Learn to track progress over outcomes. I have been teaching this for years, and it’s still one of the hardest things for me to do. I’ve committed to tracking the inputs, the leads, that get me the outputs, the lags, I want. Doing this lets me focus on the process, measure the steps, and focus less on the destination. When you commit to the small steps, you’ll grow so flipping fast! Track the number of times you go to the gym, the number of posts online, the number of emails you send about your product, or the number of books you read. Focus on the steps!
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 Aaron Velky.
Aaron is a keynote speaker, CEO and coach. His career has been dedicated to building movements, companies and leaders. He’s coached and led workshops, retreats and leadership training for hundreds across the US, and continues to write, speak and create content for other emerging leaders and companies.
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’?
My story has largely been unclear, and I was often counted out.
I’m listening, as I write this article, to Nico & Vinz’ song Am I Wrong, and this line stands out. “Am I trippin’? For havin’ a vision?”
I’ve had a vision for my life, as I’m sure you do, too. You may not know how. Or when. Or where to start. I’ve failed my way there, and hope that this share, this story and the lessons in this write up help you along the pathway of creating your vision.
No matter how ‘out’ you feel, keep counting on you.
Picked on in high school. Outcast in almost every way I could think of — I was always the ‘other’ guy. Finished with and left my friends to play soccer. Walked onto a D1 program, which was a big accomplishment (we’ll get to this in a bit), but failed there and felt like the degree program I was in really wasn’t for me.
I left college in a recession, and rather than leaning on the degree (financial economics), I leaned on skills. A son of a blue collar entrepreneur, I became an apartment maintenance technician at a college housing company. Yes. After college I went into fixing the outlets, toilets, tubs and appliances at another college campus. Dirty job. Gross. And people treated me like I was a piece of dirt, even though I had just finished college, with a great GPA, from a great school, and also as an athlete .
When I shared what my career step was, I was counted out. Friends laughed. Peers thought I was underselling myself.
I was. But I could see beyond the immediate next step to the long game. I’ve always played the long game.
The job led to management, to building someone else’s business renting out units, while at night I was coaching youth soccer to escape the boredom of a 9-to-5. I didn’t like making someone else rich when I thought I might be capable of doing it for myself.
My evening hours went less and less to fun, video games, and celebrating and more and more to figuring out new income streams, ways to make a difference in the world, and ways to create a life of travel, adventure and purpose — though I didn’t know those words at the time.
And through it all, I’ve known very little. I didn’t know where I was going, I didn’t know how to raise capital, start a company, build a corporation, hire, fire, look for clients, create marketing campaigns, navigate company culture.
I’m just a “make a choice and figure it out” kind of guy.
I never realized how much of a super power that was until lately.
And now, after years of making mistakes, building the wrong thing, wasting time, not setting boundaries, and deep introspective work, I’m an entrepreneur, keynote speaker, and transformational coach.
I have several companies and spend my time making other people’s lives better, working with companies that are pioneering, and using my moments to craft leaders and tell stories that motivate and inspire others to take action in their lives.
Serving others is my lane, and building movements is my game.
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?
One of the most challenging experiences as an entrepreneur came at the result of COVID-19. I had spent about two years cultivating a Money Club ecosystem, client base and set of investors, all who believed in the mission and the pathway of the business. We had set out to raise capital and develop a technology platform that would allow other individuals to learn about money in their school, their youth groups, and at home. We had invested in a platform, in tools, and had spent considerable time nurturing the investors that would help fund all the developments needed to make this a successful launch.
By the time we had cultivated the right opportunities, with over $400,000 in our pipeline, within14 hours, the opportunity was gone in a matter of seven emails. Once the COVID-19 news spread to schools, youth groups, and other youth-facing organizations, we received word that our contracts would be null and void and payments would not be sent. In a matter of moments, our entire year of staff salaries, investment, clients and impact work were gone.
I learned a few things from this. I learned nothing is guaranteed, and most importantly, looking out for your team is probably the most important element of business. We sat down as a team over several different conversations, outlining what our options were and what we would do. With barely $25,000 in the bank and a payroll of $16,000 a month, we had very few options and very little time. We set out to adjust quickly and adapt, but frankly, there were very few options for us.
Everyone counted us out. We were dead in the water. Even family and friends suggested I let it go. I couldn’t get responses to emails from clients, investors, and even mentors.
Difficult conversations were a big part of how we were able to survive. The team was given two options. Option one was I offered to find them a job, find them a position, lean on my network, ask friends, ask investors, ask anyone I possibly could to make sure everyone on the team would be well taken care of. That was really difficult for me because these were the individuals that I had invested in and had a lot of faith in and knew they could take our business to the next level. The second option was to stay with the business and my commitment was to make sure they had enough money to cover their food and their rent. I couldn’t guarantee them a salary like I had before. I could make sure they were taken care of.
To my shock, everyone decided to stay in the boat. The one contractor we had, who was not a full time employee, decided that it was time for him to go his own way and double down on his business rather than working in ours. He was already set and we were now, as a team, really committed to figuring this problem out together. When I think of how individuals deal with failure, the story of what happened in 14 hours in Covid points to taking care of your team first and letting the results follow. I hope that others do the same, even if they’re going through tough times, as many business owners will.
Money Club pivoted well, in the long game. We failed a lot through many different iterations when we were in survival mode. We now do some amazing work with industry leaders that want to help their team learn about money, create workplace equity and give their team personal development — and all from a total crippling moment.
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?
There are three traits that every good leader must have. The first is vision. Vision to see what cannot be seen and to explain it. If you can’t explain it, then it doesn’t exist to another person and our job as a visionary is to be able to paint, craft and narrate a possible future so that someone else can find their path alongside it or in it.
The second trait is listening and empathy. I put these two together intentionally. You can’t have empathy without listening, and it’s very difficult to successfully listen without empathy. These two are critical to leadership because emotional intelligence serves as the bedrock for our connection to our team, to our clients, to our mission. Without a deep sense of listening and empathy, we miss the opportunity to walk in someone else’s shoes and build products, services and solutions that meet them where they are. Often business owners will build from a perspective that they are in, not that their client is in. Listening and empathy helps this shift.
I used to hate hearing “We need to talk.” I got so anxious. What could it be? Did I do something wrong? What could this be about? And since doing some deep digging myself, I’ve realized, I can show up to the conversation and be a listener. If that’s all I can control, I want to do that really well. It really lets me relax in moments where I would normally panic and feel uneasy.
The third critical trait of leaders is humility. When you begin to lead, many of you will relate to this. You lead from a place of wanting to be the leader. I think there’s value in being the leader and wanting to be the leader when you trust yourself that much. However, at a certain point you recognize that leadership is often the position and responsibility we have, not necessarily a title and a mantle. When we learn to lead from underneath, from a place of service and from a place of nurturing, we get better results, requiring us to be humble in understanding someone else has more strength, more knowledge and possibly more expertise than us. Our job as leaders is to put that to good use. We have to be humble in our own demeanor to take advantage of it. While I can’t tell you a story of humility (what an oxymoron) what I can tell you is that I’m intentional about leaving room for others to share their expertise, about letting my knowledge and experience guide me and not projecting that my solutions will fit for everyone, and about giving more than I take regularly.
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?
People are afraid of the stigma associated with failure, not failure itself. That’s an important point to all of this work and my share. We are generally more afraid of what people will think of us than we are of the outcome or of the failure. When we begin down a path of something new and we’re very young and we don’t pay attention to others, we very seldom hesitate to fail. If you look at a young child when they learn to walk, when they learn to ride a bike, they’re not mindful of all of the attention that they’re getting or what people say or think about their failure. They simply understand that failure is part of the process.
As you work through all the components of being an adult, you would very quickly unravel failure as more of a projection of other people’s opinions than it is of ourselves. We’re also afraid of failure because we extract so much meaning from it. We take a small moment and make it a big moment. We take a small happenstance and turn it into multiple happenstances. This is what makes failure so scary. One failed phone call is projected into thousands of people telling us no. One failed pitch sends us into thinking that every pitch will end the same way. We usually are too inexperienced to isolate the moments. Let this be a reminder not to live in the micro pretending it’s the macro.
What are the downsides of being afraid of failure? How can it limit people?
When you’re afraid of failure, the opportunities that you have in your life are limited.
Failure, and your relationship with it, are a critical piece of your ambition becoming realized. The fear of failure will prevent you from taking risk, and risk is everywhere. Risk is in a new job, risk is in a new relationship, risk is in a new skill, risk is in speaking in public, risk is in asserting your opinion and risk, possibly most importantly, is in growth. If we are unable to make a mistake, we won’t take action and it is a severe limitation to be afraid of failing for the opinions of others or the self degrading talk we use internally.
In contrast, can you help articulate a few ways how becoming free from the free of failure can help improve our lives?
In contrast, a healthy relationship with failure and freedom from the fear of failure allows us to dramatically change our circumstances, our potential and our opportunity. A healthy relationship with failure allows us to be a beginner, which then powers new skills, new jobs, new businesses, new ideas and new relationships. When we begin down the pathway of growth, which often originates with frustration, we usually come face to face with a very stark reality. This reality is we are not who we want to be, nor are we getting the results that we want.
Failure, in many capacities, is the doorway to the results in the person we want to become. When we are healthy in our relationship with failure, we can very quickly identify which skills, which opportunities we want to pursue, what growth is needed and go after it. We understand the initial steps will be clumsy and will come with plenty of bumps and bruises. We no longer hesitate; we understand that it’s a part of the process and we commit to that fully, meaning that we are able to get the results that we desire much more reliably.
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?
There are two stories of failure that stand out to me most.
In high school, I was an ambitious soccer player. I was training regularly and had a dream of playing in college and later in the professional leagues here in the United States. I was incredibly committed and knew that the road ahead of me was a really long one, without any kind of club team experience or high level coaching available to me. Right before my senior year started, I suffered an injury to my right leg, and several doctors told me that I would never play the sport again. In that moment, and the months following, the walls felt like they were closing in on me. My dream was over, and I remember walking into my coach’s office with my bag of gear, ready to surrender, and let go of soccer altogether.
He looked at me and said, as the captain of this team, I can’t let you quit and I need you here to lead the other guys. They need you to be here. This request changed my perspective of what I had failed to see before. I thought the failure was my injury and my career being over. What he saw was a person that still had a purpose. It took me several months, but I got back on the field, began training, and within a few months of the season ending, could run, could walk, and amazingly, could strike a ball again.This left me with about six months to begin training to walk on to the college team, an unheard of act of resilience and grit. Twelve months later, I was a part of the Division One program at the university as a walk on and as the newest member of the squad.
That wasn’t the end of the failure, though. Over the course of the remainder of my degree, I missed plenty of shots in front of the goal, in front of my peers, in front of other students and fans. I fell, I blundered, and overall left college with a disappointing career on the soccer field. To this day, I look back and understand that my mentality was the failure. I didn’t have a strong mindset, and when dealing with adversity as an athlete, I wasn’t able to bring consistent, regular results to the field. My coach didn’t trust me because I didn’t trust me.
I learned a really important lesson about failure.
Now, as an entrepreneur, I spend an incredible amount of time (and a high five-figures of capital too) on my mindset so I can be consistent and get the results I desire repetitively. It’s the hardest thing in the world to do — to be consistent with performance.
This lesson comes directly from all of the failures across my athletic career. I learned that doctors didn’t always know what they were talking about, not because they didn’t know the body, they just didn’t know my resolve. I learned to trust myself through the process. I also learned that if I don’t work on my mindset, my body can only create so much output. This changed my whole career as an entrepreneur. If I wanted to be consistent, I had to listen to myself, build a strong mindset, and focus on the goal — not on what everyone else was saying. Mindset is everything.
A few years later, another test of mindset came my way. I was in San Francisco, touring the Pacific Northwest for opportunities to raise capital for the business. I had spent a lot of time practicing my pitch and learning the audience. I traveled for three days, back to back to back. It was the third day of my tour to raise capital and pitch in front of 75 investors. I walked into a large room in a tall glass building where you could see out over the water. The sun was shining, and everyone in the room had a confidence about them I will never forget. Pitches lasted ten minutes; six to share and four to answer questions.
I was the third presenter, and as I walked up to the podium wearing a black T shirt, black jeans and a purple blazer, I was nervous. I felt my hands shaking and my voice cracked. I was nervous because this mattered. I was nervous for the right reasons. I knew that I could fail. It felt like the right thing to do, to be pitching the business and sharing the mission. After six minutes of delivering a very good speech, I transitioned into questions. I frantically tried to respond with credibility, but largely — disappointed investors in the room with my answers. I stumbled through it and knew I missed my chance. I felt disappointed in myself as I walked out of the room.
To make matters worse, as I left the room, I heard snickers and laughter, and people made fun of the blazer that I was wearing. I couldn’t help but further chastise myself. I failed to sell the business well, and I made a fool of myself. My self-talk went wild — rampantly pummeling my confidence.
I wore the blazer to stand out, and here I was being made fun of for it. I’ve never felt so much like a failure. I was being laughed out of a room, and having worked as hard as I did to get in the room, and having paid almost $9,000 to be on this tour to present, I failed. I was disappointed in my language, my presentation and in my reception and it took me a week to really deal with the emotions that came with it. I had completely failed and I came back to the East Coast after this tour with no investors and very little confidence in myself.
This story is a reminder to me when I have a really good month, how hard it was and how much I put myself out there. I totally failed in that moment, and in that moment, I became a little better at failing becauseI kept going. I knew that it was part of the process, even if I didn’t like it. In hindsight, it’s easy to say that in the moment I wept and had a couple extra drinks to deal with what I was struggling with because I knew I had failed. I only failed in the micro and my language initially was very aggressive.
Was I a valuable person? Was I a good person? Was I capable? Could I even do this? Am I an entrepreneur or am I a fraud? This language I knew was temporary and that’s a reminder to everyone reading this. That language does not help you, and it needs to be temporary. Remind yourself of that when it’s time.
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 this moment, I struggled. I lost faith in myself, and lost faith in what I was building. I even lost sight of who I was becoming and how these hard moments were all a part of a bigger picture.
I remember counting myself out.
I knew I was in a funk, so I set out to snap it very intentionally. I started by making a list of everything I had wanted to learn when I was a kid. Over the next two years, I signed up once per quarter to learn one of those things — whether it was a class, a coach, or by building a new habit.
I studied piano with a coach, I learned Portuguese with 3 Duolingo lessons a day, I studied jujitsu, signed up for yoga, learning to dance and a few other meaningful pursuits. It rekindled a powerful belief. I was allowed to fail, expected to fail even, in these spaces. While it was frustrating, in a big way, I was also rebuilding a new pattern. I could fail in these small moments and knew that was the point. It powered the rest of my life. I took more risk, because I had totally replaced my belief of failure.
We raised capital for the business with investors who could see the vision, understood that I was the leader they were betting on, and found new clients through the covid series of adaptations and pivots.
I did learn to hone my mindset. I started coaching others, and after 10 years of coaching athletes, transitioned into coaching entrepreneurs and artists, because what I went through alone was not something I wanted someone else to experience alone. I was not good at coaching mindset to start — I failed regularly to help people over their blocks. Over time, I honed the practice and now am confident I can 3x someone’s business and income, deepen their self-awareness, and can catapult their leadership to another level. I learned to listen, hold space, and step into challenges with my palms up — offering and opening.
And all of it because failure changed for me.
I’d advise everyone here to look at the way they describe failure. If it’s a negative part of your life, you’ll never make it. Reframe it. Here’s how:
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.
- Change who you hang with. Email, DM, tweet to people that are brave. Join a community with other brave people — entrepreneurs, artists, creatives. Bravery is contagious. So go catch the bug.
- Read more. When you read stories of success, you’ll notice a distinct pattern. Failure is the ONE common denominator. Read Originals (Grant), Willpower Doesn’t Work (Hardy), Mindset (Dweck), The Obstacle is the Way (Holiday), and Failing Forward (Maxwell). Read Let Her Play too — cause I wrote it and most of that story is about failure and most of my writing experience was a failure (ask me about it!). Read a book a month and you’ll change your life.
- Write out your fears. Worst case — as dramatically as possible — belongs on a sheet of paper. Take ten minutes and dream up the worst case scenario. It will take the power away from it and give you a chance to ask the question, “Can I handle this?” The reality is: you can. And, you’ll likely find that the worst case scenario is crazy unlikely.
- Sign up for a class. Not exactly what you expected? Learning to fail is the same as learning to be a beginner. Take a class around something you always wanted to learn. You’ll find that you fail a LOT as a beginner, and it will help with your relationship with failure tremendously. You’re always a beginner if you let yourself be. The mentors I look up to the most have taught me this — and I would encourage you to adopt this mentality too.
- Learn to track progress over outcomes. I have been teaching this for years, and it’s still one of the hardest things for me to do. I’ve committed to tracking the inputs, the leads, that get me the outputs, the lags, I want. Doing this lets me focus on the process, measure the steps, and focus less on the destination. When you commit to the small steps, you’ll grow so flipping fast! Track the number of times you go to the gym, the number of posts online, the number of emails you send about your product, or the number of books you read. Focus on the steps!
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?
Aristotle didn’t know the internet, but he sure did get life. I take this to say, “Success is a single strategy.” He’s right that every success happens the same way. You will fail. Accept that. Move on. While we can all fail in so many ways, take every single one of my pursuits above; we can only succeed by marching through all the varied experiences, bruises, bumps and blemishes on the canvas of our life. Fail forward. Fail daringly.
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. 🙂
If there’s a movement to start, it would be to get more people adventuring.
Right out of college, or even high school, you fall into patterns that are largely about fitting into narratives. And when you break those rules, go see other countries and cultures, travel out of your hometown, learn to invest in education (not the same as school), your whole world changes. It’s changed my life, and I think everyone could benefit from spending time away from what they know.
So getting more people to be adventurous, fail, and power through the awkward phases where you might think you know the answers, but cannot possibly even understand the question — that to me is a worthwhile movement.
Often money is the issue — so I’d want some creative entrepreneurs to help tackle the funding so that more people can say yes. When you get perspective, you can emotionally connect, listen and learn more.
And I would love to mentor someone ready to make that movement happen.
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 🙂
There are three people that I’ve always wanted to have breakfast or lunch with.
The first is Frank Ocean. I’d like to meet the man behind the musician — his courage and clarity has always been admired in the way that he crafts his words, shares his personal journey, and creates his own independence. I’ve known him since his Lonney Breaux collection — before the before — and think that series of creations was the most pragmatic and connective R&B I’ve listened to.
The second is Khaby Lame. I appreciate his sarcasm, approach to social media, and how all of this came from change in his life that was out of his control. Plus — two football (soccer) fans in the same space is always lots of fun. As a social media influencer, it would be an absolute joy to meet him for who he is, and see how he thinks outside of the way many of us across the globe get to see him.
The third is Kevin Feige. I’m a huge Marvel nerd, ever since 1986, and have loved the way his long play of storytelling has come together. I can enjoy each particular element that he’s overseen — but more importantly respect his ability to see and play long with a vision. I’d ask him all about his process for finding the right directors, leading without asserting, and how he has fun and escapes now that he’s gotten so successful. Preferably, we’d set up a meeting through coded messages.
How can our readers further follow your work online?
Failure starts when you let fear win. If my stories help you with your journey, to be more confident, more intentional and more resilient, consider reaching out. Achieving big goals alone is not a path I would recommend. Find a leader, mentor, coach, or group of other entrepreneurs you can lean into. It’s worth every minute and penny — and you get 10x out what you put in.
If you feel counted out, and aren’t sure how to get what you want out of life, you can visit aaronvelky.com and set up a discovery call about my Get Out of Your Own Way coaching, or any of the retreats and live masterminds that host.
If you’re a business owner, ready to invest in your team and offer a life-changing benefit to the people that build your business success, you can check out Money Club and our employee wellness programs here.
This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.