<![CDATA[I Thought This Would Be Simpler]]>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.

]]>ithoughtthiswouldbesimpler.comRiverside.fm (https://riverside.com)Wed, 14 Oct 2026 23:29:53 GMTMon, 25 May 2026 14:30:32 GMT60Andy Golding<p><b>Life is complex. Let's talk about it.</b></p><p></p><p>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.</p><p></p><p>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.</p><p></p><p>I'm Andy Golding, and I Thought This Would Be Simpler.</p>episodicAndy Goldingandy@andygolding.comyes<![CDATA[Playing To Win | Bruce Whitfield | I Thought This Would Be Simpler ]]>The complexity of life, the impact of unfairness, and the challenges of information overload. This conversation between Andy Golding and Bruce Whitfield covers them all! It delves into the role of optimism, risk aversion, and the need to spot positive signals in a world of distractions, whilst also navigating the complexity of human nature and the audacity of setting ambitious goals.

Andy and Bruce have a history of interviewing together, though in the past Bruce was the one interviewing Andy, so it was a treat to have the table turned just this once!




]]>31affc41-910f-433e-a4fe-62fae0bd69fcSun, 27 Sep 2026 15:29:19 GMT<p>The complexity of life, the impact of unfairness, and the challenges of information overload. This conversation between <a href="https://www.andygolding.com/" rel="noopener noreferrer nofollow">Andy Golding</a> and <a href="https://www.brucewhitfield.com/" rel="noopener noreferrer nofollow">Bruce Whitfield</a> covers them all! It delves into the role of optimism, risk aversion, and the need to spot positive signals in a world of distractions, whilst also navigating the complexity of human nature and the audacity of setting ambitious goals. </p><p>Andy and Bruce have a history of interviewing together, though in the past Bruce was the one interviewing Andy, so it was a treat to have the table turned just this once! </p><p><br /></p><p><br /></p><p><br /></p>no00:43:53Playing To Win | Bruce Whitfield | I Thought This Would Be Simpler full<![CDATA[The Whole Human Leader | Peter Sorgenfrei | I Thought This Would Be Simpler]]>This conversation between host Andy Golding, and Peter Sorgenfrei explores the impact of high-pressure business environments on physical and mental health, the importance of self-awareness and leadership.

Peter Sorgenfrei discusses the impact of his book 'The Whole Human Leader' and the personal journey that led to its creation. He emphasizes the importance of impact and legacy, as well as the significance of rest and intentionality in work and life.

Takeaways

  • Self-awareness is crucial for leaders to recognize the impact of high-pressure environments on their physical and mental well-being.
  • Leadership requires the ability to lead oneself before leading others, and creating a safe space for vulnerability and authenticity is essential for personal and professional growth.
  • Rest and intentionality in work and life are critical.

You can follow Peter and learn more here.

]]>d28d18a5-8ed5-4c5a-ae5e-5327a6a1c37bSun, 06 Sep 2026 14:14:01 GMT<p>This conversation between host Andy Golding, and Peter Sorgenfrei explores the impact of high-pressure business environments on physical and mental health, the importance of self-awareness and leadership. </p><p></p><p>Peter Sorgenfrei discusses the impact of his book 'The Whole Human Leader' and the personal journey that led to its creation. He emphasizes the importance of impact and legacy, as well as the significance of rest and intentionality in work and life.</p><p></p><p>Takeaways</p><ul><li>Self-awareness is crucial for leaders to recognize the impact of high-pressure environments on their physical and mental well-being.</li><li>Leadership requires the ability to lead oneself before leading others, and creating a safe space for vulnerability and authenticity is essential for personal and professional growth.</li><li>Rest and intentionality in work and life are critical. </li></ul><p></p><p>You can follow Peter and learn more <a rel="noopener noreferrer nofollow" href="https://www.petersorgenfrei.com/" target="_blank">here. </a></p>yes00:53:4318The Whole Human Leader | Peter Sorgenfrei | I Thought This Would Be Simplerfull<![CDATA[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

]]>61bb744f-79b0-4f68-834d-026b3dfd09bfSun, 16 Aug 2026 09:45:49 GMT<p>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>I Thought This Would Be Simpler</i>, 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.</p><p></p><p>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.</p><p></p><p>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'.</p><p></p><p>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.</p><p></p><p><b>About Tim: </b>Tim Holmes – Senior Partner – Head of Sales, Sirdar Group</p><p></p><p>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. </p><p></p><p><b>Key takeaways</b></p><ul><li>Decide whether you are building a craft business or an enterprise—and play that game deliberately.</li><li>A business cannot become independent of its founder until the founder is willing to relinquish control.</li><li>Growth requires complementary leadership, not one person making every decision.</li><li>A board should be assembled to deliver defined outcomes, challenge assumptions and contribute experience the business does not yet possess.</li><li>Governance is less about bureaucracy than creating clear boundaries within which people can work autonomously.</li><li>Founders need perspective too; a coach or mentor can help them see what is difficult to recognize from inside their own business and life.</li><li>You do not have to wait for burnout, illness or crisis before choosing to work differently.<p></p></li></ul><p><b>Chapters</b></p><p>00:00 Welcome and introduction<br />01:34 From craft business to enterprise<br />04:03 Why founders struggle to let go<br />06:30 It’s okay not to build for an exit<br />09:45 The moment something has to change<br />14:20 Building a complementary founding team<br />17:21 What a board is really there to do<br />20:18 When and whom to bring onto a board<br />25:08 Building trust between founders and boards<br />29:32 Defining what success means for the founder<br />34:55 From scrappy startup to mature organization<br />38:49 Reframing governance as operating discipline<br />42:57 Clarity, culture and accountability<br />45:47 Why every founder needs a coach or mentor</p>yes00:48:4217Craft vs Enterprise | Tim Holmes | I Thought This Would Be Simplerfull<![CDATA[Dating After Divorce | Avril Reitz | I Thought This Would Be Simpler]]>The conversation gets into the complexities and hilarities of dating after divorce, exploring the emotional journey of self-(re)discovery, and the challenges of navigating the world of dating apps.

It also touches on the shift from performative dating to authentic connection and 'getting over' the stigma associated with using dating apps and 'making yourself an option'.

Avril's story reflects the transition from performing to being authentic, the importance of self-awareness, and the value of compassion in human connections.

If Avril and her story resonate and you want to get in touch, you can connect with Avril at: Avril@illuminateyourself.co.za

]]>2719259f-c21e-411f-803c-a9f23b44c87bWed, 29 Jul 2026 19:25:34 GMT<p>The conversation gets into the complexities and hilarities of dating after divorce, exploring the emotional journey of self-(re)discovery, and the challenges of navigating the world of dating apps.</p><p></p><p>It also touches on the shift from performative dating to authentic connection and 'getting over' the stigma associated with using dating apps and 'making yourself an option'.</p><p></p><p>Avril's story reflects the transition from performing to being authentic, the importance of self-awareness, and the value of compassion in human connections.</p><p></p><p>If Avril and her story resonate and you want to get in touch, you can connect with Avril at: Avril@illuminateyourself.co.za</p>yes00:52:2916Dating After Divorce | Avril Reitz | I Thought This Would Be Simplerfull<![CDATA[Andy Golding | Why This Show Exists | I Thought This Would Be Simpler]]>A few episodes in, and I'm finally introducing the show. I don't know about you, but I really did think this would be simpler. This 'life' thing. The complexity is beautiful and confounding and I want to talk about - which is why this show exists.

]]>72551e89-f48b-4859-9292-e8ba05fe6c9dSun, 26 Jul 2026 13:15:57 GMT<p>A few episodes in, and I'm finally introducing the show. I don't know about you, but I really did think this would be simpler. This 'life' thing. The complexity is beautiful and confounding and I want to talk about - which is why this show exists.</p><p></p><p></p>yes00:08:0014Andy Golding | Why This Show Exists | I Thought This Would Be Simplerfull<![CDATA[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 Life
  • Finding Purpose Networking beyond your comfort zone
  • The power of acknowledging the need for change

Chapters

  • 00:00 The Art of Reinvention
  • 18:02 The Illusion of Simplicity
  • 25:06 The Pursuit of Happiness
  • 31:19 Recognizing the Need for Change
  • 40:00 Inspiring Others
  • 01:10:53 Living Authentically and Inspiring Others
]]>b6f9e695-c5d3-410a-8b7c-1f4f39719040Tue, 30 Jun 2026 08:00:05 GMT<p>What happens when the life you’ve built no longer feels like the life you’re meant to live?</p><p></p><p>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.</p><p></p><p>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. </p><p></p><p>Ken shares practical insights on moving from intention to action, embracing uncertainty, and finding purpose on the other side of discomfort.</p><p></p><p>If you’ve ever found yourself thinking, <i>“I thought this would be simpler,”</i> this episode is a reminder that reinvention isn’t about becoming someone new—it’s about having the courage to become more fully yourself.</p><p></p><p>Connect with Ken: <a rel="noopener noreferrer nofollow" href="https://kenhellem.com/" target="_blank">kenhellem.com</a></p><p>Takeaways</p><ul><li>Reinventing Life</li><li>Finding Purpose Networking beyond your comfort zone</li><li>The power of acknowledging the need for change</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Art of Reinvention</li><li>18:02 The Illusion of Simplicity</li><li>25:06 The Pursuit of Happiness</li><li>31:19 Recognizing the Need for Change</li><li>40:00 Inspiring Others</li><li>01:10:53 Living Authentically and Inspiring Others</li></ul>no00:55:5914Reinventing yourself | Ken Hellem | I Thought This Would Be Simplerfull<![CDATA[Ectopic pregnancy & the curveballs of motherhood | Andi Saitowitz | I Thought This Would Be Simpler]]>In this Andy(i) heavy episode, Andy Golding is joined by Andi Saitowitz, a business psychologist and mom of three. Andi shares her experience of navigating unexpected twists in life, including an unplanned and ectopic pregnancy and the decision-making process that followed.

From life before 2020 to the diagnosis and treatment, Andi's journey is a testament to resilience and surrender in the face of uncertainty. The conversation delves into the emotional journey of navigating uncertainty, preparing for surgery, embracing vulnerability, and the strength of surrender.

It also highlights the role of a mother, the journey of motherhood, and the concept of post-traumatic growth.

You can connect with Andi here: AndiSaitowitz.com

Takeaways

  • Resilience in the face of unexpected twists
  • The power of surrender and faith in decision-making Strength in vulnerability
  • The power of surrender and support

Chapters

  • 00:00 Navigating Unexpected Twists
  • 08:53 The Decision-Making Process
  • 24:36 Surrender and Waiting
  • 30:18 The Strength of Surrender
  • 36:01 The Journey of Motherhood
  • 44:29 Post-Traumatic Growth
]]>5a0e8d36-ae38-44f1-bb0e-d06ff7fb330dWed, 24 Jun 2026 18:02:09 GMT<p>In this Andy(i) heavy episode, Andy Golding is joined by Andi Saitowitz, a business psychologist and mom of three. Andi shares her experience of navigating unexpected twists in life, including an unplanned and ectopic pregnancy and the decision-making process that followed.</p><p></p><p>From life before 2020 to the diagnosis and treatment, Andi's journey is a testament to resilience and surrender in the face of uncertainty. The conversation delves into the emotional journey of navigating uncertainty, preparing for surgery, embracing vulnerability, and the strength of surrender.</p><p></p><p>It also highlights the role of a mother, the journey of motherhood, and the concept of post-traumatic growth.</p><p></p><p>You can connect with Andi here:<a rel="noopener noreferrer nofollow" href="https://www.andisaitowitz.com/" target="_blank"> AndiSaitowitz.com</a></p><p></p><p>Takeaways</p><ul><li>Resilience in the face of unexpected twists</li><li>The power of surrender and faith in decision-making Strength in vulnerability</li><li>The power of surrender and support</li></ul><p></p><p>Chapters</p><ul><li>00:00 Navigating Unexpected Twists</li><li>08:53 The Decision-Making Process</li><li>24:36 Surrender and Waiting</li><li>30:18 The Strength of Surrender</li><li>36:01 The Journey of Motherhood</li><li>44:29 Post-Traumatic Growth</li></ul>yes00:46:0513Ectopic pregnancy & the curveballs of motherhood | Andi Saitowitz | I Thought This Would Be Simplerfull<![CDATA[Climbing Mount Kilimanjaro | Brad Shorkend | I Thought This Would Be Simpler]]>In this conversation Andy Golding and Bad Shorkend delve into the complexity of life and the challenges of climbing Mount Kilimanjaro. This episode explores the genesis of Brad's decisions to climb Mount Kilimanjaro, the importance of training and preparation, and reflections on the unexpected surprises of the first day of the climb.

The conversation covers the challenges and triumphs of climbing Kilimanjaro, highlighting the importance of shared purpose, teamwork, inner strength, and mental toughness. It explores the mindset shift, preparation, and the progression of the climb, culminating in the summit achievement and the reflection on the experience.

You can connect with Brad here: BradShorkend.com

Takeaways

  • Life is astoundingly complex
  • Preparation is key for mountain climbing, and even then - expect the unexpected.
  • Shared purpose and teamwork are essential for tackling hard challenges.
  • Inner strength and mental toughness are critical for overcoming obstacles and pushing through difficult situations, to access a deeper level of your capability.

Chapters

  • 00:00 The Complexity of Life
  • 06:30 Training and Preparation
  • 19:14 Reflections on Day One
  • 25:24 The Mindset Shift
  • 30:53 The Day of the Summit
  • 36:14 The Summit Achievement
  • 43:21 Shared Purpose and Inner Strength
]]>dd0468a2-a0d0-4a0d-ab62-f24aa4868b5eSun, 21 Jun 2026 09:03:18 GMT<p>In this conversation Andy Golding and Bad Shorkend delve into the complexity of life and the challenges of climbing Mount Kilimanjaro. This episode explores the genesis of Brad's decisions to climb Mount Kilimanjaro, the importance of training and preparation, and reflections on the unexpected surprises of the first day of the climb.</p><p></p><p>The conversation covers the challenges and triumphs of climbing Kilimanjaro, highlighting the importance of shared purpose, teamwork, inner strength, and mental toughness. It explores the mindset shift, preparation, and the progression of the climb, culminating in the summit achievement and the reflection on the experience.</p><p></p><p>You can connect with Brad here: <a rel="noopener noreferrer nofollow" href="https://www.bradshorkend.com/" target="_blank">BradShorkend.com</a></p><p></p><p>Takeaways</p><ul><li>Life is astoundingly complex</li><li>Preparation is key for mountain climbing, and even then - expect the unexpected.</li><li>Shared purpose and teamwork are essential for tackling hard challenges.</li><li>Inner strength and mental toughness are critical for overcoming obstacles and pushing through difficult situations, to access a deeper level of your capability.</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Complexity of Life</li><li>06:30 Training and Preparation</li><li>19:14 Reflections on Day One</li><li>25:24 The Mindset Shift</li><li>30:53 The Day of the Summit</li><li>36:14 The Summit Achievement</li><li>43:21 Shared Purpose and Inner Strength</li></ul>no00:47:58Climbing Mount Kilimanjaro | Brad Shorkend | I Thought This Would Be Simplerfull<![CDATA[Choosing not to have children | Nic Haralambous | I Thought This Would Be Simpler]]>Nic Haralambous and Andy Golding discuss the complexity of life choices, particularly the decision to not have children. They explore societal assumptions, pressures, and the perception of selfishness associated with this choice.

The conversation delves into the pressure to do more and the complexity of not having kids, challenging the perception that not having kids is 'simpler'.

This episode goes into the complexities of relationships, the impact of choosing not to have children, the decision to undergo a vasectomy, and the challenges of navigating life without children. It also explores the impact on relationships and the complexity of life choices.

You can connect with Nic here: nharry.com

Takeaways

  • Complexity of life choices
  • Societal assumptions and pressures and how the decision to have children or not has a profound impact on relationships and life choices.
  • Navigating life without children comes with its own set of challenges and complexities.

Chapters

  • 00:00 The Complexity of Life Choices
  • 09:43 Societal Assumptions and Pressures
  • 20:22 The Pressure to Do More
  • 27:40 The Evolution of Relationships
  • 35:36 The Decision to Undergo a Vasectomy
  • 42:06 Navigating Life Without Children
  • 50:21 The Complexity of Life Choices
]]>f2a84b32-fe3a-4e75-96f6-6594b91dde1fWed, 17 Jun 2026 16:45:37 GMT<p>Nic Haralambous and Andy Golding discuss the complexity of life choices, particularly the decision to not have children. They explore societal assumptions, pressures, and the perception of selfishness associated with this choice.</p><p></p><p>The conversation delves into the pressure to do more and the complexity of not having kids, challenging the perception that not having kids is 'simpler'.</p><p></p><p>This episode goes into the complexities of relationships, the impact of choosing not to have children, the decision to undergo a vasectomy, and the challenges of navigating life without children. It also explores the impact on relationships and the complexity of life choices.<br /><br />You can connect with Nic here: <a rel="noopener noreferrer nofollow" href="https://www.nicharalambous.com/" target="_blank">nharry.com</a></p><p></p><p>Takeaways</p><ul><li>Complexity of life choices</li><li>Societal assumptions and pressures and how the decision to have children or not has a profound impact on relationships and life choices.</li><li>Navigating life without children comes with its own set of challenges and complexities.</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Complexity of Life Choices</li><li>09:43 Societal Assumptions and Pressures</li><li>20:22 The Pressure to Do More</li><li>27:40 The Evolution of Relationships</li><li>35:36 The Decision to Undergo a Vasectomy</li><li>42:06 Navigating Life Without Children</li><li>50:21 The Complexity of Life Choices</li></ul>no00:51:5711Choosing not to have children | Nic Haralambous | I Thought This Would Be Simplerfull