Redirecting.work
Dennis Howlett
New Chapter: From Tech Fray to Purpose-Driven Living
Dennis Howlett was one of the Enterprise Irregulars, along with Naomi Bloom, who I always paid attention to before he left the fray in February 2021. He was a prominent voice covering business, finance, and enterprise analytics. He always took the buyer’s perspective in analyzing application vendor offerings. I was delighted when he reached out to me for a pivot interview. As someone who also has left the tech fray (mostly), I’m keenly interested in how others spend their time and why they pivoted. So much for me to learn.
Why Pivot?
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Dennis left the tech scene because he was exhausted from endless travel—nearly six months a year—and the physical toll was undeniable. “I was too old. Travel was exhausting and I just had to stop and ask, ‘what now?’”
While Dennis hadn’t charted a career path, he’d always made strategic pivots, although surprises—like the sudden impact of the dot com bust—sometimes interrupted his plans. After 20 years in other countries, he settled back in his home country, the UK to both wind down and then retire. “I spent two years planning my ‘exit stage left’ and that made all the difference to a smooth transition.”
Current Direction
Now, his days are devoted to things that make him smile. First, he’s paying it forward to his family, especially his wife, whom he feels has given him so much during his many years on the road. He’s become a cooking enthusiast, indulging in all the best kitchen tools. “I want all the kitchen toys but draw the line at ice cream makers. A store bought tub is my guilty pleasure.” I also notice his Facebook posts with yummy, healthy foods. He also spends time exploring history, particularly military history, as he builds intricate model tanks and delves into the complex narratives of WWI and WWII. “History has much to teach those who wish to avoid the mistakes of the past. Nowhere is that more obvious than in the study of recent military conflicts.”
Eighteen months ago, he found himself yelling at the TV, frustrated by the state of the world. Instead of just watching, Dennis took action—joining a political party, taking up the role of branch secretary, and running communications. “My wife told me to stop yelling and do something about it. So I did.” This activism gives him a sense of purpose and connection to the contemporary world around him.
Advice
His advice for others contemplating retiring? Seek out joy and purpose, but always with the intention of paying it forward. “You’ll be far richer if you help others without expecting anything in return.”
For Dennis, each day is a step forward, driven by a commitment to keep learning and a sense of grounded realism passed down from his father. “I am constantly reminded of my own failings but in the certainty that we can all suck a little less each day.”
By way of confirmation, he half jokes that his last business was registered as Suxless Daily Ltd. as a reminder of that imperative. “It was a great name because it always sparked a conversation,” says Dennis with an edge of certainty that belies his commitment to passing on lessons to his growing family. “We will be known by the memories we leave behind. I hope mine will be useful.”