In my almost 40 years of my 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 terrible, come up against extreme narcissism in my manager and challenged him in a way that hurt me, launched big initiatives that lost money, partnered with the wrong people, and more.  I’ve had some big successes as well, that have made me proud and helped me do the work that I love with people I respect, supporting outcomes I care about. 

In my Amazing Career Project career growth course, participants often talk about their “failures,” and long to dig deeper to understand these failures better. I add quotation marks around the word “failure” because so often, these events or experiences are not failures—they were smart, well-considered steps or decisions that happened to end in a direction that felt wrong, but that learning was inevitable and 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 Masters program and information 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, I learned that the actual professional identity every day of serving a therapist, and the intense darkness that I felt immersed in was not what I wanted for my life. But that training transformed every aspect of my life, and allowed me to be a much better coach, writer, and educator. So, not a failure at all.

About their own failures, my clients 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 as other people are? Or “How can I make sure this horrible 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.

Shakespeare too said about failure:

“Wise men ne’er sit and wail their loss, but cheerily seek how to redress their harms.” — from Henry VI

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 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 a big failure in life or work right now. Which one of these categories does it 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?

  1. Was it advised to you by an expert that you trusted? 
  2. Did you do research that pointed to this being the right move, but unforeseen factors emerged?
  3. 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)
  4. Did you think you knew enough about this particular project, activity, or direction but actually didn’t?
  5. 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

I’ve just experienced what some would view as a big failure. I’ve 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 highly lucrative and be of strong service at the same time.

The result – big failure. 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 pandemic. But as a marketer all my life, I know that isn’t the problem at all.

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. 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 dead wrong. 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 fact a relief to me, allowing me to see the full truth of my emotions and desires. This failure allows me to finally do what I want to—focus on what really matters most to me right now.

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 was completely unpredictable, and we simply couldn’t have prepared for it. Take the pandemic, for instance. So many small businesses weren’t prepared for what has befallen then, but why would they be prepared? The entire world wasn’t prepared.

Certainly, there are things some entrepreneurs and business owners could do and have done to help them stay viable and afloat, like restaurants innovating and pivoting, for instance, from fine dining to drive through, or fast casual to bulk meal boxes. But for many of the entrepreneurs I hear from, the very nature of their work has been upended, and their ability to pivot or shift has been severely limited.

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, that renowned Swiss-American psychiatrist Elisabeth Kübler-Ross described in her groundbreaking bookOn 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 15 years has revealed about the 7 most damaging power gaps that 98% of professional women face today. Gap #7 is Allowing Past Challenge and Trauma to Define You

I see everyday how our “failures” have crushed us, 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, 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 longing 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 transition.

I’ve seen too that there are 8 stages of career transformation, or transformation of any kind, and those stages are:

  1. Disengagement
  2. Disidentification
  3. Disorientation
  4. Letting Go
  5. Re-engagement
  6. Discovery
  7. Clarity
  8. Integration

Letting yourself flow through these stages, rather than fight and resist them—especially after a failure that has crushed your confidence, self-esteem 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 become more of who you are and who you want to be.

Kathy Caprino is a career and leadership coach, speaker, educator, and author of The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss. She helps professional women build their most rewarding careers through her Career Breakthrough programs and Finding Brave podcast.


  • Kathy Caprino

    Hi! I’m a career and leadership coach, writer, and speaker dedicated to the advancement of women in business.

    Kathy Caprino, LLC

    Kathy Caprino, M.A. is an internationally-recognized career and leadership coach, writer, speaker and trainer dedicated to helping professional women  "find brave" and close their power gaps to create more success, fulfillment and reward in their lives and work. A former corporate Vice President, a trained marriage and family therapist, and the author of Breakdown, Breakthrough and the new book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss, Kathy is the Founder of Kathy Caprino, LLC and of the Amazing Career Project online career course and the Amazing Career Coach Certification training program. She is a Senior Contributor on and leading voice on Thrive Global and LinkedIn, and a top media source on careers, women’s issues, and leadership and has appeared in over 200 of the nation’s leading publications, and on national radio and TV. Her podcast Finding Brave ranks in the top 100 Apple Career Podcasts in the U.S. and beyond, and shares compelling interviews with top business and leadership experts, bestselling authors, creatives, entrepreneurs, and thought leaders who are making a brave difference with their work. For more information, visit and, check out her new course The Most Powerful You, and connect with Kathy on LinkedIn, Twitter, Facebook and Instagram.