Week 29, 2026
People always tell Product Managers to switch off during vacation. Leave work behind. Disconnect. Be present. Before a recent seven day family holiday, I genuinely believed I could do exactly that. No laptop. No Microsoft Teams. No work email. Just family, sunshine, and the occasional nap. Unfortunately, Product Management is not something you leave in the office. After years of observing, prioritizing, planning, and solving problems, your brain starts operating that way everywhere.
Day 1 was supposed to be about relaxing. Instead, I found myself having an unofficial remote kick off meeting with exactly two stakeholders: me and the weather person on the TV. While the family admired the ocean, I was already reviewing dependencies between cloud coverage and beach outcomes. The vacation had not even started, and somehow I was already managing expectations.
Days 1 and 2 were filled with optimism. I was determined not to overthink anything. Then on Day 2, I “just” happened to check my work phone. Then my iPad. Not for work, of course. Just to stay informed. Before breakfast on Day 2, I had already built a mental roadmap for the perfect pool day. Milestone one was securing strategic towel placement before competitors arrived. Milestone two was maximizing shade coverage while maintaining access to snacks, drinks, and the pool. At 7:03 AM, I proudly informed the family that I had successfully secured prime real estate. Nobody seemed impressed. My wife asked why we were awake so early while on vacation. My son asked whether we were planning to swim or launch a military operation. In my mind, this was resource allocation and competitive positioning. In their minds, I had become the least relaxing person at the resort. The family wanted relaxation. I delivered a roadmap.
By Days 3 through 5, the frameworks returned in full force. When rain clouds appeared on the horizon, I immediately identified an emerging risk and developed contingency plans. Plan A was the beach. Plan B was indoor activities. Plan C was confidently claiming this had been the strategy all along. After listening patiently, my daughter suggested we could simply look outside if it started raining. It was difficult to argue with her logic. Day 4 introduced optimization. I became fascinated with finding the most efficient route between our sunbeds and the beach bar. After carefully analyzing several options, I shared my findings with the family. My wife informed me that nobody wanted a performance review of cocktail acquisition efficiency. Stakeholder adoption remained low. Then came Day 5 and what I now recognize as a career limiting decision: the family retrospective. During dinner I asked what went well, what we should do differently, and how we could improve next sprint. The reaction was immediate. My son asked whether attendance was mandatory. My daughter wanted to know if action items would be assigned. My wife asked when exactly vacation had become a workshop. Stakeholder sentiment dropped sharply.
Days 6 and 7 represented complete Product Manager mode. A disagreement emerged over where to eat dinner, creating what I considered a critical alignment challenge. One stakeholder wanted seafood. Another wanted pizza. Someone else wanted burgers. Believing I could help, I facilitated discussion, introduced prioritization techniques, explored trade off analysis, and proposed a decision framework. The family achieved remarkable alignment on one specific point: the framework was the problem. Every attempt to improve the process seemed to reduce everyone’s happiness. Eventually, my wife overruled the entire exercise and selected the restaurant herself. In corporate terms, governance was replaced by executive sponsorship. By Day 7, I finally remembered the purpose of vacation. I sat quietly by the sea, determined to relax. Then I looked at my work phone. Then my iPad. Then I opened my laptop. “Just checking one thing,” I told myself. Twenty minutes later, I was reading messages and solving problems. Every vacation eventually becomes a product launch.
The most revealing moment happened on the final evening. My wife smiled and said, “You know we’re on vacation, right?” Then she added, “You’ve planned every day, optimized every route, managed risks, run meetings, negotiated conflicts, and tracked outcomes. The only thing you haven’t done is relax.” She was absolutely right.
Product Managers spend so much time helping people navigate uncertainty that eventually uncertainty starts looking like an invitation. We do not build frameworks because we love process. We build them because we want to make sense of complexity. Sometimes that instinct genuinely helps. Other times it turns choosing ice cream into a prioritization exercise and a family holiday into a seven day operating model nobody asked for.
The irony is that I know the questions Product Managers are supposed to ask before investing time and energy into solving a problem. Yet during the entire vacation, I never stopped to ask myself: What problem am I actually solving? Why does it matter right now? And perhaps the most important question of all: Why? Because sometimes the answer is that a problem genuinely does not need to be solved. Sometimes the answer is that you’re standing on a beautiful beach, on vacation with your family, trying to improve an experience that was already working perfectly. I came for the sunshine and accidentally built a governance model. Product Managers need to stop thinking sometimes.
You can take the Product Manager out of the product, but you can’t take the product out of the Product Manager.
This newsletter reflects my personal views and experiences as a product manager. It does not represent the views, strategies, or opinions of my employer or any organization I am affiliated with.
