutely zero about their relative capabilities of course, but it may lead to an uneven distribution of “luck”. Consider also the way that successful new businesses arise disproportionally in certain urban centres.  Again, same issue.  People in those locations aren’t having better ideas, and they aren’t more capable. But they will – purely by virtue of where they live – be placing more bets, and exposing themselves to more volatility. And that counts for a hell of a lot.

It reminds me somewhat of when I read Malcolm Gladwell’s book many years ago. In it he demonstrated how the Silicon Valley titans like Bill Gates and Steve Jobs created their empires not primarily through genius, hard work, or shrewd planning, but rather through an extraordinary cocktail of circumstances that made their achievements almost look like manifest destiny. They were born in exactly the right places, at exactly the right times, and went to exactly the right schools etc. etc. in order to end up where they did – giving them an unassailable advantage over pretty much everyone else in the world for those particular outcomes. This isn’t in any way to say that they weren’t talented and all the rest of it. It’s one thing to be exposed to the opportunities, it’s quite another to take them. It’s simply to say that they were the beneficiaries of chaos – and if you play the game, you can make yourself such a beneficiary too.

After all, there will be a particular outcome which you will be usually well-positioned for.  It’s just you won’t know what that is until you achieve it.

Sadly the ability to place asymmetric bets has been significantly hampered in our current restricted living conditions. People seem to think that (in some cases) they can do their jobs and live perfectly adequately via Zoom, online deliveries, and so on.  And if you believe in design delusion then yes, that would appear to be true. But in the real world, it isn’t, because we have essentially stripped all the “pointless complexities” out of life – the stuff that happens between the things we intended – and thus have completely blitzed our optionality.  This is partly why I’ve always been sympathetic to the “pointless meetings” people always complain about.  Yes, they might be pointless on the face of it.  But every once in a while they’re not – and in a big way.

Anyway, hopefully soon creative chaos can return.  In the meantime it is worth evaluating how much we are inviting this potential in our current plans.  Are we doing those cheap, and perhaps often “pointless” things?

Or are we “optimising” ourselves out of the reach of fortune?

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