Main Site PETER.PITKIN Articles CV Blog
Blog Series

Reflections from
50 Years in IT

Lessons, mistakes, and realities from leading complex transformation — not theory, not frameworks, not the latest trends. What actually happens, and why.

50+
Years in the Industry
4
Series Themes
13
Posts Published
About This Series

What These Reflections Are — and Are Not

Over the past five decades, I have had the opportunity to work across a wide range of industries and roles — from real-time systems and enterprise architecture to leading large-scale transformation programmes in financial services, aerospace, healthcare and automotive. Technology has changed dramatically during that time. What has not changed nearly as much are the underlying challenges: how organisations make decisions, how complexity builds and is managed, and how transformation succeeds — or quietly fails.

This series is not about theory, frameworks, or the latest trends. It is a collection of practical reflections from someone who has been in the room — and often at the front of it — when things went well, when they went wrong, and when the difference between the two came down to factors that no methodology ever fully captures.

What This Series Is

  • Lessons learned the hard way — on real programmes, in real organisations
  • The gap between how things are supposed to work and how they actually do
  • The realities of leadership at scale
  • The human, organisational and structural factors behind success and failure
  • Observations most organisations recognise but rarely discuss openly

What It Is Not

  • A guide to best practice or another set of prescriptions
  • Framework advocacy or methodology promotion
  • Academic analysis or theoretical modelling
  • Comfortable reading — some of this may feel familiar in an uncomfortable way
  • Complete — fifty years of experience is more than any series can contain
Who This Is For
Senior Executives Programme & Transformation Leaders Enterprise Architects Technology Strategists Anyone dealing with complexity, change & execution

The Series

All 13 posts published across 4 themes

Learning the Hard Way
Early lessons, misconceptions, and the realities that only experience exposes
Published · 2027
Things I Wish I Had Known Before My First €100M Programme
Published · 2027
The Loneliness of the Programme Leader
Published · 2027
Transformation Doesn't Fail at the End—It Fails in the First 90 Days
Published · 2027
Confidence vs. Certainty
Leading at Scale
What changes when programmes become large, complex, and highly visible
Published · 2027
Why Most Executive Steering Committees Don't Steer
Published · 2027
What Really Happens After the Steering Committee
Published · 2027
The Moment You Realise You Don't Control the Programme Anymore
Transformation Reality
Why large programmes don't behave as expected — and what actually happens
Published · 2027
Why Large Programmes Drift (And How to Pull Them Back)
Published · 2027
When "Quick Wins" Become Long-Term Problems
Published · 2027
Why Organisations Resist Change Even When They Know They Need It
Technology & Strategy
A pragmatic, experience-based view of technology and architecture decisions
Published · 2027
Why Every System Becomes "Legacy" Faster Than You Expect
Published · 2027
The Most Dangerous Words in IT: "We'll Fix It Later"
Published · 2027
Data Problems Are Never About Data

Get notified when new posts are published

Posts in this series will publish throughout 2027. Leave your email and I will notify you when each new piece goes live — no newsletters, no marketing, just the posts.