I Thought This Would Be Simpler

Andy Golding

Life is complex. Let's talk about it. I Thought This Would Be Simpler. Maybe you did too. We grow up believing life will feel clearer once we’re older and more accomplished, or that success, relationships, ambition, creativity, friendships, money, marriage, and adulthood itself will somehow become easier once we “make it” or arrive at some elusive stage of certainty. In a world obsessed with polished success stories, quick wins, and perfectly edited highlight reels, I Thought This Would Be Simpler leans into the messy middle instead. Come join us as we play in the mud, instead of avoiding it. I'm Andy Golding, and I Thought This Would Be Simpler.

Episodes

  1. Aug 16

    Craft vs Enterprise | Tim Holmes | I Thought This Would Be Simpler

    What happens when the business you built around your talent, energy and instincts becomes too complex to depend on you? In this episode of I Thought This Would Be Simpler, Andy Golding talks with Tim Holmes about one of the hardest transitions a founder can make: moving from a craft business which is shaped around the founder, to an enterprise capable of thriving without them. They explore why growth demands more than new systems and senior hires. It requires founders to loosen their grip, confront the relationship between identity and control, and decide honestly what kind of business, and life they are trying to build. Not every company needs to become a unicorn, and choosing to remain a craft business is entirely valid. The trouble begins when founders play one game while expecting the rewards of another. Tim explains how the right board can bring perspective, challenge assumptions and help a leadership team navigate increasing complexity. He also reframes governance, as the boundaries, responsibilities and shared rules that give people the freedom to act with clarity, instead of simply being seen as corporate bureaucracy. Andy positions a new title for governance as 'operating discipline'. This is a candid conversation about ego, burnout, trust, accountability and the deeply personal work of building a company that is bigger than its founder. About Tim: Tim Holmes – Senior Partner – Head of Sales, Sirdar Group Tim Holmes worked in asset management and the IT industry for 26 years until moving to Sirdar Group in 2013. During his journey from data capture clerk in London to Managing Director of FinSwitch in Cape Town, he experienced most of the aspects of a good and bad board and the typical lack of understanding of what it means to be a director of a private or family business. Tim is passionate about education and making complex technical problems understandable to business people, originally with information technology and now with governance and the art of being an effective director. Key takeaways Decide whether you are building a craft business or an enterprise—and play that game deliberately.A business cannot become independent of its founder until the founder is willing to relinquish control.Growth requires complementary leadership, not one person making every decision.A board should be assembled to deliver defined outcomes, challenge assumptions and contribute experience the business does not yet possess.Governance is less about bureaucracy than creating clear boundaries within which people can work autonomously.Founders need perspective too; a coach or mentor can help them see what is difficult to recognize from inside their own business and life.You do not have to wait for burnout, illness or crisis before choosing to work differently. Chapters 00:00 Welcome and introduction 01:34 From craft business to enterprise 04:03 Why founders struggle to let go 06:30 It’s okay not to build for an exit 09:45 The moment something has to change 14:20 Building a complementary founding team 17:21 What a board is really there to do 20:18 When and whom to bring onto a board 25:08 Building trust between founders and boards 29:32 Defining what success means for the founder 34:55 From scrappy startup to mature organization 38:49 Reframing governance as operating discipline 42:57 Clarity, culture and accountability 45:47 Why every founder needs a coach or mentor

  2. Jun 30

    Reinventing yourself | Ken Hellem | I Thought This Would Be Simpler

    What happens when the life you’ve built no longer feels like the life you’re meant to live? In this episode, Andy Golding sits down with Ken Hellem to explore the messy, uncomfortable, and ultimately transformative process of reinvention. Together they unpack why so many of us mistake being busy for moving forward, how authenticity often requires letting go of identities we’ve spent years building, and why the hardest part of change is first admitting that something needs to change. From the power of expanding your network beyond familiar circles to uncovering the values that shape meaningful decisions, this conversation is a candid look at what it really takes to create a life that feels aligned—not just successful. Ken shares practical insights on moving from intention to action, embracing uncertainty, and finding purpose on the other side of discomfort. If you’ve ever found yourself thinking, “I thought this would be simpler,” this episode is a reminder that reinvention isn’t about becoming someone new—it’s about having the courage to become more fully yourself. Connect with Ken: kenhellem.com Takeaways Reinventing LifeFinding Purpose Networking beyond your comfort zoneThe power of acknowledging the need for change Chapters 00:00 The Art of Reinvention18:02 The Illusion of Simplicity25:06 The Pursuit of Happiness31:19 Recognizing the Need for Change40:00 Inspiring Others01:10:53 Living Authentically and Inspiring Others

About

Life is complex. Let's talk about it. I Thought This Would Be Simpler. Maybe you did too. We grow up believing life will feel clearer once we’re older and more accomplished, or that success, relationships, ambition, creativity, friendships, money, marriage, and adulthood itself will somehow become easier once we “make it” or arrive at some elusive stage of certainty. In a world obsessed with polished success stories, quick wins, and perfectly edited highlight reels, I Thought This Would Be Simpler leans into the messy middle instead. Come join us as we play in the mud, instead of avoiding it. I'm Andy Golding, and I Thought This Would Be Simpler.