Be kind to yourself. Trying to be free of fear of failure is a courageous journey that only a few dare to embark on. If you´re one of those who has decided that you´re not going to let fear of failure stop you from living your best life, you´re already way above the curve of where most people are. Pat yourself on the back and give yourself credit for that.

The Fear of Failure is one of the most common restraints that holds people back from pursuing great ideas. Imagine if we could become totally free from the fear of failure. Imagine what we could then manifest and create. In this interview series, we are talking to leaders who can share stories and insights from their experience about “Becoming Free From the Fear of Failure.” As a part of this series, I had the distinct pleasure of interviewing Annicken R. Day.

Annicken R. Day is an entrepreneur, published author and a leading global authority in the field of culture transformation, leadership, and high performing teams. As founder and culture strategist of Corporate Spring, she advises leaders, from startup founders to Fortune 500 executives, in how to build thriving cultures and secure business success in the new world of work. She is the author of the bestselling novel Fly, Butterfly, which has been translated into multiple languages.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

I am a native Norwegian, entrepreneur, executive advisor and writer who lives in Los Angeles, California. The last ten years I have transformed my life, reinvented myself, made choices others considered insane, and created a reality that I wasn´t even able to imagine ten years ago. None of this would have happened had I not decided to believe in myself, taken risks, faced some of my greatest fears, including the fear of failure, to design the kind of life I wanted for myself.

I knew already as a little girl what I wanted to be when I grew up. “I want to be happy” I said when the grown-ups asked me. I had noticed that adults didn´t seem to have fun and decided that I wanted a different kind of life for myself. I can still remember their overbearing laughter and comments, saying that I would soon enough grow up and realize the harsh reality of life, that work wasn´t supposed to be fun. My six-year-old self, however, decided that one day I would prove them all wrong. I think it is fair to say that I have. For the last 20 years I have built a career around building inspired, happy workplaces, from within large corporations as well as from the outside, as a consultant. I have been invited to speak around the world about the importance that fun, joy and happiness has on creativity, innovation, performance, and business results. I have also written a novel about a leader in a cut-throat corporate world who reinvents herself, and her business, when she realizes what really matters in life. You write about what you know they say.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

In my early 30s, I landed my dream job as a Chief Culture Officer at a Norwegian videoconference company called Tandberg. I knew I was home when I learned that one of their values was “Fun and Profit”, based on the founders´ beliefs that when people enjoy their jobs and have fun at work, profit follows as consequence (and of course they were right!). I was hired to “take care of the corporate soul” as we grew rapidly and globally over the next ten years. The company was later awarded the Best Place to Work in Norway three years in a row. We became a global market leader in videoconference and was sold to Cisco in 2010 for 3.5 billion USD. But I´m getting a bit ahead of myself…

The story I wanted to share is from my first week in that job.

I was excited and nervous, and eager to impress the founders that had hired me. One day I was sitting in the office filling out some documents that had landed on my desk. As the company´s first head of HR, there was a lot of catching up to do. I was deep into it when one of the founders of the company showed up in my office. “What are you working on?” he asked. “Oh, I´m just filling in these forms for the authorities” I replied, feeling proud and important about it all. He stared at me and asked: “Why are you doing that?” I was confused. He repeated his question and I replied: “Because they asked me to?” “What will happen if you don´t do it?” he continued asking. “I don’t know” I had to admit.

He then walked over to my desk, took the paper I was working on and threw it in the waste bin. “If you don´t know why you´re doing what you´re doing, it is clearly a waste of your time.” He nodded towards the waste bin. “If that document is important, someone will be chasing it. And if they don´t, it´s just a proof that it wasn´t that important to begin with.” I think I must have held my breath the entire time he was speaking. I had no idea how to respond.

“Never waste your time on things you don´t know why you are doing. Now, go and make yourself useful” he said and left my office.

That experience formed my career, it made me conscious about how easy it is to fall into the trap of busyness without purpose. In fact, I have later been telling people I have hired, led, and coached what the founder told me: if you don’t know why you are doing something, and no one can explain it to you, spend your time on something more meaningful instead.

Too much time is wasted on meaningless tasks in most companies. It´s a waste of people´s time and energy (and motivation) and it´s ineffective and unproductive for the businesses that promote this way of working.

To this day I ask myself the question: “Why am I doing this? What purpose does it serve?” And if I don´t know the answer, I do something else instead.

You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The three-character traits that stand out the most to me are my passion, optimism, and can-do attitude. I don´t think I would have survived as a leader, or even as a human, without those three qualities. Life and work throw us many curve balls, and I know that my way of dealing and thinking about those challenges is what not only has helped me survive, but also thrive, in the face of them.

Being passionate by nature, I have a strong inner drive, and a fire in my belly that gets ignited when I feel I am living with purpose and according to my values. If it hadn´t been for my passion, I would not been able to embark on my personal and professional transformation the last ten years, including moving countries multiple times “because I wanted to”. And without my passion, I would not have managed to build a business based on a philosophy and ideas that still, to many leaders and companies around the world, feels a bit “out there”. I´ve been speaking about the importance of inspiring, authentic leadership, meaningful work, happy employees and thriving work cultures for the last 20 years. I´ve spoken at conferences with thousands of suits with skeptical faces, looking at me as if I just fell from the moon, because I tell them that by being more human, they will get better business results. If I hadn’t wholeheartedly believed in what I am saying, if I hadn’t had tremendous passion for what I speak about, I couldn’t have been able to do it, or impact people in the way I know I have.

As for my optimism, it is my ability to always look for the good in situations and in people, to see possibilities where others see problems, and to not let negativity or naysayers get the better of me. When I left my well-paid corporate job to start my company Corporate Spring, based on the dream of making the corporate world a happier place, some people thought I was insane and reckless, especially since I was a single mom. I didn´t know how it all was going to play out, but I did know that, somehow, I was going to figure it out, just like I always have. My belief in the good of people and the possibilities that come with new experiences, and the habit of saying yes before no, have given me many opportunities. If something hasn´t turned out the way I wanted it to, or someone wasn´t as trustworthy as I hoped, well, then I learned and moved on, a bit wiser, but not less optimistic.

For my “can-do attitude,” I must credit my childhood book heroine Pippi Longstocking. Her expression: “I have never done that before, so I´m sure I can do it” has been my life philosophy for as long as I can remember. I have never been afraid of doing new things or making mistakes. Pippi taught me that it was all about the attitude, the learning, and the experience. If you don´t define mistakes as failure but as learnings, why would you beat yourself up or feel bad about learning new things? Whenever I´m in a new situation that I have no idea how to handle, I channel my inner Pippi Longstocking, tell myself I´m sure I can handle it since I´ve never done it, and know I´ll be just fine.

A situation when all these three-character traits came into play was when I decided to apply for the US green card a few years ago. I went for the EB1 visa, “alien with extraordinary abilities,” also known as the “Einstein visa.” I grew up in a country where thinking you were extraordinary in any way was almost considered a sin (very different from American culture, in other words) and even though my inner critic had its doubt, and people warned me that it was nearly an impossible feat, I believed that I could, and therefore I did.

Passion, optimism, and can-do attitude is a powerful combination and I have learned that my inner voice always knows best, and that when I listen to it, amazing things can happen.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the concept of becoming free from failure. Let’s zoom in a bit. From your experience, why exactly are people so afraid of failure? Why is failure so frightening to us?

I have seen so many great people not realizing their full potential because of their fear of failure. Having worked globally, I have seen this fear in people across all cultures. As briefly mentioned earlier, I grew up in a culture influenced by “The Law of Jante” which basically stands for “You shouldn´t think you´re anything special,” which is like the “tall poppy syndrome” you find in some other cultures. I still know many people who are afraid of standing out, being different, or being ridiculed. Even in the US I am sure many might experience this, however there is a much stronger “winning” culture here, a more individualistic culture where success tends to be more admired than envied. Hence, the fear of “losing” may be more dominant in the American culture. The lack of safety net, job and social security is also more prevalent in the US than in Europe, so the fear of speaking up or simply just being yourself at work is something I see people being more afraid of in American work cultures than in others.

Lately, however, thanks to new findings within neuroscience, social psychology, and biology, we are learning that the feeling of fear has a lot to do with our humanness; our need to feel safe, to belong, and to be accepted. Fear is our brain´s response to external stimuli that threatens our most basic and fundamental needs for survival, which can sound very dramatic but is perceived as very real by our brains. Our world and our lives have dramatically changed from the time when we used to live on the savannah, but our brains haven´t changed that much.

There´s been a lot of studies around psychological safety as a prerequisite for well-functioning teams. Research shows that our brains aren´t functioning optimally if they constantly must scan for danger in its environment. To our brains, the feeling of insecurity, uncertainty and loneliness can be perceived just as dangerous by the brain as a hungry lion on the savannah was some five hundred thousand years ago. When we understand this, we can learn to be more tolerant and compassionate for our own and other´s fear.

We often hear the expression “get out of your comfort zone” and while I personally think that is a good advice, we also need to understand that doing so can be scary for some, even though they rationally may know that it´s not dangerous. In those cases, I recommend asking questions about what it is that scares them, what they think is the worst thing that can happen to them and help them see that their fears may come from stories they are telling themselves in their minds, and not from reality. I have seen it happen many times, the a-ha feeling people get when they realize that what is standing between them and their happiness, are made-up stories that they themselves have the power to change.

What are the downsides of being afraid of failure? How can it limit people?

Fear of failure can hinder people from progress, from moving forward in their lives and careers. Fear can shut people off from amazing opportunities and possibilities, make them think less of themselves, prevent them from realizing their talents, their potential and from living their lives to the fullest. It shuts the door to happiness, because how can you live a happy life, how can you learn, grow, and have new experiences, when you walk around being afraid of failure?

In contrast, can you help articulate a few ways how becoming free from the fear of failure can help improve our lives?

Learning about mindsets and our ability to choose more positive, less fearful mindsets can be a game changer. When we stop wasting energy on everything that can go wrong, and start focusing on everything that can go right, we move into a solution-oriented mindset and more positive opportunities will follow as a result. When we let go of the need of controlling the outcome, which is typically what we try to do when we´re afraid, and instead move into a more trusting, go-with-the-flow mindsets, we become more creative and open to new and better solutions to the challenges we may have.

When we steer our minds towards more positive thinking, looking for opportunities instead of problems, great outcomes instead of bad, we start creating those situations. What we focus on becomes our realities. Stopping to think of failure as something bad, and instead look at it as something we will learn from sets us free, helps us grow, and certainly makes us feel a whole lot happier, because fear and happiness rarely go hand in hand.

We would love to hear your story about your experience dealing with failure. Would you be able to share a story about that with us?

By now you know that my perspective on failure is more focused on what I´m learning from it and how my failures help me grow, but that doesn’t mean that I haven’t felt like a failure from time to time. I like to think of failure as a short-lived thing; it hurts, I learn, I grow, I move on. However, the story I´m about to share is not one of those. This one lasted for many years, years when a part of me felt like an absolute failure while the other part of me went about with her life, trying to ignore the devastating realization (a story dictated by my mind) that I was a total loser.

In 2013, I went to Kauaí in Hawaii and as I landed on the island for the first time, I got an idea for a story which I knew I just had to write. Filled with passion, optimism, and can-do attitude, I decided that I was an author even before I had written a single word.

Excited I shared the news with friends and family, convinced that I would have this book written within the next 6 months. I started writing, and I told everyone who wanted to listen how great it went while I was struggling with getting the story inside my mind into meaningful words. I had already told people I was an author, so I was too embarrassed to admit that I didn´t manage to write.

Months and years went by. I still spoke enthusiastically about the book but while I was telling people I had written a lot more than I had, I started doubting my abilities as a writer and feeling like a total failure.

Mean voices started speaking inside my mind. Who did I think I was? Did I really think that I could write? Years passed by. I was busy building my business, which went well, but the writing, not so much.

After a few years, friends and family stopped asking me how the writing went. If I happened to mention it myself, I could feel the silence, the looks, the embarrassment, the “poor disillusioned wannabe-writer Annicken” that I was sure they said behind my back.

Then one day, I came across two random quotes. One was by Maya Angelou “There is no greater agony than bearing an untold story inside you,” and the other was Toni Morrison “If there´s a book you want to read, but it hasn´t been written yet, then you must write it.”

I wish I could have seen my own expression in that moment. It felt like being struck by lightning, and suddenly I realized why I hadn´t been able to write the story. I had been thinking that I should write the story for someone else, but then I realized that the story needed to be written, not for someone else, but for me.

That realization changed everything, and the words started flowing through me, as the movie that I first had seen in my mind when I landed in Hawaii started playing again.

When my dad got sick and later died from cancer in 2017, I was reminded that life is too short to procrastinate and not do the things that mattered to me. I put everything else aside for a while, wrote night and day, and was finally able to finish the book.

As I was writing the last pages, I realized the book had taken the time that it needed to take. My struggles to write had never been a failure, it was about me not being ready yet. There were things I needed to learn and things I needed to experience and grow into before I was able to write the story that needed to be told.

A year after my dad died, the story was finished, the first publisher I shared it with picked it up, and today it is a bestselling book translated into 3 languages with more to come.

Lesson? There are no failures. Not everything is supposed to happen the way we think, and when we trust the process and the timing of all things, we are able to see that so-called failures can be our greatest gifts and best teachers in life.

How did you rebound and recover after that? What did you learn from this whole episode? What advice would you give to others based on that story?

I am humbler about creative processes, about journeys and about not letting my critical and limited mind get the better of me. In a world focused on goals, deliverables, achievements, and success, I want to be a champion for the journey, for trusting the process, for not pushing through but let things grow and evolve the way they are meant to. It was wonderful getting my book published, having it become a bestseller, getting amazing feedback from my readers etc., but what I am most proud of with Fly, Butterfly is that I wrote it for me, not for anyone else. If it never had been published, if it had never been read by anyone else but me, I would still not have considered it a failure.

Fly, Butterfly was a story that needed to be told, and I was the one to tell it. It was also a book I wanted to read, and that didn’t exist, so therefore I had to write it.

Fantastic. Here is the main question of our interview. In your opinion, what are 5 steps that everyone can take to become free from the fear of failure”? Please share a story or an example for each.

  1. Redefine failure. There´s a saying “What would you do if you knew you couldn´t fail.” I think a better questions to ask is “What would you do even if you knew you could fail?” The answer to that question tells you where your true purpose and passion is and what matters so much to you that you are willing to take the risk of failure. And what´s so bad about failure anyway? Failing is a sign that you´re trying something new, taking risks, pushing yourself out of your comfort zone. It´s how we grow, it´s how we create, innovate, and change things for the better. Our fear of failure keeps us from taking risks and keeps us from doing something new. When we redefine failure as growth, innovation, and courage, we realize it is nothing to be afraid of.
  2. Replace worst-case scenarios with best-case scenarios. When we are worried or afraid, it is easy to fall into the what-if followed by worst-case scenario mindset. “What if I fail/make a fool of myself/lose everything?” But what if you replace worst-case scenarios with best-case scenarios: “What if I succeed/grow/become happier than I´ve ever been.” Our brains are wired to look for problems, but it is also flexible and can be trained into a more optimistic and positive way of thinking, which again will make it less fearful.
  3. Visualize your desired outcome. Whatever you dream about, are hoping to achieve and want to do, think about it as if you´ve already achieved it. Then visualize the journey that will take you there and know that whatever bump in the road or challenge you will meet, you will overcome them effortlessly. Many great athletes do this, they feel the emotions in their body before they have won the game. By this visualization exercise, they are programming their minds and the bodies for best possible outcomes. They are also preparing themselves for the journey that will take them there. Think of yourself as the writer of a story with a happy ending and believe that what you visualize will happen.
  4. Practice your fearless muscles. Practice makes master, and that also goes for fear. Think about fearlessness as a muscle that gets stronger the more you activate it. When you do things that scare you it might feel very uncomfortable at first, but the more you do it, the less scary it will feel. As your fearlessness muscle strengthens, your quality of life will strengthen too. To use myself as an example, ten years ago I was a single mom with a well-paid, steady job, living in the suburbs of Oslo, Norway. Today I am a business owner, entrepreneur, and bestselling author, living in Los Angeles, California. This journey had me living outside my comfort zone for the last decade! I have taken many risks and faced some of my greatest fears on regular basis. It hasn´t been easy, and not everything has gone as planned. But today I am living the life I wasn´t even able to visualize those ten years ago, and I can tell you that my fearlessness muscle is well trained by now. I have proven to myself that facing my fears takes me to amazing places, and I have no intention of stopping here.
  5. Be kind to yourself. Trying to be free of fear of failure is a courageous journey that only a few dare to embark on. If you´re one of those who has decided that you´re not going to let fear of failure stop you from living your best life, you´re already way above the curve of where most people are. Pat yourself on the back and give yourself credit for that.

Some of our fears of failure come from self-doubt, imposter syndrome, being judged, ridiculed, and seen as a failure by others. But whatever others may say or think, remember that they are not you. They´re not on your hero´s journey. You are. So be kind to yourself. Look at what you have achieved and how far you´ve come. Be proud of the fact that you´re trying, practicing, getting braver and stronger all the time. When you stop being afraid of failure, you´re setting yourself free. Free to live the kind of life you want and deserve, the kind of life that makes you happy.

The famous Greek philosopher Aristotle once said, “It is possible to fail in many ways…while to succeed is possible only in one way.” Based on your experience, have you found this quote to be true? What do you think Aristotle really meant?

My personal view and experience are that you also can succeed in many ways, that success can mean different things to different people, and that failing can be success too, if your goal was to take risks, try something new, learn and grow. I think many have a narrow way of defining success, that you must be number one at something, or achieve a certain outcome to be considered successful. But what if just being on a journey, wherever it may take you, is success in itself? Maybe more people would be less afraid of trying something new if they were more focused on the process and less on the end goal.

What Aristotle’s really meant with that quote, well that beats me, haha.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

I would create a movement to inspire people´s change of mindsets. Repeatedly, I see how simple mindset shifts can transform lives for the better. Many people waste so much energy being frustrated and angry of things they have absolutely no control over, blame other people for whatever is wrong in their lives, and focus on limitations and problems instead of opportunities and solutions. Fear-based mindsets tend to send people into a downward spiral, only leading to misery and negativity. We all know that misery seeks companionship so the ripple effects of such negativity can quickly spread and create a lot of unhappiness.

One of my missions in life is to remind people that there is another way. Inspire them to make different and better choices for themselves and show them ways they can turn that negative spiral around by introducing more positive, solution oriented and self-empowering mindsets. To give people hope, see opportunities, and feel courageous enough to go out and live their best lives. If I can start a movement that helps people do that, I will have achieved what I believe to be the biggest purpose of my life, in addition to being happy and enjoying my life on this planet.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them 🙂

I have always wanted to meet Richard Branson. I have been inspired by him for the last 20 years and have always loved his wisdom, passion, positivity, entrepreneurial spirit, and his slightly crazy can-do attitude. But even more so, I think we will have a great time with fun conversations and lots of laughter. I once passed him on an empty street on Notting Hill in London and I wish I had walked over and introduced myself. If I had, I´m pretty sure we would have been friends now. But then again, it´s never too late. Next time I will for sure say hi. Or even better if you read this Richard, let´s have lunch, laugh and be friends!

How can our readers further follow your work online?

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.


  • Savio P. Clemente

    TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor

    Savio P. Clemente, TEDx speaker and Stage 3 cancer survivor, infuses transformative insights into every article. His journey battling cancer fuels a mission to empower survivors and industry leaders towards living a truly healthy, wealthy, and wise lifestyle. As a Board-Certified Wellness Coach (NBC-HWC, ACC), Savio guides readers to embrace self-discovery and rewrite narratives by loving their inner stranger, as outlined in his acclaimed TEDx talk: "7 Minutes to Wellness: How to Love Your Inner Stranger." Through his best-selling book and impactful work as a media journalist — covering inspirational stories of resilience and exploring wellness trends — Savio has collaborated with notable celebrities and TV personalities, bringing his insights to diverse audiences and touching countless lives. His philosophy, "to know thyself is to heal thyself," resonates in every piece.