Be curious. Having an open, questioning mindset about your feelings, your resistance and whatever may go wrong will help you to learn and grow from the experience. When something does not go right in my business- perhaps it is a program launch, I like to be curious and ask why the launch did not go as I had projected. What were my goals? We they achievable and measurable goals? What steps could I have taken to attract more leads or build excitement for the program? What went well with the launch? What would I like to do differently next time?

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 Tiphany Kane of KaSa Media Productions.

Tiphany Kane, M. Ed. is the “The Heck Yes! Coach”. She is an entrepreneur, public speaker, podcast host, and writer, who brings her passion for the art of the spoken word to people who need help finding their voice. Tiphany is passionate about coaching women to turn life’s painful “no’s” in life & business into empowered opportunities to find the “Heck YES!”. She weaves in her personal experiences of escaping a cult-like religion, leaving an abusive marriage, and starting a new business after 20 years in public education to connect with women overcoming challenges. In addition to being the Heck Yes! Coach, Tiphany is the co-founder of KaSa Media Productions, LLC as well as the host of 2 podcasts; “Radical Audacity in Love & Life” and “Mastering the Podcaster Mindset.”

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’?

We all have major turning points in our lives. For me, my first turning point was based on my deep inner-knowing and morals. I was raised in a very strict, cult-like, patriarchal religion. At 19 years old, I decided to leave this religion and create a life on my own. I made this incredibly difficult decision, which meant that I would lose my family and friends, because I did not agree with the morals of the religion regarding people of various sexual identities and so forth. I packed up my little 1982 blue Toyota Corolla hatchback and drove 3,000 miles across the country to start a new life.

My second major turning point was 20 years later when I left a toxic, abusive marriage. I had two young children and left my newly renovated home to live in a tiny less-than-600 square foot apartment with my two young children. This turning point is my life-saving turning point. Living in a toxic relationship had created so much stress and pain in my life that my body was in terrible shape. I had been admitted to the hospital twice, once with a code stroke called on me. I was on more than a dozen medications to control my blood pressure, kidney issues, thyroid issues and so much more. Within a few years of leaving the marriage, I ran multiple marathons, finished a 100-mile bike race, earned a Master’s degree, and was no longer on a dozen different medications. I was mentally, emotionally, and physically healthy.

My third turning point is my most recent turning point. This is a turning point of Radically Audacious Freedom!! I had a career in public education for more than two decades. After receiving the Master’s degree, I explored moving into educational administration. I moved out of the classroom and into a leadership position training teachers and creating professional development. I quickly found that I felt less and less in alignment with my true core. The defining moment that propelled me to great change was when my supervisor informed me that I had “too much passion” to move up into administrative leadership opportunities. At that moment I had to decide, do I conform to what they want from me or do I create my own way in the world where my passion is valued?

That is when I launched a podcast, co-founded my media production company and became my own boss. I am now on a path where my passion is what drives my business.

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?

The most interesting story from my career was the day my supervisor told me that I was too passionate and that I would have to change to be able to move forward in district leadership. At first, that comment took me by complete surprise. How can you be too passionate when it comes to public education? After my initial shock came my moment of reckoning. I had to really sit with myself to truly understand what this would mean for me. Did I want to continue I this career I had worked so hard in for the last two decades? Or did I want to explore what other options were out there for me? What could those options even be?

I decided that there was no way I was going to dim my light, or contort myself in to pretzels to become the good leadership soldier the school district wanted me to be. This decision led me to open my eyes to some of the possibilities around me. I joined an entrepreneurial course. I decided to start a podcast and that podcast opened the doors for me to co-found a media production company.

My biggest take-aways from this story:

  • When you feel like you are coming up against resistance every time you are trying to grow and expand- take a step back. Be curious about this resistance. Dig deep inside yourself and listen to your inner knowing. Figure out why that resistance is happening.
  • Once you know the source of the resistance, take steps to move in another direction. I call this finding the “Heck Yes!” in a “hell no” situation. When a door is closed to you, there are always other doors & paths you can take if you just look for them.
  • Trust my inner knowing! I felt called to start a podcast. I didn’t have a clear idea of what I would do with that podcast. I had a vague idea that maybe I could be a relationship coach. Even though I was not super-clear on my vision- I started. And from that first episode, EVERYTHING changed. My self-confidence grew. The fascinating people I interviewed became friends and collaborators. People started asking me to teach them how to start their own podcast and from that a media production business was launched.

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?

There are so many important character traits, it is hard to narrow then down to just three. However, these three have been the most pivotal traits for me.

  1. Passion- passion for your purpose is vital. Think of purpose less as the actual thing you are doing and more as the person you are being. For example, I have a passion for being a change-maker. My purpose is to change certain aspects of the world. It doesn’t really matter what I am doing as long as I know I am making a difference. I can be a classroom teacher, a sales person, or a business owner…the title does not matter. Passion for your purpose is what truly matters.
  2. Collaborator- being a collaborator is vital. For one thing, none of us have all the answers on our own. We need a variety of perspectives and experiences to help create a thriving business. Plus, collaborating with others opens up incredible opportunities!! One of my collaborations started with a me being a podcast guest, then turned into me being featured in that podcasters book, Women in Podcasting. From the feature in the book, I was invited to be a guest on their livestream. This collaboration continues to open doors for my business.
  3. Curiosity- Curiosity is vital when you are building your business!! Leaders should be curious about failures. Leaders should be curious about successes. Leaders should be curious about learning form others. Our brains are in their most active learning state when we are in a state of curiosity. The brain lights up when faced with a question and a problem to solve. If we can approach our challenges from a place of curiosity rather than from a place of fear or frustration, growth is able to happen. For example, when I had a program launch that performed much lower than I had projected, rather than viewing that launch as a failure, I looked at it from a place of curiosity. Where did my message fall flat and not connect with my audience? Were there other ways I could have nurtured leads? How could I have built more excitement? These are powerful questions that lead to great change for my next successful program launch.

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?

Rather than seeing failure as a growth opportunity, society has conditioned us to believe that failure is a sign of not being good enough for something. Humans need connection. Connection is vital for our survival. We all want to be liked, to be accepted, and to feel like we belong. Many times, failure is wrapped in shame that gives us the misinformation that we do not belong, nobody will like us, people will ridicule us, and we will not be accepted. This leads people to debilitating mindset beliefs such as perfectionism and imposter syndrome. This fear of failure puts us in a place of being frozen and not able to move forward.

For example, in that moment when I decided to start my podcast, I was so scared of what my co-workers and friends would think. I started my podcast and did not tell anyone I knew. My fear of what they would think was strong. However, because I was a member of an entrepreneurial course group, I knew my course-mates would have compassion for my learning curve. I asked for feedback from them. And this feedback helped me to grow. Within a few weeks, my fear of failure dropped away and my sense of pride in what I had accomplished started to shine. Once I felt that pride and started sharing my podcast, my confidence increased ten-fold. As my confidence increased, my fear of failure fell away. I knew what I was doing was important and I was no longer afraid of what others would think.

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

Fear of failure is absolutely debilitating! It raises our anxiety. It limits our ability to move forward. Fear of failure keeps us from trying new and scary things. It keeps us from growing and exploring. It keeps us in our head and out of our hearts. Fear is an emotion that is supposed to protect us.

Fear is important in a life and death situation. If a tiger is charging at you, fear will kick in to save your life. The fight, flight, or freeze response can keep you safe. However, our brain doesn’t understand the difference between a tiger threatening our life or a new leadership opportunity that feels scary. Being able to calm our brains and let our bodies know we are safe will allow fear to take a back seat and allow growth to happen.

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

Your question includes the words “free of failure”. There is freedom when we can teach ourselves to view “failure” as a learning and growth opportunity rather than a thing to be ashamed of. Let’s look at a few examples:

  • You have started a new leadership position and you are asked to speak at a conference on your area of specialty. You have prepared a terrific presentation, arrived early to the presentation room, and are all set up ready to go. Minutes before the presentation, the sound in your room stops working which means the videos you have in your presentation no longer work. You feel your heart pounding. What can you do? This exact scenario happened to me. I took a deep breath. Let everyone know what the issue was and that I would need to adjust, and then I made a joke of it! Everyone in the audience relaxed. I could hear an audible release of breath. Throughout the presentation, I made small, light-hearted jokes about the sound issue. I also brought in the lessons I was learning about mental flexibility on the spot into the presentation. It was a live opportunity for the participants to see the concepts I was speaking about in action.
  • As a new business owner, you are trying to “do all the things.” You feel like the harder you work, the more things are falling through the cracks. You just can’t do it all and can feel yourself becoming afraid of failing. Then you realize that you have resources at your fingertips to help and you call upon those resources. An example in my business is when I was having a difficult time managing my multiple Facebook communities. I just could not keep up with all the tasks that needed to be done. Instead of letting my “failure” stop me, I reached out to someone in my community that I knew had a strong background in social media community management. I told her about my problems, told her my goals, and brought her in to manage my various communities. This freed up my brain space to do the work I loved and created a collaborative friendship that I value to this day.

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?

In my public education career, many people would have seen that moment when I did not get the promotion as a failure. I “failed” to get the position. I “failed” to move forward in my career that I held for two decades. But for me, rather than seeing this as failure, I saw it as an incredible growth opportunity. I saw it as a time to step back and reflect on exactly what I wanted in my life. What path did I actually want to be on? What goals did I truly have?

I remember sitting down and mapping out a path that included business ownership, writing a book, public speaking, and a podcast. That vision was so strong, so exciting, and never would have happened if I had gotten that promotion. Now as an entrepreneur and a leader, I get to work with people I never would have met if I stayed in public education. I have collaborated with actresses, an Oscar-winning Broadway producer, multiple best-selling authors, coaches and other inspiring entrepreneurs. My universe has expanded immensely…because of the thing many would have described as a failure.

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?

My rebound & recovery from not getting the job promotion and being told I was too passionate came from a place of deep inner reflection. I took the time and space to sit down and reflect on what it was that I really wanted in my life. I asked myself what path I truly wanted to take. I tried to erase all the “should” messages and focus on my own personal wants and desires.

Once I identified my wants and desires, I took action. I invested in myself and joined an entrepreneurial group where I learned how to start my own business from the ground up. I collaborated and learned from the other people in the entrepreneurial group, I asked questions, I was curious, I explored. I tried new things, I failed and tried again.

My biggest piece of advice regarding fear of failure is to look at failure simply as a learning and growth opportunity. Approach “failure” from a place of curiosity. What does this experience teach you about yourself? What does this experience teach you about your leadership? What does this experience teach you about your business? A curious mind is a non-judgmental mind. Do not judge your failure negatively. In fact, stop talking about it as a failure. Look at it instead as the stepping stones on the path of your personal growth journey.

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.

The five steps:

  1. Step back and take a deep breath. Try to look at the failure from a different perspective. Here is a visualization to help with this. Imagine a fly buzzing around a big, beautiful plate glass window. The fly can see a luxurious picnic happening on the green grass outside and the fly has a deep desire get out to the picnic. The fly’s desire is so strong it flies full-speed at the glass and BAM it knocks into the glass and bounces backwards. The fly tries again & again- each time it gest hurt worse and worse. Eventually that poor fly falls exhausted and in pain on the window sill unable to try again. However, there is another fly in the room that also wants to go out to that luxurious picnic. This fly takes a moment, zooms back into the room, looks around and sees an open door just a few feet away from the plate-glass window. This second fly zooms easily through the open door and lands on the picnic basket outside. Lesson: taking a moment to step back, look around, and see your options will help you to calmly find a path to meet your goals!
  2. Be curious. Having an open, questioning mindset about your feelings, your resistance and whatever may go wrong will help you to learn and grow from the experience. When something does not go right in my business- perhaps it is a program launch, I like to be curious and ask why the launch did not go as I had projected. What were my goals? We they achievable and measurable goals? What steps could I have taken to attract more leads or build excitement for the program? What went well with the launch? What would I like to do differently next time?
  3. Seek help. Do away with the notion that you have to do it all yourself. Seek help and guidance from a coach, mentor, collaborator or someone skilled in this area of challenge. I am very fortunate to have an excellent business partner. We co-founded KaSa Media Productions and his skill set is a great asset to my skill set. When I am confused, frustrated, or feeling significant resistance, I can brainstorm with him. Find someone that can brainstorm and problem-solve alongside you.
  4. Take steps to move toward your goal. Failure is a great indication that you are moving forward. You are trying new things. You are getting new skills sets. Make sure as you learn these new things, you take direct action to continue to move toward your goal. One of the things I always commit to is investing in working with a coach or mentor to keep my forward learning momentum going. I have a personal goal of finding a new coach or mentor every year and investing my money into learning from them.
  5. Reflect on your growth and what you learned from the experience. Reflection is a powerful growth tool. We are constantly learning, growing, & changing. If you are able to look at “failure” and reframe it into an opportunity to reflect on growth, failure no longer becomes scary. You almost welcome it when it happens because you know dynamic growth will happen as a result.

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?

As with any quote, when it is taken out of context it is often misinterpreted. Aristotle lived in a time of great excess- the Greeks lived with opulence, violence, and passion. Aristotle believed in temperance, deep thought, and deep questions. He worked hard to have people look at the world around them differently. And he was a bit extreme in his goals. He wanted people to live virtuous lives and felt strongly about what virtue meant.

While I may not agree with the specifics of what Aristotle is saying in this quote, I do believe there is a powerful lesson to learn. Yes, it is possible to fail in many, many, many ways. At the same time, success is only possible when we are no longer afraid of these many ways to fail. Success is only possible when failure is seen as a tool for growth and a building block for our goals.

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 am passionate about inclusivity in the media. Podcasting is my main platform. Women and non-binary people make up more than 50% of podcast listeners, but only 20% of podcast hosts. We need more women, more people of color, more LGBTQ voices, and more perspectives from those with less privilege. Every time I teach a course, I identify a few people to award a scholarship. I’m also planning on starting a foundation that will help BIPOC, LGBTQ, and female identifying podcasters the opportunity to not only start their podcast but to grow the influence of their podcast. I would love to find partners to start this foundation!

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 am a huge fan of the singer, P!nk. I am inspired by the way she lives her life by her own rules. She does not feel the need to be anyone other than who she authentically is. Music is a powerful force and P!nk uses her song-writing to connect, tell stories, share pain, uplift, and shine a light on issues. She creates her own rules about what it means to be a mother, a wife, an entertainer, and a woman. Anytime I feel overcome by life, I put on one of her songs and instantly feel stronger.

I have a very beautiful memory and P!nk plays a large role in this memory. My best friend from childhood, Noni, had terminal breast cancer. Shortly before she passed away, we attended a P!nk concert together. When P!nk’s song “Try” came on, Noni & I turned to each other with tears streaming down our faces and connected on such a deep soul level. A year after Noni passed away, I performed an aerial hoop dance to this very same song in Noni’s memory. This performance is another example of pushing through the fear of failure. I had only just started learning aerial hoop a few months before this performance. I was 42 years old and by far, the oldest person performing. But I embraced those butterflies, let my tears stream down my face, and performed from my heart.

How can our readers further follow your work online?

I can be found on all the socials as Tiphany Kane. I am most active on Instagram and Facebook, although you can find me on LinkedIn, Twitter, & YouTube as well. My podcasts are: Radical Audacity in Love & Life; Mastering the Podcaster Mindset.

My websites: &

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.