When the Obstacle Becomes the Way
There was a period in my life marked by serious consequences. Everything that had once given me a sense of stability was gone. My job, my home, my relationship, and my reputation had all fallen away. What remained was fear, uncertainty, and a deep sense of exposure. At the time, it felt unbearable. In hindsight, it became the turning point.
During that season, I leaned into an idea that went against every instinct I had. Instead of trying to outrun fear or numb it, I considered that what I was most afraid to face might actually hold the answers I was searching for. Joseph Campbell captures this powerfully when he says, “The cave you fear to enter holds the treasure you seek.” That sentence stopped being poetic and became practical. Avoidance had shaped my life for years. Turning toward what I feared became the beginning of change.
Ryan Holiday explores this same principle in The Obstacle Is the Way. Drawing from Stoic philosophy, he reminds us that obstacles are not interruptions to the path. They are the path. One example from the book that deeply resonated with me is the Stoic practice of reframing adversity as training. Instead of asking, “Why is this happening to me?” the question becomes, “What is this asking of me?” That shift does not remove pain, but it gives pain direction.
As a recovery coach, this distinction shows up constantly in my work. Not all pain is equal. Some discomfort is necessary for growth, such as honesty, accountability, grief, and learning to tolerate emotional intensity. Other pain is unnecessary, including shame, secrecy, and self punishment. A large part of the coaching process is helping men learn which pain to move through and which pain to put down.
I work primarily with men who struggle with sexual integrity and sex addiction. Many of them experience the obstacle as internal rather than external. It often looks like slowing down, getting honest with themselves, and asking questions they have avoided because life has been too fast, too loud, or too overwhelming. The work is not about forcing insight. It is about creating enough safety and structure to stay present with what is already there.
One practical tool I often share is to treat moments of discomfort as signals rather than problems.
A simple practice: Turning toward the obstacle
Pause when discomfort arises rather than acting on it immediately.
Name what you are feeling in the body, such as tightness, heat, restlessness, or pressure.
Identify the urge without judging it. This might be to escape, distract, control, or numb.
Ask a grounded question: What is this moment asking of me right now?
Choose the smallest action that aligns with integrity rather than relief.
This practice does not remove difficulty, but it builds trust in your ability to stay present. Over time, what once felt overwhelming becomes workable.
Call to action
If you find yourself avoiding certain questions, emotions, or conversations, consider that these may be pointing toward meaningful change. Choose one small area of discomfort this week and practice staying with it a little longer than usual. Growth rarely comes from eliminating obstacles. More often, it comes from learning how to meet them directly.
