Jon de la Motte initially failed his first Stripe interview because he was over-prepared and focused too much on demonstrating high craftsmanship, which led him to perform poorly on the actual interview question.
Jon decided to take the riskier route of joining the new JS Infra team at Stripe because he wanted to try something challenging and different, even though it was more difficult and risky.
Jon worked on migrating the company's largest JavaScript codebase to a new bundler called Metro, which reduced the development startup time from 15 minutes to 30 seconds, a massive win for the team.
Jon received a 'partially meets expectations' performance review because he struggled with project management and bringing other team members into the project, even though he had a successful project.
Jon faced a personal crisis when his wife threatened to leave him and take the kids, which led him to seek therapy to address his issues and improve their relationship.
Therapy helped Jon overcome his math anxiety by uncovering the root cause—shame and fear from his childhood—and allowing him to relearn and understand math without those emotional barriers.
Jon decided to leave Stripe because he was struggling with burnout and realized that his deep-seated issues with work and his father were affecting his mental health and performance.
Jon learned that his identity and performance were deeply tied to childhood traumas and family expectations, and that by addressing these issues, he could find a more authentic and fulfilling life.
What if leaving your dream job was the way to discover your true self?
Jon de la Motte failed his first Stripe interview, but he didn't give up. It was his dream job, a company that connected with his father's work in finance with his software ambitions.
At Stripe, Jon faced challenges. He joined a risky JavaScript infrastructure team and struggled to find his footing. Eventually he found his way, built a great team and then it all started to fall apart again.
Discover how Jon's journey reshaped his life and what it means to balance personal and professional priorities.