I noticed a few things when I felt I was done with mainstream journalism.
I was going to media parties and meeting the same people, mostly older than me, complaining about freelance rates that had not moved in 20 years. They moaned about the food that was being laid on for them for free.
And in a room full of genuinely accomplished journalists, not one of them had ever really worked inside a business.
I'd absolutely loved journalism, but I needed to learn more about business before I could come back to it. I felt like I needed to get schooled.
So I left the newspapers behind, knowing I was also giving up recognition - and some brilliant travel opportunities.
That was the hard part - to get over my massive ego and leave that behind in pursuit of new learning that would be and was really, really tough.
Setting up shop
The first business I ran was in publishing. I was such a cocky twat when I started, only to be quickly humbled when I had to learn to sell.
This was 2007. Back then almost nobody was using WordPress or Twitter so I was early and I built audiences cheaply. Before long I had 50,000 people a month coming to a site I ran from my bedroom, and sponsors from global companies spending upward of £30,000 a month. As a news reporter I had been on £29,000 a year.
What struck me through all of it was that despite the pay grades, executives buckled when they had to tell their story. That set me thinking about the single most valuable piece of paper I could write.
The executive summary
I decided it was the executive summary on the biggest deal in London. There must be a billion-dollar deal being done right now. The problem was I did not know who was writing those summaries, or how I would ever get near one.
Now I do not believe in manifestation, but sometimes when you are turning a thing over in your mind, the world answers. A friend trying to sell his company called. He needed a journalist to look over a bid that would unlock a new valuation if he won. When I read it I saw he needed serious help. He subsequently won his deal.
After a couple of startups and a lot of failures, what I found when I got inside corporates was very simple.
Landing a deal came down to three things.
1 - Asking good questions.
2 - Listening properly to the answers.
3 - Telling a brilliant story for the audience.
Not so different from journalism.
I don't really know how it happened, but within weeks of the win I mentioned, one of the biggest technology companies in the world called asking me to do the same thing at a far larger scale. "Come and look at why we are losing," they said. "We aren't relevant in front of our clients any more and we are telling the wrong story."
It turned out to be a piece of deep cultural change. The company had been so successful for so long that it had leaned on its past, assuming it could keep selling the way it always had. The pitches were pretty bad. The decks looked like they were from 1991 and there was rarely a coherent story. The deals were worth north of £500m.
The company found it really hard to let go of the approach that had made them successful, and that was exactly the problem. They weren't thinking apps for CEOs, they were thinking 'how many people can we bill for?'. That's the tail wagging the dog. What the client wanted was control. They wanted relevancy for their customers. They wanted to know they were cutting edge and that it was driving growth.
The story is just the wrapper. The mindset was where the real internal change had to take place.
What makes a company relevant today?
So fast forward to today and ask the same question:
What makes you relevant and fit to land a deal in today's market?
It is still whatever the market wants - only that changes direction faster than a ping pong ball being smacked around a room by a wall of paint shakers on horse back.
The reason is AI.
Ask a buyer a good question on AI now and they often cannot answer it because so many companies do not actually know what they want from AI.
They know they are meant to want it, and that is not the same thing. Listen carefully and what you hear is hype they half believe, tangled up with a fear they cannot name.
MIT last year found that 95% of enterprise AI pilots produce no measurable impact on the bottom line, and that the failures are not about the quality of the models but about how badly they are fitted into the business.
Roughly 3 in 4 of those failures are organisational rather than technical. They fail because nobody asked the right question or told a story the organisation could follow.
Leadership is missing.
But that is your opportunity.
It does not help that many of the companies selling AI services have not yet done it for themselves. They have not worked out how to make their own business agentic, so their credibility is thin before they have said a word.
In order to lead ourselves, we have to let go of what came before. Even if it was brilliant and it worked. There is every possibility now that it is no longer relevant.
Take Perplexity's Computer. A year or even a month ago a vendor could sell a client an AI solution built around a single model and call that a strategy and it felt solid, proven, the safe thing to pitch.
Now Computer runs a whole stack of models at once, sending each part of a job to whichever model handles it best and pulling the results back together. The single-model pitch that looked like strategy last month looks thin this month.
Even OpenClaw, which everyone was raving about, is now overtaken by this.
And then take price.
A top tier AI model runs at around £200 a month, and for that you get a generous allowance on something genuinely good. It feels cheap for what you get. A bit like free cigarettes in a bar to get you hooked.
But everything you put through it travels through someone else's system and the moment you move to enterprise pricing you are paying per job, token by token, with the meter always running.
Some models feel built to swallow as many tokens as possible by padding their answers, and whether or not that is by design, you can spend a great deal to get very little.
Uber's own CTO admitted the company burned through its entire annual budget for AI coding tools in 4 months, and its chief operating officer then said out loud that he could not draw a line between all those tokens and any real rise in what the company actually shipped.
It's called tokenmaxxing.
And the moment AI gets expensive enough, employees start to look relevant again, because the cost of a human and the cost of a machine begin to converge.
So don't write yourself out of the story. Just be ready to adapt.
Anthropic has just filed to go public at a valuation near a trillion dollars, and plenty of people who watch this closely point out that none of the big AI firms can yet support themselves on the income they make, which is precisely why the valuations have to be so large.
While the work is cheap or close to free, people will use it in abundance. If the real price arrives, and a serious workload costs thousands a month rather than a couple of hundred, the maths flips, and hiring people may turn out cheaper than feeding the meter.
I would not write off the things that look finished. If the largest AI companies miss their numbers when they go public, the money that keeps them sprinting dries up, and the market tilts back toward open source and local models, delivered by the human-led technology companies that have been doing this for years.
What looks done today might not be...
Which brings me back to my point.
Relevance is whatever the market wants or needs. That market is going through a midlife crisis right now and has no idea what it wants.
But it will be back shortly - and it's your job to read and study enough to bring it through.
I know you thought you'd mastered your career - and in many ways you almost certainly have. But there's now some new stuff you have to take on board to be at the front of the pack.
The hardest part of staying relevant is the willingness to let go of the thing that feels comfortable - whether that's recognition, the pitch that always worked, the model you just bought or the price you assumed would work.
All of that is up for grabs.
The craft of asking, listening and telling the story survives all of it, precisely because it is loyal to no single answer.
Letting go of what once made you relevant feels like letting go of who you are. The only question that ever matters is whether you can bring yourself to move with it, before it decides it no longer needs you to.
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