100. Customer Success Career Advice: Stop Blindly Following Traditional CS Paths

Episode notes

What if the reason you feel stuck in your Customer Success career has nothing to do with your performance and everything to do with the path you’re blindly following? On today’s episode, I’m unpacking the uncomfortable truth about traditional CS career paths and why doing “the next logical step” can quietly derail your growth, happiness, and earning potential. We’ll talk about why promotions that look good on paper can feel miserable in real life, how following the crowd leads to boring roles and regret, and the simple mindset shift that changes how you make career decisions inside Customer Success. By the end of this episode, you’ll walk away with a completely new way to think about success in your Customer Success career, one that’s built around what you’re actually good at, what you enjoy, and where you want to end up, not what everyone else is doing. If you’ve ever felt pressure to go enterprise, become a CSM, or say yes just because it’s “the path,” this conversation will give you clarity, confidence, and permission to choose differently.