Goal Setting and Iterating Quickly

  • How do we choose our goals?
  • How do we avoid doing the wrong thing?
  • How do we avoid wasting people’s time and money?
  • What happens if we’re wrong?
  • How do we learn from our mistakes?

How do we learn from our mistakes?

These are all questions that have difficult answers. The danger, as it happens, is not doing the wrong thing — the danger is doing nothing. And, I believe, the source of our paralysis is actually the goals we’ve chosen. In this I discuss some pitfalls in choosing goals and ways to choose them in a way that makes us more willing to try seemingly risky solutions and iterate faster.

Working Together to Reveal Truth

It is not for us to assume that we can understand the variables that affect others’ decisions. How we interact with the world somewhat of a mystery. It is that mystery that makes life challenging, inspiring, surprising, and unknowable. Struggling with our own selves is a grim reminder of the difficulty we have in understanding others’.

The fog of the future ahead and the facts of the past behind. Both are tainted by our own senses, our own experiences and our own biases. As such, the decisions we make our tainted by the very same.

Minimizing these biases can only be done through honest discourse with those who walked similar paths but came to different conclusions. Weaving experiences together is the best way to reveal truth. While stubborn allegiance to our own viewpoints is the most assured path to feed falsehoods.

With this in mind, mistakes are not made through incorrect conclusions but through reserved opinion.

Types of Goals

The difficult part of knowing where you want to go is distinguishing between your destination and your next step. The latter is a means to an end while the former is the end itself. As obvious as this may seem, it is often forgotten or never considered in the first place.

So there’s a nuanced difference between setting your sights on a general goal and locking in on a specific, unwavering outcome. The first is a destination you want to arrive at while the second is marked by a specificity which can actually limit your ability to apply creativity to your solutions.

Having a detailed goal in mind implies that you know more about your environment than you actually do. Goals that we are speaking of here are inherently non-specific. They are light through the fog not a signpost in a clearing. Expecting the latter will have you fumbling in frustration when you encounter the fog.

As with any agile approach, as you approach the goal, it will become more clear giving you the ability to waver less on the path you set for yourself. But in order to do this you must accept and understand that you’re perspective is limited by your own experience. Reject the notion of infallibility and open your mind to possibilities. If you accept that diversity of opinions can you open your eyes to unexpected solutions then you are well on your way to a successful project.

Choosing Your Path

A humble attitude is a requirement that weaves its way through each of our lessons in different forms. Approaching any problem with a defiant stubborness of opinion is far more likely to move you down a wrong path than eagerly soliciting others thoughts and opinions.

This behavior is often seen as weak or indecisive in our corporate culture. But the truth here is that soliciting opinions and deliberating on them is not indecisiveness until you are unable or unwilling to choose one of these options.

Taking too long to choose a path suggests that you have defined your end goal with too much specificity and are now worried that your solution won’t address each requirement as expected. But the truth is that we can never know for sure if a chosen solution will solve a specific problem until it is tried. But we can know that a chosen solution can move us in the right direction toward a more conceptual goal,

So, once again, success in crafting your goal is the catalyst that triggers subsequent decisions and success. A goal that falls too far in either direction (precision or vagueness) will lead to a more difficult journey.

And the act of crafting your goal and taking your first steps is an exercise in humbleness. Have confidence in what you know and solicit opinions for what you don’t. But be honest with yourself when deciding what you know and what you don’t. That might be the hardest part.


As I finish this, I recognize that what I’ve written so far reads like a self-help essay and not a practical approach to goal-setting. But it occurs to me that so much of this is more art than science. I, like most, would like these tasks to be deterministic. But by ignoring the reality that in many cases, there are too many variables to accurately predict the future we have to give ourselves the room to be wrong and to make errors a fundamental and critical part of our process.

By all means, do everything you know to do to pick the right path but don’t let it paralyze you. Be courageous enough to make decisions despite the threat of wrong choices and humble enough to recognize that you will make them. Being humble encourages you to solicit other opinions and the courage helps you take a step when your path is unclear.

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