AI changed the game you trained for.

How I won out after being laid off, what I got wrong and how to change the rules.

The Dark Room

I am exhausted and finally surrender to my body's demand for rest. On entering the bedroom, I turn off the light. The darkness is total; I freeze at the shock of it, silently cursing my poor judgment. A primal fear wraps around me like a cold fog from a misty marsh. I reach out, gingerly checking for the wall which I expect to be there and yet—nothing. Do I drop to a crawl and step back toward the light switch in humiliation, or continue?

One more step; then my heart stops as fingers brush against something totally unexpected. It is a chair, with clothes thrown over the back. Oh, I forgot. Relief floods in. I keep feeling my way forward until my toe smashes into the foot of the bed with a loud click.

Once the flashing stars and unspeakable words subside, I settle into what just happened. The wall, the chair, and the bed frame stayed where they were. Yet I panicked, my heart jumped against my ribs. In my defense, I allowed something older than me to sort them out: the grounding scent of lavender, the rough grain of wood against my feet, the head wrecking rhythmic creak of that loose floorboard that kept me going.

"Midway along the journey of our life

I came to myself in a forest dark,

for my true path was lost."

That is (my version) of Dante, opening his Commedia about seven hundred years ago, and it is a permanent mantra of mine . My night terror is nothing next to his exile. But when I reach out in the dark with no idea what is solid, his words return to me. That is exactly how it feels to work with AI these days.

When the rulers of Florence changed the game Dante loved and exiled him under threat of death, he didn't try to win on their terms. He didn't write in Latin, as serious writers of his day were required to do. Instead, he wrote in the vernacular Italian people actually spoke, using a rhyme scheme he invented to carry it.

He changed the carrier - the actual medium itself - so a different brain could receive the signal. He changed what the game was, and his poem helped make his native Tuscan the basis of modern Italian.

That is the Dante Move: and it is one that can be used again and again to thrive in this new Age of Experience. I cleave strongly to this term because it delivers new life to those of us who have been around a long time. Used wisely, it becomes straightforward to turn the tables on the pretenders who are stuffed with algorithmic bulshit. However it relies on a pearl beyond price - lived experience. This is the one thing to hunt for above all else.

So when the ground changes beneath you, and all seems lost, the person who comes out ahead is rarely the one working harder at the old game, or frantically fighting the algorithm. It is the one who changes the rules. Because Hell is an algorithm, and I have seen this play out before, in my career.

How to change Home Base

Changing the rules was not new to me. Years before my first startup, I was a sales director facing entrenched incumbents. We knew we could not win on their terms because they owned the customer's idea of what a good supplier looked like. I call that Home Base: the ground the buyer assumes the contest is played on, so every comparison starts there.

So we stopped playing on their pitch. We changed what Home Base meant and made the customer a new emotional promise. Thanks to an incredible team effort, we went from unknown to global leader in our sector in three years.

Working harder on an old pitch that has already shifted is a trap. If you look closely across history, every leap forward comes from someone who recognized that the ground had moved and refused to play on the incumbent’s Home Base:

• Visual Art — Pablo Picasso (1907): Rather than mastering 19th-century perspective, Picasso painted Les Demoiselles d'Avignon, breaking up form and space to view objects from multiple angles simultaneously. He changed visual art from representation to perspective.

• Music — Miles Davis (1959): After years in fast bebop, Davis recorded Kind of Blue, built on sparse modal scales rather than hyperactive chord changes. He stopped playing faster and gave soloists room to breathe.

• Artificial Intelligence — AlphaGo (2016): In Game 2 against Lee Sedol, AlphaGo played Move 37—a shoulder hit on the fifth line that human commentators called a mistake. It wasn't playing by human positional tradition; it calculated a new geometry for the board.

Each of them saw that the surface had shifted and stopped competing on the old terms.

Now, the machine is the incumbent. AI beats us at the old game: it answers faster, remembers more, and never tires. Competing with it on speed, volume, or raw output is playing on its Home Base. You lose.

So do not tell me you are funny. Make me laugh.

The Mistake: Confusing the Tech for the Ground

Despite losing my job, and with three young children to provide for, I was strongly against rejoining the corporate sector. So I set myself a challenge with a high success bar and decided that if I could succeed in that challenge I would have whatever it takes to go solo. The challenge I set was to secure and deliver 30 face-to-face CEO meetings over 30 days. This was around the time when the LEAN startup was published, and a new sense of independence and can-do was in the air.

To survive as a solopreneur, I needed to learn how to stare through the fog and keep going. I needed the skill of finding humans—engaging real decision-makers in ways that were raw, compelling, and immediate. It took tenacity, street smarts, a learned humility and a willingness to shut up and listen.

I passed the challenge. I thought that was enough.

Then came the mistake that took twenty months to burn through my pocket: I fell in love with the technology and took my eye off the human it was there to serve. I also got endlessly confused between the customer and the consumer of the service I was providing.

A hard lesson that will never grow old. A business dies from a lack of connection. A machine can draft an email, synthesize data, or generate a pitch, but it cannot sit across from another human being who is putting their livelihood on the line.

Changing the Carrier: Your New Rules

Many years on, fortified by experience, I am once again embarking on the solopreneur, in what I hope turns into the Age of Experience, where pretenders will be mercilessly uncovered, hiding behind their agentic engines.

Recently, I am bitten once again by the automation bug. I started using AI to automate my outreach, polish my thinking, and speed up my workflow. Without realizing it, I slipped right back onto the machine's Home Base. Decades of corporate sales-speak had dulled my natural voice, and relying on automated tools only buried it deeper under layers of the new synthetic "Latin." I was generating noise faster, but I wasn't connecting. Sleepwalking to the wood chipper, as the saying goes.

So where is all this going? That sudden shock in the dark was a wake up call, and so I have written down some lessons learned from my experience to date. Hopefully you can save a considerable amount of time and effort.

Learn from the past to reach the future, so to speak:

If you want to win in a world dominated by AI, you must accrue earned experience. It is waiting for you at the crossroads of skill and patience, and thereby you get to develop your personal Dante Move. You must abandon synthetic corporate speak and shift the game to the one domain AI cannot replicate: unfiltered human presence and critical verification. It hurts. Maybe it's meant to.

Go find some humans and practise.

Scanning for Cliche

Here is how my personal pledge today:

Rule 1: Trade Synthetic "Latin" for Raw "Tuscan"

Dante abandoned Latin to speak directly to the people. I learned that there is no escaping the ‘hard yards’, daily exercises in order to ground my humanity. I do this in part by running daily flow-writing exercises—writing without a single pause, non-stop for 10 minutes until my inner corporate censor expires from anxiety and “I” is the only voice left on the page.

I do not allow AI to write my thoughts, because even after many years of practice I still find myself prone to AI anxiety, a kind of ‘what would Claude say?”. I warmly embrace AI to handle administrative background noise, but I keep my outward voice unpolished, direct, and unmistakably human. When everyone else is publishing AI-generated consensus prose, authentic human vulnerability becomes a distinct competitive advantage.

Rule 2: Step Off the Machine’s Home Base ("Find Humans")

When I relied solely on networked tools, I was living in a digital nursery. Every time an AI tool delivers a strategy, an email, or a conclusion, I now force myself off the screen. I get up, walk around, and validate the insight by taking it to a real person. Building real-time human relationships is the ultimate Home Base advantage that no model can ever automate.

Rule 3: Touch It Before You Trust It (The "Lead the Witness" Test)

The sudden shock I experienced in that pitch-black room landed hard. I cannot always trust what appears to be obvious - that sense of being entitled to a given reality can be a trap; Now I often pause, ground and re-centre. Agentic AI is getting to the stage where it can re-write the paste, pre-judge a future, and this is as dangerous as a carbon monoxide leak. Learning to sense what delusion feels like is a super power that will only become more valuable with time.

So tonight, recall a sense of being lost and alone in pitch darkness. Pick a real decision you are facing.

Open your mind to two opposing outcomes and let them superimpose on one another. Stay open and rest by saying, today is enough, tomorrow will clearly let me know the direction I need to take.

If rest proves elusive and you feel that a swift answer is required, let that answer be “No”.

This is no simple homespun wisdom. The world is now changing at such a pace that things which loom large today may become irrelevant, literally, within weeks. It is an early example of what I am calling real-time living. Adjust your perspectives accordingly because this state of affairs is only going to accelerate. Get some rest.