In this episode of Remote Work Conversations, Lucas and Luna explore the concept of career checkpoints—a structured, forward-looking alternative to annual performance reviews for remote workers. They break down how a checkpoint is different from a retrospective, using a concrete example: a product designer at a fintech startup who set a checkpoint every 90 days to assess her portfolio, skills, and network. The hosts discuss how to choose meaningful metrics, how to bring data into the conversation, and how to turn a checkpoint into a springboard for a raise or a pivot. They also share practical tips for scheduling, documenting, and following through. If you've ever felt stuck in your remote career or unsure how to measure progress, this episode offers a clear framework to take control of your growth.