I've made more career transitions than most people make in a lifetime — from competitive gymnast to startup founder to Facebook PM to executive coach and author. Each transition taught me that pivoting isn't about abandoning who you are; it's about finding a better expression of it.
These articles are for anyone in the middle of a professional shift, whether you're leaving a job, switching industries, or trying to figure out what comes next. The common thread is that career transitions are rarely linear, and the people who handle them best are the ones who learn to sit with uncertainty while still moving forward.
Navigating Uncertainty
- The Double-Loop Pivot — A structured framework to decide whether to stay the course or change direction
- Optionality Is a Trap — Stop keeping all your doors open and commit to the path that matters
- The Dizziness of Freedom — Kierkegaard's insight on why too many choices paralyze instead of liberate
- There Is No Best Choice — Accept that every career move is a tradeoff and make yours deliberately
Timing & Pressure
- Off Track at 30 — Honest perspective on the panic that hits when your career doesn't match your timeline
- The Tyranny of Thirty — Push back on the cultural myth that your career must be figured out by 30
- The New Thirty — Challenge the Full House Fallacy and rethink what modern adulthood actually looks like
- Diminishing Returns on Merit Badges — Recognize when collecting credentials stops advancing your career and starts stalling it
Reinvention in Practice
- Burned-Out Tech CEO to Warehouse Associate — What radical career reinvention looks like when you hit rock bottom
- Ridejoy: Lessons Learned — Transferable lessons from a failed startup to fuel your next chapter
- Finding Your Edge — The unique intersection of skills and experiences that defines your next move
- Dark Horse — The unconventional paths that high achievers actually take to find fulfillment
Getting the Job
- The 10x Job Application — Stand out from the pile with applications that demonstrate genuine fit and effort
- Signaling Quality — Why presentation opens doors that substance alone cannot
- How to Conference Better — Turn conferences into career accelerators through tactical networking and visibility
- Go to More Parties — Use social occasions as catalysts for the connections that change your trajectory
Building Your Own Path
- Expertise Is a River — Treat your expertise as something that flows and evolves rather than a fixed credential
- Best Practice — Find your personal best practice instead of blindly following industry norms
- From Zero to Unicorn — The full arc of a career trajectory from nothing to outsized impact
- Process Over Outcome — Focus on the quality of your daily work instead of obsessing over where it leads
My book The Path to Pivot goes deeper into career transitions. Get the book at jasonshen.com/books or work with me directly at jasonshen.com/coaching.