You can't be afraid of failure and you can't be afraid of

Host: The gentle hum of the evening filled the room, creating a calm space for reflection. Jack sat at the table, his fingers lightly resting on his cup, considering Dave Van Ronk’s words. Jeeny stood near the window, her gaze directed outward, reflecting on the deeper meaning behind the statement.

Jeeny: “I’ve been thinking about what Dave Van Ronk said: ‘You can’t be afraid of failure and you can’t be afraid of success, because either one gets in the way of your work.’ It’s such a powerful statement, isn’t it? The idea that both fear of failure and fear of success can hinder us from fully engaging in our work or creative process. It’s about being free from those fears so that we can truly create or perform.”

Jack: “Yes, exactly. Van Ronk is showing us that both success and failure can create paralysis if we let them control us. If we’re too afraid of failing, we won’t take risks or push ourselves to try new things. But if we’re too focused on the fear of success, we might hold ourselves back, not allowing ourselves to fully embrace our potential. In both cases, we end up getting stuck and not doing the work that matters.”

Jeeny: “Right. And I think it’s also about how we define failure and success. Both of these concepts can be so overwhelming when we place too much importance on them. Van Ronk is encouraging us to detach from these expectations and focus instead on the work itself, on the process, rather than the outcomes. When we can do that, we create freely without being bogged down by fear of either success or failure.”

Host: The stillness in the room deepened as they both reflected on how fear can hinder creativity and progress. Jack’s fingers rested on the table, while Jeeny’s expression softened, considering how both success and failure can be distractions if we let them control our actions.

Jack: “It makes me think about how often we become paralyzed by expectations—whether it’s the fear of failing or the fear of living up to our past successes. Van Ronk is reminding us that if we get too focused on either extreme, we stop moving forward. We let those fears dictate what we do, rather than just doing the work. Success and failure are part of the journey, but they shouldn’t control the journey itself.”

Jeeny: “Exactly. Van Ronk is showing us that work itself is the focus, not the outcome. Fear of failure makes us hesitant, and fear of success makes us avoid our potential. Both fears can create mental blocks that prevent us from doing what we’re truly capable of. The only way to really make progress is to let go of those fears and just immerse ourselves in the process of creation or work.”

Jack: “And I think that’s what makes this so freeing—it’s about focusing on what you’re doing, not on the fear of what might happen. Van Ronk is reminding us that if we can let go of the pressure of success and failure, we can put our energy into the work itself, which is where the real value lies. It’s not about the external recognition or the fear of not measuring up; it’s about doing the work with authenticity.”

Jeeny: “Yes, and I think this is why creativity or any type of meaningful work thrives when it’s done from a place of freedom and joy. If we’re not attached to the outcome, we can approach the work with a sense of openness and curiosity. Van Ronk is saying that when we’re not worried about success or failure, we give ourselves the space to experiment, to grow, and to truly express ourselves without restrictions.”

Host: The quiet in the room grew deeper as they reflected on how freedom from fear can unlock creativity and progress. Dave Van Ronk had shown them that both fear of failure and fear of success can stop us from doing the work that matters. Jack leaned back slightly in his chair, while Jeeny’s gaze turned from the window back to him, both of them understanding the deeper meaning of Van Ronk’s words.

Jack: “So, Van Ronk is really showing us that to do meaningful work, we have to let go of both fear of failure and fear of success. When we’re focused on the process and not the outcome, we can create freely and fully, without being blocked by either of those fears.”

Jeeny: “Exactly. Van Ronk reminds us that work is about expression, not expectation. When we stop fearing failure or success, we free ourselves to do the work that’s most important, without the mental constraints of how it will be judged or whether it will lead to something big. The process itself is where the magic happens.”

Host: The evening had fully settled in, the quiet understanding between them a reminder that creativity and progress come when we release the fears of success and failure. Dave Van Ronk had shown them that doing the work—without the pressure of outcomes—is where true growth and expression occur. The world outside had darkened, but inside, there was light—a recognition that the process of creating is more important than the results we fear or chase.