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Everyone talks about running multiple ventures — but almost no one talks about how to do it sustainably without burning out or neglecting the business that pays the bills. In this episode of The CEO Lounge, Derrick Thompson breaks down the exact calendar system he uses to balance multiple ventures while staying focused, profitable, and sane. Derrick isn’t sharing theory — this is lived experience from a CEO who runs a digital marketing agency, community initiatives, multiple podcasts, and passion projects without chaos. In this episode, we cover: • Why planning your week on Monday means you’re already behind • How Derrick plans his entire week before Monday (weekend planning strategy) • His exact weekly structure: Monday: Client relationship & check-ins Tuesday & Thursday: Batched meetings Wednesday: Work on the business (systems, strategy, execution) Friday: Creative work, vision, and future ventures • Why your “main thing” must stay the main thing — even with exciting side projects • How to avoid shiny-object syndrome while still building long-term ventures • The calendar, systems, and tools that make managing multiple ventures possible This episode is for entrepreneurs who feel pulled in too many directions and want clarity, structure, and sustainability — not hustle culture. Chapters: 0:00 When entrepreneurs lose control of their time 0:29 Welcome to The CEO Lounge Podcast 2:18 What it really means to balance multiple ventures 3:19 Why planning your week on Monday puts you behind 9:40 Monday as Client Relationship Day 15:51 Why batching meetings reduces burnout 21:19 Structuring your week to protect energy and focus 27:24 Systems and tools that keep businesses running 38:30 Why your main business must stay the priority 47:10 How new ventures are built sustainably 58:00 Final takeaways + CEO Weekly Operating System 👉 FREE RESOURCE: Download the CEO Weekly Operating System + Calendar Framework Website - www.theceolounge.net Direct Resource Link - https://www.theceolounge.net/download... 🎧 Subscribe for weekly conversations on leadership, business growth, and running your week like a CEO. 🔔 #BalancingMultipleVentures #EntrepreneurLife #CEOSystems #BusinessLeadership #TimeManagement #WorkweekPlanning #TheCEOLounge