How to Fail Forward

He had already repeated a grade in elementary school and now found himself placed in the lowest division of the lowest class. Worse yet, he then went on to fail the entrance exam to military college twice. This unknown child failed many times in different aspects of life, until at age of 62 when he became the man known as “Winston Churchill”.

Unfortunately, it does not matter who you are – Winston Churchill or (your name goes here) – you will inevitably and consistently fail in your attempts towards many goals in life.

Goals such as losing weight, eating healthy, being a better person, or doing better in school.

How is that the highly successful people failed many times before accomplishing their goals? If there is no fail-proof way to your goal, how do you fail forward?

How can we come to understand failure as a normal part of life – and not shy away from it?

Hurdle Race

Our journey towards our goals is much like a hurdle race where we overcome unknown barriers as we go further. When we start, we are seldom aware of the barriers that lie ahead.


Goal Roadmap
Goal Roadmap


Here is my personal example.

Goal: Gym Routine – Going to the gym twice a week.

On day one. This is how my roadmap looked like – full of barriers I was not fully aware off.

Goal: GYM
Goal: Gym Routine

Two weeks into my goal, and am already struggling to go to the gym twice a week. The barriers are poor time management, lack of accountability, and lack of purpose.

Goal: Gym – Barriers to Overcome

To successfully move forward, my goal temporarily becomes to overcome these three barriers. Therefore, I improve my time management (by scheduling it in advance), I get a gym buddy to have more accountability, and I explicitly write down why I want to go to the gym twice a week and its positive effects on my. Having overcome these barriers, I’m ready for the next one.

Goal: Gym - Overcame Barriers
Goal: Gym – Overcame Barriers


The process repeats itself until you get to your end goal. (I am still in-progress)

goal check
Goal: Gym – CHECK!

It is hard to identify obstacles that make you fail – i.e. lack of work habits, lack of motivation etc. These obstacles are hidden under human ego or our unwillingness to accept our mistakes  – or our tendency to point out words instead of in words.

Lessons Learned

  • Identifying barriers are just as important as identifying the end-goal.
  • Failing is inevitable, thus, you must learn to fail forward.
  • Persisting at things gives you greater insight in what barriers to overcome to get your your goal.
  • It’s not the failproof method that we should be aiming for, but rather fail forward method.
  • “Always focus on how far you have come, instead of how far you have left to go”

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