The Pain of Learning

Growth, by its nature, isn’t always comfortable. In fact, the pain of learning can be as disorienting as it is rewarding. At every level of leadership, stepping into a new skill, embracing unfamiliar challenges, or allowing yourself to make mistakes means letting go of old markers of success, previous accomplishments, identities, or even established reputations. For many, this growth requires something deeply challenging - the courage to embrace vulnerability.

Learning means letting go of the need to look like you’ve got it all figured out. Ironically, the more experienced or senior you are, the harder this can feel. By then, many people assume they need to be the expert, have the answer, or uphold their credibility. 

Mature leaders understand something essential. Credibility isn’t the result of always being right, it’s rooted in the courage to say, “I don’t know.” This honesty fosters trust and garners respect. Leaders who are willing to show that they’re still learning create more space for others to grow, inviting their teams to move forward in confidence.

Learning is messy, sometimes awkward. Yet, leaders who take on new challenges, even in areas they know little about, tend to be the ones who grow stronger and earn more respect over time. It’s also common for highly coachable people to lean into this process openly, while uncoachable people may blame circumstances or others, avoiding personal responsibility. 

Self-awareness, and understanding your own blind spots, strengths, and limitations, is crucial for growth. This willingness to adapt is perhaps one of the most important traits in leadership. When a leader is open to learning, they signal their commitment to their future self and their team’s success.

When leaders take the role of a learner, they also gift others the chance to teach. Asking for input and valuing others’ expertise creates a learning environment that invites collaboration and trust. Leaders who are comfortable with experimentation cultivate a culture where learning becomes a shared pursuit. 

Try running some “safe experiments’” Take on a new challenge, get a little uncomfortable, and allow the outcomes to unfold as they will. It may feel unfamiliar, but with practice, this way of learning will become a normal part of growth. You will also create a new normal with expanded mastery.

A friend of mine, a former Olympian, has a poster on her bathroom door that reads: “Do something every day that scares you.” It’s a mantra she lives by, acknowledging that true growth means stepping out of our comfort zones. She actively seeks out activities where she can start as a novice, fully aware of the value in humbling herself and trying something new. With her background in mastering one field, she values the process of intentionally putting herself in places where she “is a bit shit” (her words).

Nothing builds rapport faster than humour, especially in the midst of learning something new. Being able to laugh at your mistakes not only helps you grow but creates a more human environment where others feel safe to try, and fail as well. Leaders who make space for humour demonstrate a grounded confidence. They invite connection, make learning enjoyable, and give permission to others to embrace the reality of growth and vulnerability.

Learning is a process, a series of confidence-competence loops where practice not only improves skill but builds resilience and belief in yourself. True confidence, after all, isn’t about knowing everything -  it’s about the willingness to keep showing up, keep learning, and keep building the future through each experience.