Podcast Episode 37: From Banking to Tailoring...to Teaching

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From boring invoice processing to bespoke tailoring, from extras work on film sets to teaching maths in schools, this episode has it all. Multiple career changer Neil O’Dwyer shares the unlikely chain of events that turned a “sensible” banking career into a life full of creativity, variety, and bold reinvention. Neil’s story is a masterclass in what happens when you stop forcing yourself to stay on the wrong path.

Neil explains how a chance catch-up with an old friend in tailoring opened his eyes to tangible, hands-on work, why networking and saying yes kept leading to the next opportunity, and how one small creative experiment eventually reshaped his whole career. You’ll discover how Neil worked his way through London on tiny budgets, side jobs, and sheer resourcefulness, and how teaching unlocked confidence, public speaking, and the skill of storytelling.

If you feel stuck in a safe job that pays the bills but drains the life out of you, this episode is for you. Neil’s path proves that the next opportunity often comes from the last one you almost didn’t take, and that a messy, unconventional route can still lead somewhere meaningful. This is essential listening for anyone craving a more creative, varied, and self-directed career.

Listen to the episode below via Spotify. Also available on Apple Podcasts, or you watch the conversation on YouTube.

Alice Stapleton

About Alice

Alice offers Career Coaching for those in their 30s & 40s designed to help professionals feel less stressed (through somatic and nervous system regulation tools), as well as helping career-changers gain a clear vision of what career is right for them, and how to achieve it. She is also an accredited Coach Supervisor, and host of The Career Change Diaries podcast.