Live Like Pirates

Discover why we need to ‘Live like Pirates’ after this notice…

Live Like Pirates – Clarity Is Not Coming First Anymore

I did not expect a pirate party to teach me anything beyond how committed some adults are to a bad pirate accent. But there we were, sixty people in costume, to live like pirates, escaping reality and hunting for a map to Willie’s hidden treasure, when it hit me. We are living through a strange moment where the old maps do not match the coastline anymore. You can feel it in politics, in work, in relationships, in the way everyone seems tired in their bones. And when the coastline changes, the only thing left is navigation.

I know. It sounds dramatic. Possibly ridiculous. But hear me out.

I am not usually a fancy dress person. But it was the celebration of a close friend’s joint birthday, so I said yes to ‘live like pirates’ for a day, with a pirate themed murder mystery. And honestly, it was a lot of fun.

Suspicious side eye across the bar. People taking character roles way too seriously. The whole event was built on one premise: you do not get all the information upfront. You are given partial clues, mixed signals, and your own assumptions. Then you beg, borrow, and steal your way through conversations, trying to work out who did it, while stacking up as much cash as you can along the way.

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Clarity is not coming first this time. It comes after motion.

Gregg the Artivist

What surprised me most was how quickly it cut through the usual small talk.

Instead of the normal polite scripts, it gave us a shared mission. A reason to talk, to listen and to pay attention. And somewhere between the fake murder and real life conversations, about work, burnout, money stress, meaning, relationships, uncertainty, our whole messy existence, I realised we don't know how to live like pirates.

Most of us are trying to navigate the future like it is a well lit path with clear signs and a map marked with an X.

Yet, we are all acknowledging that the future feels more like the ocean. Salty fog, crashing waves, sudden storms, shifting currents and a horizon that refuses to sit still.

So why are we still acting like clarity is a requirement before movement?

The old deal we were sold

As I reflect on this, I keep coming back to the contract we were raised on. The one that goes something like: Be productive. Be sensible. Work hard. Plan well. Do the right steps in the right order. Then you get certainty.

Or at least, you get the feeling of certainty. Which is what we were really chasing.

School trained us to believe there is a correct answer. Work trained us to believe our value is measurable. Culture trained us to believe busyness is virtue and idleness is suspicious, or at the very least, laziness.

Even our language gives it away. In small talk situations, I continually catch myself asking:

What do you do? What are you working on? What is next? and What is your plan?

They are meant as questions of engagement. Genuine curiosity. But it is also worth asking: whose script is this? Why is this the default way we measure a human life?

So when we find ourself 'off map' and feel as if we are in the ocean, we do what we were trained to do.

We grip harder. We plan more. We optimise. We push.

And I am sure I am not just speaking for myself when I say we tell ourselves: if I can just get organised enough, consistent enough, productive enough, I will regain solid ground. But the ground is not solid. Not right now. And maybe it has not been for a while. We are just waking up to it.

Back to the party for a moment. On arrival a friend of a friend greeted me with: “Hey, Gregg the Artivist. I’ve been listening to your podcast.” It is always a nice surprise, and it also makes me weirdly nervous. I never quite know what to say beyond, “Oh wow, thank you.” The reason I mention it is this: today’s article ties closely to an early episode of Rewrite Reality, S01E06, Living with Uncertainty. If you want the audio version of this theme, you might like to listen here:

Rewrite Reality S01E06 Living with Uncertainty

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The new reality: clarity is not coming first

At the party, I caught myself saying something like: we need to live like pirates because we are living through a transition where the old maps do not match the coastline anymore. It helped that my character was a pirate geographer, which is a sentence I never expected to write in my life.

We were talking about how politics feels reactive. Systems feel overstretched. Institutions feel slow. People feel exhausted. Every week brings new inputs, new threats, new distractions, new reasons to feel like you are behind.

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Productivity is doing things to maintain an identity. Purposeful is doing one thing that reduces confusion.

Gregg the Artivist

And I realised something important. When that is your environment, waiting for certainty becomes a trap. Because certainty does not arrive. And the longer we wait, the more anxious we get.

Then our brain does the thing it always does when it feels unsafe. It tries to regain control. And in our culture, and definitely in my own habits, control often looks like productivity.

So we end up in this loop:

Uncertainty makes us anxious. Anxiety makes us chase productivity. Productivity becomes identity. Identity becomes a prison. Then we burn out and wonder what is wrong with us.

And we are convinced something is wrong with us, when nothing is. We are responding normally to a world that is not giving the kind of stability we were promised. This is why I keep coming back to this thought:

Clarity is not coming first this time. It comes after motion.

And I cannot stress this enough: I am not talking about perfect motion. Not heroic motion. Not the kind of motion that proves you are special. Just the next honest step.

Productivity and identity: the quiet addiction

Whether we like to admit it or not, we are addicted to a lot of things. Here is another uncomfortable belief I have come to hold as true: A lot of productivity is not about contribution. It is about identity maintenance.

It is a way of saying: I am still a good person. I am still relevant. I am still safe. I still belong. It is a way of outrunning the feeling that if you stop, you will collapse. Or get lost. Or become nothing.

This was one of the big takeaways from my own burnout.

When you have been trained to equate output with worth, slowing down can feel like disappearing. When you live in a system that turns humans into metrics, rest can feel like rebellion. When the future looks unstable, planning can feel like prayer.

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I'm finding purpose is more often small and slightly unglamorous.

Gregg the Artivist

So when someone asks, why do you think you have to be productive, you can feel the truth in your bones before you can explain it in words.

Because without it, who am I? Because I need money. Because I am scared. Because I have been conditioned. Because I do not know what comes next, and I want to feel in control.

At some point, I think I saw this as weakness.

Now I think it is simply human. But here is the problem.

If productivity is holding your identity together, then uncertainty becomes unbearable. Because uncertainty threatens the very thing you are using to feel okay.

So we need a different anchor. Not less ambition or care or action. Just a different way of relating to action.

Purpose is not productivity - Live like pirates

So I keep playing with this idea that:

Productivity is doing things to maintain an identity and purposeful is doing one thing that reduces confusion.

That is it. Purpose is not a five year plan nor a grand vision that makes me feel enlightened. I'm finding purpose is more often small and slightly unglamorous.

The phone calls I keep avoiding, an honest conversation, a first draft, an application for the job I can tolerate while building a bridge to something better.

Purpose is a walk (despite how miserable the weather is) that resets my nervous system so I can think again or making a decision to turn something into a next step. When I find myself in fog, I have to remind myself: purpose is not about speed. It is about reducing confusion.

Which is why sailors make sense.

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The future is not a neatly labelled spreadsheet. It is a mystery on open water.

Gregg the Artivist

Live like pirates: Why they might be the right teachers now

Pirates, and sailors more broadly, did not have the luxury of pretending the ocean would cooperate. They could not demand stability. They could not argue with weather. They could not negotiate with currents.

They had to read conditions, set a heading, make adjustments, and rely on the crew. They made decisions with incomplete information, then learned fast.

I'm starting to realise that is not chaos. That is navigation. And deep down, I honestly believe that is what this moment is asking from us. Not certainty. Navigation.

So if you feel stuck right now, consider this:

Maybe you are not stuck. Maybe you are waiting for a kind of clarity the ocean does not offer. And the moment you accept that, your life changes.

It is the same muscle I explore in Radical Acceptance, Do You Dare To Play: Radical Acceptance Do You Dare To Play

Because then the question is no longer: what is the right plan? The question becomes: what is my best next adjustment?

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Adjust Your Sails: A Mini Toolkit for Uncertain Times

If you want the practical steps from this section in a simple printable format, download my PDF guide Adjust Your Sails: A Mini Toolkit for Uncertain Times here.

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Live like Pirates: From Party to Practice

There was a moment at the party where I realised something simple. To try and live like pirates for the event was fun because it did not demand perfection. Nobody was expected to know everything. You were allowed to be wrong. You were allowed to change your mind. You were allowed to play your way toward the truth.

Imagine if we gave ourselves the same permission in real life.

Because right now, the future is not a neatly labelled spreadsheet. It is a mystery on open water.

So take one step. Gather one clue. Find your crew.

And if you are going to do it, live like pirates.

When the wind shifts, do not panic.

Adjust your sails.

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FAQ's - Live like Pirates. Clarity Is Not Coming First Anymore

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Additional off site Reading:

• Beware a Culture of Busyness - A Harvard Business Review essay on how modern culture mistakes constant busyness for achievement, and how that mindset damages real performance and wellbeing.  
• What VUCA Really Means for You - A breakdown of volatility, uncertainty, complexity, and ambiguity, and why each requires a different response instead of treating uncertainty as one big vague problem.