Simon O'Regan

Hi, I’m Simon.

Past:

TikTok Global Head of Monetization Integrity Services.
Mastercard Director of Product Innovation.
Head of AI and Data Platform Products at Zalando.
PhD in Machine Learning for neonatal neuroscience.

I build products and services at the intersection of design, data and AI.

I write about:

AI products from idea to execution.
Design fiction, Biophilia and possible futures.
Progress and Possibilities.

In 2023, I published a fortnightly newsletter, Design Fictions: Biophilia Futures that offer glimpses of possible futures that bend towards Biophilia - the human tendency to be drawn towards life and life-like processes.

In 2020 and 2021, I published an occasional newsletter, The Deployment Age, that focused on tools from Design, UX of AI, Product Management, Futures, and Innovation Management broadly applicable to the knowledge work of creating new things.

I am the author of 500 Whys: Writing Your Purpose Statement, a short book written with the singular aim of illustrating a wide range of personal purpose statements so that others may more easily define theirs.

I’m from Cork in Ireland and believe remote is the future of work.

Creativity is a muscle best grown under constraint. I take a photo a day with my phone. 1,000 posts and counting.

Book addict with a penchant for paper and pens.

I write to organise my thinking. I publish to share that thinking with a fictional past self - what I wish I had read 6 months ago.

This tangle of topics is constantly evolving. Currently, my ‘favourite questions’ are:

I. DEEP PAST

What can the deep past tell us about tools: how we use them, and how they remake us?
How does a mind reach out into the world, through hands, materials, images and imagination? Can we follow that reaching back into minds long gone?
What can ancient DNA tell us about the flows of people and things? Can it bring us closer to knowing our ancestors and the landscapes they lived in?
What did our ancestors know, make and do that has been forgotten? What is worth recovering and handing on?
Who were the peoples of the Atlantic and North Sea sea-roads? Did they live off the sea, or just near it?
What does it mean to know a place by taking part in it? How does knowing its deep history change that?

II. PRESENT

What is worth paying attention to? What should I hand over to machines, and what should I ignore?
How do we cultivate attention and seek resonance? How do we tell curiositas from studiositas, in research and in making?
What is good knowledge-seeking, and what is worth knowing?
How does lyrical, textured language change how we know and understand? Can it be exact enough for science and scholarship?
What kind of thing is the new machine intelligence, and what does it reveal about our own minds?
Can the deep past help re-enchant the present?

III. PREFERABLE FUTURES

How do we move between possible and probable pasts, and possible and preferable futures?
How can I best prepare my children to live well in a world of thinking machines, screens, and networks built to reward our lesser instincts?
Where do genuinely new things come from? Can we harness that and steer it toward the good?
How do we make and build well when we can’t use only, or even mostly, natural materials?
What is worth building with the second half of a life?