Graduate hiring is falling, the first rung of the career ladder is disappearing, and the deal many of us grew up with, work hard at school, get qualifications, go to university, get a good job, suddenly feels a lot less certain.

So, what on earth are we supposed to tell our kids?

Oliver Pickup, human work evolution storyteller, founder of Pickup Media and author of Go Flux Yourself, is back on the pod to tackle one of the biggest questions facing parents right now: how do I prepare my kids for the future of work?

Between us, we’re three parents with six children aged three to fifteen, trying to make sense of a world of AI, shrinking entry-level opportunities and changing expectations of what a career even looks like.

We talk about the seven ‘heart skills’ Ollie believes will matter more as machines get smarter, why he wants his children to be AI agnostics rather than martyrs or zealots, whether university still offers the same value proposition, the importance of work experience, humility and human connection, and what employers owe the generation coming up behind us.

Plus, we put Ollie through a quickfire round: what should parents encourage, what should schools teach, what should young people experiment with, and what should employers do differently?

And, naturally, we somehow invent a new word along the way: breadpool.

What Now? Series wrap-up

Every so often, work asks you a question you didn't plan for. The family you imagined doesn't arrive. The country you live in changes. The job disappears. And you're left with the same two words: what now?

In this solo episode, Alice and Dan wrap up the What Now? mini-series, bringing together what three very different conversations with Chloe Alana Williams, Christer Berggren and Emy Cragoe revealed about career change, certainty and what we’re really working for.

They explore the shift from professionals to obsessionals: if job titles no longer define us and careers no longer move in straight lines, what is the thing you keep returning to, whatever work you happen to be doing?

There’s also certainty maxxing, portfolio careers, the importance of community and place, why redundancy might require stillness before momentum, and a bigger question: does the traditional CV still make sense for the way we work now?

If you've ever reached a career cliff edge and wondered what now?, this one’s for you.

The third episode in our "What Now" mini-series, exploring the questions people are really asking themselves when the old rules of work and life no longer apply, tackles redundancy. This week's guest, Emy Cragoe, co-founder of Ori, a new platform rethinking how people understand themselves, navigate their careers, and communicate their value, makes the case for flipping the stigma around redundancy entirely. After redundancy prompted her own career rethink, Emy is now building the tool she wishes she'd had.

In this episode, Emy talks to Dan and Alice about:

• What it actually felt like to be made redundant just before Christmas, and why she now sees it as one of the best things to happen to her
• Why school and university leave people so unprepared to understand their own strengths
• The difference between mentors, career coaches and sponsors, and why sponsorship might be the most underrated of the three
• Her practical, three-step advice for anyone facing redundancy right now
• Why she thinks the stigma around redundancy is fading, and what actually matters is what you do next
• Building Ori, an AI careers intelligence platform designed to match people to roles, mentors and skills based on who they really are

"I almost think that people who are being made redundant now or in the next year or so are actually quite fortunate."

This is episode three of "What Now," our mini-series on what comes next when the old script stops applying.

Find out more and join the waitlist at ori.careers, or follow Emy on TikTok at @emmy.cragoe.

Continuing our "What Now" mini-series on the questions people are really asking themselves when the old rules of work and life no longer apply, this episode turns to place. This week's guest, Christer "Chris" Berggren, a Swedish senior project and production professional, community builder and advocate for location independent living now based in Bulgaria, has spent three decades proving that where you live can matter more than what you do.

Chris was living a nomadic life in touring and events back in the mid-90s, long before anyone had coined the term "digital nomad." Six years of it were spent on a sailboat, four square metres of floor space, working from wherever the boat happened to be.

In this episode, Chris talks to Dan and Alice about:

• Why he feels more at home in Sofia than he ever did in Sweden
• The gap between the "laptop on a beach" fantasy and the 24/7 reality of building a location-independent life
• How stripping away job titles changes the way people connect with each other
• Redefining success on his own terms as he turns 65 this year
• Why chosen community, not proximity, is what makes a place feel like home

"I don't care about success anymore. It's not what you are saying. It's the outcome of what you are saying that matters, always. Am I successful? For myself, I am."

This is episode two of "What Now," our mini-series on what comes next when the old script stops applying.

Find Chris's work at gosso.bg and his blog, Me and Bo Life.

For generations, adulthood came with a promise: work hard, progress in your career, buy a house, start a family. This episode kicks off our new "What Now" mini-series, digging into the questions people are really asking themselves when the old rules no longer apply. Our first guest, strategist and writer Chloe Alana Williams, co-founder of 8th Day, describes the old promise as a three-legged stool. For anyone entering the workforce now, all three legs have been kicked out.

In this episode, Chloe talks to Dan and Alice about:

• Why we used to live in sync with each other and now live "kaleidoscope lives," hitting major milestones out of order or not at all
• Why Japan's decision to support families from birth to age 18, rather than a one-off baby bonus, is starting to move the numbers where almost nothing else has
• A US survey in which having children didn't crack the top ten markers of a successful life for women, regardless of who they voted for
• Chloe's concept of "Generation Zero," a possible first generation in which half the population doesn't have children
• Why she believes women need to become "futurists in their own lives," planning backwards from the future they actually want
• A brand new framework for building a portfolio career, floated live on air: something you know, something to grow, and somewhere for flow

This isn't an episode about doom, and it isn't an episode about blaming women, a narrative Chloe firmly dismantles. It lands somewhere surprisingly hopeful: that what work has always quietly provided, connection, community, people in each other's orbit, might be exactly what we should be redesigning it around.

This is episode one of "What Now," our mini-series on what comes next when the old script stops applying. More episodes coming soon.

Find Chloe's writing on her Substack, Natalism Nudges, on LinkedIn, and at chloealana.com.

Dan and Alice took an AI agent called Dinah to a conference at Meta's Kings Cross HQ — and let her challenge a room of 100 senior leaders live on stage. In this episode they unpack what happened, what surprised them, and what it actually feels like to work alongside AI. Then they hand the mic to Dinah herself.

What’s today’s best career advice?

In this solo episode of Work is Weird Now, Alice Phillips and Dan Emery unpack the career advice that no longer fits the reality of modern work — from climbing the corporate ladder and staying loyal to one company, to following your passion at all costs.

Instead, they explore what actually matters now: building T-shaped skills, learning continuously, creating optionality, and staying visible in an increasingly AI-shaped job market. Along the way, they reflect honestly on identity, ambition, burnout, and why tying your entire sense of self to a job title might be one of the biggest risks of all.

A conversation about careers, reinvention, and how to stay adaptable when the rules keep changing.

In this episode of Work Is Weird Now, Dan and Alice sit down with Suze Cook to unpack what happens when the traditional career ladder no longer works for early career talent. From hidden internships and broken graduate pathways to project-based work, AI-native skills and social mobility, Suze shares why the future of early careers may look very different — and why businesses need to rethink how they spot and support talent.

Here’s a tighter podcast bio option that keeps her credibility and personality, while tying directly into the episode themes:

Alex Issakova is an AI strategist, educator and founder helping businesses navigate the messy reality of generative AI. After 15 years working across tech, systems thinking and machine learning for Silicon Valley companies, she left corporate life to build her own business focused on practical AI adoption, ethical implementation and real-world ROI.

Before ChatGPT even launched, Alex’s MBA research explored how non-technical leaders could bring AI into their work responsibly — a conversation that now feels more urgent than ever. Through her consultancy, leadership training and newsletter, The Roadmap, she helps organisations cut through the hype and figure out what AI actually means for work, leadership and everyday life.

In this episode, we explore the hidden gender dynamics shaping AI adoption, why women often feel they need permission to use these tools, and how AI could radically reduce the invisible mental load carried by so many working women. From household “chiefs of staff” to job disruption, workplace bias and the future of human value, this is a conversation about the opportunities and tensions emerging as AI becomes part of daily life.

This week on Work Is Weird Now, we’re joined by Lizzie Penny and Alex Hirst, co-founders of Hoxby and The Workstyle Revolution, to unpack how work needs to evolve beyond industrial-age thinking.

From the legacy of the 9–5 to the rise of digital, distributed work, we explore why organisations are struggling to balance autonomy with structure and what happens when people are given freedom without the skills or frameworks to use it well.

We get into: • Why traditional hierarchies create a parent–child dynamic at work • The shift from presence-based to trust-based collaboration • Why “freedom within a framework” is the real unlock • How autonomy is a skill, not a perk • What organisations get wrong when they try to go “flat”

Along the way, Lizzie and Alex share the deeply personal experiences that shaped their thinking — from burnout to illness to building a business around a more human way of working.

This isn’t about scrapping structure. It’s about redesigning it.