Part of Kathy Caprino’s series “Becoming The Most Powerful and Confident You”
In my 40 years of work, I’ve experienced some colossal failures that anyone would consider undesirable and some would say were embarrassing and humiliating. For instance, I was blindsided by a brutal layoff from my high-level corporate VP role in a way that shattered my confidence. I’ve been passed over for promotions, assumed new roles that ended up being very wrong, come up against extreme narcissism in several leaders (and challenged them in ways that ended up hurting me), launched large initiatives that lost money, partnered with the wrong people, and more. I’ve had some strong successes as well, which have made me proud and helped me do the work that I love with people I respect, supporting outcomes I care about.
In my professional development course The Most Powerful You, people often talk about their “failures,” and long to dig deeper to understand these experiences better. I add quotation marks around the word “failure” because so often, these events or experiences are not failures at all — they were smart, reasonable, well-considered steps or decisions that happened to end in a direction that felt wrong, but the learning that ensued was powerfully valuable and in truth, essential for their growth. So why would we call that a failure?
That same experience happened to me when I became a marriage and family therapist. I loved the Master’s degree program and concepts I learned. I loved the training and three years of study, but once my actual internship started, and even after launching a therapy practice with two partners and engaging in therapeutic work for some time, I learned that the actual everyday living identity of serving as a therapist — and working with the intense challenges and darkness that many of my clients were dealing with — was more difficult for me than I anticipated. I finally accepted the fact that I had different longings for the work I’d be doing in the remaining years of my professional life, and becoming a career and leadership coach, writer and speaker called to me. But my therapeutic training and work transformed every aspect of my life and allowed me to be a much better coach, writer and educator (and parent). So…not a failure at all.
About their own failures, my clients often ask: “Why didn’t I see this coming?” or “How is it that no matter what I do at this job or company, I’m not recognized or rewarded like others?” or “How can I make sure this painful experience doesn’t happen again?”
Failure is a concept that has been written about for centuries. Some experts have shared that “failure” is all about how you look at it. Others have explored the idea that there really is no “failure”— it’s only feedback. Others have proposed that there are certain structures of failure, and the key is to understand this structure so you can avoid the fruitless and damaging blame game. Finally, scientists researching the topic have found that failure is a prerequisite for success.
The problem with many of these definitions is that they don’t actually address the disappointment, grief and confusion we often face when we experience what we see as failure — the pain we feel when we don’t achieve the key outcomes we think we so desperately need and want.
To cut through all the academic discussions of failure and figure out how we can bounce forward quickly and learn from what we’re facing, I’ve seen there is one simple question you can ask yourself to help understand the failure you’re experiencing and extract the most benefit from it so you can get to your new, better goals faster.
That question is:
In looking at this experience, action or event that I see as a big failure, what was the ONE true root cause of it and what can I learn now from it?
Did I fail because of:
1) A tactical error
2) A lack of recognizing or honoring my true emotions and desires
3) Not being able to foresee what was coming down the road
This week, take some time to examine what you experience as the biggest failures in life and work over the years. Which one of these categories do your “failures” fall under?:
A tactical misstep
Did this failure emerge from taking a step that moved you in a direction you now see and feel as wrong?
If so, think about why you took this step. What motivated the misstep?
- Was it advised to you by an expert that you trusted?
- Did you do research that pointed to this being the right move, but unforeseen factors emerged?
- Did you simply think that it was going to lead to a happier professional life (as I believed, when I became a therapist), but you didn’t vet the direction well enough? (This is often due to what I call the Pendulum Effect)
- Did you think you knew enough about this particular project, activity, or direction but actually didn’t?
- Did you move too fast, without recognizing the full potential impact of this one step?
Typically, tactical errors are made with the best intentions, but we don’t have a crystal ball. They sometimes take us to new places that we haven’t vetted properly, or even if we did vet them, life is not linear—you’ll frequently experience things you were never going to be prepared for.
Tip: If it was a tactical misstep that led to the failure, look more closely at why you engaged in that tactic, and uncover where in the process you could have perhaps elicited or learned some new information that might have saved you the pain of that step.
Often you’ll find there was nothing you would have done differently. Meaning, you did the best you could given all the information you possessed and given the person you were at that time. But if you do make this type of tactical error repeatedly, you’ll want to get to the bottom of why this is a repeating pattern in your life.
Unrecognized emotions and desires
Several years ago, I experienced what some would view as a big failure. I launched a program that I believed: 1) I truly wanted to deliver, 2) would be helpful to thousands of people around the world, and 3) would be lucrative and be of strong service at the same time.
The result – those dreams and goals didn’t materialize. In short, there was very little demonstrated interest.
Entrepreneurial or business experts would point me to the marketing and sales process I engaged in to promote this program, and they’d immediately blame the marketing steps or the difficult economic times we’re in. But as a marketer for many years, I know that wasn’t the full extent of the problem.
In thinking long and hard about this, I realize now that I really didn’t want to deliver this program as it was presented, not in my heart of hearts. So why did I pursue it? Because I didn’t validate or honor my truest feelings (and in some cases wasn’t even fully aware of my deepest feelings). I pushed forward because I thought it would be a good business move, and because I fell prey to what so many entrepreneurs experience each day — the belief that just because others are doing something similar that looks easy and lucrative, and because we have the skill to do that same thing well, we should pursue it.
Lesson learned: That’s not a productive way to live and work. Just because you can do something, doesn’t mean you should do it. For me, my heart just was not in this endeavor, and it was focusing on an audience that is not my passion to serve. If I’m honest, the failure was in the end a relief to me, allowing me to see the full truth of my emotions and desires. This failure allowed me to do what I wanted to—focus on what really matters most to me right now and on the communities I want to serve, deep in my heart.
Tip: Spend some time this week thinking deeply about this “failure” you’ve experienced. In what ways has it opened new doors, or released you from a job, career path, relationship or outcome that deep down, you no longer want or is no longer needed.
How has this failure set you free? If it has released you to pursue something closer to your heart, would you still think of it as an abysmal failure?
Not being able to predict the unforeseen
Often we blame ourselves for failure to achieve a goal when what prevented that goal achievement was completely unpredictable, and we simply couldn’t have prepared for it. Take the pandemic, for instance. So many small and large businesses weren’t prepared for what transpired and were negatively impacted — but truly, who could have been prepared for a global pandemic? The entire world wasn’t.
As the inspiring futurist April Rinne has shared, “People often assume that, as a futurist, I’m in the business of ‘predicting the future.’ This is definitely NOT what I do, not least because ‘the’ future doesn’t exist; it’s only a concept, a figment of our imagination. Rather, I help people and organizations navigate a world — and a future — in flux. This means understanding and preparing for many different possible futures… which we are all contributing to every day.” (Stay tuned for another riveting interview with April coming up on my Finding Brave podcast in September!).
Certainly, many entrepreneurs and business owners found ways to stay viable—such as restaurants pivoting from fine dining to drive‑through formats or fast‑casual chains offering bulk meal boxes. However, for numerous professionals and entrepreneurs I talk with, the nature of their work has been fundamentally disrupted—often in ways that make rapid pivots difficult or impossible. This holds true today as well, amid dramatic workforce shifts, the proliferation of AI, supply chain volatility, and ever-evolving consumer expectations.
When you face a huge, unforeseen challenge, something you couldn’t have seen coming, being as flexible, open and innovative will help you deal with that challenge. Learn as you go, become more nimble and embrace new strategies that will help you rethink your approach and strategies, and goals, rather than stay stuck in anger, fear and resistance.
Tip: If you’re experiencing grief from this failure (and so often, grief does accompany our feelings of personal or professional loss and failure), it’s helpful to understand the five stages of grief, which renowned Swiss-American psychiatrist Elisabeth Kübler-Ross described in her groundbreaking book On Death and Dying. She explained that the grief process can be divided into five stages. Her observations came from years of working with terminally ill individuals.
The five stages of grief are:
- Denial
- Anger
- Bargaining
- Depression
- Acceptance
Which stage might you be in now? Not everyone goes through these five stages when grief is experienced, or we may not go through them in this order. But I’ve found that when we perceive ourselves as failing in ways that hurt and humiliate us, grief is almost always involved.
Now it’s time to bounce forward, not back
In my book The Most Powerful You, I share what my research over the past 18 years has revealed about the 7 most damaging power gaps that 98% of professional women and 90% of men face today. Gap #7 is Allowing Past Challenge and Trauma to Define You.
Here’s more about it:
I see every day how our “failures” have internally crushed our self-trust, confidence, and self-esteem, and how the pain and shame of these failures stay with us, often for years and even for a lifetime. Among numerous stories of inspiring women who’ve faced and overcome these damaging gaps, Chapter 7 shares the riveting story and insights of Cheryl Hunter, who experienced a devastating and horrific event in her teens that changed her life forever. Years later, as one who helps people tell a different story about their lives, she shares that we need to stop trying to “bounce back” to a former way of life or to a previous “self,” and instead focus on bouncing forward to a new, more rewarding and life-affirming way of being.
One way forward after failure is to understand that there are many stages, phases and events that punctuate our lives and careers. Again, success is not a linear path — it’s a fluid process of a living organism. Years ago, in learning more about this process, I was fascinated by the work of William Bridges and his book Transitions: Making Sense of Life’s Changes in which he talks about common stages of life transition.
I’ve seen too in coaching clients that there are 8 stages of career transformation, or transformation of any kind, and those stages are:
- Disengagement
- Disidentification
- Disorientation
- Letting Go
- Re-engagement
- Discovery
- Clarity
- Integration
Letting yourself flow through these stages in a more organic and fluid way and looking at what new avenues may be possible now, rather than fight and resist them — especially after a failure that has crushed your confidence and self-worth — will help you bounce forward, integrate the new information you’ve learned from what’s emerged in your life, and get on the Finding Brave path to becoming more of who you truly want to be in this world — and more of what the world needs you to do and be.
Join me for a private 60-minute Career Consultation — designed to help you uncover the key insights and next steps you need to move forward with greater clarity and confidence. I’d be honored to support you.
Kathy Caprino is a career, leadership and personal growth coach, speaker, educator, and author of The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss and creator of The Most Powerful You 8-week coaching/training course helping professionals address their power and confidence gaps to build the lives and careers they long to. Move forward to build your most rewarding and fulfilling career through Kathy’s Career Breakthrough programs and Finding Brave podcast, and speaking/training programs.Sign up for Kathy’s weekly personal newsletter here.
