Layla Shaikley has built an unusually nonlinear career. She completed gruelling studies in architecture (twice!) with the objective of contributing to post-war reconstruction of Iraq. She was an unlikely candidate for programs at NASA and MIT but got herself in anyway. She then landed her dream job at UN Habitat, went to Iraq to work on the reconstruction and decided it wasn't the right role for her. She went on to co-found a successful tech company Wise Systems and become a writer and creator with a huge following on multiple platforms.

Along the way she has had to navigate stereotypes, rejection, public scrutiny, and the pressure to fit into other people's ideas of who she should be.

In this episode we talk about:

• What boredom taught her about creativity
• Overreach and applying for things you're "not qualified" for
• Rewriting the stories people make up about us
• Learning to tolerate rejection and embarrassment
• Walking away from a dream job, and choosing what not to become
• Confidence, Capacity, and Creating more "surface area" for luck

Mentioned in this episode

• "How to Increase Your Luck Surface Area" by Jason C. Roberts
• "The Red Sneakers Effect" by Silvia Bellezza, Francesca Gino and Anat Keinan, Journal of Consumer Research.
• "The Surprising Lessons of the 'Muslim Hipsters' Backlash" by Layla Shaikley, The Atlantic
• "The cost of success is embarrassment" by Layla Shaikley
• The Confident Mind by Dr. Nate Zinsser
• The Stimulated Mind by Dr. Tommy Wood
• Tiny Experiments by Anne-Laure Le Cunff

Follow Layla

• Substack: laylool.substack.com
• Website: laylashaikley.com
• Instagram and TikTok: @laylool

Chris Connors takes us from a childhood in Belfast during the Troubles, through his career as part of an award-winning fashion design team in the late-nineties London fashion scene, to the painful losses that sent him on spiritual journey and new career path.

We talk about:

• Growing up in a war and what constant fear does to a young nervous system
• Burning his suit after a year in advertising, and what came next
• Grief, PTSD, and the difference between suffering and our attachment to it
• Holding many identities at once and the absurdity of linear thinking
• Why the linear career is a fiction, and what our right brain is worth in an age of AI

Follow Chris's Work:

• Chris's site: chrisconnorscc.com
• OPO: opo.world
• Chris on Instagram: @christopherconnors
• Slow Academy at Flussbad Campus, Berlin: flussbad.com

Join the Conversation:

Instagram: @myunlikelycareer

Substack: myunlikelycareer.substack.com

Ahmed Rashad has built his career by chasing interesting problems and betting on the right people. From an oil rig in the Gulf to studying at MIT to joining the rocketship, Scale AI, in Silicon Valley, his path has never been predictable or planned. Along the way, he's learned to trust his intuition, take the right risks, and move on when comfort starts to feel like a trap.

We talk about:

• How to take the right career bet and evaluate risk
• Importance of building intuition from making mistakes
• Dangers of outsourcing your thinking to AI tools
• Knowing when stability starts to feel like a trap
• What curiosity and obsession actually look like in practice

Follow Ahmed's Work:

• Perle AI: perle.ai
• Linkedin: linkedin.com/ahmed-rashad-perle

Join the Conversation:

Instagram: @myunlikelycareer

Substack: myunlikelycareer.substack.com

Former VP of Talent & Insights at Index Ventures, Dominic Jacquesson shares his remarkable journey from publishing to tech and venture capital and the decision to leave it all behind to become a student once again, now in his fifties. His story is a powerful reminder that the dreams and curiosities we carry through our lives don’t have to be left behind and that the path we take along the way can help make them possible.

We talk about:

• Following your curiosity throughout your career
• Creating the conditions to pursue your passions
• Making a career pivot later in life
• And some big questions around consciousness, AI, and what comes next

Follow Dominic’s Work:

• Dominic at Index Ventures: indexventures.com/team/dominic-jacquesson/
• Scaling Through Chaos: indexventures.com/scaling-through-chaos/
• Rewarding Talent: indexventures.com/rewarding-talent/

Join the Conversation:

Instagram: @myunlikelycareer

Substack: myunlikelycareer.substack.com

Bella Pollen began her career at nineteen as a self-taught fashion designer, founding her own label and becoming one of Britain’s best-known young designers. She later reinvented herself as a journalist and novelist, writing for publications including Vogue, The Financial Times and The Observer, and publishing five novels, among them the bestselling Hunting Unicorns and the critically acclaimed The Summer of the Bear.

Her work has increasingly taken her beyond the worlds of fashion and literature. After first visiting Afghanistan in 2013, she became deeply involved in education for Afghan girls as the cofounder and UK trustee of 30 Birds Foundation, supporting Afghan women and girls through education, mentorship and opportunity.

Bella has followed an instinct for finding possibility in unexpected places. Her story illustrates that even though our lives and careers may not always go to plan, we can use what we learn along the way to achieve more than we ever imagined possible.

We talk about:

• Career reinvention and adaptability
• The importance of resilience and hard work
• Balancing motherhood and entrepreneurship
• Lessons learned from success and failure
• The impact of personal values on professional choices
• The significance of community and responsibility

Follow Bella's Work:

• 30Birds Foundation: 30birdsfoundation.org
• Jonah X Projects - jonahxprojects.org
• Bella’s Website - bellapollen.com

Join the Conversation:

Instagram: @myunlikelycareer

Substack: myunlikelycareer.substack.com

© 2026 Unlikely Careers. All rights reserved.

Welcome to My Unlikely Career. In this podcast, we share honest conversations with people who followed their intuition and built non-linear career. These are stories of courage, reinvention, and redefining success on your own terms.

This trailer introduces the vision behind My Unlikely Career and what you can expect from the show. If you've ever questioned your chosen path, wondered about changing direction, or simply love hearing remarkable human stories, you're in the right place.

Subscribe now and join us twice a month for new episodes.