Celebrating 500 Posts on Driving Digital Transformation

This is my 500th post on this blog, Social, Agile, and Transformation (and almost 700 across all websites), so I hope you will celebrate this milestone with me!

I started this blog back in 2005 when a friend told me that my startup needed to be "plugged into the blogosphere." I interpreted that to mean that I should start a blog and called it CTOtoDevelopers. I imagined using the blog to share technical best practices, and my first posts on application logging and on using agile to develop coding best practices remain classics.

500 Posts by Isaac Sacolick

The Technical Early Years of CTOtoDevelopers

A Dashboard of Isaac Sacolick's Posts
Dashboard of Isaac Sacolick' Articles

Every year I adjusted the topics I covered. The posts from my first couple of years were technical, and I shared our learnings on java web 2.0 application development. I also have some real classic posts, including this letter to Michael Dell, my thoughts on Oracle buying MySQL, and my two cents on Google buying YouTube.

Mind you, I was just writing what was on my mind. I had no aspirations at the time to write a book, become a speaker, develop agile certification courses, run digital transformation workshops. or launch my company, StarCIO.

In 2007 I pivoted and left the world of startups to being a CIO at companies that were thrown into digital transformations well before the buzzword became popularized. 

For the next decade, I shared my advice and learnings on leadership, culture, agile practices, innovation, and architecture. Some of my favorite posts from the early years of my CIO days include:

As CIO: Rebranded to Social, Agile, and Transformation

I rebranded the blog Social, Agile, and Transformation to reflect three pillars of my leadership principles and style. Then from 2010-16, I started to cover bigdata, data science, DevOps, digital transformation, and citizen development. I celebrated my 300th post in 2016, and my favorite posts from this period include:

StarCIO IT Culture

Digital Transformation




Driving Digital and StarCIO

2017 was a milestone year. My book Driving Digital came out, and I focused the blog on providing best practices beyond what I covered in the book. 2017 is also the year I launched StarCIO, where we guide organizations of all sizes and across industries on developing strategic advantages with data and technology.

Here are some of the top posts from the last few years.

StarCIO Proactive Data Governance

AI, Data, and Analytics

Agile, DevOps, and Architecture

Digital Transformation and Leadership

Digital Leadership 2025 - 2030

Since last year, my writing and speaking are more focused on the next decade of digital transformation. I have finished a new book and am working on editing and publishing it. 

Thank you for all the support. The best way to track all of my writing is to sign up for my free Driving Digital Newsletter.

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