“Perfection is not just about control. It’s also about letting go. Surprise yourself so you can surprise the audience. Trancendence!”

– Thomas Leroy

A common saying in the field of entrepreneurship is the notion that you should plan for success. You should set goals for yourself, measure the progress and pursue your plan with laser-like focus. However, as seen in numerous projects all across the world – a plan is rarely successful. In fact, more often than not, a plan is missing crucial information that is impossible to know beforehand. So if following a plan is ineffective, how can we cultivate success?

A Rare Bird

Imagine for a second that you are an well-decorated ornithologist (a scientist in the study of birds) in 16st century London. You sit in your dark leather armchair by the fire, and have invited the most intellectual peers you know to your home in order to discuss the field of birds. You are exceptionally ambitious, and your plan is that these gentleman can provide you with key assistance in becoming the most noticeable ornithologist of your time.

Today the particular topic of discussion is the swan. Beautiful, majestic, pearl-white swans. While your peers lovingly illustrate how swans are amazingly pure creatures born of light, an impostor ornithologist across the room proposes a theory that perhaps not all swans are white, but some might actually be black. Preposterous!

You and your peers laugh from the depths of your bellies, and throw out a regularly used age old expression from roman at the man –

“Rara avis in terris nigroque simillima cygno”

(“A rare bird in the lands and very much like a black swan”)

– to describe such impossible occurrences. Naturally, you hastily fire the impostor and make sure he never sets foot in your team again.

Later – in 1697 – you uncover that this impostor has guided dutch explorers on an expedition to western Australia and found conclusive evidence that there are – in fact – black swans. His discovery grants him world renown and he quickly overtakes you as the most celebrated ornithologist.

The Black Swan

This is the concept of a ‘Black Swan’, popularized by a man named Nassim Nicholas Taleb in 2007. It is used to describe highly unusual events that are impossible to predict before-hand, but have extreme impact on the world. Although the black swan example above is chosen mostly because of the ease of storytelling – notable black swan events include the unexpected attacks on the world trade center – or the more recent COVID-19 outbreak.

Every single plan in the world has a risk of spectacularly failing because of these unknown black swan events. This problem with planning is also coined the ‘problem of induction’ by philosophers. The issue here is that every plan is based on assumptions and experience from the past. In doing so, you fail to take into account that your plan can spectacularly fail based on unknown black swan events. The infinity of reality cannot be accounted for in finite models.

Contrasting to spectacular failure due to Black Swan events – extreme success are also usually not part of the plan. Do you honestly think the original plan of Facebook was to become the largest global social media network? It was just a fun project in the basement!

I’m sure everyone has experienced this in your life. An unexpected death, divorce or sacking completely hay-wires everything you planned for in life. In a positive contrast, did you plan to meet the love of your life – or did it happen spontaneously and you simply jumped on the opportunity?

Planning without taking into account the possibility of extreme fluctuations to the normal will leave you blind to unexpected opportunity and open for blindsided attacks.

That is okay for low-risk projects, and most of the time you will be fine. For higher stake projects however, such as your life as a whole, I’m arguing that you can’t afford to rely on a plan. The things that will exponentially grow your success or completely hammer you into the ground will be the unexpected – the out of the ordinary – black swan events that you cannot predict.

The Wealthy Pig

Allow me to give you another example; Imagine this time you are a pig. An actual pig in a farm. Every morning, after sunrise, your farmer comes to you and feeds you lots of delicious grains.

Your plan for getting enough food is easy, you simply stay put and wait for the farmer every morning. A great plan based on previous experience. As far as pigs go, you feel pretty smart about yourself. You soon become fat and content.

One morning, the farmer is late.

What is happening, you wonder? Was my plan – based on the assumptions that I was to be fed – incorrect?

Fortunately, you are an unusually smart pig, and it had happened before, so you saved some food under a pile of mud for occasions such as this. You arrogantly oink to yourself that you’ve identified sufficient risk and create a risk mitigation plan.

That evening, however, the farmer comes in, snaps your neck and you are cooked in a pan that evening.

It must have been either that particular pig or Socrates that said:

“ The only true wisdom is in knowing you know nothing. “

The Alpha Predator

To stay in the realm of the animal kingdom; Popular western reasoning of planning for success essentially makes you into an Cheetah, an alpha predator with extreme focus with an all-or-nothing attitude to success. In fact, the alpha predator mindset is idolized in western civilization. Elite athletes are compared to the Cheetah, being the best and the fastest and the strongest as a result of their single-minded focus.

In reality, a cheetah is wildly ineffective in real life scenarios.

Let me elaborate. A Cheetah hunting and survival tactic is the creation and execution of a simple plan; Be the fastest to run and subsequently run after an antelope until it is caught. A Cheetah – in this sense – is the ultimate hunter and executor of the plan. Rarely does a cheetah fail to catch his prey.

What happens afterwards is interesting. The Cheetah, having expended all his energy of the plan, is extremely tired and needs to recover to catch his breath. At this point, the cheetah is dead in the water and is unable to defend himself against opportunistic lions or scavengers stealing away his meat.

So even though the Cheetah made a plan and executed it perfectly, he failed to react to unexpected external events and has lost the meal.

The Opportunistic Chameleon

I would challenge you – the reader – to instead take the spirit of a Chameleon. When people think of the Chameleon, they initially think of their color-changing camouflage skin as their prime attribute as they use this to blend in with any environment.

More interestingly, a key component in their evolutionary victory is their opportunistic hunting method. Their claws are specially developed to be able to lay still on a branch and wait for hours if they have to. Their eyes are uniquely developed to spot literally the tiniest opportunity (insects) and expertly induce the depth towards the target. When the timing is exactly right they will – like a military sniper – assassinate the target with pin-point precision using their uniquely developed tongue muscle. A Chameleon will only move to hunt if no target comes along.

Contrast this opportunistic styled Chameleon to the single-plan Cheetah and you will see the massive difference with respect to Black Swan events. If we assume Black Swan events can occur – and will be the main driver for exponential success or failure – we must be able to sit on a branch and wait for opportunity to arise.

Blend the environment with you

One last word on the Chameleon analogy, before I move over to practicality; A Chameleon’s skin color actually cannot adapt to every environment. If you put it in a completely foreign environment it will have significant problems in camouflaging itself. It’s the other way around. A chameleon chooses his environment to be able to effectively camouflage.

Which brings us to the practicality of this topic. If planning is setting yourself up for failure – how do you ensure success? I’ve written before on lessons we can learn from ants, and many of these apply here as well.

My main proposal here is to steer away the focus from a time-tabled plan and focus instead on setting your environment up for success. Make sure you naturally gravitate toward success and are able to respond with full military force once an opportunity or danger arises that you can react upon. Stay flexible and ready.

Some concrete steps that you can implement now to improve your environment for success:

• Have a large financial buffer. Not just enough to weather financial headwinds, but buckets of cash to opportunistically jump on opportunities.

• Remove toxic people from your life and instead surround yourself with successful people that give you positive energy.

• Continuously expand your knowledge by reading.

• Explore – Fail and experiment – on many different paths.

• Take action – anything! Without making some noise and rippling the waters of your life, there is no way opportunity will arise.

Success lies not in being able to execute a plan in the fastest, most straightforward method. But in making sure your environment is perfectly attuned to your particular skill set. Then, patiently lay in wait and be an expert in spotting opportunities and capitalizing on them with expert precision.

Be a Chameleon, my friend.