Patience and Humility

My wife and I are standing on the porch in Florida, waiting for the school bus to arrive. The heat is building—both outside our house and inside our bodies. We’ve received several alerts today from the county school portal about missing assignments. We see school as our kids’ job. We work hard to give a stable, loving environment. In turn, we expect them to work hard to fulfill their age-appropriate responsibilities. Completing class assignments isn’t just how they learn the material—it’s how they build work ethic.

Our second oldest can tell we’re waiting for him and slows his pace. We launch into our interrogation as he approaches. He’s only nine and quickly tears up. This isn’t how we want to parent. We need a new approach.

Dad + admin = Dadmin

I’m an arranger.

I make the bed every morning and love a freshly cleaned car. I’m fascinated by the Theory of Constraints and love aligning groups toward a common goal. I’ve re-engineered physical production control across a 2,000-person industrial facility and knowledge work in the C-suite of a 42,000-person organization.

I’m also focused.

Over time, I’ve learned that I’ll forget something if it isn’t in my calendar or task manager. I need a system that tells me what to do and when to do it to break my attention. It should also help manage my time holistically across roles. This way, I avoid local optima.

My wife and I settled on weekly family meetings as our new approach. The six of us took turns expressing gratitude and provided feedback before diving into the logistics of the upcoming week. Alas, they fizzled out after a few months. My inner nerd began to overwhelm my wife’s free spirit. Two of the kids began to seek the gold star that would come each weekend. The other two began to dread what became known as Dadmin.

I had reduced loving check-ins with each other and gentle nudges of our kids into a production meeting. My well-intentioned questions had again turned into an inquisition. We again needed a new approach.

The system

Cal Newport teaches that any good productivity system does three things:

1. Easily captures open obligations in a trusted repository
2. Allows for configuration by due date, status, context, etc.
3. Helps you control time allocated to the top priorities

Simple in theory, but not always easy in practice.

I’ve been iterating on my system for about a decade. Some improvements were technology-related, others came from feedback by those it touched. Over time, two principles emerged:

1. Keep the technology easy for the user
2. Allow for others emotional self-pacing

Yes, I rediscovered the importance of user experience…

Tiago Forte calls my style “the architect.” I view the world through systems and enjoy discovering their structure. This shows in my Notion workspace with through APIs, relational database properties, and artificial intelligence. It has become my second brain.

But this integrated ecosystem of tasks, notes, projects, and areas is WAY too complicated for my family. They don’t find personal productivity nearly as fun as I do! They prefer Apple’s simpler suite of calendars, reminders, and notes that can be easily shared.

So, I pull tasks from my various task managers and deliver them to a specific family member through an intuitive app carried in their pocket that includes a reminder:

• Our integrated, color-coded Calendar helps us find the best slots for doctor appointments and triage rides when we’re double-booked.
• The smart grocery list in Reminders lets everyone add items. It organizes them by aisle and whoever is shopping can simply check them off.
• We use shared Notes for everything from the kids building their Christmas lists to saving ideas for renovating our backyard.

It took me only a few years to learn this first principle. The second continues to be an area I work on. An obvious extension of focusing on the user experience is to meet others where they’re at.

For example, I learned the hard way that my wife dreads our budget review and my daughter her grade book. What I see as teamwork, they see as me asking difficult questions they aren’t ready to answer. After some trial and error, I now do the detailed analysis independently and send them the highlights. We then review together when they’re ready.

Considering their user experience balances my need to get things done with my family’s need to not be micromanaged. Besides the above examples, my wife considers these use cases a success:

• Car maintenance on vehicles rarely in our driveway
• School communications and tutor coordination with slightly less teenage attitude
• Medical bills for young adults learning to navigate insurance paperwork
• Preventative house maintenance aligned to our the specific context of our house and location

“You’re willing to sacrifice your relationship for his future.”

My wife said this to me a few years back.

We were struggling at the time to help our second oldest align his aspirations and effort. She meant it as a compliment, and I took it that way. In fact, he later presented me with the mentor pin at his Eagle Scout Court of Honor. It was his way of appreciating my help in getting him across that particular finish line….within days of the age cutoff.

Looking back, though, I only had to risk my relationship because I didn’t recognize his emotions.

I’m used to professional process improvement implementations. I’m versed in breaking down functional stovepipes in the pursuit of an overarching organizational goal. I’ve been taught to acknowledge, but generally remove emotions from the decision process.

This was my mistake: emotions matter, both at home and at work. I didn’t realize that my big picture could be his small—especially in the moment. I only considered my user administrative experience, not his emotional.

While writing this post, we asked our son for his best and worst Dadmin memories. His answer for both: accountability.

He appreciates that my system provided the scaffolding he needed for the professional path he’s on today. It was also hard facing reality when he struggled to meet expectations, ours or his own. A checklist review in front of his siblings that highlighted those moments made it even harder.

My wife and I do hope our kids carry on the Dadmin tradition. I just hope they do so in a more emotionally and user experience attuned way.