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Power of Iteration

We are our enemy

When we are trying to make a significant change in our lives or when we have an ambitious goal we want to achieve, our biggest struggle isn’t necessarily with the work itself or even the effort needed to complete it.

Our biggest obstacle is our own attitude, our own intimidation and insecurity. We measure the scale of our desires against our estimation of our abilities and find ourselves wanting, regardless of the actual reality.

This is not a new problem and most suggested solutions involve breaking the overall goal down into smaller, supposedly more manageable steps.

However, that just replaces the intimidation of the sheer magnitude of the overall goal with the intimidation of the sheer number of smaller tasks. It does nothing to address our perceived disparity between the needs of the goal and our own abilities.

If we felt inadequate before, it is unlikely that this approach will fix that.

Fear is our personal reality

Another way we could possibly get through this impasse is to lower the bar, to reduce the level of our ambition to the level of our insecurity.

But that doesn’t feel right. It feels like giving up because it is giving up. We shouldn’t lower our expectations before we engage just because we are intimidated.

Intellectually we know this. But the thing about something intimidating is that it’s intimidating. The actual reality of the goal may be that is achievable but our reality is our intimidation.

Feelings are motivational and none more so than fear so this intimidation is not something that we can easily talk ourselves out of no matter how much we intellectually know we can handle things.

So how do we decrease our perceived gap between our ability and the need of the moment while at the same time still preserving our ambition?

Practice vs Failure

The answer is to build in failure from the start.

We plan from the beginning to make more than one try. If we execute our plan knowing that we will be making subsequent tries then the results of the first try become less individually important. We can afford to screw up because we know we’re going to try again.

That is to say we plan on iteration.

Iteration is not repetition

Iteration is very different than merely doing something over and over again.

It’s not that you started off intending to do it perfectly, failed, and are now trying again. There is a conscious decision to do things more than once and as a result it’s easier for your ego to accept that the first try doesn’t have to be perfect.

We are lowering the bar, but temporarily. And that makes all the difference.

In addition, by breaking that seal and allowing yourself to be less than perfect you set a precedent for yourself so that you don’t hold as tightly to this need for perfection in general. As a result even your subsequent tries don’t feel so fraught with meaning.

But iteration still means holding yourself accountable, in two specific ways.

Iteration is a set of complete cycles

The first is that when you are using iteration to refine your process you are taking it from end to end for each pass. You are not trying different steps of the process, you are doing the whole thing through from start to finish just at a lower standard.

This way, we mentally and emotionally scope things so that instead of dealing with this open-ended amount of work, we are able to grasp it’s extent. Even if it is a lot of work, a known amount is always going to be easier to deal with than an unknown amount.

To be sure, if you start down a pathway and discover that it just isn’t working out the way you thought there is no reason to blindly stay on that path. But you start with the intention of finishing things through the end, and then doing it again through the end, over and over until it’s good enough or you have satisfactorily demonstrated that it is a wrong path and you back off and choose a different one.

The key is to choose the right starting and ending point so that it is long enough to be meaningful but short enough that you can do more than one cycle.

How well did we do?

The second way to hold yourself accountable is evaluation. After each pass, you evaluate your success and adjust accordingly for the next pass. The change may not take the form of an improvement per se, perhaps it is just trying something brand new.

In fact part of that evaluation is to determine if that goal is still what you should be working towards.

This implies we trust our judgement as to what is good enough. Since you are evaluating success at each pass, while at the same time each pass becomes just another one rather than your only example, you are also practicing trusting your judgement in a less high stakes way ego wise.

Just finishing something from end to end is, in and of itself, an accomplishment even if the quality wasn’t perfect. That makes us feel good about ourselves which helps combat the effect of our insecurities.

You start to trust yourself more in general. We may still attach our ego to our results but by giving ourselves this drumbeat of success we insulate our ego from the results of any one pass.


Iteration is practice and progress and ego-building all at once. It gives us permission to be imperfect as well as helping us to trust our judgement more generally.