Certainty is a Liability

Since starting my journey working on startups and in life, there is this thing that has become a reoccurring theme. Whenever I say something will be done, the world does everything in its power to make sure it doesn't happen. It's frustrating. So in this blog I am going to discuss how to avoid being certain and the motions the world rewards. (Based on my experiences thus far)

Why Does Certainty Guarantee Failure?

Short answer, no one knows, but let's talk about some of the consequences of being certain. If I am certain and proclaim to the world that I will do something, then I have a lot to lose if I don't deliver. Some tasks are much more certain than others, like going to the grocery store to get milk. However, there are other tasks that are much less certain, and often revolve around one's career. My examples include getting to a number of users on our website or getting funding for the company. These are ambitious tasks that require careful planning and execution. Being certain of dates and deadlines is a surefire way to immediately fail.

So what happens if you fail to deliver on time? First things first, personal credibility takes the first hit, but there are second order consequences. You get used to not delivering on time and it becomes normal, which in turn builds habits that are not healthy. This impacts Investors, employees, and even family. You become unreliable and unreliability gets buried somewhere deep in your human psyche. Not only does it not feel good, but it also impacts your sense of self worth. This is when the wake up call happens to start delivering on time, but you've built a habit of being certain, and so the cycle continues.

Now it's possible to be certain and right. These events are rare and only exist in a vacuum. These are situations where failure risk is low because you, as the owner of the task, own the majority of the risk associated with the success of the task. In addition, the risk of disruptions from outside influence is abnormally low. Let's go back to the example of going to get milk from the grocery store. Most people have done this before, meaning there is low experience risk, low risk in the commute, low risk in having the available funds, and low risk that the store does not have milk. Most of the risk is in the operators control and knowledge. The probability of success is high.

Most cases are not like this, especially if you are doing things for the first time. My rationale to answer the question 'why does certainty guarantee failure' is because you can't possibly predict or quantify every possible risk on the path to an outcome. Therefore, your proclamation of certainty is not based on any reality. It's an uneducated guess - the worst kind.

To summarize, if it can go wrong, it will go wrong, and if you don't even know what can go wrong - you're losing before you even started.

How to Avoid Certainty?

Let's preface this section by laying out my belief that human beings are great at getting things done. I think it's amazing how much we can get done. So to me there is an abnormally low risk that humans can successfully produce amazing outcomes. Outcomes, in my view, are inevitable successes - provided the person or team commits to doing the necessary work are relentless.

Lets make up some scenario:
Planning to get to 15k instagram followers in 10 weeks, organically. This attempts to control an outcome in by a certain deadline. Using timelines is suitable if the jobs to be done have abnormally low risks of failure. This situation does not fall int that category since the outcome is not in our sphere of influence. However, we can control the frequency and content of the posts we publish to instagram. These tasks are a function of the outcome but do not dictate the timeline of the goal. there are too many external forces, like algorithms and users. Plan only what is in the sphere of influence.

How to not realistically plan for success: Creating a goal that we are going to get to 15,000 followers in 10 weeks while our social media page is currently at 0 and this is our first time running a business page. This over confident goal is going to fail. However, It doesn't stop someone from being absolutely positively sure about the outcome.

Let's unpack this a bit: The correct eventual goal is to get to 15K followers. The projection of certainty that we will get there in a certain time frame is a feel good bandaid over the fear that we never get there. It's a comforting and possible goal until the day has come to deliver the number. This failure feels worse than admitting we couldn't achieve the goal.

So how do we do planning? First we have to be honest about how much risk lies just in the lack of experience. How much does the team or person need to learn to produce a small amount of work? Factor this into the deadlines. Next, only plan things that are in the sphere of influence. Do we have the talent and experience to do it ourselves? Are there existing resources to do the work for us? These are all factors to your planning and certainty levels.

How Do We Project Our Goals to the World? (And Maintain Credibility)

This is easy. Don't include deadlines for outcomes. But if you have to, take your best estimates and then triple the time necessary. Otherwise just say we will get to this task when the current set of things are accomplished. This is more realistic approach is called milestone based planning. It's the best tool for aligning teams on the work to be done and when it is time to do it.

The world has taught me that having longer timelines is better than missing deadlines. Being right is more important than how quickly something is done. So next time you are certain about an outcome think again. Be certain about getting the job done but remember to give yourself a hedge against timelines to accommodate for the unexpected risks in life.

Enadi

Thank you to William Gaty and Christiana Ferencz for proof reading this essay.