How To Overcome Obstacles Using The ‘5 Why’s’ Technique


When learning how to break bad habits and form good ones that stick, it’s not uncommon to experience a dip in your motivation and quit – and often right on the edge of a breakthrough.

These losses can be chalked up as failures on our part and affect our self-esteem, or worse: discourage us from trying again in the future.

The reality is, our problems are seldom behavioural, but situational. It isn’t us that’s the cause of our challenges, but the system we’re using. In other words, it’s not that we’re demotivated; quite the contrary – it’s that we haven’t identified the real obstacles that stand in our way.

The obstacles in question may seem obvious – “I didn’t go to bed before midnight because I was watching a movie” – but there’s often an underlying root cause and classifying it is paramount to building the right solution.

The Five Whys

The Five Whys is a technique adapted from the Toyota Production System. Taiichi Ohno, considered to be the father of the Toyota Production System, describes The Five Whys as:

The basis of Toyota’s scientific approach [and] by repeating ‘why?’ five times, the nature of the problem as well as its solution becomes clear. [1]

Often, at the root cause of all our obstacles are habits, that either aren’t working well or simply don’t exist. But by asking “Why?” five times, we can drill right to the core and strategise a solution.

For example, let’s assume you’re on a diet and you had a willpower failure by eating a meal that wasn’t on your diet plan.

The Five Whys would look like this:

The Problem: “I ate a pizza for dinner”.

Why #1: Why did you eat a pizza for dinner?

  • Answer: I didn’t feel like cooking.

Why #2: Why didn’t you feel like cooking?

  • Answer: I had a bad day.

Why #3: Why did you have a bad day?

  • Answer: My boss criticised me.

Why #4: Why did your boss criticise you?

  • Answer: I’m underperforming.

Why #5: Why are you underperforming?

  • Answer: I’ve been going to bed late.

Now we’ve got something! You’ve identified that the real reason you had a willpower failure and failed to commit to your diet, wasn’t because you couldn’t summon the effort to cook a meal, but because you were tired.

In that case, the root cause of your dietary challenge isn’t the diet itself, but another behaviour; one you previously would not have considered a problem had you not made a self-enquiry.

If you were to prioritise sleeping seven to nine hours a night – in other words, make going to bed early a keystone habit – imagine what your end result would look like? You would perform at an optimum level, impress your boss, feel happier and motivated to lose weight, and commit to your diet.

This is a very Kaizen way of solving problems because it invites you to take baby steps and improve at a rate that’s sustainable. 

Identify Your REAL Obstacles

There are two rules when using The Five Whys:

1. Be tolerant of all mistakes the first time.

2. Never allow the same mistake to be made twice.

In his book, The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses, Eric Ries explains the first rule encourages you to get used to being compassionate about making mistakes, after all, mistake are inevitable and it’s how we learn. The second rule gets you to start making proportional investments in prevention. Once is a mistake, twice is a choice. [2]

Only when you develop an accurate understanding of the root causes of your obstacles, can you begin to create widespread change.

If you lose enthusiasm for going to the gym, you may confess it’s because you’re not gaining muscle, but when you dig deeper, you may be surprised to learn the root cause is because you believed muscle would lead to more confidence. Lean into your fear: confidence will follow.

Keep forgetting to floss? You might conclude it’s because your forgetfulness keeps getting the better of you. But by becoming a choice architect and redesigning your environment – say, leaving your floss in plain sight and flossing immediately after brushing – you identify the real reason: your environment was hindering you rather than helping you.

Excusing yourself from habitualising a new habit – like writing 1,000 daily – because you’re “busy” and “don’t have time”, may seem like realistic excuses. But with a little self-enquiry – like using The Five Whys – you may expose the truth: you’re afraid. Afraid of judgement. Afraid of what others may say. Afraid of the “what ifs?” Procrastination is often an opportunity for introspection, so listen up and just start.    

A Final Word

There are many more examples we could discuss, but as rule of thumb: when encountering an obstacle, ask “Why?” five times to determine its root cause. Remember, it’s often a broken process or alterable behaviour.

Obstacles are to be learnt from, so don’t run from them. People do not fail, processes do, so if need be – learn a new process. All will become clear in the end. Thought Catalog Logo Mark


[1] Ohno, T. (1988) Toyota Production System: Beyond Large-Scale Production, Portland: Productivity Press.
[2] Ries, E (2011) The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses, New York: Random House.

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