Problem Solving Orientations

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.

Consider an archetypical scenario: a monkey sees a grove of banana trees, and, in approaching the bananas, is scared away by a tiger. From the top of a tree a safe distance away, the monkey stares at the bananas, which make the monkey hungry and make it want to approach, but knows that the tiger is still in the grove, which makes the monkey afraid and makes the monkey want to stay away. The monkey had previously perceived the situation as one of unmitigated gain, which led to its action of approaching the trees incautiously. With the new feedback presented by the tiger’s chase, the monkey can not longer proceed as before; something has to change.

Modify the External Motivational Environment

If you can’t win, change the rules.

― Peter Diamandis

The first step in the causal chain leading to action is the environmental motivation. Wherever you are, there are opportunities present to you in the environment, and also threats. The motivations we have use the opportunities as a foundation, so that our motivation is conditional, that is, our motivation is restricted to situations where we see the opportunity presented to us.

Sometimes, the “environment” we find ourselves in is mainly metaphorical. Given a computer, we are all presented with a vast set of opportunities, a plethora of possible actions and responses at our fingertips. Our social environment as well presents us with a world of possibilities within every interaction. Our choices might be so numerous and consistent as to seem ubiquitous, which might engender the illusion that our motivations are deeply coherent, but as we have discussed before, we are not nearly as consistent as we think we are.

Recognizing, then, that our motivations are conditional given our environment, changing that external environment is one approach to resolving a problem. If the tiger in the monkey’s environment threatens its ability to pursue bananas, one solution for the monkey is to drive away the tiger so it can eat its bananas in peace.

By focusing and resolving the conflict in the external environment, that environment is now conflict-free; the environment itself is improved. In situations where the environment is one you will be participating in frequently or repeatedly, it is often worth the investment to upgrade the external environment in this way. On the downside, of the four approaches this one can be the most confrontational; you share the environment with others, so changing the environment might put your interests at odds with theirs. The monkey might earn a scar from confronting the tiger; the tiger’s future absence may or may not be worth the price.

Modify Your Internal Motivational Environment

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

― unknown

Next in the chain to action is your internal motivational environment. Triggers of context and content from the environment may cause motivations within you, but ultimately it is your interpretation of the world around you which lets those trigger have that effect. Your motivations are not beyond your control; by reflection we are able to rein in our emotions and make them serve us, rather than the reverse.

There are many ways to change our internal motivational landscape, for the sake of this essay we will consider the primary method of prioritization. In seeing some object of desire alongside its risks, we might deprioritize the goal as not worth the potential cost. Or, if we were a monkey, we might think that the bananas we see in the tiger’s grove are probably not particularly tasty bananas anyway.

Whenever we set goals or expectations, we are emotionally investing in that area of our life. It can be tempting to see the release of a goal or a lowering of an expectation as a failure or a retreat, but in fact, it can simply be a good investment decision not to spend more emotional energy or mental effort in unimportant parts of our lives. 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 drive forward exhausts us. 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, being willing to lower our expectations can be an excellent way to focus our energies into other areas of our life.

Change Your Technique

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.

In a sense, this is “inside-the-box” thinking; we are given some question from the environment and from our interpretation of the environment, and we seek out an answer to that question. In some sense, each of the other approaches changes the question in some way.

But we should not think that “inside-the-box” thinking is somehow lesser or uncreative -- there is a good reason this is often our default approach! When you change your techniques to solve a problem, you accumulate more tools and skills which follow you to other problems as well. If you change your techniques in the right way, you are solving not only the problem in front of you, but also a host of problems you might encounter in the future.

Returning to our monkey example, perhaps the monkey might discover a way to swing from branch to branch in the trees’ canopy, never exposing itself to the danger of the tiger on the grove’s floor. For that grove and every other, it now has a safer means of transit, which could open a whole new world of opportunities.

Switch Your Environment

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

― Coco Chanel

The last method of obstacle resolution is 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.3

In our example, perhaps our monkey might remember any of the other places it has found fruit in the past, or any of the places where it hasn’t yet searched. Seeking out new environments encourages us to explore, and can lead to a reduction of aggressive competition if you can find a new game to play without hostile opponents.4


Approach Pros Cons
Modify the External Environment Environment is improved for everyone; often leads to status Often involves some conflict for status
Modify Your Internal Environment (Lower Your Expectations) Fewer resources invested in the problem, more resources for other problems Inferior outcomes in this problem
Change Your Technique Accumulates tools for future problems Mentally difficult, sometimes impossible
Switch Your Environment Explore other opportunities, can find situations with less conflict and higher reward No guarantee that the grass will be greener on the other side

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.


  1. See the well-traveled road effect and the familiarity principle for more info.

  2. See the sunk cost fallacy.

  3. Sometimes referred to as the “Grass is Greener Syndrome”, or weighting too heavily on the “explore” side of the “explore-exploit tradeoff”.

  4. Mauborgne, Kim. Blue Ocean Strategy, 2004.