There’s a useful distinction between assets that depreciate and assets that compound. In creative work, execution skills now depreciate faster than at any point in the last fifty years. Strategic skills, cultural intelligence, and client relationships compound. The five-year framework is about deliberately building the compounding assets before the depreciating ones stop covering the bills.
Year 1: Master AI in Your Current Practice
Don’t change your work — change how you do it. Build efficiency using AI tools so you have time for strategy. You should be spending 30% less time on execution by end of year one. Use that time to develop strategic offerings, not to take on more execution work.
Year 2–3: Package and Price Strategic Work Separately
Start selling strategy as a standalone service. Strategy Brief: $2,500. Brand Positioning Workshop: $5,000. Creative Direction Retainer: $3,000/month. These feel ambitious. That’s the point. The market will tell you quickly whether your positioning is credible.
Year 4–5: Build Recurring Revenue and Authority
By year four, execution should be a proof point for strategy, not the primary offering. Develop a recurring revenue product — retainer, subscription content, licensing. Publish your thinking. Speak. Become the practitioner that other practitioners cite. This creates the kind of market position that AI cannot undercut.