Fail Early, Fail Fast, Fail Often: What lessons can we learn as leaders?

Rishi Khanna
5 min readFeb 1, 2021


People who know me have heard me say, “Fail Early, Fail Fast, Fail Forward”. I have always believed in progress over perfection. I have even taken it to the next level to say, “Fail Cheap”.

If you’re into reading self-help books, you’ve likely heard of ‘Fail Fast, Fail Often: How Losing Can Help You Win’ by Ryan Babineaux and John Krumboltz. I recently read this book and found it to have furthered my mindset. The psychologists, counselors, and creators of the Stanford course ‘Fail Fast, Fail Often’ has revolutionized the way we think about failure, by taking lessons from some of the most successful entrepreneurs and packaging them into one foolproof lesson.

That lesson is that successful people spend less time planning and more time doing. They are less afraid to fail and as a result, they fail a lot, however this actually leads to a quicker process of growth. There is also a growth opportunity in the organization by preaching this to your teams to move fast and focusing on moving the needle and not be afraid of a dent along the way.

There are so many amazing lessons hidden within this book, from thoughts on the nature of innovation to the ways that top entrepreneurs operate. I am rounding up some of the most insightful learnings from this book to give you a quick rundown. Take a look…

1.Failing Means Learning

One of the most important lessons from the book is that we need to reshape how we think about failure. So often we can feel down and depressed about failure, like we’ve really done something wrong and that there is no way out. In reality, failure is often the first step to really understanding something and therefore it should be reframed as a stepping stone to success.

At the end of the day we are all human and no one really knows what we’re doing the first time round. When it comes to innovation and entrepreneurial thinking, this involves trying new things by its very nature and therefore it’s reasonable that you will fail. Failure should be thought of as an essential part of learning. It’s actually a good thing. Afterall, Failing is a prerequisite to learning and growing.

2. A Fun Life Will Lead You In The Right Direction

People often opt for the hard route in life, believing that the harder something is the more they will be rewarded. Perhaps this is some kind of message we pick up from school-age? Either way, somewhere along the line we’ve inherited the belief that the harder we work/ the more we study/ the less enjoyable it is, the more likely we are to succeed. We go into work with the same mindset, thinking that the more we study, stress, and spend time on something, the more likely we are to reap the rewards.

In the real world, this isn’t true. When we struggle and don’t enjoy what we’re doing, we give off negative energy that affects every aspect of our life. Conversely, when we follow the path that is more fun, that we genuinely enjoy, the world seems to open up to us and offer more opportunities. Follow the fun.

3. Take Risks

How many times has the fear of failure held you back? Or the fear of being embarrassed, doing something wrong or letting people see you in a vulnerable light? The truth is that none of us like to admit we’re wrong, or that we’re vulnerable — our ego really doesn’t like it. However, that commitment to the ego can be what holds us back. In order to succeed, we need to fail, and we need to take risks.

This book teaches us to take risks and be less afraid of the outcomes. We don’t have to wait to act, we can start right away. Be confident, be unafraid, and take the calculated risks that you believe in.

3. Reclaim Your Innocence

Children see the world in such an amazing way — they bring an innocence to the world that makes it more fun, more open and more full. As a child, you probably rarely worried about failure, you’re just in a state of doing and experimenting all the time. As we get older, we get conditioned to forget this part of our nature, and as a result we can become stuck in patterns of thought that confine us.

Don’t be afraid to ask questions as a child would, you are not supposed to know everything. As soon as we drop out ego and look at the world in terms of play, we start to make amazing changes.

4. Think Of A Career As A Marriage

So many of us jump into careers that we don’t know enough about, or that we don’t truly love. In reality, a job or career is a lot like a marriage — it will be there with us for the rest of our lives and will impact our day to day lives so much more than we realize when we first embark on those steps to start a career.

The book teaches us to spend time investing in a career as we would a marriage and not to go blindly into a career path without understanding it fully.

5. Have A Hobby You Love

Having a hobby can take you away from the daily struggles of life, reset your mind and help you refocus. It really doesn’t matter whether you’re good at it or not, so long as you enjoy it that’s all that matters.

Having this mental break from reality can be amazingly helpful in both our lives and our careers and can keep us out of trouble when times get tough or stressful. If we have something we really love and have goals with, we can get happiness from life even when work and career goals are not being met.

6. Don’t Travel The Journey Alone

No one can do it alone. We all need people to help us along the way, whether that is in a mentorship role, a coach role, a friend role, a partner role, or otherwise. This book teaches us not to try and do it all alone, but to trust others as we move through the business world. As the saying goes, “if you wish to go fast, go alone, if you want to further, go together.”

The more people we know, the more we network, the more likely we are to have opportunities open up to us and light up the way.

Want to read the book for yourself? You can find a copy on Amazon. Let us know what you think of these takeaways and get in touch if you want to discuss the lessons in this book.



Rishi Khanna

Thought-leader, Culture Building, and Growth CEO. A leader in the following companies: ENO8, ISHIR, BorderlessMind, DigitalSuccess, and AnythingCloud.