How Will Work Be Weird in 2026?
A live conversation with Oliver Pickup
Season 5 Kickoff of Work Is Weird Now
Work has never been stranger, and 2026 is shaping up to be the year everything breaks, accelerates, or mutates. To launch Season 5 of Work Is Weird Now, we’re going live with award-winning future-of-work journalist Oliver Pickup to explore the trends set to define (and disrupt) the year ahead.
Ollie brings seven big provocations:
1. The AI readiness reckoning
Three years after ChatGPT, only 28% of organisations outside tech are prepared for AI. In 2026, the gap between AI-enabled teams and everyone else becomes impossible to ignore.
2. The collapse of the graduate pipeline
Entry-level jobs requiring degrees are down 67% since 2022. With university pathways costing £53k and offering diminishing returns, what replaces the old system?
3. Loneliness goes mainstream
40% of workers have no friends at work. Meanwhile AI companions are exposing millions of conversations. When do organisations finally treat human connection as a performance issue?
4. Resenteeism reaches breaking point
93% of workers are frustrated, yet only 4% are quitting. People have been planning “revenge quitting” for 13 months. Does the dam finally break in 2026?
5. Learning velocity becomes the new competitive advantage
77% of AI users are self-taught. Leaders who model learning and create space for experimentation pull away from those who simply roll out tools.
6. The side hustle economy matures - or collapses
57% of Gen Z have side hustles, increasingly for survival, not passion. Does this evolve into true portfolio careers, or does economic pressure push people back into traditional work?
7. The four-day week stalls (again)
Even with overwhelming evidence of success, structural resistance holds the four-day week back. In 2026, the tension between what works and what organisations actually do becomes harder to ignore.
What you’ll get from the session
A clear, unflinching look at the forces reshaping work in 2026
Practical insights for leaders, teams, and individuals
A live audience Q&A
A first look at Season 5 of Work Is Weird Now
About Oliver Pickup
Oliver Pickup is an award-winning journalist specialising in technology, digital transformation, and the future of work. His writing appears in the BBC, The Economist, WIRED, The Times, and more.
Tuesday, 13th of January, 2026 at 12:30 pm (GMT)
Live on LinkedIn