Customer success leaders spend a lot of time trying to reduce pain. But the truth is, pain is unavoidable. The real choice is when and how it shows up. In this session, we’ll explore why the pain we avoid in customer success almost always reappears later as churn, escalations, burnout, or broken trust. From avoiding hard conversations and unclear success definitions to letting scope creep and misalignment slide, small discomforts compound into big problems if left unaddressed. This talk reframes pain as a signal, not a failure. Attendees will learn how strong CS leaders use early discomfort to create clarity, drive adoption, build trust, and protect renewals. Through real-world customer success examples, we’ll look at how confronting issues early leads to healthier customers, stronger teams, and better retention outcomes. Because in customer success, the goal is not to eliminate pain. It’s to use it wisely.