No, You Don’t Always Have To Start With Why

Here’s a simple exercise for today.

The Ladder Of Why is a tool for gaining clarity in your work. Specifically, clarity on the relationships between the tasks you’re working on and the objectives you’re moving toward.

There are only two rules:

1. To move up the ladder, ask ‘Why?’

2. To move down the ladder, ask ‘How?’

Where To Start

Take anything you happen to be working on. An article you’re writing; a song you’re composing; a script you’re coding.

Every task you’re engaged in belongs somewhere on your own unique Ladder of Why.

Toward the top, we have our objectives — the things we’re hoping to achieve through the completion of various tasks.

Asking, ‘Why should I do this?’ is the way to take one step closer to understanding those objectives.

Toward the base of the ladder, we have our actions — the things we actually need to do in order to achieve our objectives.

Asking, ‘How can I achieve this?’ is the way to take one step closer to understanding which actions are needed.

Where to start?

Start wherever you are, with whatever you’re working on, and move in whichever direction you feel you need more clarity on.

Moving Up The Ladder

Take this article as an example:

  • Why should I write this piece today?

→ Because I want to build a library of resources, exercises and tools for creators, and this piece will contribute to that library.

  • Why should I build a library of resources for creators?

→ Because I believe the creator economy is more unstable than it needs to be, and that building better infrastructure to support it — including simple libraries of resources — is a valuable thing to do.

  • Why is supporting the creator economy a ‘valuable thing to do’?

→ Because I believe it facilitates a mode of working that allows for a unique level of agency and autonomy — which will ultimately lead to a better and more fulfilled society if the systems and structures can be built to make it viable.

You’ll notice that the reasoning is personal. Subjective. Without any rigorous proofs or research to back it up.

The purpose of the exercise isn’t to produce a rigorous objective proof — it’s simply to get me to a point where I have enough clarity to begin taking action.

Photo by Ethan Johnson on Unsplash

Moving Down The Ladder

Moving in the opposite direction is equally important.

If I begin at some high level objective, vision or mission, I need to be able to navigate my way down into the weeds of the ‘How’.

‘How’ questions are typically more difficult to pin down. They do not have a single source as do many ‘Why’ questions, and so the branches for what could be done are numerous.

This is why implementing is hard. It’s why having a good idea at the high level is worth very little if you cannot demonstrate and work your way through the ‘How’.

Doing the work of being precise on the ‘How’ means being explicit in asking the question.

An example of moving down the ladder:

  • My mission is to build structures which facilitate the creator economy, because I believe it will lead to a more fulfilled society.

→ Okay, how are you going to do that?

  • From my research and experience, it seems that instability and uncertainty are major issues in this domain. I’m going to build tools that reduce uncertainty for creators.

→ Okay, how are you going to do that?

  • Uncertainty can be reduced with better data points. So, I’m going to help creators leverage their data to be more informed and lower uncertainty.

→ Okay, how are you going to do that?

  • For the software-driven data solutions, I’ll help facilitate the build of tools with my technical co-founder. For the items which can be produced more ‘manually’ — templates, exercises, articles, discussions, forums, etc. — I’ll create them steadily and distribute by publishing to an audience of creators.

… and so it goes.

It’s worth noting that the process of finding your ‘How’s is a branching one. This means that for every ‘Why’, there will be multiple ‘How’s.

At the end of the process of moving down the ladder, you should have a list of several tasks that need doing in order to fulfill the Why at the level above.

Counting Steps

Moving down the ladder is effectively the process of backward induction. It’s one of the most powerful mental models I’ve come across, and sincerely worth investing the few hours it will take to learn and absorb as a toolkit in your own life.

With decision trees and backward induction in mind, one useful thing to note while doing the Ladder of Why exercise is:

‘How many steps removed am I from the end objective?’

  • If the step count is greater than 3, you can consider the ‘Why’ abstracted;
  • If the step count is 3 or fewer, you can probably keep the ‘Why’ within view while working on the task, without much difficulty.

For ‘far removed’ objectives, it’s worth making a visible note of what your objective is and returning to it often.

This is what those ‘vision boards’ are all about. It’s positive affirmations; it’s visualizing your success; it’s reading back your goals each day.

Photo by Ameer Basheer on Unsplash

I think these tools are important only for a certain type of objective — that is, for abstracted goals.

The logic for this is simple.

Some of our goals are complex and have been abstracted away from daily actions. If our end goal is 7 steps removed from ‘writing this article, today’, it’s a cognitive strain to walk up and down the Ladder of Why with each and every writing and daily task.

Instead, jumping up the ladder with a pre-made reminder of the higher ‘Why’ can speed up the motivational circuit needed to do difficult work, today.


  • The Ladder of Why is a simple, 2-rule exercise for connecting the ‘Why’ and ‘How’ of a given task or objective;
  • Ask ‘Why’ when you are lacking motivation, or simply don’t understand the need for the task at hand;
  • Ask ‘How’ when the why excites you, but you don’t seem to be making any tangible progress;
  • For tasks that are 3+ steps removed from their ‘Why’, create a shortcut with a physical reminder that states it explicitly. The more time you invest into creating this ‘token’, the more meaningful it will be (and the more likely you are to find it inspiring).

Happy climbing.


Gerrard + Bizway AI Assistant

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