Lesley Michaels On Becoming Free From The Fear Of Failure

Lesley Michaels On Becoming Free From The Fear Of Failure

I’m a 3rd generational feminist and my life has been lived in a circle of women. I did a stint in corporate oil and gas back in the early 80s but found the environment too punishing. Following this, I spent years building and either selling or crashing several small businesses, while simultaneously building a reputation as an international speaker and professional mentor.

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

One of my favorite stories from my long and diverse career revolves around when I was the Visionary Founder of a 501c3; HonuaOla. Organizational Focus:

?Generating international programs and support for the dis-enfranchised peoples of the earth with special focus on the indigenous.

?Creation of focused emergency relief support efforts and resources for those affected by natural disasters.

A launch event of significant scope was planned to develop recognition. I served as Executive Producer for, HonuaOla; The Event I had never produced an event of this size but was passionate about the mission. A friend from the entertainment industry arranged a call with the top person in field of large-scale outdoor events. After an hour of being brutally ridiculed for daring to attempt an event of such scale, with no previous history, by end of the call I was convinced I had made the mistake of a lifetime and could not possibly succeed. I drove home in a daze and fell onto my bed completely undone. The fears had taken over. What was I thinking and what am I going to do about all the money that has already been received and paid out?

At the end of a very long day, without intending it to happen, my thoughts wandered back to planning. By the following morning I awoke ready to take the chance on failing miserably, if that did prove to be the outcome, but committed to working to make this event more than had I had originally imagined.

After fourteen months of jumping hurdles, falling down and struggling back up again, sleepless nights and constant push, we featured 111 presenters and performers from 7 countries on 3 stages over the course of two days. It was a spectacular event featuring 3 Grammy award winning artists, a Bagpipe Band from Scotland, a Kodō Drum group from Japan, public servants, human service organization directors, a State Senator, national leaders in Social Justice, international environmental experts, and international Human Rights leaders. We were even bestowed with a Mayoral Proclamation naming February 5, Honua’Ola Day, “For services to humanity”.

The organization has continued to work with disaster support for global events from Haiti to Puerto Rico. They also initiate programs on island countries who have large, marginalized indigenous communities.

My greatest take-aways were to keep going when there is a passion burning inside to accomplish something. I didn’t know how the expert in the field would have done it, but that didn’t mean it was the only way. Most importantly, I was committed to the project and the potential benefits a successful outcome would have on the lives of the people the organization was meant to serve. Myself, my ego, and my fears all had to take a backseat, with the organization and its purpose for being becoming the singular focus.

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?

Tenacity, resilience, and a capacity for deep listening. My tenure in the corporate world was during the early days of women in leadership. At that time the majority of women were hyper-protective of the little piece of real estate they had struggled to secure. Despite often referring to this as my period of being kicked through the fences, it is not in my nature to quit, so my quarterly numbers were consistently and unquestionably above par. Throughout my years in the industry, I paid close attention, and absorbed everything I could, including many things beyond my scope of authority. By the time I moved on, I had absorbed so many insights to successful team building, what works and what must be nipped in the bud, that small business building was an exciting adventure.

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?

Instead of being taught to apply critical thought to our mistakes and shown how to draw every bit of useful insight from them, to position for future success, we are taught fear of failure from the time we are small. Further we are not taught to see a project as a failure, but to believe that?we?are the failure. Consequently, fear of failure is not just personal but cultural. We’ve all heard the stories of someone, their plan or company, spoken of as having failed. We’ve felt the ridicule or pity that accompanied those statements. None of us want to be on the receiving end of being judged as a failure. The very thought of it puts pock marks in our self-image and drives us to work harder, and rarely smarter, to avoid this conviction.

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

The primary downside to fear of failure is the assurance one will experience

it repeatedly. Chronic fear of failure results in perfectionism. Because life is ever expanding and we are constantly evolving, perfection is a staid destination point that, at best, can only be achieved for a fleeting moment. The net result being an ongoing revisiting of the crushing sensation of failure. Rather than view these changes as growth, we view them as a result of our own ability to achieve.

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

Letting go of fear of failure is the most direct path to audacious courage. Whether that be expressed daring to build one’s next business, pursuing the professional leverage one’s always aspired to, or simply bringing a project in on time, on budget, and at a level of overall excellence. Most significantly, doing this free of fear of failure allows the experience to be fulfilling, versus merely experiencing relief at the completion of the endeavor. Without this fear, we get to enjoy the journey and the process of learning and growth.

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?

One of my notable successes led to one of what I came to see as one of my greatest failures. In the mid-1980s, I was one of the first women to achieve executive status in corporate oil and gas. In a reasonably short timeframe my P&L’s, turnover, and shrink outdistanced any of my colleague’s numbers. The environment was challengingly harsh, but I was committed. So, it wasn’t that I loved my role, but rather that I was determined that ‘they weren’t going to beat me” and whatever they did I was going to do it better. A truly self-brutalizing mindset that did ultimately render its predictable impact.

By the time I did realize leaving that environment was necessary for my mental and emotional health, I was so depleted that it took months to recover from the impact of those years.

How did you rebound and recover after that?

I took several months off for traveling. During that time, I consciously focused on what had originally fascinated me about my previous role and what I had allowed to reduce my self-respect to the point of driving myself into the ground. Along the way, I encountered a number of women who had founded their own businesses. Spending time in deep conversation, I asked about why they loved it, and what it was costing them, emotionally and intellectually. Ultimately, I realized this was a path that would suit me. The loyalty of my employees in my former role had shown me I was a leader, and now it was time to determine for myself the direction and purpose.

What did you learn from this whole episode?

Humility was the most powerful lesson gained from this experience. I was young, smart enough to succeed but not wise enough to know that my ego had been driving me, forcing me to push beyond what was reasonable or healthy.

What advice would you give to others based on that story?

Listen to your body and internal wisdom. When pushing beyond your limits is the only option for avoiding what you perceive as failure, it might be time for a change. It’s easy to get caught in the idea that we can’t leave, can’t find another position that supports us in the manner we prefer. There are many avenues to failure. Working in a manner, at a pace or in an environment that is taking a toll on our fundamental well-being, is potentially the most devastating failure of them all.

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. By being clear and intentional when reviewing a mistake, you can avoid letting negative emotion of feeling like a failure run away with you. Perfection seeking was a fatal practice I carried for many years. It boxes us into a corner of either being a failure or perfect in all applications. A completely unrealistic and yet broadly practiced mindset. A highly effective means of stopping this cycle is to pause for reflection. Consider the outcome from several vantagepoints.


  • What was working well until it started to fall apart?
  • What wasn’t working or acknowledged as faulty soon enough?
  • What was the initial indicator the project/initiative was becoming incohesive?
  • What could have been done differently? This may have multiple answers as you notice that there were several points at which there could have been a successful turnaround.

Summary: What are the beneficial understandings gained for future application?

Rather than condemning it and yourself as a failure, you have turned the mistake into a positive learning experience.

2. Have an accountability and mastermind partner to help you remain focused on the big picture. When building a big project, it’s easy to become afraid of taking the time for these two crucial components for success. I fell into each of these when I was a younger businessperson, and the effects were devastating. The harder I would drive myself, the less time I took for evaluation and consultation, the greater the fear of failure. What I realized to be true is that these two actions calm the fear of failure because you know you have someone else to talk through the most challenging situations with, for course correction. Additionally, weekly accountability charting lets you track when you are off course before you are too far down the wrong path.

3. Delegate and appreciate. Feeling you are the?only?one who can take on too many responsibilities effectively is damaging to you, and your project. This mindset is rooted in a fear of failure, and distrust in others ability to perform up to your standard. Positioning yourself as the single source of excellence will make failure a self-fulfilling prophecy. Any project that is to be sustainable and scalable requires a team, whether in-house or through consultants. Being able to delegate tasks, teach those on the team to understand the ultimate objectives and appreciate their contributions relieves great amounts of pressure on all involved. Creating a cohesive team vastly reduces the potential and fear of failure.

I have always enjoyed leading with teams, within my own businesses and other organizations. Learning to delegate and appreciate has been an ongoing journey that continually produces greater outcomes. Additionally, stepping up to claim responsibility when the team is not performing at top level has shown me the degree to which teams appreciate and perform better for a leader over a boss.

4. Taking time away. For years I was the absolute worst at taking time away from a project to rejuvenate and reframe. I was always afraid the entire project would fall apart if I didn’t work relentlessly, and I would end up failing. What I have learned is that I made more missteps by not taking the time to rejuvenate and reframe. These periods consistently prove to be times of new inspiration that I can bring back to the project to allow it to become more than it was before. Life is organic and evolving and the breaks allow my vision to catch up to that naturally evolving process.

Granted it is important that the breaks be well timed. So, designating rotating periods into the calendar for you and the members of the team to each refresh, reinforces faith and enthusiasm, eliminating the fear and result of failure.

5. There is no way to track the number of times I’ve been approached by a woman who was struggling with her project or company and on the verge of panic that she was going to fail. When I referred them to a mentor, business coach, or other valuable consultant, too many times they have immediately responded with protests of not being able to justify the expense. Later I would hear the project had collapsed. The justification of the expense for working with a high-level support person cannot be overstated. And it is a lesson I learned early on, after crashing two of my earliest businesses by making the same mistake as the women I mentioned.

It is completely common to take a deep dive into fear of failure when taking on a new project that requires skills we will need to develop along the way. While initially it may feel like a stretch to factor that into the budget, the return on investment will prove the wisdom of having made that choice. The confidence a high-level support person will imbue, while offering the most direct path to upleveling the necessary skills will soothe the fear of failure. This becomes new energy you will now be able to focus into more productive applications.

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?

I fundamentally agree with what I believe to be Aristotle’s intended teaching in this sentiment. Specifically, I see the only way to succeed is by believing in oneself at a core level combined with a belief that the chosen direction is both sustainable and a solid fit for one’s skills and talents.

Beyond that, there are many paths to a single destination and being willing to listen deeply to one’s internal leadings and guidance is key to knowing which will serve best in a specific circumstance.

What do you think Aristotle really meant?

This has been debated by scholars throughout the ages. The one thing we do understand clearly is that he was referencing?virtue. In that age the word spoke to a state of moderation. I believe Aristotle was counseling against leaning into extremes on either end of any spectrum. Specifically, I believe he was offering caution to remain clear of the intensity of self-depreciation and egoic grandiosity, associating moderation with an internal state of balance.

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. :-)

For women to begin supporting each other fully through development of Strategic Alliances. Men have long had the Secret Handshake and the Old Boy’s Club, and they have served each other well through these relationships. With women being 50–53% of the population and claiming only 33.7% of the national yearly income, I believe that by setting down the old fears of lack of real estate, their long-taught negative competition and comparison, women can rise to claim the equity they deserve. And numerous studies indicate that when women win, so too will men, children and all of society.

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.

Emmanuel Acho. I have tremendous respect for courage he demonstrated in creating Uncomfortable Conversations with a Black Man. Since then, I have become fascinated with his book, ILLOGICAL, and the video reels he’s released on that topic. It would be informatively fascinating to have a conversation on both topics, and specifically, the processes he has developed for his personal knowing of when following the illogical is following his spirit and destiny.

What would be far more beneficial is to learn to see mistakes, even significant ones, as opportunities to learn from.

How can our readers further follow your work online?

https://lesleymichaels.com/

Omolara McCloud

\S/enior Accountant | Helping purpose-driven business owners save the world, one financial statement at a time!

1 年

Thanks for sharing!

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