Mid-Season Review: Portfolio Careers, AI Anxiety & What’s Next

In this mid-season review of the Work Is Weird Now podcast, hosts Alice & Dan reflect on season five, one year of WIWN, and the ideas that keep resurfacing in the future of work conversation.

From Dan’s early “accidental” portfolio career (four-star McDonald’s badge included) to interviewing at Sainsbury’s after leaving corporate life, the episode explores how identity, income and purpose are becoming less linear and more layered.

The conversation moves from shift-based work platforms across Europe to the psychological freedom of “just doing your shift and walking away.” They also unpack AI’s double edge: creatively liberating, economically unsettling.

With thousands of listeners now tuning in across the US, Canada, Eur ...