Learning How to Fail Well

No one ever tells you that one of the most essential parts of your life is learning how to fail. 

Whether big or small, you will make mistakes. That reality has been ever present this year as I have been working in my first post-grad professional position. For most of my academic career, things felt predictable. If you learned a teacher’s expectations, knew the syllabus, and studied, you could achieve the desired outcome. There were benchmarks and examples at every turn. There was always a measurable definition of success. 

But work, especially in a new organization and in a remote position, doesn’t operate on a syllabus. Sometimes you are learning how to get from point A to point B while simultaneously writing the manual for how you do it. You are building or improving the process as you go. And in that space, mistakes are inevitable. 

This year has taught me that failure and mistakes are not interruptions to growth; they are often the vehicle for it. 

As Pittsburgh Fellows, we often talk about the integration of our faith into our work and our professional lives. I’ve come to believe that this integration begins with humility. Scripture reminds us, “God opposes the proud, but gives grace to the humble”. (James 4:6) Humility in the workplace looks like admitting when you do not know the answer. It looks like receiving feedback without defensiveness. It looks like understanding that your own and others’ competence is developed over time, not overnight. 

Tim Keller in “Every Good Endeavor" reminds us that work is one of the primary places where God shapes our character. He explains that through work God refines us, not only in skill, but in heart. And when we fail, our idols of control, perfection, and/or approval are exposed.

Truly how you handle failure is tied back to what you think about yourself. If you believe that you are a chosen and beloved child of God who has to die to their sins every day but who has the grace of Christ, you will live into Paul’s statement in 2 Corinthians 12:9, “My grace is sufficient for you, for my power is made perfect in weakness”. If you don’t, ultimately, you will feel crumbled under the weight of expectations, uncertainty, and overthinking every step. 

Ultimately, learning how to fail well means asking better questions after a mistake: What can this teach me? Where did I assume instead of clarify? How can this strengthen the process next time? Take a step back and a deep breath away from the situation and answer this as someone who is not dependent upon the answers being a reflection of your character. Because they aren’t. When you get to this point, you can celebrate wins and acknowledge and learn from mistakes without shame. 

-Written by Sarah Westmoreland, Class of 2026

Sarah graduated from Eastern University and works at Her Safe Haven as a Pittsburgh Fellow.