Marc Winn
Marc Winn, close-up black and white portrait against a dark background, half smiling in a knitted jumper

About

Part soul magician. Part trickster.

Someone once called me a modern-day alchemist. I liked that.

The short version

I work with founders, business owners, leaders, investors and private individuals at consequential moments: a big decision, a business that has outgrown its shape, life after an exit, or making sense of what rapid technological change means for them. Life and business rarely stay in separate boxes, so I do not pretend they do.

I co-founded a mail-order business and helped transform it into an e-commerce company, growing it from zero to a million customers before we sold it. I know what it takes to build and scale a business while technology changes the rules.

Since then, my work has moved through business mentoring, thousands of conversations and more than a decade of community work in Guernsey. I bring that mix of commercial experience and human curiosity to consequential decisions.

I have spent decades in rooms where something was not working and no one could quite say why. I walk in, and somehow the knot loosens. Not always. But often enough that I have stopped pretending I do not know what to do.

I live in Guernsey, a small island in the English Channel. Islands teach you something about perspective. The rest of the threads are below.

The longer story

The accidental diagram

In 2014 I originated the Ikigai Venn diagram by joining the word ikigai to Andrés Zuzunaga’s existing purpose Venn diagram. I was not trying to make something viral. I was trying to help myself think.

Versions of it have since travelled far beyond my original blog post, shared, adapted and reused around the world. It took on a life I never intended or controlled.

It taught me one thing. The things that travel are not the things you engineer. They are the things that help people see what they already feel. That lesson shaped everything that came after.

Ten thousand coffees

Years before the diagram, I started an experiment. I wanted to understand how change actually happens. Not in boardrooms or strategy documents, but between people. So I started having coffee with strangers. Fifty at first. Then hundreds. Then thousands. Ten thousand, and counting.

What I found is that conversations are the unit of change. Not decks. Not frameworks. Not workshops. Conversations. The kind where someone says the thing they have been carrying but have not yet spoken aloud. That is where shifts begin.

The 50 Coffee Adventure became a workbook, a journal designed to help change-makers build social capital around their missions. The real insight was simpler. The best way to understand anything is to sit across from someone and listen properly.

The islands

Islands teach you something about perspective. When you can see all the edges, you understand the whole differently. You notice connections that get lost in larger, noisier places.

That instinct led me to work with other island nations, helping them reimagine themselves as living test beds for the future. Places small enough to experiment meaningfully, connected enough for the experiments to matter elsewhere.

Back home, I spent over a decade helping my community use its smallness as an advantage. Conditions for people to see clearly together, then act on what they saw. No grand strategy. Just clarity, then movement.

Granite cliffs on the Guernsey coast meeting a calm sea under warm hazy light

When you can see all the edges, you understand the whole differently.

The wand

Somewhere along the way I noticed that I do my best work when I am playing. Not entertaining, playing. Treating the room like a living thing. Breaking the spell of seriousness for long enough that the truth can walk in.

The wand is a reminder that a serious question can benefit from a little play. Humour can loosen a fixed assumption and give us room to try a different approach.

If you want to go deeper

I write at The View Inside Me, where I think out loud about purpose, perspective, and work that matters. A few years ago I explored what becomes possible when a whole community decides to care. That became a TEDx talk that captures much of the philosophy behind the work.

Public recommendations

In other people’s words.

Words people use afterwards

Now you know the threads. If something here recognises you, let’s talk.

Working togetherArrange a conversation

What Could Possibly Go Right? Marc's weekly letter on technology, business and the strange possibilities of ordinary life. Every Friday.

Read a recent letter first