How to Fail and Still Win: A Guide to Not Losing Your Cool

We hear more commonly now that to succeed we must become good at failing. Fail fast and fail repeatedly but ensure you don’t make the same mistakes. Admitting failure can be extremely hard to do. We are declaring we are vulnerable. We open ourselves up to criticism and self-deprecation as well as suffer great guilt and shame in disappointing and letting down the team that has been supporting us all along. If you are a business owner, CEO or senior executive the consequences of your failings can be far greater. You might not just be impacted financially. Your relationships outside of business can suffer terribly and not just for the short-term either.


Despite all of this, there are solid ways to keep your cool whilst your claw your way back to dignity through this mental and emotional hurricane. Here are some key steps to help you tap into the upside – yes, there are inevitable upsides – to failing that ultimately are your keys to your future success.

1. Become better at accepting you have failed.

When you have truly failed to meet the goal or target that was set, trying to resist and deny it only compounds the emotional and mental load you carry. When feelings of disappointment, embarrassment and sadness arise within you, start strategically dedicating time to experience them. By doing so, your brain’s emotional center will process these faster and free up your mental capacity to step into a growth mindset.

“Identify and quantify a failure before it compounds over time.” ~Fran Tarkenton

If anyone knows how to fail forward, it’s Jeremy Bloom. By saying “I have failed”, Bloom explains you’ve literally set yourself free of the weight of it. Developing this acceptance process and using it repeatedly, Bloom has gone from being an Olympic and world champion skier to an NFL player and now founder of the Wish of a Lifetime charity and software company Integrate. For Bloom, accepting failure is a highly liberating experience.


However, this acceptance phase cannot last forever. Move through the emotional phases but put a time limit on it. Set a deadline for when you will step into stage two.

2. Start embracing the multi-dimensional nature of failure.

Failure is a matter of perception and your definition of it will often mean something completely different from one person to the next. If you view failure as something that needs to be avoided at all costs, it is likely you have developed deeply unhelpful values and self-defining labels that staggered your potential. If you don’t start reframing them, they will continue to keep you prisoner. You can start turning this around by inviting yourself to look at failure as a multi-dimensional experience.

3. Look for the lessons.

World-renowned former quarterback for the Minnesota Vikings Fran Tarkenton learned early to expect to fail a lot. He learned to shift his focus to learning and improving:

“Losing a game always taught me more about a game than winning one.”

After winning a game the team would celebrate going out with family and friends and having a wonderful time. But after losing a game, Tarkenton would study. He would study what needed to change, go back and review where he could have done things differently. He always learned something which improved his game.


Review your original goal and your preparation to achieve it. Examine what worked and what didn’t and look for the reasons why and why not. If you have a chance to attempt that goal again, start developing a different strategy of attack and brainstorm the alternatives to get there.

4. Remind yourself you are on the cusp of greatness; you just can’t see it yet.

After being devastatingly fired from his own company, Steve Jobs did not lose his passion upon exiting Apple in 1985. In fact, he described it as being one of the most freeing periods of his life as he was no longer under the heavy constant pressure of being successful. Jobs chose to embrace this new ‘lightness’ he felt and started NeXT Computing, Inc., NeXT Software, Inc. and then Pixar Animation Studios which has become one of the most successful animation studios globally.


Let part of your grief process for your defeat entail stepping into creative thinking. Don’t just reflect on what you could have done differently. Start asking yourself explorative questions about the different directions your current crossroads could take you. When you practice and increase your time expanding your focus and thoughts to possibilities, your brain will be activated to develop faster and greater clarity on what your next best steps need to be. Ask yourself: “Where else can I go from here?”

5. Review your self-talk; practice remembering your thoughts and emotions don’t define you.

We often automatically ascribe ourselves self-deprecating labels of never being good enough, hopeless, a waste of other peoples’ time, useless….and the list goes on. We learn essential life skills when intense emotions are coupled with valuable experiences. But the downside is that this mechanism also anchors unhelpful thinking that comes alive when we experience intense negative emotions.


You, yourself are not a failure. In truth, the product of your actions, thoughts and behavior resulted in your failure. Failure does not define you. Nor do your thoughts and feelings. By starting to catch yourself in the midst of using any negative, self-demeaning labels you instantly help yourself to keep your cool because you are creating distance between you and your thoughts. Your mind generates your thoughts and feelings. They come out of you but they don’t define you. How can they when they can change so quickly from one second to the next??

About Malachi Thompson

Dr. Malachi Thompson III has cracked the code to creating a life that enables sustained levels of high performance. He has spent nearly 20 years as a coach, adviser, friend, mentor, and creative spark plug to elite athletes, CEOs, senior sports industry leaders, senior military leaders, and people who want to get more out of themselves and their lives. His expertise has been featured in Entrepreneur, CEOWORLD Magazine, Lifehack, Thrive Global, and Addicted2Success.

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About this blog

I’ve shown up to write every day for the last decade. Not because I had to, but because it's how real change happens—through consistent effort and a willingness to question everything. If you’re a reader, you’re in the right place. But be warned: I’m not here to comfort you. I’m here to challenge your assumptions, flip the script, and push you to see the world in a whole new way. Ready? Let’s go.

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