Forgive yourself. If you decide now that you’ll forgive your failures, they’ll be a lot less scary. Forgiveness can give us freedom from fear of failure.

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 Dia Bondi.

Dia Bondi is a Communications Catalyst helping C-level leaders, VC backed founders and ambitious professionals find their voice and lead with it. She’s the author of Ask Like an Auctioneer: How To Ask For More and Get It which aims to help 1 million women ask for more and get it.

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’?

When I was a kid, growing up in Northern California, I wanted to be a long-haul truck driver. I loved the idea of being on the open road, in an unlikely job for a woman (it was the late 70’s and 80’s), and living a life of freedom, independence and adventure with the opportunity to meet and connect with all kinds of folks. I knew I wanted to live a life on my own terms.

Fast forward, and in some way, I’ve lived, and live that life now. As a leadership communications coach and author my work has had an incredible mix of adventure and deeply connected experiences with people from every sector and around the world. I’ve always been a bit of a rebel and my rebel spirit was a key driver in finding the world of professional development which was nascent when I started twenty years ago.

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?

My work has given me the great opportunity to work on high-stakes, high-profile projects with high-impact people. Like my work helping Rio de Janeiro win the right to host the 2016 Olympic Games, working with the biggest brands in the world and with founders building new technologies that have a profound impact on our world. But one of the most interesting journeys I’ve had is one that was by accident. When I took a sabbatical, I followed my curiosity and learned to be an auctioneer as an impact hobby for fundraisers benefiting women and girls. I had no idea that little adventure would lead me to write my first book. I saw a connection between what I was learning in that impact hobby and how to make strategic asks in our businesses, careers and lives. It was a great surprise to me that it would lead me to write my first book, allow me to learn that I love writing and catapult my career in a new direction. The lesson here is to follow your curiosity and don’t be afraid to try things even when they feel or seem far afield from your current trajectory or domain. That follow-through on a desire to learn something can have a big impact on your life, your creativity, your career and your idea of what you think is possible. I mean, auctioneering? Who would have thought it would do more than give me a chance to have a fun hobby and wear a nice gown now and then?

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?

My experience in leadership is in leading in ideas. Bringing folks along with me and enrolling them in having an impact with those ideas.

In that, three important character traits that have helped me lead and have the impact I want are enthusiasm, openness, and courage.

Enthusiasm has been critical. If I’m not enthusiastic about the ideas I’m leading with, nobody else will be. Equally, it’s paramount I’m enthusiastic about the feedback and ideas I get in return and in reaction to what I’m sharing. This creates a momentum that is generative vs. defending my ideas in a way that stops the conversation or limits thinking together with others. One pitfall of enthusiasm I’ve had to guard against, is being so enthusiastic that there’s no room for others in the conversation. It’s a delicate and important balance. Inviting others to share their ideas with simple phrases like “What do you make of this as it relates to your goals?” and “What do you think?” and “Where do you see the gaps?” helps to make room for other voices.

Openness has been less of a character trait and more of a learned behavior for me. I have cultivated my openness very intentionally to ensure that I am in a position to collaborate with my client, teams or stakeholders in a way that allows new ideas and creative innovations to occur. I don’t think I would have seen the connection between what I learned in Fundraising Auctioneering and my career of leadership communications if I wasn’t open to seeing how ideas collide in productive and surprising ways. Especially when those ideas challenge conventional thinking or a comfortable status quo.

Without courage I would never make the impact I want to have. I remember once working with a very influential leader, human right activist and globally recognized prize winner, I was challenged to see how I could help him. As we started to work together in a private session, I could see that I wasn’t able to quickly assess where to start. The easy thing to do would have been to just default to where I would always start and lean on tactics that I knew would work but were lower value. Instead, I accessed my courage and asked one very simple, very clear question- one that risked looking naive and risked losing my credibility. That one courageous question had the exact opposite effect. His answer gave us what we needed to decide exactly where to start. And we were very successful in our engagement. This is a small but meaningful example of where courage serves me in my leadership and impact. When we have a choice to have more impact with courage, and when we have the willingness to take the risk using it, we can lead more effectively.

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?

First “failure” as a word, can be big, all-encompassing, and not specific enough to help us grapple with it. Once we can get more concrete and specific, we can deal with it, see choices in the face of it, and its power shrinks. “Fail at what, specifically?” is a good question to get started on knocking it down to size.

Further, we are afraid because we conflate success with our worth and worthiness. It triggers our anxiety about being left out, left behind, isolated, embarrassed, and humiliated. It can become existential.

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

One downside of that fear is it can limit our ability to act, paralyzing us and never letting us see what’s possible. But it also captures our attention in a way that constricts our thinking, makes us less resourceful, and focuses our energy and problem solving on what “not” to do instead of on the wonderful questions “what if?” and “how might I?”

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

First, we have fear of failure across lots of aspects of our lives and leadership. One thing I see a lot of are folks feeling fear of failure around not securing funding for their start-ups, securing their next promotion, getting that raise, or getting a new client to engage. That fear can paralyze action. One idea I learned in my time auctioneering that I share in the book is that price is a measure of value not worth. That’s to say what someone will pay or do is a way to see what they value and how they value it, not a way to define your worth or worthiness. This takes the pressure off “failing” to get that raise. And instead, it allows that failure to give us a line of sight into what’s important to the person on the other side of the conversation. It’s not failure, it’s information. And that information is empowering because we can do something with it.

Second, in the thousands of communications coaching sessions I’ve executed over the years, I’ve seen that it’s important to remember in high stakes moments, that you can get help. Get help recovering from a failure, get help while live in the room when you may stumble on stage, get help from your community on what next steps you might take. Help is everywhere. And like my earlier example, failure gives us information we can use to collaborate with others on what we might do next. Running up against failure works like a treasure hunt to find our way forward. So, if we remember we have and can get help, taking the action that exposes us to possible failure feels less like failure and more like an experiment. That is freedom from failure.

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?

Except for a small stint in the middle, my career has been one where I have been an independent professional running my own business. I went in-house with a client once as an experiment and then a few years later to another organization. I quickly saw that I’d made the wrong decision when I moved to that second organization. I saw that wasn’t going to be successful there. It felt like a failure. I felt like a failure. But I knew that I couldn’t let it paralyze me in taking action. So, I quit. Nearly immediately after I realized I wouldn’t be successful, I got into action. For me, there was a lot to learn in that situation, but one thing I really worked to do was to see it as a misalignment, not a failure. I acquired a lot of information about where I needed to go next and what I was really looking for. It was an experiment, and the beaker broke. “Okay.” I said to myself “Move on and try something else with the information you have from that experiment.” And that’s exactly what I did.

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?

Action solves a lot. I took a sabbatical, but I got into action around the question “what do I want now?” And the answer came.

It’s important we know what question we’re trying to answer after a failed experiment. And then get into action around that question. Even if the action is examination, journaling or exploring a feeling. Action that connects us with the greater world can stop us from spiraling or obsessing on a failure and help us start to connect dots, get new ideas and see what’s next.

In your opinion, what are 5 steps that everyone can take to become free from the fear of failure”?

Step 1: Put your upcoming potential “failure” into the context of your longer-term goals or journey. If you are looking out onto the horizon of your life or career, and place this “failure” in that context, the fear that comes with that potential fail moves into perspective and becomes a speed bump, not a cul-de-sac.

Step 2: Plan what you’ll do next. Before you pursue the thing that might fail, decide now all the things you’ll do after it “fails”. Once you’ve done that, you may see that its power shrinks and you become more free of that fear.

Step 3: Take the action and watch the impact like an experiment. Something didn’t work? Instead of internalizing it, notice what new information you have so you can fold that into your next experiment. This will give you some distance from the outcome such that it’s not about “you”, it’s about the experiment.

Step 4: Gather your community. We all have our professional and personal circle of colleagues, friends, mentors, and family who can help you through anything. Find those people and gather them around even before you take a risk. Put them on your unwritten team so you have the support around you to take the risk, see how it goes and not have to be alone with it.

Step 5: Forgive yourself. If you decide now that you’ll forgive your failures, they’ll be a lot less scary. Forgiveness can give us freedom from fear of failure.

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?

This quote sounds like the only way to succeed is through failure. It’s a natural and necessary process. I do believe that we can’t expect ourselves to be numb and perfectly neutral to the feelings that come with failure or the potential of failure. We are feeling beings. What we can do is recognize that failure is a necessary part of success and cultivate skills and perspectives that help us be courageous and resilient.

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 amplify and accelerate the movement for equality for women. When women have equal access to education, can live free from violence in any form and opportunities to create financial security for themselves, it benefits us all.

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 🙂

David Byrne. His willingness and drive to experience a full range of his creativity is astounding and courageous to me. He is a model for me and demonstrates a refusal to be boxed in.

How can our readers further follow your work online?

See all Dia’s work here:

Get free tools and Dia’s book Ask Like an AUctineer: How To Ask For More And Get It Here:

Follow and connect with Dia here:

Listen to Dia’s Podcast Lead With Who You Are here:

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.