How to penetrate complexity?

“Start with what is easy”, ” Do the hard job first”, ” Chunk your goal”!

There are much advice out there telling us how to approach our execution process but none of them talks about contexts and timing. And We end up more confused than ever.

If we always focus on the easiest part, we won’t make any substantial progress. Our internal voice will remind us we are running away from the real job that can help us to move the needle.

On the other hand,if we always start with the most difficult , we end up postponing the starting point  because we feel it is going to be hard.

There is one efficient framework that you can use to penetrate any situation that seems complex.

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To begin with, we need to understand the difference between CRITICALITY and DIFFICULTY. These concepts are always intricate.

Criticality helps to assess the risks of not doing something for someone within a certain horizon of time.

To evaluate criticality the question is: What might happen at worst case scenario if I don’t accomplish the task within in a certain horizon of time?

Difficulty on the other hand helps to measure the energy you should invest to accomplish a task.

To evaluate difficulty the question is: How much effort should I put in at minimum to have this task done within  a certain horizon of time?

Rule 1: Always start with the most critical task

Chronic procrastinator struggle to follow Rule 1  because of  our identity.

Even if we perceive the risks involved in not working on something at a logical level, somehow at an emotional level we underestimate it on the balance of decision-making.

So we will naturally make our first analysis under the spectrum of difficulty.

It gives a thinking process like this:

  • “Oh it sucks”
  • “I don’t like it”
  • “It is so boring”
  • “I have better things to do”

These are all reactions of our unconscious mind when our attention quickly spot a critical task  that is also a difficult one.

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Rule 2: if a task seems difficult, start with its easiest subtask . If a task seems easy, start with its most difficult subtask.

The moment we shift our focus from the big critical goal to its small easiest subgoal , suddenly all the anxiety goes. we stop being harassed. It helps us to focus because worries like the  following disappears automatically: ” How I am going to finish, It is still a long way to go”, ” Am I not running away from the most import part?”.

On the contrary,  Starting with the difficult part when the subject looks easy compensates the cases when we underestimate the difficulty level  involved.  Procrastinators are champions of wishful thinking:  ” it is almost finished” ,” I already have xx, I will be ready to do it, don’t worry”. Starting with the difficult sparks our motivation since there is still a challenge from our eyes, otherwise we neglect it.

Now let us take a hard look at how it applies in real life:  we will consider the most common case: when the critical task is also a difficult task.

  • Step 0: Fix the horizon of time H

    • Which horizon do you consider to analyse? ? 1 day, 1 week, 1 month, 3 month,1 year?
  • Step1:  what is the most critical task of your list? 

    • What will happen if I don’t complete task T for client C in the horizon H?
  • Step 2: Start with the easiest subtask within the most critical task

    • What are the intermediate subtasks I can list now and which of them request little efforts?
  • Step 3: Continue with the most difficult subtask within the most critical task

    • What are the intermediate subtasks I had listed and which of them requests much effort?

Example 1 Employee at Office

Context:I have a lot to do today. Phone calls, meeting reports, travel to prepare, powerpoint presentation, project’s reviews, Boss weekly meeting.  I don’t have enough time and paper are everywhere. I don’t know how to proceed.

  • What is the  horizon? 1 day
  • What is the Most critical task: “be ready for boss meeting review” ( because not being ready will slow my career)
  • What is the Easiest subtask: “issues on track”
  • What is the Most difficult substast:  “Issues that happened recently and I don’t clearly understand their root cause.” There is a need to delve deeper to explain them to my boss.

Execution plan

  • Step1: I summarize the latest news about topics on tracks .
  • Step 2: I start looking for information about issues I don’t fully capture: calling colleague  to get answers, reading mails with attention.

I challenge you to apply this simple framework to a complex situation you encouter today.

Example 2: student preparing for exams

Context: There is too much to study for:Mathematics, physics, english, french, geography, electronics.

  • What is the  horizon? 2 weeks
  • What is the Most critical task: “be ready for Math test” ( because not being ready in maths will give me bad grades. It  is an eliminatory criteria for concours I plan to apply for later)
  • What is the Easiest subtask:” subjects I had understood well”: like complex numbers, geometric sequences.
  • What is the Most difficult substaks: “subject too abstract”: like algebra .There is a need to delve deeper

Execution plan

  • Step1: I do exercise on complex numbers
  • Step 2:  I focus on understanding algebra courses ( reread personal.notes, call a friend, do old algebra exercises)

Example 3: entrepreneur building his business plan

Context: I  am looking for investments and I have to talk to different kind of people; Investors, bank,  future team members, partners.  I need to build a business plan and it has many parts:  Problem statement, Solution , market study, competition, Go-To market strategy, finances, team,

It is a tedious tasks to build a  business plan. However I would like to spend my time building the product and serve customers. I am  not used to  do financial projections . Moreover I already know these projections won’t last long because there is always many unespected pivots.

How shoud I approach investing my energy to build the business plan giving my scarce time resources?

  • What is the  horizon? 2 weeks (because I am meeting with the Bank in 2 weeks)
  • What is the Most critical task:
    • Criticality level 1“Problem statement” Because if someone does not understand   the problem you solve, there is nothing to be discussed. The people you are talking  to have to be convinced there is demand  linked to a problem. If they don’t quickly understand what is you are trying to adress,  It is over.
    • Criticality level 2 “Finances” . Because The Bank is concerned by money. If there are convinced there is a need, the second thing there are going to  be interested in is your financial projections. Are the hypothesis you choose realistic? What is their Return of investment? So you better have something ready to share even a low level document is enough.
  • Criticality level 1“Problem statement” What is the Easiest subtask:
    • ” framing the problem with technical words” (I am technical so it seems easy)
  • Criticality level 1“Problem statement”What is the Most difficult substaks:
    • ” reframing the problem with simple words” (I am technical, so it is difficult)
  • Criticality level 2 “Finances”: What is the Easiest sub-task
    • How much people do I need   for the next 6 months? ( I can evaluate it  based on the  short term perspective  easy to process)
    • What is the annual revenue of  similar companies than yours after 3 years? ( I can find the answer with Google)
  • Criticality level 2 “Finances”: What is the Most difficult subtask:
    • How  to model the financial flux of the company? ( I can’t find it on google and even if I do, there will still be  a need for deep understanding )
    • Which KPI should I use to drive the company later? ( same remark than above)
    • How  to adapt the workload with the resources? (  there is a need to build different scenarios)

Execution plan

  • Step 1: I focus on framing the problem in technical terms
  • Step 2: I focus   on re-framing the problem in simple easy-to-understand terms
  • Step 3: I focus  on evaluating the resources required for the next 6 months and the revenues I could expect in 3 years
  • Step 4: I focus on modeling the financial flux  of the company.

I challenge you to apply this simple approach to a complex situation you face now.


HEUDOU TCHIHIKOU Aubin

A Master chronic procrastinator who chose to execute on its dreams because of frustration and self-criticism.

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