Kenneth Jackson has spent over fifteen years as a freelance digital strategist and consultant, working with clients ranging from solo entrepreneurs to Fortune 500 companies. After spending his first five years in the industry trapped in the feast-or-famine cycle that plagues most independent professionals, he made a conscious decision to restructure his business around recurring revenue. Within eighteen months, he had replaced his project-based income with retainer clients, and within three years, he had doubled his income while working fewer hours.
Since then, Kenneth has helped hundreds of freelancers make the same transition through his coaching practice, online courses, and speaking engagements at events including the Freelance Business Summit and Creative South. His approach is grounded in practical, actionable systems that work for real freelancers in real markets—not theoretical advice from someone who has never managed a client roster.
Kenneth lives in Portland, Oregon, with his wife and two children, where he continues to run his consulting practice while writing and teaching. When he's not working, you'll find him trail running in Forest Park or experimenting with sourdough baking. He believes that freelancing should be a path to freedom, not a different flavor of corporate exhaustion, and he's on a mission to help as many independent professionals as possible build businesses that support the lives they actually want to live.