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How to Plan a Week That Actually Brings People Together

Posted by: RealEfforts Posted on: June 1, 2026

There is a particular kind of spreadsheet that only exists for one reason: love. It has columns for flight numbers and arrival times, rows for Airbnb addresses and rental cars, and a color-coded grid of who is sleeping where on which night. It is, on the surface, a project management document. But what it’s really tracking is the effort a family is making to be in the same room together.

I’ve been part of planning a few of these gatherings — the kind where people fly in from all over the country and scatter across Airbnb’s and hotel rooms, where the group text has seventeen people in it and someone is always asking what time dinner is. The logistics are real. The coordination is genuinely complicated. And it is absolutely worth every minute of it.

The gatherings that work best share a few things in common.

First, they have an anchor event. Not the whole week — just one moment that everything else orbits around. A memorial service, a milestone birthday, a dinner in a historic vault downtown. When there’s a clear center of gravity, everything else — the morning walks, the pickleball games, the impromptu lunches — can be loose and spontaneous without the whole thing feeling unstructured.

Second, they leave room for the unplanned, but nobody is required to go. The neighborhoods invite walking. The evenings have a dinner but not a schedule. The best conversations happen in the margins, not the main events.

Third, they mix the generations deliberately. When it’s only the adults or only the kids, you lose something. When a ten-year-old is at the dinner table next to a seventy-five-year-old, stories get told that wouldn’t otherwise surface. Questions get asked that adults have stopped asking each other. Something transmits.

The families who gather regularly — who make the plane reservations even when it’s expensive, who take the days off work, who sleep on uncomfortable air mattresses in someone’s living room — are building something. Not just memories, though those matter. They’re building a fabric of relationships that holds people across distance and time.

The spreadsheet is worth it. Make the spreadsheet.

RealEfforts

My name is Martin Fenton III. I created Real Efforts because I've reached a point in life where I find myself spending less time asking, "What's next?" and more time asking, "What did it all mean?" Like most people, my life has been filled with chapters I never could have predicted. I've lived overseas, built businesses, worked for large companies, raised children, fallen in love, made mistakes, started over more than once, lost people I loved, and discovered that many of the things I was certain about at thirty look very different at sixty. For many years I focused on building a career and supporting a family. Today, I find myself increasingly interested in understanding the lessons hidden inside those experiences. Real Efforts is my attempt to do that. This isn't a business website. It's not a memoir. It's not a collection of answers. It's a collection of observations, stories, questions, lessons, and reflections gathered over a lifetime of trying to figure things out. Some of these thoughts are about family. Some are about work. Some are about friendship, purpose, aging, reinvention, and the strange ways life unfolds despite our plans. Many of them are simply attempts to make sense of experiences that felt confusing while I was living them. The older I get, the more I realize that life is less about arriving somewhere and more about paying attention while you're traveling. I've learned that relationships matter more than accomplishments. That starting over is never as easy as people pretend. That success and happiness are not always the same thing. And that some of the most important lessons don't become visible until years after the experience itself. I originally created this site for my children. I wanted them to have more than photographs and dates. I wanted them to understand how I thought, what I struggled with, what I learned, and what I hoped for them. Over time, I realized these thoughts might be useful to others as well. So this site became something larger. A place to collect life chapters. A place to preserve family stories. A place to explore purpose. A place to ask questions that don't always have answers. Most of all, it's a place to leave behind a little context. Because someday, when we're all gone, the stories disappear unless someone takes the time to tell them. This is my effort to tell them.

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