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In this conversation, I’m chatting with Tim Gailey, one of our current d.MBA members. Tim has one of the most genuinely squiggly career paths I’ve come across: teaching, landscaping, biochemistry, healthcare, and then into UX and product design. A few years ago, that kind of background could feel like a disadvantage. These days, it might be exactly the point. We talk about what it means to be a generalist in 2026, why labels and titles are mostly made up, and how building business confidence changes the way designers show up with clients and stakeholders without losing the human part of the work. We also get into practical stuff: workshops, relationship-building, how to bring non-designers along with you, and why “fast” is not the strongest value proposition (especially now that AI makes speed feel cheap). Topics we cover: • Squiggly careers and why they are suddenly an advantage • The scientist mindset in product design • Teaching, mentoring, and learning by explaining • Business strategy as “more lenses”, and how not to overwhelm yourself • Why workshops are such a powerful tool for influence • Side projects as hobbies, not hustles • What juniors are up against right now, and what companies get wrong • The “waiting for permission” trap, and how to build agency Tim lives online here: • linkedin.com/in/timgailey/ • timgailey.com If you’re curious about d.MBA, it’s our membership for designers who want to build real confidence around business and strategy through practice, not just theory.