How to Reinvent Yourself

Lessons Learned from My Career Transition and How to Find Your Next Great Thing

 
In August 2021, I resigned from my role as COO at ConvertKit. I sold most of my stock and set aside funds for a sabbatical of undetermined length. In the 18 months following my departure, I transitioned industries; pursued three six-month career experiments; experienced deep anxiety and depression; and came out the other side, more aligned to myself than I’ve felt in years.

A career transition can be an opportunity for a step change in personal and professional growth. I know this is true, and yet the more senior I’ve grown in my career, those transitions have actually felt riskier. We need more people to talk publicly and openly about how they go about making big mid-career changes.

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