The Calendar as a Treasure Map

I flew to the United States this week for the wedding of an old friend, Chris, who I first met almost exactly twenty years ago in a hostel in Antigua, Guatemala. Back then, we were both taking a bit of a detour from the expected track of life. I was a South African travel agent on a sabbatical with a backpack, he was an aspiring doctor from Colorado, and somehow we ended up travelling together for six months through Central and South America. It was a friendship that has endured ever since as our lives took on different shapes on our home continents… but one thing we both stuck with was the effort to make it a lifelong friendship, not a seasonal one. He was at my wedding, and of course I would be at his.

This trip was different from that original odyssey. I packed a suit and golf clubs, went shopping at Lululemon along the way, rented a hybrid EV instead of taking the bus, stayed in the fancy wedding venue retreat, and wasn’t on the ground long enough to properly shake off my jetlag. Having said that, I approached it with some of that same adventurous backpacking spirit. I was flying solo, I had five nights in the States, and I decided not to make it a simple in-and-out wedding trip. I turned the calendar into a little treasure map and added a few side quests with other old friends. I had a couple of fantastic meals (we just don’t do Mexican food as well in South Africa), spent some time in Arizona in addition to the wedding in New Mexico, played the TPC PGA course in Phoenix, and generally tried to squeeze a bit of adventure into the gaps without losing sight of the reason I had gone in the first place.

That idea of the calendar as a treasure map stayed with me through the trip, and it became particularly vivid when I started noticing the Waymos in Phoenix. If you have not seen one, they are the driverless cars quietly moving around American cities, and they are strangely mesmerising to watch. They know where they are going, they have a map, but they are not simply following a line. They constantly read their surroundings, noticing other cars, pedestrians, cyclists, traffic lights, construction, and whatever other bits of chaos humans throw into the system. They have a destination, but they continuously adjust to get there safely.

It struck me that this is not a bad metaphor for proactivity.

We often reduce proactivity to being organised. Plan ahead, make the list, put things in the diary, get there early. All useful, but Stephen Covey’s idea in The 7 Habits of Highly Effective People is more interesting than that. Proactivity is really about recognising that between what happens to us and how we respond, there is still a choice. We do not control the road, but we do control how we navigate it. The map matters, but so does the ability to notice what is changing around us and make the small adjustments that keep us moving towards what actually matters.

The wedding gave me another example of this. By wonderful, or perhaps cruel, coincidence, it fell on the same day as the fourth and final Test in the Springboks versus All Blacks series. Anyone who knows me will understand this was no trivial clash. A version of me could have tried to engineer a hybrid arrangement: phone discreetly under the table, one eye on the vows and the other on the score, perhaps a tactical bathroom break at halftime. It would have been entirely possible to be physically present at the wedding while mentally somewhere else.

But I had decided beforehand that I was there for Chris. That was the objective. So I let the rugby go.

I stayed present. I enjoyed the wedding, the people, the speeches, the dancing and the fact that after twenty years of friendship I got to stand there and watch my friend marry the person he had chosen to build a life with. Later that night, when the party had wound down, and I was back in bed, I calmly watched the highlights. Nothing had really been lost. In fact, I think I gained something, because I had not diluted one important experience by trying to consume another at the same time.

We do this constantly, of course. We try to answer emails during meetings, half-listen to our children while looking at our phones, take calls while driving between appointments, and keep so many things running simultaneously that we confuse activity with progress. Sometimes proactivity is not about fitting more in. Sometimes it is about deciding in advance what deserves your full attention and being prepared to let the rest wait.

The same theme came up again the night before the wedding at the rehearsal dinner. Chris had asked me beforehand to say a few words, along with about ten other people. What struck me on the night was how thoughtful the speeches were. People had stories, structure and a clear sense of what they wanted to say. It was obvious we had all spent time preparing. That sounds like a small thing, but it is not.

Chris had created the conditions for people to do a good job. He had given us notice, and because he had, we could honour the moment properly. Compare that with the dreaded spontaneous request at a function, when someone suddenly says, “Would anyone like to say a few words?” and a room full of people immediately starts studying the tablecloth. The brave souls that do take the mic often do a rambling salutation, and kick themselves afterwards for what was left unsaid. Maybe it’s because this was an older crowd, maybe it was because of the quality of people Chris and Taylor surround themselves with… or maybe it was just that my old buddy began with the end in mind.

There is a leadership lesson in that. We often complain that people are not thoughtful enough, prepared enough or proactive enough, but then we give them no time to be any of those things. We ask the important question in the meeting. We brief the presentation the night before. We hand over responsibility without context and then get frustrated when the quality is not there. If we want better outcomes, we often need to create better conditions before the moment arrives.

My speech (and, as it happens, many of the others that stood up) focused on what I know and love about my buddy (and his new bride): Abundance mindset.

Scarcity thinking assumes there is not enough to go around. Not enough time, not enough recognition, not enough opportunity, not enough success. When you live from that place, you tend to become reactive because you are constantly protecting what you already have. Abundance thinking is different. It assumes that there is more possibility available, that other people can succeed without diminishing you, and that giving someone more context, more trust, or more room does not somehow leave you with less.

Win-Win, in the Seven Habits, sits on that foundation. But I think it is hard to live with an abundance mindset unless you are proactive first. You have to decide what matters, think ahead, create the right conditions and be deliberate about where your attention goes.

Otherwise, the environment makes the choices for you.

That is perhaps what I liked most about the Waymo metaphor. It does not confuse having a plan with being rigid. It knows where it is going, but it keeps reading the road. It adapts without losing the destination.

Man, the robots keep teaching us how to be better humans, hey.

PG’s Pro Tip

This week, choose one area where you keep finding yourself reacting under pressure and redesign it before the next version arrives. It might be a meeting that always feels rushed, a team member who repeatedly needs rescuing, a conversation you keep postponing, or simply a calendar that has become so crowded that everything now feels equally important.

Ask yourself what the real objective is, what you could decide or prepare earlier, and what you are willing to ignore so that the important thing gets your full attention.

Then try this prompt with ChatGPT:

I want you to act as my proactive planning partner. I am going to describe a recurring situation in my work where I often end up reacting under pressure. Help me work backwards from the ideal outcome and identify what I could anticipate, prepare, communicate, delegate or deliberately ignore earlier. Show me the real objective, what currently makes me reactive, what I can decide in advance, what signals I should monitor as circumstances change, what distractions I should consciously deprioritise, and what small adjustments I should make in real time. Then turn it into a simple, repeatable playbook I can use next time.

The point is not to predict every obstacle.

It is to know where you are going, pay attention to the road, and choose your response before the noise chooses it for you.