A reflective piece by a licensed therapist on how fear of failure limits growth — and how Stoic philosophy can help you face fear, build courage, and live without regret.
Updated on
October 8, 2025
I once knew a man who told me, as he approached the end of his life, that his dream had always been to write a novel. He wasn't fantasizing or suggesting that he would have written a New York Times best selling book, he was just wishing he would have written one during his lifetime.
Now that his life was coming to an end it was one of his deepest regrets he held. I asked him why he never went ahead with writing the novel and wondered aloud if it was because of time or money or circumstance. I remember him looking over to me and saying that none of these excuses were the reason he failed to write a novel. The real reason, he told me, was he feared creating something that could fail.
I was surprised, because this man, who I had only ever known to be a confident, bold individual, let fear stop him. I never would have thought he'd ever let anything get in his way, nonetheless fear of failure. It's a moment I'll never forget and I think of it often. I do my best to use it as a reminder to push through my own fears that trick me into inaction.
Now before we get started, let's identify how fear of failure lies to us. Fear can show up as wanting to be overly prepared, convincing us we won't fail if we practice just one more time. Fear delays action by persuading us that it just isn't the right time to try a new project. Fear influences our choices by convincing us that we are being cautious, after all, we aren't risk takers.
While some preparation can be helpful, we tend to overdo it based on fear of failure, which often leads to paralysis. These excuses feel rational, but if we take a good look they are protective walls meant to keep us from trying. There are plenty of times I've done this in my life. I'm sure you have too. Take some time to think about moments in your life where you let fear, disguised as caution, dictate your actions.
Our task becomes working through this fear of failure by knowing what's at stake. We need to know that if left unchecked, failure will threaten our entire sense of self worth. When something we're working on fails it's easy to confuse, "This idea failed" with "I am a failure."
As a psychotherapist, my concern is not for the failure itself, it's for the diminishing of one's own worth based on that one failed attempt. That is a real wound that left unchecked multiplies and wreaks havoc on our self-esteem.
I often iterate to clients that these small little moments of failure are not their entire story. They are not the entire "book" of their life. They're just one line, in one chapter of the book. We need to keep things in context of their importance. Fear creates a distortion that is larger than the actual outcome. Nine times out of ten, your worst fear does not happen.
So now let's pivot from fear being a problem we feel we can't overcome and revitalize our courage as a practice for life. As the Stoics often remind us, our life is not defined by what happens to us, but how we react to what happens to us.
Marcus Aurelius said "Everything that happens is either endurable or not. If it's endurable, then endure it." Most of the things we fear, be it failure, embarrassment or criticism are not only endurable but also pass quickly. Think back on your life and how failure tends to pass through rather quickly. Marcus continues, "Just remember; you can endure anything your mind can make endurable, by treating it as in your interest to do so." Marcus invites us to shrink the fear down to actual size and ask how long it's going to hurt. Is it going to be a day or a week? Will it even be remembered a year from now?
Like the man in the story at the beginning of this post, we all need to make sure we account for the cost of "never trying" into our decisions. After all, the regret was far less endurable for him at the end of his life, than any perceived failure would have been.
The Stoics would also ask us not to measure our life by outcomes or by how many accolades we may receive. Rather, we should be measuring our impact on the world by if we've acted with honesty and courage. After all, courage is not the absence of fear, but the decision to step into the fear and act in accordance with our values.
Now, even with all this said, I'm well aware that fear will not disappear for any of us. It will always be whispering in our ear. Coming up with reasons to delay starting a project or to stay safe in what we're doing. Eliminating fear is not going to happen just by quoting a Stoic or journaling about fear more often.
Moving forward, let's agree to view fear of failure and regret as if they are on separate paths. Failure stings for a bit, but it passes. Regret stays with us much longer, often for the rest of our lives. Here's a call for all of us to move forward with boldness and measure our lives by our courage to act.
Try journaling through your fear of failure in the Stoic app. Each reflection helps you recognize fear’s voice — and write a story driven by courage, not regret.