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”

14 comments On How to Fail Forward

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  • Really loved your inspiring post and thought your little obstacle diagrams added a lot!

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  • I really love the idea and have many times tried in many areas of my life, sometimes I succeeded, sometimes I didn´t. What I find hard is that I often end up doing it alone because I don´t seem to find people that can help me and held me accountable for my actions. I know it´s my job but, I know, at times, two is better than one.

    Any suggestions on how to do it so I can truly find partners/support for these kind of changes?


    btw: You are a truly handsome man.

    • Hey, that is a very valid question. I am happy that you are so self-aware that you know having good accountability friends can help you excel further.

      Here are some tips to do that (I follow them too):
      1. Call Your Closest Friend / Mentor / Family Member – Talk to them about it and say that you want them to hold you accountable for it.
      2. Join our Facebook group – There are many people who want an accountable buddy too. I am sure that I can help you find one!

      Hope to see you around! 🙂

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  • Hi Jawwad I really like your expression failing forward! I’m wondering how or if you decide there too many barriers? For me being active and keeping fit is very important but I know I can’t stand gyms! So instead I walk or dance or enter fundraising events to motivate me and help others. My fit bit tracker has connected me with walkers all over the world and we have friendly competitions too, that really spurs me on!

    • You bring up a good point and something I agree with too. Focusing on the outcome is important and not just the activity. For example, you dance and walk whereas I bike and workout – both activities achieve the same outcome of living a healthy life which impacts all other areas of life!

      • Yes ☺ and another way to view it is to figure out what the underlying need is that you want to meet and then look at your best options to help you achieve it. Ive just had this vision of doors instead of hurdles. I will draw it in my journal…Thankyou for your inspiration.

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  • thankyou for your blog. It is very interesting. I used to journal in my 20s a lot and i stopped in my thirties … I want to restart . I have seen that whenever i wrote strong post it notes and placed for myself like FOCUS, you can do it and set time to regularly medidate and write what i did that day and i monitored myself for weeks sometimes and identified pain points and i worked better when i internalized it and kept it to myself. I live with my parents and i feel ashamed now to do the same ….

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