Five Questions with_ Oliver Pickup

Hi Ollie, You took on several new ventures last year, launching both a new podcast and a newsletter. As we approach the first anniversaries of Go Flux Yourself and Upper Bottom (congratulations!), we wondered if you could tell us a bit about what the experience has been like. As a print journalist by trade, do you enjoy exploring other formats?

Thank you for the opportunity to feature as the opening guest of TFD’s 5 Questions With series. It’s a great idea and an example of the innovative and agile approach to content that we need. I would encourage it in a world where 90% of all online content in 2025 is likely to be synthetically generated by AI, according to Nina Schick. If you have so many pieces of content trained on other AI-written articles, average content will become lower in quality and less human. It’s like serving up margarine. I’m a full-fat butter person, for sure.

The experience of launching the two new ventures you mention has been genuinely liberating and enriching. Both Go Flux Yourself, the monthly newsletter I set up in January 2024 chronicling what I’m thinking and what I’m hearing in the tech and business space, and Upper Bottom, a weekly sobriety podcast I began a month later, came from my “AI-induced FOBO” – fear of becoming obsolete.

As a technology and business writer with a print newspaper background, I was conscious that AI would nibble my bottom line if I stood still, and relied on a business-as-usual approach. A chance tarot card reading in late 2023 (at a Turkish cafe while my car was being serviced) suggested exploring different communication formats and going out of my professional comfort zone. That advice has proven invaluable, leading to the newsletter and my podcast, which have become incredibly useful tools for connecting authentically with audiences.

These ventures have allowed me to be more human, more discoverable, and it’s been more fun for me, too, as I’ve learnt a lot. This process has helped to chisel my values (community, health, understanding, and interconnectedness – CHUI) and, in turn, made me focus on “human-work evolution”.

I’ve coined this term, human-work evolution, as I think the “future of work” so often considers humans an afterthought. It can often be too heavily focused on whizz-bang gadgets, and so many people in the tech space fall into the Turing trap, where we create technology that can pass the imitation game set by Alan Turing over 50 years ago. But, really, we don’t want technology to do what we do as humans. We want technology to do the things we can’t do, to plug those gaps, to make our lives easier. As author Joanna Maciejewka wrote a viral tweet in March 2024: “You know what the biggest problem with pushing all-things-AI is? Wrong direction. I want AI to do my laundry and dishes so that I can do art and writing, not for AI to do my art and writing so that I can do my laundry and dishes”.

More recently, I’ve also co-founded Pickup_andWebb , a thought leadership company helping businesses and their leaders stand out with human content. Additionally, I’ve added keynote speaking to my list of talents and am looking to take to the stage more in 2025. Please reach out if you are looking for a speaker, moderator, or podcast host.

You have spent years working for a number of national newspapers throughout your career - how have newsrooms changed during that time, and what do you think newsrooms will look like 20 years from now?

Throughout my career, I’ve witnessed the remarkable evolution of newsrooms. I started at The Observer sports desk 20 years ago, and it certainly feels like a different era. With it being a Sunday paper, the staff didn’t head into the office until Thursday, having been off since Saturday. The sports editor would constantly have horse racing on the TV, and it was very boozy – Fleet Street was famous for that culture.

The last newsroom I worked in about a decade ago was an open-plan office with a command-and-control hierarchy. Since then, it’s been incredibly challenging for media organisations, particularly newspapers, following the advent of the Internet. The traditional business model has been completely upended – essentially, most newspapers are now just managing decline because they haven’t worked out how to organise the advertising model effectively.

I’m part of the problem: apart from my Financial Times Weekend subscription, I can’t recall the last time I bought a newspaper – it must be two years or more. The situation has led to an explosion of clickbait content, making life even more difficult in our post-truth world.

As Mark Twain supposedly said: “If you don’t read a newspaper, you’re uninformed; if you do read the newspaper, you’re misinformed”; This feels particularly relevant today, where we’ve seen the damage caused by misinformation, not least during the Coronavirus crisis. It makes me somewhat ashamed to be a member of the media, given some of the mistruths peddled during that period that we’re still struggling to deal with.

Looking ahead 20 years, while AI agents will handle much of the admin work, there will always be a place for authentic journalism. However, we’re seeing concerning trends, particularly in local journalism. Cities and towns are losing their local news outlets, though it’s heartening to see publications like The Mill and The Londoner starting to gain momentum. For a while, crucial local stories were going missing, and that truth – so valuable to communities and society–was absent, leading to growing mistrust.

Perhaps we won’t even have physical newsrooms in 20 years – I don’t see why you’d necessarily need them when modern communication technology enables remote command-and-control style leadership. The bigger question is how to maintain journalistic integrity and teach the next generation, including my own children, to navigate news consumption in this post-truth world. The key, I believe, is to remain curious and question everything.

As a journalist committed to covering the future of work, what impact do you think emerging tech such as agentic AI is going to have on the way humans work and collaborate?

There’s no question that AI will change things fundamentally – it already is, though perhaps we just don’t know it yet. As William Gibson famously noted: “The future is already here – it’s just not very evenly distributed.”

We’re seeing glimpses of both the positive and concerning aspects of AI. One development that particularly worries me is how AI is creating and accelerating a desire for faux relationships. There’s been an astronomical rise in AI girlfriends and boyfriends, particularly among young people. This trend towards artificial relationships is genuinely concerning for society.

Take Jensen Huang’s vision for NVIDIA, which was announced in October – he wants a workforce comprising 50,000 humans and 100,000 non-humans, essentially AI agents. While that might sound desirable to some, there are significant seen and unseen consequences to consider. For instance, what permissions do you grant those non-human workers? There are serious safety and security implications we need to think through carefully. Moreover, what does this mean for human workers? For remote working? For those vital water-cooler moments? For workplace loneliness?

We’re facing a loneliness epidemic, and that’s the biggest threat AI presents. People talk about how technology and AI will democratise access to technology – the bar is being lowered constantly, and we’re now in the no-code era. That’s brilliant in theory, but it feels as though those who invest time and energy in AI now – whether learning better prompting techniques or creating custom GPTs – will become part of what some call the ‘AI class’.

I’ve been exploring this myself, not because I necessarily want to be in that class, but because there’s likely to be a gulf of knowledge developing. As they say, better the devil you know.

What is the best part of your job?

The best part of my work is its constant evolution. I started as a sports journalist, but since having children, I’ve become fascinated by what technology means for their future in an increasingly digital world. This drives my curiosity and powers my investigation of these topics. I’m constantly learning and being stimulated, all while ensuring we don’t leave humans behind in this technological revolution.

Looking ahead to 2025, I’m excited to collaborate with organisations and individuals who share my passion for human-centred innovation. Whether through thought leadership consulting with Pickup_andWebb, keynote speaking engagements, or new podcast ventures, I’m committed to exploring how we can harness technology while preserving what makes us uniquely human.

I’m particularly keen to engage with audiences about human work evolution and how businesses can improve this process in meaningful, sustainable ways.

And finally, for any PR professionals reading, we wondered if you could tell us how you source your stories as a freelance journalist, and when the best time is to pitch you a story?

When I started out in journalism over 20 years ago, we had a firm rule: you needed at least two primary sources for any story. That principle was instilled in me early on, and it remains crucial today - perhaps even more so in our post-truth world.

Journalism has had a rough reputation in the last decade because the Internet has completely changed the business model. The constant pressure for clickbait articles that generate more hits has sometimes led to less rigorous sourcing and fact-checking. We saw this during the pandemic, where claims were sometimes exaggerated or not scrutinised as thoroughly as they should have been.

As a freelance journalist, you’re only as good as your last piece of work. That’s why I believe it’s critical to interrogate sources properly and always go to the primary source – whether that’s conducting an interview or accessing original data rather than relying on quoted statistics. This commitment to truth is essential for society and communities, particularly as we navigate an increasingly AI-driven world.

When’s the best time to pitch a story? Whenever, really. If the angle is strong enough and interesting enough, I’m always ready to listen. But I’d emphasise the importance of authenticity and originality. With 90% of online content predicted to be AI-generated by 2025, there’s never been a greater need for genuine, well-researched stories that offer real insight rather than just recycled content.

For PR professionals specifically, I’d recommend focusing on stories demonstrating genuine impact or innovation in human-work evolution.