How will work be weird in 2026?

Work is Weird Now is back — and we kicked off 2026 with our first live episode on LinkedIn. We sat down with award-winning journalist and future-of-work commentator Oliver Pickup to frame the year ahead.

Ollie brought seven big shifts shaping how work will feel in 2026 — from AI readiness and the graduate pipeline, to loneliness, side hustles, and the rise of “resenteeism.” The through-line: we’re entering a year defined by tension — between accelerating automation and a growing hunger for human connection, purpose, and trust.

Ollie argued that 2026 is landing at a pivotal moment. On one side: the “automate everything” energy coming out of major tech agenda-setters like CES, with talk of physical AI and robotics. On the other: a widening conversation about what we’re losing when we optimise everything — creativity, meaning, relationships, and agency.

His hunch (and hope): we’re seeing the early signs of a backlash against tech for tech’s sake, and a renewed value placed on real human work.

1) AI readiness: the promise vs the reality

We’re now years into the generative AI era — and yet many organisations still don’t know what to do with it.

Ollie shared that outside the tech sector, businesses may be far less “AI ready” than the hype suggests, with leaders often pushing adoption without investing in the workforce capability, learning time, or practical strategy required to make it work. The result is a disconnect:

• Leaders feel pressure to “use AI”

• Employees are left to figure it out alone

• Many initiatives struggle to show ROI (or even clarity on what ROI should mean right now)

We also talked about the cultural consequences of rushing: productivity theatre, distrust created by bot-heavy meeting culture, and a flood of synthetic content (“work slop”) that makes human authenticity more valuable, not less.

What we landed on: 2026 is a year for pause, focus, and workforce investment — not blind acceleration.

2) The graduate pipeline collapse (and why it’s personal)

This one hit home. Between us, we’re raising kids who are moving through a school system still selling a “traditional” pathway — while the labour market underneath it shifts fast.

Ollie shared a stark picture: entry-level roles are thinning, degree debt is huge, and businesses adopting AI are often being short-termist about talent pipelines. If early career opportunities vanish, we don’t just lose “junior jobs” — we risk breaking how future leaders learn.

That led us to a bigger question: if the old path isn’t guaranteed, what replaces it?

Ollie’s answer wasn’t “ditch education,” but double down on the human skills and truth literacy young people will need — and be honest that careers will be less linear, more fluid, more portfolio-shaped.

3) The six human skills that matter more now

Ollie named six “C” skills — once dismissed as soft, now increasingly the edge:

• Collaboration

• Communication

• Compassion

• Courage

• Critical thinking

• Creativity

He also shared a line we loved (via Minouche Shafik):
“Jobs were once about muscles. Then they were about brains. Next they’ll be about the heart.”

The warning underneath: if we use AI to imitate humans (rather than augment what only humans can do), we fall into a trap — chasing automation at the expense of the very qualities that make organisations resilient.

4) Loneliness at work goes mainstream

We moved from macro trends to something deeply human: connection is breaking down, and it’s showing up in the workplace.

We discussed the sobering reality that many people now report having no real friends at work, alongside wider social patterns: less going out, less community, more isolation — even while people still crave connection (sometimes expressed through memes, Slack culture, and “micro-moments” of shared humour).

The organisational challenge: loneliness isn’t just wellbeing; it becomes performance, retention, creativity, and trust.

What helps? Not forced fun. Not manufactured culture. But intentional environments:

• workplaces designed for different needs (including neurodiversity)

• leaders modelling connection

• teams brought together for real collaboration (not office days spent on Zoom)

• rituals and communities that help people “find their tribe”

5) Return-to-office tension (and what good looks like)

We’re both office advocates — when the office earns its place.

Ollie shared examples of companies investing in great spaces without harsh mandates — treating the office as a pull, not a punishment. But we also named the barriers that rarely get said out loud: commuting cost, lunch cost, and the fact that a “return” can feel pointless if it’s just a change of backdrop.

The takeaway: the future isn’t “remote vs office.” It’s designing work on purpose.

6) Resenteeism: staying, but mentally checking out

Quiet quitting had its moment. Now we’re seeing what Ollie called resenteeism: people staying in jobs (for stability, uncertainty, lack of alternatives), but feeling disconnected, frustrated, and directionless.

We also referenced wider engagement research pointing to how many employees don’t even know what’s expected of them — a huge leadership gap that shows up as low energy, low ownership, and “coasting.”

Our angle: this isn’t laziness. It’s often a broken psychological contract.

7) Learning velocity: the skill that changes everything

If there was one practical thread we kept coming back to, it was this:

People need time and permission to learn.

Not everyone needs to become an AI expert — but everyone needs the confidence to experiment, build capability, and stay adaptive.

We talked about small, doable approaches (like 15 minutes a day of AI play) and the leadership role in making learning real — because if learning only happens “after hours,” it won’t happen equitably.

The question we ended on

We asked the audience (and ourselves):

If a four-day week became real, what would you do with the extra day — and what’s stopping you now?

It sparked a bigger point: if AI gives time back, what do we want to do with that time? More scrolling — or more health, community, learning, creativity, contribution?

What you’ll take away from this episode

• Why 2026 will feel like a reset year: dialogue, trust, and purpose pushing back against pure automation

• How to think about AI as augmentation, not replacement — and why the “human edge” is growing

• Why the graduate pipeline matters to everyone, not just students

• How loneliness is becoming a workplace issue, not a private one

• What resenteeism looks like — and how leaders accidentally create it

• Why learning velocity is becoming a non-negotiable organisational capability

Learn more about Ollie Pickup and his writing on LinkedIn.