My Enlightening Books to Read in 2023 for Digital Transformation Leaders

I know Digital Trailblazers commit to lifelong learning, and recent Pew research shows that 75 percent of adults read books in any format - either print, digital, or both. So, while we all read blogs, watch videos, and listen to podcasts, there's much to learn and an opportunity to relax with a good book. 

So, as in past years, I am sharing my top book reads of 2022. There are five I am calling out as must-reads for digital transformation leaders, and others depend on your interests and cover agile, innovation, AI, and the metaverse. I also added one special topic about humanity.

Isaac Sacolick's 2002 Book Reads

Five must-read books for aspiring transformation leaders 

Five books are at the top of my 2022 stack and collectively represent a very balanced reading list for digital transformation leaders.

  1. This is How They Tell Me the World Ends: The Cyberweapons Arms Race by Nicole Perlroth - A CIO/CISO friend recommended this book to me when I asked for a recommendation on an infosec 101 book. Perlroth’s book is not a technical or leadership book about security and is more like a collection of cyber horror stories. Perlroth, an award-winning NY Times journalist and dove into the zero-day exploit bowels to describe the marketplace. She tells the stories of the hits that made the news, others that never made it to the front page, and the very near disasters. It’s a must-read for every IT, security, and digital leader. 
  2. Ascend Your Start-Up: Conquer the 5 Disconnects to Accelerate Growth by Helen Yu - Helen takes you on two parallel journeys in her book. The first is a very personal one about her journey to Mount Everest, where she shares her grit and emotions throughout her mission to bury her grandmother’s ashes. Her second story is about bringing a new idea to market. She includes many secrets beyond her “5 disconnects” as you learn about developing minimally viable products, creating a pricing strategy, and inspiring a cultural collaboration. Her book is a checklist of the 26 decisions entrepreneurs will face in developing and executing a go-to-market strategy. 
  3. The Cold Start Problem: How to Start and Scale Network Effects by Andrew Chen - You’ll hear marketers target and talk about their campaign “going viral” and the flywheel effect to grow a business. But before you start experiencing feedback loops and other network effects around a product or business, you have to get that first spark of interest from influencers in your target audience. Andrew tells stories and lessons around the cold start problem from his days at Uber, but with many other examples from companies like Twitch, Tinder, Wikipedia, LinkedIn, and Reddit. 
  4. The Power of Regret: How Looking Backward Moves Us Forward by Daniel H. Pink - I admit that I was apprehensive when a friend recommended this read, as I always believed it’s stronger to look forward than back. But Pink helps you see things differently by describing the four core regrets, telling stories behind them, and sharing advice on how reflecting on them can make us smarter and stronger people. I learned a ton about myself from this book and highly recommend it to everyone. 
  5. Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership by Isaac Sacolick - It’s on my list because of what readers shared with me after reading it. Marlene Veum says it’s “an invaluable resource for anyone looking to successfully lead a #digitaltransformation. It will make you laugh.” Gil Press shares, “Sacolick successfully flashes out the do’s and don’ts of many aspects of digital transformation, delivering an excellent guide.” But my favorites come from fans that sent me private messages like “the humor you bring to the space has me in stitches most mornings” and “this is the book I always wanted to write. Your approach is spot-on.” 

Reads on Specialized Topics: Agile, AI, Metaverse 

I read on a wide range of topics and recommend the ones below for the subjects that interest you.

More to come in 2023, and you can connect with me on GoodReads to track my progress.

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.