The Hardest Thing You Try May Change What You Believe You're Capable Of
Introduction
There are decisions that seem small when we make them. We say yes to an unfamiliar opportunity, sign up for something intimidating, or ask a question without knowing where it might lead. Only later do we recognize that one ordinary moment changed what we believed was possible.
The outcome matters, of course. But sometimes the more lasting change is not what we accomplish. It is what the attempt teaches us about our own capacity to face uncertainty.
That distinction runs through the story of Ray Dillman, a retired U.S. Army major who served in Special Forces and later became an educator and founded Discipled Warriors. One unplanned detour early in his military career gave him an experience he would draw on for decades.
Why This Post Matters
Confidence is often treated as something we need before taking action. We wait until we feel qualified, prepared, certain, or somehow ready. Yet the experiences that build durable confidence frequently begin when those feelings are absent.
This matters well beyond military training. A new job, a creative project, a difficult conversation, a return to school, or a decision to change direction can all present the same uncomfortable question: What if I cannot do it?
The answer is rarely available in advance. We learn more by engaging with the challenge than by endlessly rehearsing the possibility of failure. Trying does not guarantee success, and not every risk is wise. Still, refusing every uncertain opportunity has a cost of its own: we never gather new evidence about what we might be able to do.
The Unexpected Doorway
As a young infantryman reporting to Fort Bragg, Ray Dillman could not find the replacement detachment where he was supposed to report. Frustrated, he wandered into the JFK Special Warfare Museum. There, a master sergeant approached him and asked whether he wanted to try Special Forces.
Ray said yes. The man turned out to be a recruiter. Soon, Ray was on a path toward assessment and selection. When asked which specialty he wanted to pursue, he asked for the hardest one. The answer was the medic course, even though he had no medical background.
It is an almost comically understated beginning to an extraordinary challenge. No grand plan, no years-long declaration of destiny. A wrong turn, a conversation, and a willingness to try.
What makes the story useful is not the notion that everyone should choose the hardest available path. It is that Ray did not require certainty about his ability before taking the first step. He could learn what the challenge demanded by entering it.
What the Mountain Changed
Looking back, Ray described the deeper impact of that decision in a single reflection:
“By doing that, by climbing that mountain, I think that ⁓ that gave me the confidence to just try everything else that I did in life.”
— Ray Dillman
Retired U.S. Army Major and Founder of Discipled Warriors
That confidence was not simply the satisfaction of finishing an especially demanding course. It became permission to consider other possibilities without first having to prove that he already belonged there.
Confidence Has a Memory
Ray connected that early experience to later choices: pursuing advanced education, teaching at West Point, and even finding the courage to ask the woman who became his wife on a date. Those decisions were different in kind and consequence. What carried across them was a growing willingness to try.
One demanding experience did not make every future challenge easy. It gave him a reference point. When something new appeared intimidating, he could remember that he had once faced an unfamiliar and difficult undertaking, stayed with it, and learned what he was capable of.
That is a more useful understanding of confidence than the idea that confident people never doubt themselves. Confidence can be a record of having acted despite doubt. It can be built through preparation, effort, feedback, support and the discovery that discomfort is not always a signal to stop.
Failure can contribute to that record too. An attempt that does not succeed may still reveal skills to develop, assumptions to revise or a direction that is not right for us. The valuable evidence is not always that we can win. Sometimes it is that we can recover, adapt and decide what comes next.
The Challenge Is Not a Solo Performance
There is another important detail in Ray’s story. Although his training was highly specialized, he repeatedly emphasized that no one succeeds on a battlefield alone. Each person has a role, and the team depends on those roles being fulfilled.
That perspective complicates the familiar image of courage as solitary toughness. Taking on something difficult does not mean refusing help. Asking questions, learning from people with experience, accepting guidance and recognizing the contributions of others are often what make a demanding challenge possible.
Ray spoke about the humility of doing the work rather than advertising the achievement. That matters here too. The purpose of a hard experience is not to collect a dramatic story to tell other people. Its quieter reward may be a changed relationship with your own limitations.
Lessons for Living Life Audaciously
Living audaciously does not require choosing danger or proving something to an audience. It can begin with a thoughtful yes to an opportunity that matters, even when you cannot yet see every step.
Consider one challenge you have been postponing because you do not feel ready. Is the hesitation pointing to a genuine risk that needs attention, or is it asking you to know the outcome before you begin? Those are different problems, and they call for different responses.
You might prepare more carefully, ask someone for guidance, start with a smaller commitment, or take the first step while uncertainty remains. Whatever the decision, pay attention to what the experience teaches you. Not only whether it worked, but what you learned about how you respond, adapt and persist.
Years from now, the most important result of a difficult decision may not be the credential, job or accomplishment attached to it. It may be the next decision you were willing to make because you had already learned that unfamiliar territory was somewhere you could find your way through.
