Sundry Surpassings

Learning is transformation. Each failure engenders inadequacy and dissatisfaction. In the moment, a failure drives you towards some change, any change, any resolution to continue forward, but the paths from failure are not all the same. There are four kinds of transformations that a obstacle can prompt, which all lead to different forms of resolutions.

Change Yourself

The road to wisdom? ― Well, it's plain,
    and simple to express:
Err, and err, and err again,
    but less, and less, and less.

― Piet Hein

Throughout most schooling, we are taught one way of overcoming problems: by improving our skills until the task becomes easier. Through learning new tools, new frameworks, or through practice, we harmonize our actions with the goals in our environments, producing fewer errors.

When hiring for a new employee, considerations most often turn to their collection of skills. As an employer, you are setting up some problems for them to solve; if self-improvement has been their path for overcoming obstacles, then they are most likely able to overcome the challenges in their role. In this sense, changing yourself, which seems at first to be a solitary approach, can be the most collaborative, since the change is contained internally, it is most flexible to varying external circumstances.

Change the Rules

If you can’t win, change the rules.

― Peter Diamandis

When presented with an impossible question or quest, another common road to resolution is to change the terms of the game. This is often the most confrontational approach, as it requires you to xx your will on your motivational environment. xxx

This approach can have far-reaching benefits for others. If you encounter a situation where the rules seem unfair or inconvenient, then by changing the rules for yourself, you can potentially correct them for others as well. On the other hand, this propensity for affecting others means this approach can also hurt others, possibly by skewing a situation in your favor and against someone else. With the most external consequences, this approach should be undertaken carefully, and with special attention paid to ethical considerations.

Change Your Standards

Happiness is not having what you want, but wanting what you have.

― unknown

At times, the problems we encounter come, not from external forces or rewards, but from within ourselves. It can be healthy to be your own harshest critic ― self-scrutiny can be one of the most efficient tools for improvement, as you can provide yourself far more voluminous feedback because the feedback never needs to leave your head.

Nevertheless, at times the standards we set for ourselves can hold us back. Pursuing excellence in any dimension carries the implicit cost of not pursuing excellence in another dimension; in pursuing some good, we might easily miss out on some other, higher good. Sometimes the good we leave behind is our own tranquility and peace of mind, as an indefatigable x forward exhausts us and xx. Sometimes, the goals could remain exactly the same, but the timeframe can be loosened to allow for more play, improvement, and hope. Regardless of the exact form, “settling” can be an excellent approach to resolve a problem, especially when those problems are not high priorities.

Play Another Game

Don't spend time beating on a wall, hoping to transform it into a door.

― Coco Chanel

The last method of obstacle resolution is simply to give up. In this vast world there are many games to play, careers to pursue, or partners to date. Sometimes the prize is not worth the growing cost, and another goal would be more worth your while. Even if you don’t end up switching, it is valuable to keep in mind alternative paths, so that you can be positively motivated, instead of being negatively motivated by feeling trapped.

Switching paths does come with a cost, and evaluating the costs and benefits can be quite difficult. We have a tendency as humans to overestimate the value of goals we’re familiar with and underestimate costs we are used to paying.1 We also tend to consider as losses costs already paid.2 On the other hand, countering these status-quo biases and pursuing constant novelty can lead to a loss of focus, or abandoning projects or relationships too early and never making progress.


Each of these strategies for overcoming obstacles has its place. Being aware of which strategies you’re choosing, and matching them to the problems you encounter can help you focus your energy towards meaningful progress, and avoid wasting time.