I use ChatGPT a lot.
Probably every day.
Running a small business means constantly jumping between completely different things — accounts, VAT, marketing, boats, technical problems, emails, contracts, weather, equipment and all the little questions that come with trying to do most things yourself.
ChatGPT is incredibly useful for that.
There are plenty of things I would previously have outsourced, spent hours researching, or simply put off because I didn’t know where to start.
Of course, you have to be careful. ChatGPT gets things wrong, sometimes confidently wrong, so I cross-check anything important.
But used properly, I think it is extraordinary.
What I hadn’t expected was for it to make me question how I was living my life.
A slightly strange experiment
A friend recently sent me a prompt.
It asked ChatGPT to look at everything it knew about me and identify my developmental “leading edge” — the thing about myself that I couldn’t quite see yet.
The instruction was deliberately provocative.
Don’t be nice.
Don’t tell me what I want to hear.
Look for the pattern beneath the pattern.
Tell me what is just outside the way I currently see the world.
I thought I’d give it a go.
Now, I’ve done quite a lot of therapy over the years and spent a frankly enormous amount of time reflecting on myself.
Why I work the way I do.
Why I burnt out.
Why I left corporate life.
What motivates me.
What kind of father and husband I want to be.
What success actually means.
So it takes quite a lot these days to present me with a genuinely new interpretation of myself.
I pressed enter without expecting much.
Then I started reading.
And stopped.
“You escaped the corporate cage, but you brought the operating system of the cage with you.”
That was one of the lines.
Ouch.
The argument was actually very simple.
For much of my adult life, if something matters, I learn about it.
I understand the system.
I prepare.
I get qualified.
I buy the right equipment.
I identify the risks.
I make a plan.
Then I take responsibility and get on with it.
That worked well in corporate life.
And it works rather well on boats.
But ChatGPT suggested something I hadn’t really considered.
Maybe competence wasn’t simply something I had.
Maybe I had made it part of who I was.
Its summary was brutal:
“I am safest, most valuable and most alive when I am competently making things happen.”
And then came the uncomfortable part.
Perhaps I had left one achievement system and simply constructed another.
I had swapped meetings, targets, bonuses and executive responsibility for boats, qualifications, ocean passages, refits, racing, houses, Navaia, volunteering and projects.
A much better life.
But perhaps powered, at least partly, by the same engine.
That really landed.
Freedom isn’t the same as optionality
There was another idea that stayed with me.
I like options.
I like understanding what might happen, knowing the alternatives and maintaining the ability to change direction.
ChatGPT made a distinction I hadn’t really considered:
Optionality says: “I could still become many things.”
Freedom says: “I don’t need to.”
For years I’ve talked about freedom.
Freedom from corporate life.
Freedom to sail.
Freedom to choose my work.
Freedom to spend more time with my family.
But perhaps another level of freedom is not needing to continuously turn that freedom into something.
Not every experience has to lead somewhere.
Not every skill has to become useful.
Not every boat needs improving.
Not every chapter needs another mountain at the end of it.
Perhaps sometimes you’re already there.
This is where ChatGPT became slightly frightening
Up to this point, ChatGPT had mostly felt like an extremely powerful tool.
This felt different.
It wasn’t giving me generic advice about work-life balance.
It was drawing connections between my old career, sailing, Navaia, racing, family, property, qualifications and even the way I deal with uncertainty.
It found a pattern underneath them.
And, frankly, it was pretty much spot on.
The response was long, detailed and comprehensive, but the themes were incredibly clear.
I read the whole thing once.
Then I had ChatGPT read it aloud to me.
When it finished, I played it again immediately.
Not because I hadn’t understood it.
Because I wanted to hear it again.
There were things in it that felt more specific and more immediately useful than insights I had reached after years of therapy and self-reflection.
That sentence makes me slightly uncomfortable to write.
ChatGPT isn’t a therapist.
It doesn’t truly know me in the way my wife, children or close friends do.
It only sees the parts of me that make it into conversations.
And it can be completely wrong.
But none of that changes the experience.
The mirror it held up was remarkably accurate.
“What if nothing needs to be next?”
That was perhaps the biggest theme.
I am quite good at “next”.
Next passage.
Next race.
Next boat improvement.
Next business opportunity.
Next project.
Even personal development can become the same thing.
Find the weakness.
Understand it.
Work on it.
Become a better version of yourself.
And then ChatGPT pointed out the irony.
I had effectively asked:
What is my next developmental level and how do I get there?
Which might itself be exactly the behaviour I needed to notice.
Perhaps there wasn’t another improved version of me waiting to be constructed.
Perhaps I didn’t need to endlessly upgrade myself either.
The sailing analogy
This is probably why the message resonated so strongly.
Good seamanship is largely about preparation.
Weather.
Tides.
Navigation.
Boat.
Crew.
Safety equipment.
Contingencies.
You do everything you reasonably can before leaving harbour.
And then you leave harbour.
At which point reality takes over.
The wind doesn’t care about your forecast.
The sea doesn’t care about your passage plan.
Something breaks.
The front arrives early.
The boat goes slower than expected.
Good sailing isn’t the ability to control all those things.
It’s having enough competence that you don’t need to.
You respond to what actually happens.
The phrase that stayed with me was:
“Competence without psychological dependence upon control.”
Perhaps that is just good seamanship.
Perhaps it is also quite a good way to live.
Then came the question that really hurt
ChatGPT gave me a thought experiment.
Imagine Navaia never becomes particularly big.
Bossy Boots never wins anything important.
Nobody particularly notices my ocean sailing.
My houses are simply houses.
My corporate career slowly becomes an anecdote.
There is no magnificent second act where everything suddenly combines into an elegant story proving why I left my old life.
Instead…
My marriage is good.
I’m close to my children.
I sail a lot.
I teach some people who remember me.
I race because racing is fun.
I fix ridiculous things on boats.
There are evenings at anchor when nobody needs anything from me.
I get old.
And eventually I die.
Nothing was maximised.
Nothing scaled.
Nothing proved anything.
Then came the question:
Was that life enough?
That question has stayed with me.
Because intellectually the answer is obviously yes.
The more interesting question is whether I actually live as though the answer is yes.
So what?
This is the bit that surprised me most.
I actually took the advice seriously.
Not in a dramatic way.
I’m still me.
There are still boats to fix.
There are still races I want to do.
I’m still running Navaia.
I’m still ambitious.
But something has shifted slightly.
I’ve noticed myself trying less hard to turn every experience into progress.
I’ve been a little less interested in what comes next.
I’ve been more present with my wife.
More present with the girls.
And strangely, that seems to have brought us even closer.
Not because I’ve introduced some clever new strategy.
Almost the opposite.
Less fixing.
Less improving.
Less needing the moment to become anything.
Just being there.
It is a small shift.
But it feels significant.
The bit that amazes me — and scares me
I still don’t quite know what I think about all of this.
Part of me finds it astonishing.
We have built technology that can take thousands of fragments of information, recognise patterns across them and produce an interpretation capable of genuinely changing how somebody sees themselves.
That’s extraordinary.
Another part of me finds exactly the same thing frightening.
Because if ChatGPT can do this now, where does it go next?
What happens when people begin outsourcing not just administration, research and writing to machines, but reflection, judgement and meaning?
There are huge questions around dependence, privacy, truth and the authority we give something simply because its answer sounds profound.
And occasionally ChatGPT produces complete rubbish.
That may be one of the most important points in this article.
But blindly dismissing it because it can be wrong seems as foolish as blindly believing it because it can sometimes be remarkably right.
Perhaps the interesting place is somewhere in between.
Curiosity without surrendering judgement.
Amazement without worship.
Caution without fear.
Use the tool.
Cross-check it.
Challenge it.
And every so often, perhaps allow it to challenge you back.
The original response ended with this:
“You already know how to leave harbour.
You already know how to navigate.
You already know how to make the boat better.
Perhaps what remains is to discover that there was nowhere you had to get to.”
I’m still thinking about that.
And perhaps, for once, that’s enough.