Planning for Everything

Once upon a time, there was a happy family. Every night at dinner, mom, dad, and two girls who still believed in Santa played a game. The rules are simple. Tell three stories about your day, two true, one false, and see who can detect the fib. Today I saw a lady walk a rabbit on a leash. Today I found a tooth in the kitchen. Today I forgot my underwear. The family ate, laughed, and learned together, and lied happily ever after.

There’s truth in the tale. It’s mostly not false. We did play this game, for years, and it was fun. We loved to stun and bewilder each other, yet the big surprise was insight. In reflecting on my day, I was often amazed by oddities already lost. If not for the intentional search for anomaly, I’d have erased these standard deviations from memory. The misfits we find, we rarely recall.

We observe a tiny bit of reality. We understand and remember even less. Unlike most machines, our memory is selective and purposeful. Goals and beliefs define what we notice and store. To mental maps we add places we predict we’ll need to visit later. It’s not about the past. The intent of memory is to plan.

In reflecting we look back to go forward. We search the past for truths and insights to shift the future. I’m not speaking of nostalgia, though we are all borne back ceaselessly and want what we think we had. My aim is redirection. In reflecting on inconvenient truths, I hope to change not only paths but goals.

We all have times for reflection. Alone in the shower or on a walk, we retrace the steps of a day. Together at lunch for work or over family dinner, we share memories and missteps. Some of us reflect more rigorously than others. Given time, it shows.

In Agile, the sprint retrospective offers a collaborative context for reflection. Every two to four weeks, at the end of a sprint, the team meets for an hour or so to look back. Focal questions include 1) what went well? 2) what went wrong? 3) how might we improve? In reflecting on the plan, execution, and results, the team explores surprises, conflicts, roadblocks, and lessons.

In addition to conventional analysis, a retrospective creates an opportunity for double loop learning. To edit planned actions based on feedback is normal, but revising assumptions, goals, values, methods, or metrics may effect change more profound. A team able to expand the frame may hack their habits, beliefs, and environment to be better prepared to succeed and learn.

Retrospectives allow for constructive feedback to drive team learning and bonding, but that’s what makes them hard. We may lack courage to be honest, and often people can’t handle the truth. Our filters are as powerful as they are idiosyncratic, which means we’re all blind men touching a tortoise, or is it a tree or an elephant? It hurts to reconcile different perceptions of reality, so all too often we simply shut up and shut down.

Search for Truth#section2

To seek truth together requires a culture of humility and respect. We are all deeply flawed and valuable. We must all speak and listen. Ideas we don’t implement may lead to those we do. Errors we find aren’t about fault, since our intent is a future fix. And counterfactuals merit no more confidence than predictions, as we never know what would have happened if.

Reflection is more fruitful if we know our own minds, but that is harder than we think. An imperfect ability to predict actions of sentient beings is a product of evolution. It’s quick and dirty yet better than nothing in the context of survival in a jungle or a tribe. Intriguingly, cognitive psychology and neuroscience have shown we use the same theory of mind to study ourselves.

Empirical science tells us introspection and consciousness are unreliable bases for self-knowledge. We know this is true but ignore it all the time. I’ll do an hour of homework a day, not leave it to the end of vacation. If we adopt a dog, I’ll walk it. If I buy a house, I’ll be happy. I’ll only have one drink. We are more than we think, as Walt Whitman wrote in Song of Myself.

Our best laid plans go awry because complexity exists within as well as without. Our chaotic, intertwingled bodyminds are ecosystems inside ecosystems. No wonder it’s hard to predict. Still, it’s wise to seek self truth, or at least that’s what I think.

Upon reflection, my mirror neurons tell me I’m a shy introvert who loves reading, hiking, and planning. I avoid conflict when possible but do not lack courage. Once I set a goal, I may focus and filter relentlessly. I embrace habit and eschew novelty. If I fail, I tend to pivot rather than persist. Who I am is changing. I believe it’s speeding up. None of these traits is bad or good, as all things are double-edged. But mindful self awareness holds value. The more I notice the truth, the better my plans become.

Years ago, I planned a family vacation on St. Thomas. I kept it simple: a place near a beach where we could snorkel. It was a wonderful, relaxing escape. But over time a different message made it past my filters. Our girls had been bored. I dismissed it at first. I’d planned a shared experience I recalled fondly. It hurt to hear otherwise. But at last I did listen and learn. They longed not for escape but adventure. Thus our trip to Belize. I found planning and executing stressful due to risk, but I have no regrets. We shared a joyful adventure we’ll never forget.

Way back when we were juggling toddlers, we accidentally threw out the mail. Bills went unpaid, notices came, we swore we’d do better, then lost mail again. One day I got home from work to find an indoor mailbox system made with paint cans. My wife Susan built it in a day. We’ve used it to sort and save mail for 15 years. It’s an epic life hack I’d never have done. My ability to focus means I filter things out. I ignore problems and miss fixes. I’m not sure I’ll change. Perhaps it merits a prayer.

We also seek wisdom in others. This explains our fascination with the statistics of regret. End of life wishes often include:

While they do yield wisdom, last wishes are hard to hear. We are skeptics for good reason. Memory prepares for the future, and that too is the aim of regret. It’s unwise to trust the clarity of rose-colored glasses. The memory of pain and anxiety fades in time, but our desire for integrity grows. When time is short, regret is a way to rectify. I’ve learned my lesson. I’m passing it on to you. I’m a better person now. Don’t make my mistakes. It’s easy to say “I wish I’d stood up to bullies,” but hard to do at the time. There’s wisdom in last wishes but bias and self justification too. Confabulation means we edit memories with no intention to deceive. The truth is elusive. Reflection is hard.