Entrepreneurs are psychologically unique. In a world where up to 90% of startups fail, the most enduring visionaries will push through, energized by the idea of experiencing freedom and success alongside the 10% who beat the odds. They’re resilient. They’re adaptable. They’re extreme risk-takers. The most successful entrepreneurs tend to run toward uncertainty and threat instead of running away. Why? The reason, at least according to psychologists, is that successful entrepreneurs tend to have one mindset about fear that the rest of us simply don’t share, at least not to the same extent: If harnessed in the right ways, understanding our fears and anxieties can lead us to breakthrough self-discoveries, innovation, and creativity. For exceptional entrepreneurs, noticing fear is a competitive advantage; it’s an emotion that we dive into with curiosity, passion, and a hunger for exponential growth.
The good news is, these critical mindsets around fear can be learned.
Serial entrepreneur and executive coach Justin Milano has experienced success and failure — but it’s the failure that changed his life. “I was building a company to solve one of the greatest environmental challenges we face today: food waste,” he says. Then, his greatest fear became a reality. The company failed, and in the soul-searching that followed, he saw his motivations in a truer light. “I realized there was an unconscious part of me looking to do something grandiose because I didn't fully value and love myself. I was trying to prove my self worth.” He wasn’t afraid of his business failing, he was afraid of feeling like a failure. There’s a big difference between the two, but they’re often strongly related.
At least, that’s what Milano learned after a satisfying bit of symmetry. What seemed like his greatest failure led to his greatest success: co-founding Good Startups, an executive coaching company for startups that focuses on cutting-edge leadership psychology, neuroscience, and emotional intelligence. What he had started to understand intuitively, his eventual cofounder, Dr. Daniel Cordaro, Director of Wellbeing at the Yale Center for Emotional Intelligence, had already been studying across cultures for nearly a decade. In 2015, they teamed up to use their mix of scientific expertise and on-the-ground startup experience to help founders and their teams identify and manage their fears and anxieties, and more importantly, understand the deeper psychology blocking them from self mastery and sustainable high performance.
There are a lot of entrepreneurs out there unconsciously trying to prove their self-worth through their companies.
In this exclusive interview, Milano and Cordaro break down a 4-step process to transforming your fear and anxiety into a competitive advantage. You will learn:
The important difference between fear and anxiety
How to uncover the sources of your anxiety
The neuroscience behind reliably transforming your fear into creative power
Effective tools for navigating fear in the moment
When you practice and master these tools, the result is better decision-making, expanded performance and energy, more inspirational leadership, and a doorway to self-mastery. It’s scientifically evidenced.
“The best entrepreneurs of our time experience fear,” says Milano. “It's their relationship with fear that differentiates them.”
First things first: to transform your relationship to fear and anxiety, you need to define what you’re dealing with. “Fear is a raw emotion that happens instantly to ensure our survival and safety, like getting out of the way of a moving car,” says Cordaro. “With anxiety, we are anticipating future threats based on our imagination, or trying to avoid painful experiences from the past, again based on mental projections. Fear typically lasts seconds, and anxiety is often chronic and can last for days or even months.”
Milano offered one of his favorite quotes from Mark Twain to demonstrate anxiety in action:
I’m an old man and have known a great many troubles, but most of them never happened.
As entrepreneurs, every day we are faced with uncertainty and risk, and when things are unknown, it’s natural to have anxiety. Some common anxiety thoughts include: “What happens if we run out of money?” “What if this product launch fails, will I get fired by the board?” In Milano’s experience, even his clients that are thriving at the highest level experience chronic anxiety thoughts like “Where is the next big win going to come from,” or “How do I continue justifying this massive valuation?”
The key point is that 99% of the time when people say they are experiencing fear, they are actually experiencing anxiety around events that may never happen. When this anxiety is playing like a broken record in our subconscious mind throughout the day, we are hanging out in our limbic brain, specifically the amygdala, which is responsible for our reactions to threat. When we are seeing the world through the lens of threat, we experience tunnel vision and limited possibilities.
When we only see limited possibilities, “this dramatically impairs our decision-making ability, which as an entrepreneur, is one of our most important leadership assets,” said Cordaro. “Whether we like to admit it or not, every decision we make goes through an emotion filter first, and fear is one of the most powerful emotion filters. Think of it this way: Are your decisions different from a place of joy and happiness versus sadness and despair? Most often yes, so it’s important to recognize that emotional intelligence is an essential skill set for entrepreneurial leaders.”
Once you recognize that what you are experiencing is most likely anxiety, the question becomes how do you release the grip of anxiety so you can operate with expanded awareness and creativity?
Milano offers that the first step toward uncovering the source of your anxiety is to pay attention to your attachments to certain outcomes and identities. “Anxiety is the fear of more fear. It’s fueled by attachment. It is rooted in the need to control the things around us to keep our reality known and safe.” Milano suggests that founders suffering from anxiety walk themselves through these questions:
What expectation, idea, or outcome are you attached to? A specific investor? A specific client? A certain type of product working? Being cash positive in six months?
What identity is driving the attachment? Have you created an image of yourself as the next game-changing entrepreneur to investors, the press, and your team?
Consider this example: A founder tells her investors that the company will be cash positive in six months. Then inevitable obstacles set in, and it becomes clear that goal is unattainable. It would be easy to descend into a morass of anxiety and what-ifs: Will the board let me go? Will the team start questioning my leadership?
A leader who has practiced uncovering their attachments, on the other hand, can see things in a more productive way. “The healthy thing to do is acknowledge the attachment to a certain outcome, soften your grip on it, and use your creativity to design a new path based on reality,” says Milano. “You get to what's really true and face what's actually happening. Then you can say to your team, from a place of integrity and clear-headedness, ‘Looks like it won’t be six months. Looks more like 12 months. Now that we know that, here’s what we’re doing about it.’”
Attachment to identities can be harder to relinquish, but it’s critical to consider. Many founders, whether through their own strategy or the attention of the press, assume the mantle of “the next big thing.” Suddenly, they’re not just building a product and running a company, they’re living up to very public expectations. “Now if your product launch isn't working very well, it starts to threaten that identity. Not only is your product broken, but you’re a fraud, a common human fear.
That’s one of entrepreneurs’ biggest fears: I went out there, I sold all these friends and investors on the next big thing, and it didn’t work. I’m a fraud.
“What this speaks to is the power of humility,” says Milano. The most inspirational leaders know that it’s not about them. They acknowledge challenges and respect the competition, and they are prepared for ups and downs. And importantly, they communicate this to their team and investors. “They say, ‘This isn't about me. This is about all of us collectively working together to achieve this beautiful mission. We’re going to face some bumps along the way, and what’s important is we navigate them together, as a team and a board.’
Cordaro adds, “It’s important to know that it’s ok to have certain identities, it’s totally natural and part of being human. Just know that all these identities come with hidden expectations that can add up quickly. It’s much more pleasant to make decisions as a leader from a place of what’s best for the company and society, as opposed to maintaining a personal identity.”
Once Milano and Cordaro support their clients in identifying their unconscious attachments and identities, they go a few layers deeper into the three main sources of fear, which they call “the three cultures of fear.”
The Culture of Scarcity: The belief system that there’s not enough resources (e.g. time, money, etc.).
The Culture of Aversion: The belief system that says “I’m having the wrong experience,” or “I shouldn’t be feeling this emotion.” (e.g. shame, guilt, etc.)
The Culture of Unworthiness: The belief system that “I’m not enough, just the way I am.”
The Culture of Scarcity is familiar to most entrepreneurs who are often scraping by financially or working 16 hours per day to achieve the next big thing. In relation to time scarcity, Cordaro says, “What’s interesting is that Silicon Valley is one of the most abundant places on the planet in regards to financial resources, yet when it comes to time, it is one of the most impoverished places on the planet.”
Milano and Cordaro offer that the Culture of Scarcity is a myth, deeply rooted in unconscious societal programming that can be transformed with awareness and new habits. This practice is important according to Cordaro because “when scarcity dominates, selfishness, hypercompetition, and creative stagnancy do too. When abundance dominates, generosity, cooperation, and rapid transformation are there too.”
When working with clients, Milano and Cordaro take people deep into their individual scarcity programming to write new, more empowering stories for their lives.
Reject the Culture of Aversion
Cordaro notes that the goal should never be to eliminate fear, but rather to acknowledge and accept it. He sees the same pattern unfold with all the entrepreneurs he coaches: First comes a great idea, and the drive to make it a reality. “It's very exciting and really fun. It's very desire and creativity-driven.” Then they start actually building a company, and things get in the way — and anxiety sets in. “Now there are things that are getting in the way of my vision; there are things that are coming up against these visions I have for how I want the world to be. Fear is a natural part of this process.”
Adopt this mindset, and fear stops looking like a threat; it’s merely part of the package.
In Milano and Cordaro’s experience, the following shift in mindset can have a profound influence on founders. When a product fails, when the new app gets two stars in the App Store, when funding isn’t coming through, successful founders don’t get caught up thinking, “This is the wrong experience. This isn’t the way it’s supposed to be.” Instead, they accept those obstacles as part of their experience — the only one they can and should be having. They use the experience as a growth opportunity to become better, stronger, and more inspirational leaders.
“When your product isn’t working, you need that feedback in order to actually create a product that people do want,” says Milano.
“Every time you're experiencing fear and anxiety, there's information and data that wants to be uncovered.”
Anxiety lets you know when you need to kick into gear. The problem, Milano notes, is when you simply stew in anxiety all day, every day. These emotions will not serve you well if they become chronic. And where there is chronic anxiety, there is almost always avoidance or aversion.
That app with the two-star rating? Customers don’t like it — it needs to change. “The person with a healthy relationship with fear can say, ‘This is what's happening. I'm going to accept that, embrace that, and receive the information. Now what can I do creatively to solve this?’” says Milano. Leaders with an unhealthy relationship to fear, on the other hand, often lose the opportunity to course-correct. Stuck on how things “should” go, they miss the valuable signal that it’s time to pivot.
Moreover, avoiding feelings of fear only prolongs them. “All emotions are here to provide us with information about the world around us. That's why we've evolved to feel them. Emotions are data; they’ve helped us survive for tens of thousands of generations. If we're not listening to an emotion, if we're not receiving that data fully, it's going to keep coming,” says Cordaro. When you allow yourself to fully feel and accept an emotion, it dissipates very quickly, often in as little as 30 to 90 seconds.
Seen that way, accepting fear isn’t just a nice idea — it’s a serious competitive advantage. That broken product or low-rated app isn’t going to fix itself. But you can effectively halve all of your problems by listening to your fear and letting it go. Cordaro asks: “As an entrepreneur, do you want to double every single problem that you have, or do you just want to deal with the things that actually need to be worked on?”
Be an example for your team: Entrepreneurship is a roller coaster. Let’s accept that and fix what we can. There will be no freaking out.
Develop an Unshakeable Sense of Self Worth
The final culture of fear is the Culture of Unworthiness. “This one goes beyond entrepreneurship, it is an epidemic of the human species,” says Milano. The belief system is that “I’m not enough just the way I am, I need to achieve something extraordinary to generate fulfillment.” This is the culture that had hit Milano the hardest so many years ago.
Often when Milano asks his clients if they are looking to prove something to themselves, their family, or society by building their company, the answer is a quick, reactive ‘no.’ “Most people are not consciously aware of how powerful the Culture of Unworthiness is until they make a major mistake or ‘fail.’ I certainly wasn’t aware of it.”
Milano offers that one of the quickest ways to determine if you have some work to do around your own sense of worthiness is to ask yourself the question “If my company completely fails and I fall flat on my face, will I still love and accept myself unconditionally.” When Cordaro and Milano ask this question in their virtual group coaching sessions you can often see people stop breathing even through the video conferencing technology. "It’s a powerful and shaking experience," Milano says.
We live in an entrepreneurial culture that “glorifies entrepreneurs as modern gods,” says Cordaro. “We worship those who achieve impossible tasks and create things that few have only dreamed of, kind of like what Elon Musk is doing with electric vehicles and clean energy. These are extraordinary people, for sure, but when we pin all of our self-worth on becoming exactly like them, however, we’re asking for trouble.”
“When we are faced with the loss of our dreams and ideals, a natural response is a feeling of low self worth,” says Milano. For him, this was the greatest gift of his food waste startup failure.
“Through that experience I was forced to marinate in my feelings of failure and low self worth, and learn the vitally important lesson that no success and achievement will ever fill the gap of self worth within," he says. "No expensive houses, shiny cars, or flashy press headlines will ever provide true fulfillment. I am now experiencing what it feels like to be of service and create for the sheer joy of it, without the requirement for my company to validate my self worth. In my opinion, this is one of the most important skill sets an entrepreneur can cultivate.”
Through that experience, Milano now leads his clients into their unique personal experiences that are the sources of their Culture of Unworthiness. “Maybe your parents didn’t tell you that you were good enough, and you’re trying to prove that you’re worthy,” he says. Other times, the sabotaging hang-ups are professional in nature — the traumatic experience of having been fired as CEO is a prime example, and now you want to prove you can be CEO.”
In Cordaro’s experience as a psychologist, learning to conduct this sort of self-enquiry can be transformative for founders. “One of the most powerful things that I've seen people do is simply develop a curiosity about who they are and why they behave the way that they do,” he says. “It’s that kind of attitude that allows people to be the most impactful they can possibly be in society.”
Once you do the courageous work to defuse your unique sources of anxiety, you are then free to transform your anxiety into something far more useful, like creativity and innovation. Cordaro shows us how to do this through cutting-edge neuroscience.
“If you remember one thing from this article, remember this: Every fear is mirrored by a desire,” says Cordaro. “They are two sides of the same coin.”
Terrified of public speaking? That’s because you desire to share a compelling, well-articulated message. Worried you won’t get funding? That’s your strong desire to raise money and build a successful business. Afraid of failure? What’s underneath that is your desire to have a positive impact on humanity.
This isn’t just a hunch; it’s actually deeply rooted in neuroscience. Most of us are at least vaguely aware of the amygdala, that part of the brain, right behind the temple, that perceives threats — the “fight or flight” portion of the brain. When the amygdala perceives a threat, one of its jobs is to stop sending information to the cortex, where we engage in higher level thinking and rational decision-making.
What most people don’t know is that right next door to the amygdala is the nucleus accumbens, which is responsible for desire and all things that make us crave feeling good. “Scientists have tried to find where the nucleus accumbens stops and the amygdala begins, and they can't find it. These portions of the brain are intrinsically involved with each other. When the amygdala fires, the nucleus accumbens is firing as well,” says Cordaro.
Entrepreneurs are typically driven by massive desires — to solve big problems and change the world. It’s natural, then, that they experience more fear than the average person, too. “But when you're aware of what's happening in your brain, you can reliably shift from your fear-based limbic brain, which is where the amygdala is, into the neocortex, which manages higher-level functions like judgment, decision-making, and creativity.”
A healthy relationship with fear is the doorway to the part of your brain that optimizes judgment, decision-making, and creativity.
Milano and Cordaro developed a five-question exercise to help their clients understand what their anxiety is telling them in the moment, and shift toward consciously pursuing their creative desires. Why is this process important? Very simply, it gets your brain unstuck from fear-based, animalistic reactions and allows you to rapidly shift into creative problem-solving mode.
What's the fear or anxiety?
Where do you feel it in your body?
What is the desire being mirrored? What is the desire underneath that anxiety?
Once you discover the desire, do you choose to take action on it?
If so, what are the creative action steps?
Let’s put this system to the test by bringing in a real life example of the number one most feared concept across all of humanity (it even beats death) — public speaking. In a few months, you’re going to give a high-profile talk regarding your company’s vision on stage in front of 2,500 thought leaders and influencers. Anyone would feel some level of anxiety, especially for those of us who aren’t public figures for a living.
What’s the fear or anxiety? This should be an easy one, but this is where awareness begins. Failure. Bombing the talk. Being the subject of ridicule and scorn, or even worse, silence, from this massive audience. Missing an extraordinary opportunity to inspire major influencers in your space.
Where do you feel it in your body? Milano and Cordaro recommend taking time to get out of our heads and into our bodies. “When it comes to anxiety, living in your mind only leads to rumination and getting even more stuck in our fear stories,” says Milano. Take a moment to notice where the fear and anxiety sensations live in your feet, legs, torso, arms, and face. Cordaro says that for him, anxiety feels like “my heart is beating faster, palms are sweating, and I have a slight tightness in my chest and throat. When I feel that, I know that anxiety data is incoming.” Milano most often notices fear and anxiety in his belly, and “by simply locating the sensation of anxiety in my body, and taking a deep breath into it, I move into a place of presence.”
What is the desire being mirrored? “This is your big opportunity to flip the coin to the other side,” says Cordaro. It turns out that your anxiety stories aren’t rooted in what can go wrong, but rather what you want to go right. For the talk, you want to be a source of inspiration and an amazing representative for your company. You want to deliver a clear message and be heard. You want to activate like-minded people and invite them to join your mission. “Do you feel the shift in how you feel when you move out of fear and into your desires?” asks Milano. “It’s a game changer, because you’ve just opened up your brain to higher levels of thinking.”
Make the choice. Fear feels like we’re being backed into a corner, like we can’t escape, but it turns out that we’re simply denying ourselves a critical freedom: the choice to tackle this challenge and act on our desire. Milano and Cordaro teach that by asking ourselves “Do I choose to get creative and make this desire a reality?”, we open up the possibility of releasing our fears completely. “Fear shows up when we experience the illusion of being out of control, and desire is exactly the opposite - it’s the illusion of being in control,” says Cordaro. “Making this choice calms the mind and allows us to move forward with clarity and determination. In the end, we want to find the balance between desire and fear, and release our attachment to both. It’s walking the edge of the coin, instead of getting stuck on one side.”
Get creative. “Now that you’ve started to release the grip of fear and anxiety,” says Milano, “it’s time to use the power of your cortex to start coming up with innovative solutions to act on what you really want.” You want to be an inspiration and a great representative of your company? Learn the dynamics of great storytelling by watching TED talks, or hire a writer to help you craft the perfect message. You want to deliver a clear message and be heard? Take some public speaking lessons and practice that talk in front of your team (and strangers) as a top priority. You want to activate like-minded people and invite them to join your mission? Have your team work on getting intel on all of the major attendees, and create a networking strategy that sets you up for success before you even get on stage. “The list goes on, and that’s the point. You’ve opened yourself up to possibilities, and freed yourself from the rigidity of fight-or-flight mode.”
So you’ve gone through the process of understanding fear, uprooted your cultures of fear, and transformed your fears into desires. But how do we deal with in-the-moment spontaneous feelings of fear that may arise, let’s say, in the middle of your talk when someone asks a piercing and unexpected question? In Milano’s experience, there are several common physical experiences that are dead giveaways you’re having a fear reaction: sensations in the belly, sweaty palms, increased heart rate, rapid breathing, and even accelerated speech.
Become adept at recognizing these physical manifestations, and you can also develop the skills to overcome fear as it strikes. Whether you’re standing at a podium or opening an investor email that’s unlikely to contain good news, a few simple actions can jog you out of paralysis and into presence. Milano and Cordaro offer three examples here.
Breathe: You’re about to get on stage for your talk, and you feel like you might hyperventilate and forget everything you wanted to say. It’s time to breathe. Get comfortable and close your eyes. Feel yourself breathe cool air in through your nose and exhale warm air through your mouth. Repeat this for a few breaths, then open your eyes and notice the space around you.
Move: You make it on stage and are about to begin, when you feel a crippling paralysis. Your knees are frozen, and you have that deer-in-the-headlights look on your face. It’s time to move. When your body freezes in fear, by gently wiggling, shaking, or bouncing you can stop that fear in its tracks. If you are feeling the adrenaline rush of a “fight or flight” response, plant your feet firmly on the ground to experience that sensation of rootedness, like a redwood tree. These simple body movements are fear “pattern interrupters” developed by Milano’s friend Dr. Kathlyn Hendricks, who is an expert on Body Intelligence.
Match: Match the experience, that is. “There is a great quote by Fritz Perls, who said, ‘Fear is excitement without the breath.’ When you are feeling fear, you are often excited,” says Milano. So lean into that excitement and match it with your words. When you’re speaking, for example, start by telling your audience, “I’m excited to be here.”
Research shows that the second you match your experience by saying ‘I'm excited,’ your nervous system relaxes.
Just as founders need to recognize fear in order to move past it, they also need to recognize creative energy so they can welcome it with open arms. Here, too, the body offers the most reliable indicators: “You feel spacious, balanced breathing. Your gut relaxes, and your adrenals and heart chill out. You begin having fun, seeing more possibilities, generating a sense of trust, and the world looks friendly. You make clear decisions from a place of balance,” says Milano.
If you experience anxiety daily — if you move through every day thinking, “I’m overwhelmed,” for example — odds are good that you’re not letting yourself feel anxiety fully and understand why it’s there. That’s when taking the time to get present is the most powerful tool in a founder’s arsenal. Stop. Walk through the “fear melters.” Establish a meditation practice. “Mindfulness is all about being aware of what's going on so you're not at the mercy of it.”
The goal of meditation is not, as many people assume, to be more calm and peaceful (although those are certainly positive side effects that you can expect from a regular practice); it’s to see one’s experiences through a different lens.
One of the main reasons we engage in mindfulness practices is to sharpen our attention muscle so that when these feelings of fear and anxiety come on, we can catch them at a much earlier stage and simply let them go.
Then, in turn, you can choose how you will respond, prioritizing the actions that will most benefit your unique offering to the world.
Sure, fear and anxiety will eventually make themselves known without help from mindfulness, but left unchecked, they’ll do it by landing founders in a state of total burnout. “At the end of the day, when it's four in the morning and you haven't gone to the bathroom or eaten all day, that's when you’ll notice that you need to do something to improve your well-being,” says Cordaro. That kind of passive anxiety management isn’t just personally taxing; it drains your company’s most important resources, too. “It's so much easier to live each day kind of like a judo master, working through the energy of your emotions, than to have to take a month off to recuperate, come back full steam, and then just do it all over again. Most of us can’t afford to do that, and we shouldn’t have to.”
The reality of emotional intelligence, is that it needs to be developed. As with any new skill, it takes practice; new muscles must be flexed. But as you do that, you will begin to find your relationship to your work, and your colleagues, meaningfully changed. Herein lies the competitive advantage of fear, understanding it, and learning how to transform its energy into massive creative potential.
“You can change your neuroplasticity. You can go from being a completely hyper, worried, caffeinated, crazy entrepreneur —because I was—and come to a place with more balance,” says Milano. “As you start to apply these practices and tools, and you rewire your brain, you’ll start to have a different experience in this world. One of the biggest payoffs to doing that is that the world no longer looks unfriendly. It has just as much potential as you do.”