S3 Episode 05 Kieron 'The Boy' Bailey : Recovering Loudly … Failure, Grief, and the Courage to Start Again

We Recover Loudly – Unfiltered Stories, Unapologetic Recovery

In this honest and powerful episode of We Recover Loudly, host Shell sits down with Kieron Bailey : a hospitality industry veteran, leadership coach, and creative disruptor! They explore his raw and relatable journey through recovery from grief, and professional collapse.
Kieron shares openly about growing up in a chaotic, and busy council estate home surrounded by siblings. He talks about his early passion for hospitality, with an early start in the world of pubs and restaurants, and how years of emotional suppression, career overdrive, and personal loss led to a turning point. From being the life of the party to losing his sense of purpose, his story is filled with brutal honesty, dark humour, and as to be expected from Kieron, lots of wisdom.
Together, Shell and Kieron unpack what it really means to recover from systems, roles, and identities that no longer serve us. They discuss the emotional toll of hustle culture, the importance of boundaries in leadership, and how redefining success means getting uncomfortable, taking responsibility, and learning to live with uncertainty.
Now focused on building psychologically safe workplaces and disrupting toxic leadership norms, Kieron brings deep insight into what it takes to rebuild — not perfectly, but authentically.
If you've ever felt burned out, stuck in a role that doesn’t fit, or like you’re holding it together on the outside while falling apart inside then this conversation is for you.
CONNECT WITH KIERON :

Instagram - @theboybaileyspeaks

https://www.linkedin.com/in/theboybaileyspeaks/

For more information on We Recover Loudly and to reach out for speaking engagements or support email [email protected]

@werecoverloudly
www.werecoverloudly.com

Chapters

1. Welcome and Introduction to Kieran Bailey (00:00:00)

2. Kieran's Journey in Hospitality (00:03:37)

3. Sibling Dynamics and Personal Growth (00:06:27)

4. Career Setbacks and Recovery (00:09:45)

5. Transitioning to Branded Hospitality (00:21:32)

6. Unexpected Encounters and Coffee Culture (00:27:46)

7. The Art of Hospitality (00:28:27)

8. Challenges in the Service Industry (00:29:33)

9. The Value of Upselling (00:31:46)

10. Balancing Kindness and Niceness (00:34:08)

11. Starting and Running a Business (00:36:27)

12. 39:19 Navigating Business Partnerships (00:40:14)

13. Personal Reflections and Accountability (00:41:35)

14. Dealing with Grief and Loss (00:54:06)

15. Living in the Hospital: A Son's Commitment (00:54:47)

16. PTSD and Rage After Loss (00:55:14)

17. Support from Chris During Grief (00:56:34)

18. Navigating Identity and Self-Worth (00:58:30)

19. The Power of Kindness and Compliments (01:09:44)

20. Turning Pain into Purpose (01:18:11)

21. Final Reflections and Gratitude (01:23:19)