Leading from the fear of regret
We’re all afraid of something. But what if we let our fear guide us to what really matters?
When we take the time to understand the source of the fear, we can also tune into what it’s asking of us.
A fear of loss might be telling us to appreciate our friends and loved-ones. A fear of loneliness in old age might be encouraging us to cultivate closer connections now. A fear of change might be pointing to a need for more adventure in our life.
And a fear of regret? For my guest on this week’s Fearless Forward podcast, Happy Startup School co-founder Laurence McCahill, that fear is a driving force.
For Laurence, the very thought of wasting talent, an idea, a dream, or a relationship – drives him to do the opposite.
“For many people, the fear of getting it wrong is greater than the fear of regret. But for me it’s always been the other way around. I’d rather get it wrong than not try.”
In my conversation with Laurence, I explore where all this comes from. The early-life and intergenerational influences that have guided his purpose and direction. Living most of those years above a pub – various pubs – in North London. And his father’s struggles with alcoholism.
Laurence grew up in a world full of warmth, music and belonging – and with conflict and addiction. The former helped him navigate the latter, and they still do.
Looking back on his relationship with his father, he’s taking forward not a polished lesson, but a practice of noticing what he’s inherited, keeping what feels true, and trying not to pass on what caused harm.
All this and more has informed Laurence’s need to build community – through the Happy Startup School he co-founded 14 years ago with his childhood friend Carlos Saba. Together they create spaces where people can feel more at home, be themselves, and be curious and open-minded.
“We create what we most need in the world, I believe. And one of the joys of this work [for me] is connecting great people and seeing what unfolds.”
If you’re looking for a story that’s inspiring and deeply human, I hope you’ll give this episode a listen.
This episode will help you:
- Hear how to prioritise long-term happiness, purpose, and genuine human connection over traditional corporate metrics when building a meaningful business.
- Discover how to create safe, human-centric environments that foster authentic relationships, trust, and organic collaboration among like-minded leaders.
- Learn to cultivate self-acceptance and trust in your own value so you can lead authentically without trying to fit into rigid industry expectations.
Highlights:
- [00:00:34] Introducing Laurence McCahill
- [00:01:55] Growing Up in a Pub
- [00:03:52] Navigating Conflict and a Father’s Temper
- [00:04:40] Early Career Disconnect
- [00:07:25] A Father’s Influence and Irish Heritage
- [00:09:12] Understanding His Father’s Struggles
- [00:12:36] Compassion and Hindsight
- [00:14:25] Conversations About the Past
- [00:18:10] Parenting with Conscious Intention
- [00:22:31] Creating Experiences Over Owning Things
- [00:25:28] The “Anti-Career” and Finding Purpose
- [00:28:46] The Problem with Traditional Networking
- [00:31:32] The Birth of the Happy Startup School
- [00:35:02] The Ongoing Quest for Happiness
- [00:39:08] The Joy and Frustration of Building Community
- [00:40:14] The Power of Trust
- [00:42:57] Facing the Fear of Loss and Regret
- [00:46:12] The Gift of Being Yourself
- [00:50:21] What “Fearless Forward” Means
Links:
- Laurence’s LinkedIn
- Website: The Happy Startup School
- TED talk: The Art of Being Yourself by Caroline McHugh
