The Discipline of Letting Go | Joey Pinz Digest Nov. 15
Reading Time: 4 min
Hi friends,
Joey Pinz Digest
November 15, 2026 | Second Issue
The Discipline of Letting Go
Earlier this month, I wrote about gratitude, lessons from the road, and the discipline of slowing down. This time, I want to explore another part of growth: knowing when to let go.
Discipline often brings to mind doing more. Showing up. Staying consistent. Following through when we would rather quit.
But holding on takes effort, too. And sometimes we keep putting that effort into something we need to release.
A responsibility someone else is ready to handle. A routine we have outgrown. The expectation that everything has to happen our way.
There is a question worth sitting with:
What am I holding on to that is making it harder for me—or someone around me—to grow?
That applies well beyond work. It can show up when we offer advice before someone has asked for it, step in before another person has a chance to learn, or keep saying yes because we have always been the person who handles everything.
Daniel Blank’s upcoming episode, Great Leaders Know When to Let Go, gives us a starting point for this reflection.
Letting go still requires care. We may need to explain what matters, set expectations, or accept that someone else will approach things differently.
This week, choose one thing you can hand over, step back from, or stop trying to control. Notice what becomes possible when you give it some room.
Who Are You When Things Change?
When someone asks us about ourselves, how quickly do we reach for a job title?
Our work matters. So do the roles we play in our families and communities. Over time, those roles can become a familiar way to explain who we are.
Then something changes.
A career takes a turn. The kids become more independent. A skill we spent years developing becomes less central to our work. Suddenly, we have to find a new answer.
Several upcoming podcast guests work in an industry moving through rapid change. Their episode topics raise a question that reaches much further:
Which parts of who you are can help you through a new chapter?
Curiosity travels with us. So do patience, judgment, generosity, and the ability to learn.
As you think about next year, consider one thing you would like to learn simply because it interests you. Give yourself permission to be a beginner before you have everything figured out.
Coming November 18, 2026
#973 — Hans ten Hove: “Why MSPs Must Stop Selling Technology”
A conversation about looking beyond technology to the problems people need help solving and the value businesses provide.
#974 — Phylip Morgan: “The MSP Is Dead? Why Managed Intelligence Is the Future”
An exploration of a changing industry that raises broader questions about adapting our skills and staying relevant.
#975 — Adrien Gendre: “The AI Security Threat MSPs Are Missing”
A look at AI-related security threats and the importance of staying alert as technology changes.
#976 — Lane Brannan: “The AI Revolution, Pax8’s 8OS & the Discipline of Leadership”
A discussion connecting technological change with the discipline required to lead people through uncertainty.
#977 — Raffael Marty: “Can AI Replace Human Connection?”
A timely question about the role of human relationships as AI becomes more present in our lives.
Coming November 25, 2026
#981 — Daniel Blank: “Great Leaders Know When to Let Go”
A leadership topic that connects directly to this digest’s theme of releasing control and giving others room to grow.
#978 — Matt Linn: “The Future of MSPs: AI, Automation & Human Connection”
An exploration of how automation and human connection fit together as businesses evolve.
#979 — Kristof Orts: “The Death of IT Tickets: What’s Next?”
A look at changing approaches to IT support and what happens when familiar ways of working give way to new possibilities.
#980 — Mase Issa: “Can AI Scale Your MSP Without Losing the Human Touch?”
A conversation about growing a business while preserving the personal attention that helps build relationships.
November 18, 2026
#977 Raffael Marty: Can AI Replace Human Connection?
November 18, 2026
November 25, 2026
#979 ITNation 2026: Kristof Orts| The Death of IT Tickets: What’s Next?
November 25, 2026
#981 ITNation 2026: Daniel Blank| Great Leaders Know When to Let Go
November 25, 2026
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Back in October, I had the honor of delivering a TEDx talk at Bates College—an experience I’m deeply grateful for. The talk was officially published on the TEDx platform in December, allowing the message to reach a wider audience. Sharing the stage at Bates College was both humbling and meaningful, and it reinforced the importance of thoughtful, disciplined conversations around growth, intention, and long-term impact.
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