How to Reframe Failure and Find Courage with an Experimental Mindset

How to Reframe Failure and Find Courage with an Experimental Mindset

The original article was posted here on the outstanding women’s business blog Stilettos on the Glass Ceiling.


“Perceived failure can become a catalyst for profound reinvention.” Conan O’Brien


Hello SOTGC community! Ok … lets get right to this topic of failure.

You were let go from a job, the business didn’t work out, you made a mistake on a project, you weren’t picked for an assignment, or perhaps you could have done better on that presentation last month. We all know that mistakes and failures are part of our life. And most of us know that it is how we deal with actual failure, perceived failure, or a fear of failure that matters.

Why is failure so hard to deal with if we know its part of life and we know it’s a possibility?

Lets start with the basics. What does it mean to fail?

To Fail (v.): “to fall short of success or achievement in something expected, attempted, desired, or approved” (

To Fail (v.): “Be unsuccessful in achieving one’s goal” (Oxford dictionary)

So, to fail you:

  • Must have a goal
  • Must make an attempt

Since we all have had goals and made attempts at them in our past … we also have had failures and successes. Looking back at your failures and successes – how did you feel when you failed? How did you feel when you succeeded? You felt so much better when you achieved that goal versus fell short right? When you won that award, landed that project, or got the promotion, it just feels great to achieve those goals.

When we look at past failures, we can usually vividly recall that sinking feeling of being sad, frustrated, and disappointed with the outcome. We can’t fail if we don’t have anything to lose. If we don’t put ourselves out there, have a goal, and make an attempt, then we aren’t living. Instead, we are watching and waiting for the perfect time…the perfect moment to jump in and start.

Yet, when you set out to achieve ANY goal, you don’t know if the outcome will be a success or failure. The essence of any goal, attempt and action is really an experiment from the beginning.

An experiment (n.): “A course of action tentatively adopted without being sure of the eventual outcome” (Oxford dictionary)


How can you embrace an “Experimental Mindset” in your work & life?


1) Reframe Your Past Failures – What Did You Learn?

“At the age of 47, after twenty-five years of obsessively pursuing my dream, that dream changed. For decades in show business the ultimate goal of every comedian was to host ‘The Tonight Show’. It was the Holy Grail. And like many people I thought that achieving that goal would define me as successful, but that is not true. No specific job or career goal defines me and it should not define you.” Conan O’Brien

We are all guilty of being WAY too hard on ourselves. How can we realign to the ACTUAL reality of what REALLY happened? How can we be kind to our “self” as we look at our past failures?

When we attach our ‘self’ to a past outcome, we feel the failure MUCH bigger than it really is. We are not defined by our successes or failures unless we decide to be. When we use language like “I should have known better”, or “it happened to me”, we are not able to observe, reframe, and restart. We are stuck in defining and attaching our ‘self’ with the failure.

The opportunity is to reframe our ALL past failures and successes as experiments. When we do this, we look at our experiences with a lens of a scientist. Scientists observe, experiment, learn, and reflect. Then, they pivot, retest, retry to observe again, experiment again, learn again, and reflect again.

Here is a personal example. While I was in graduate school, I was interviewing for full-time positions at Fortune 500 companies. I knew how to answer all interview questions except for one. “Why didn’t you get a full-time offer after your internship this summer”? I was a summer intern at a known Fortune 500 company, and I was one of the few people who did NOT get a full-time offer. I didn’t know how to answer this question until my brother asked me this question: “What did you learn?” In that moment, my perceived failure became my story of growth because I knew the answer. I was ready to share the experience of what I would do differently next time based on what I learned. In the end, I did get that exact question from a VP in a final round of interviews.   And, I was excited to accept the full-time offer from that company.

In your work & life, think about a perceived failure. Now think about what you LEARNED from that experience. Be a scientist. From what you knew at the time, you made the best choice. Now looking back, what would you do differently?


2) Reframe Your Fear of Failure – What Can You Learn?

“Today I tell you whether you fear it {failure} or not, disappointment will come. The beauty is that with true disappointment you can gain clarity, and with clarity comes conviction and true originality.” Conan O’Brien

Watch these talks below as reminders of why we MUST move forward despite our failures and fears.

Do you want to be in the game or watch the game? You decide. Neither success nor failure define who you are…its the art of showing up that matters. You will feel resistance. That is the memory of your past failures trying to protect you from failing again.

Tara Mohr, an expert on women’s leadership and well-being, shares that to reframe your fear of failure it is helpful to give yourself permission to learn.

Think of goals that will push you to play bigger in your work & life. Pick a two-week goal that you could start tomorrow (and that scares you a little or a lot). Before you start that goal, write down what you want to learn in that “experiment”. Reframing a goal, a day, a project in terms of what you CAN learn, will help you shift toward an “experimental mindset”.

  • What do you GET to learn today?
  • What do you NEED to learn today?
  • What do you WANT to learn today?


3) Reframe Your Mindset – How Will You Attempt Your Goal?

To fail or succeed, we must have a goal and then attempt that goal. How we show up and attempt that goal matters.

Ask yourself in your current situation: Do you have a “perfectionism mindset” or an “experimental mindset”?

When we show up with an “experimental mindset”, we see the goal and our efforts as a learning experience. We are less attached to the outcome of success or failure. Rather, we are focused on the actual experiment, which then forces us to be in the moment. Author Carol Dweck has done extensive research on the benefits of a growth mindset versus a fixed mindset.

“In a fixed mindset, people believe their basic qualities, like their intelligence or talent, are simply fixed traits…In a growth mindset, people believe that their most basic abilities can be developed through dedication and hard work—brains and talent are just the starting point. This view creates a love of learning and a resilience that is essential for great accomplishment. Virtually all great people have had these qualities.” Carol Dweck, author of Mindset

When we see our goals from the lens of growth, we empower ourselves to make attempts with curiosity. Like scientists, we wonder what might happen, we set up the experiment, and we start. We focus on doing great work, reflecting, and pivoting in the moment. Carol Dweck’s use of the work resilience is key. When we make attempts and make mistakes or miss the mark, the key is having the resilience to get back up and try again.

One of the challenges we face in getting back up is something called “perfectionism”. When we attempt a goal with a perfectionism mindset, we go into paralysis mode. Brene Brown talks about perfectionism in her book, Daring Greatly.

“The fear of failing, making mistakes, not meeting people’s expectations, and being criticized keeps us outside of the arena where healthy competition and striving unfolds”. Brene Brown, author of Daring Greatly.

Our challenge in work & life is to have that goal, make those attempts, and still get up again and again regardless of that fear of failure. Integrating an “experimental mindset” helps us attempt our goals with a lens of learning and resilience. And on the other side of that fear of failure … is courage.

“I learned that courage was not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear.” Nelson Mandela



As you feel those failures and fears in your work & life – empower yourself with an “experimental mindset”:

  • Reframe Your Past Failures – What Did You Learn?
  • Reframe Your Fear of Failure – What Can You Learn?
  • Reframe Your Mindset – How Will You Attempt Your Goal?


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Kara Smith is a talent development / HR leader and is the founder of the Soul of Work project:, a think tank and not for profit learning lab.  The mission & intention of the Soul of Work project is to bring best practices, tools, and practical insights from thought leaders to help professionals get hired, build more sustainable economic fulfillment in both work & life, and do their best work.  As part of this mission, the Soul of Work project is dedicated to actively fundraise and donate to aligned non-profit organizations.  Learn more here:  Kara is a working mother who believes we do our BEST work when we align work with our life.