The Courage to Face Fear
“Show me a guy who's afraid to look bad, and I'll show you a guy you can beat every time.”
-Lou Brock
I'm embarrassed that I've been 'that person' who has been afraid to look bad ever since I entered the working world.
While entrepreneurs and founders who I admire have started, failed, tried again, and succeeded, I've chipped away. I've done well, but I know that for the past 15 years I've had more to give. Fear of looking foolish and failure has loomed. A lack of courage has held me back.
I went walking with a friend last week, and through our conversation unpacked that there have been three times in my life when I've found the courage to set that fear aside. And guess what? Each time I survived.
No. I more than survived. Each time I found that fear, a door opened to bigger version of my life than what I imagined possible before.
The first time was in 2005 when I chose to go to a university 2 hours from home after a comfortable up-bringing in a small town. I didn't know anyone at the school or in the city—no friends and not even my girlfriend went there but I chose to go anyway.
The Other Side: I shook off other people's ideas of who I was and became my own person. I met people who worked in fast growing and exciting companies which eventually led to a connection at the company where I launched my career—Desire2Learn (thanks Gary!).
The second time was when I started selling cheese at a farmer's market in 2012. Yes, cheese. Gourmet cheese, to be more precise. For context, I did this when I was building a high-flying sales career in the tech sector while also battling crippling anxiety (more on this in a future blog). The appearance of taking a part-time job on the weekend could not have been further from the person I thought I was supposed to be. But I did it anyway.
The Other Side: One day, over the counter, I met the CEO of Axonify (a fellow cheese lover). That connection led me to join the company, where I grew into an executive and experienced the most fulfilling years of my tech career. Even better, my time in that environment helped me build the confidence to tackle hard things and reinforced that, with focused energy, I could make anything work.
The third time was in 2020, navigating my first wife Allison's short battle with brain cancer. Beyond the heartbreaking sadness and trauma of losing my partner of 15 years, I had to navigate countless impossible decisions to keep my life and our three young children's lives from veering WAY off course, or derailing entirely. I sold my house and moved my three kids into a small condo. I ignored strong suggestions from in-laws and some 'friends' and did what I felt and knew in my heart was right.
I got therapy. I got a Costco membership. I steered the ship.
The Other Side: I found out that my intuition is right and that I need to trust it more. I have kids who see their dad as someone who truly has THEIR backs, no matter what. I also found and built a life with an incredible partner, where we embrace and respect each other's entire pasts and strive to create a future that is uniquely our own.
It's easy to look back on how courageous I've been throughout my life, but it isn't that simple.
While I recognize how formative those hard times were, after each period of courage, I slipped back into routines where change felt scary and intimidating. Each time, fear crept in again. Each time, I let left my courage on the sidelines. I wasn’t fully all-in, like I had been during those three pivotal moments.
What I’ve learned is that every time I’ve confronted my fears and leaned into courage, those decisions have paid off in ways I never could have imagined. Over time, it’s become clear that the founders and entrepreneurs I admire aren’t any less afraid than I am—or than you are. They're just more willing to confront that fear than I have been.
So...what's the point here, Boyd?
Maybe you've felt this surge of courage before, have faced your fear, and can relate to the experiences that I've shared. If that's you, you've felt how powerful you can be...I bet you want to feel that again. As Ryan Holiday says in one of my favourite books, Courage is Calling,
"Once you dine on courage—and freedom—and have stood up for yourself, the taste of fear is much harder to tolerate".
Amen to that.
But maybe in reading this you struggle to think of when you've faced down fear and have acted with courage. Maybe it has been a long time and you've forgotten. Fear has held you back and continues to hold you now. If that's you then know you're not alone.
Perhaps it’s time to find a place in your life where fear is holding you back, and it’s time to confront it. It isn't easy and it isn't necessarily natural, but it IS possible. For me, it has been 5 years, and as you read this, I'm leaning in myself to find that courage, and face fear again.
Maybe 2025 is the time to start fresh.
You can do it too.