Observability is an essential component in digital transformation and cloud journeys, providing crucial insights into system health and performance to ensure seamless digital experiences. Effective observability can empower developers to deliver resilient services and improve customer experiences, but it becomes increasingly challenging and costly as cloud workloads grow. Key challenges include managing data quality, tool proliferation, user access control, and escalating costs due to large data volumes. Best practices to address these challenges involve unifying data analytics to reduce mean time to recovery (MTTR), segregating data to manage permissions, optimizing data storage, and implementing data quality processes to derive actionable insights. The choice between SaaS and self-hosted solutions involves a trade-off between avoiding vendor lock-in and saving engineering resources, with SaaS options like Logz.io offering managed services to alleviate maintenance burdens. Observability responsibilities are often consolidated under a dedicated team in an Observability Shared Services Model, which can enhance efficiency, security, and data sharing across an organization. Implementing a robust observability strategy can mitigate risks, reduce costs, and ultimately protect revenue by ensuring reliable digital experiences for customers.