Face those fears. Practice what you would do differently in situations that trigger your fears. For example, I am fearful of certain people not validating my worth. I will practice acceptance and not needing validation from those people through intentional thinking.

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 Kerry Wekelo.

Kerry Wekelo, MBA, is the Chief Operating Officer at Actualize Consulting, a financial services firm. Her book and program, Culture Infusion: 9 Principles for Creating and Maintaining a Thriving Organizational Culture and latest book Gratitude Infusion, are the impetus behind Actualize Consulting being named Top Company Culture by Entrepreneur Magazine, a Top Workplace by The Washington Post, FORTUNE Best Small & Medium Workplaces™, and Best and Brightest ELITE National Winner in Strategic Company Performance category. In her leadership, Kerry blends her experiences as a consultant, executive coach, award-winning author, mindfulness expert, and entrepreneur. Kerry received the 2021 Women with Vision Award and has been featured on ABC, NBC, NPR, The New York Times, Thrive Global, SHRM, Inc., and Forbes.

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’?

Each of us has our unique life story that shapes who we are, how we show up, and how we look at and feel our way through life. All the moments, from small to large, leave imprints that mold our essence.

First, it is vital to note that I am and have always been a sensitive person. This is relevant because until recently, I did not realize my true essence nor the gifts of being sensitive and intuitive. As a result, I felt out of place and wanted to blend in rather than standing out in fear of others getting too close and seeing my true self — fear of being a failure in front of others. As a sensitive being, I have always wanted to hide. But the days when I interact, overcome fears, spread love and compassion fully, and contently listen and engage are the days when my heart expands and life flows. Fears give anxiety a home, and anxiety feeds fear.

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?

Upon reflection, I realize that my career development began in childhood. Because my mom worked full time and our family was in the manufacturing business, my brother and I were exposed to more than my friends were and given high levels of responsibility at an early age. I learned about business and hard work from spending time at our family’s manufacturing business. I worked during the summers at the age of five and continued through college. I started with pulling weeds, making copies, and taking inventory, and ended up performing every function within the company at some point. I had completed the equivalent of a hands-on Business 101 course before I even started college! While my mom was at work, my brother and I took care of each other while building a foundation of trust. There are countless stories of Chad and me supporting one another. I remember when I was in the fourth grade, we were constantly hungry before our mom could get home to make dinner, so I took it upon myself to learn how to cook. Chad was always in my math class, even though he was one year behind me in school, so he would tutor me in math. Since our closest neighbors with kids were over a mile away, we would take turns playing games. We learned the value of compromise and give and take at an early age.

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?

Effective communication emphasizes listening, empathy, and seeing challenges as an opportunity to find solutions. As COO of Actualize Consulting, these are a few of the skills I must rely on.

When an employee (we’ll call her Alice) approached me with a grievance she had about being over-committed within her practice group, I knew it was best to stop what I was doing and give her my full attention. After listening carefully to her concerns, asking her clarifying questions, and repeating back to her what I was hearing about her situation, it was clear that Alice was feeling overwhelmed. She was working many hours and spinning in circles trying to get her job done while also dealing with many other factors in her personal life. I decided to start with what things Alice could do to make more time available for herself so that she would know that I understood that something needed to be done and that she could confide in me at any time, knowing I would support her in finding a resolution to her issues.

I had empathy for what she was going through. I guided her to reset her expectations by letting her know I had felt this way before as well, then shared what I did to handle the feeling of being overwhelmed by my day-to-day responsibilities. I shared how taking a break or two each day helped me readjust my priorities throughout the day and that in doing so, I could focus and become more productive. As our firm culture encourages, taking a walk outside for fifteen minutes or taking five minutes to practice a breathing routine can help the mind to regroup and organize our daily activities.

After my conversation with Alice, we both committed to the accountability of doing these things for ourselves as a daily practice. Through this, I felt assured that Alice would continue to come to me to talk things out or for guidance at any time, therefore endorsing our open-door policy at the firm.

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?

Failure can be frightening because of how it feels. If you are afraid of failing, you feel pain and judgment when you do fail. This judgment can be internal or external, or both. Because I am a Type A and Enneagram Type 3, I can be hypercritical of myself and have in the past attached my self-worth to my accomplishments. When self-worth and pain are on the line, people become afraid of them.

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

Fear of failure can be paralyzing with long-term effects to personal and professional growth. Growth is a feeling of expansion, while fear is a feeling of being constricted. When we are in a constricted tense state, we cannot access what should be free-flowing information, energy, and solutions. On a daily basis, it can be just as debilitating when trying to accomplish tasks. Taking risks, being creative, and trying something new cannot exist while being afraid to fail. Imagine going for a walk and suddenly stopping and unable to move forward. You are stuck in the same place.

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

A powerful method to help free yourself from the fear of failure is to pay attention to your self-talk. There are judging questions that reinforce the fear of failure, and they sound like this.

• Why did you fail again?

• Whose fault is this?

• Why can’t you get this right?

• When will you learn? (Yes, rhetorical questions also have an impact.)

Questions are powerful tools that can either hinder or catapult forward movement. As Albert Einstein said, “It is not that I’m so smart. But I stay with the questions much longer.” He was constantly asking learner questions. So instead, train yourself to ask learning questions which will free you from fear of failure. They sound like this.

• Why do you feel this happened?

• Could we go in another direction?

• Are there untapped resources we could utilize?

• What happens if we shift our focus to…?

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?

I entered college as an accounting major, and in my first official accounting class, I could not comprehend as all seemed backward with debits and credits. I got my first ever “D” in that class, which justified my mom allowing me to switch to a double major in Finance and Marketing. Fast forward to my career at Actualize and a recent shift we experienced in our accounting department. The accounting function has always reported to me, and I could easily review and provide input. But with turnover in this role over the years wearing me down each time, I would end up resisting the work that would allow me to learn more about the nuts and bolts of the function.

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?

After experiencing two situations like this, I decided that moving forward would require embracing my inner accountant. These are the steps I took to rebound and recover.

  • Setting and verbalizing my intention: The decision to embrace my inner accountant versus my previous negative mindset needed verbalization and accountability.
  • Utilizing existing skills to automate and streamline the accounting processes: I leaned on the skills I had already developed to problem solve efficiently.
  • Dividing the role: Previously, only two people did the majority of the work. Using this strategy ensures coverage should a person be out of the office or leave the firm and limits key person dependency.
  • Sourcing the right people: Networking is a crucial way to ensure this. I found the right resources with my network as it is always better to have people and firms recommended by personal connections.
  • Finding the joy in numbers: Numbers never lie, and there is comfort found in the certainty they provide. It removes any gray area and allows you to see exactly what is happening financially and statistically.
  • Celebrating with the team: As we were enhancing, I kept saying to my team, “It is going to be better. We got this!” Celebration during growth allows you to strengthen camaraderie and cohesively come together to have a more robust accounting function.

Resisting because of fear of failure stops you in your tracks. But, by leaning into your strengths and talents, you can move forward through your fears. When you lean–you flow as eloquently as water flows.

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. Find a supportive group of people you can trust to be yourself without fearing judgments or projections of their struggles on you.
  2. Be honest about how you are feeling. Write down your feelings, use an app on your phone, or verbalize them to a safe person.
  3. Seek professional help. Coaches and counselors offer a third-party confidential perspective.
  4. Understand your triggers. What are you fearful of? As I mentioned, I am afraid of failure and not being perfect.
  5. Face those fears. Practice what you would do differently in situations that trigger your fears. For example, I am fearful of certain people not validating my worth. I will practice acceptance and not needing validation from those people through intentional thinking.

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?

I agree because everything always works out as it should. You may fail, yet that failure brings opportunities for growth and success. It brings you to exactly where you need to be.

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 like to inspire the act of sharing daily gratitude with those around you. I have seen how gratitude transforms organizational cultures, communities, families, and individuals. I believe in its ability to change the world.

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 🙂

Brené Brown has inspired me personally with her unique ability to research data and reveal it via riveting storytelling. If you have not seen her speak, I recommend taking some time to watch her videos; she’s captivating. One of my favorites is her Netflix special Brené Brown: The Call to Courage. In it, Brown talks about her research on gratitude and how she incorporates gratitude with her family.

How can our readers further follow your work online?

I am very active on LinkedIn and would love to connect with you there. I post regularly about events, programs, tips, and articles. Visit Actualize Consulting to learn about my interactive sessions and sign up for our email list here.

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


  • Savio Clemente

    Board Certified Wellness Coach (NBC-HWC, ACC), Media Journalist, #1 Best-selling Author, Podcaster, and Stage 3 Cancer Survivor

    The Human Resolve LLC

    Savio P. Clemente is a Board Certified Wellness Coach (NBC-HWC, ACC), media journalist, #1 best-selling author, podcaster, stage 3 cancer survivor, and founder of The Human Resolve LLC.  He coaches cancer survivors to overcome obstacles, gain clarity, and attract media attention by sharing their superpower through inspiring stories that make a difference. He inspires them to get busy living in mind, body, and spirit and to cultivate resilience in their mindset. 

    Savio has interviewed notable celebrities and TV personalities and has been invited to cover numerous industry events throughout the U.S. and abroad.  His mission is to provide clients, listeners, and viewers alike with tangible takeaways on how to lead a truly healthy, wealthy, and wise lifestyle.