Do the Thing You’ll Remember Best: A Rule for Life Choices

It’s been a long workweek. We feel like going home, eating Gelato, and watching a few episodes of LOST. But let’s say we’ve also been invited to go snowboarding for the first time, or to go to a new restaurant with good friends, or to stay late and grind out a major work project with our colleagues until 1 AM in the morning.

What do we do when we’re faced with a choice among options like this?

I’ve been testing out a loose sort of rule for these situations: do the the thing that you’ll remember best.

We all want our lives to be great stories. And we all want to look back and remember long, vivid lives. The best way to achieve both ends is to do the thing which will leave the healthiest (AKA best) and most distinct (AKA memorable) memory: the best-memorable experience.

It’s actually quite easy to pick the experiences that will be most memorable for us. Rarely will they ever be things that we do on a regular basis – things that we already know. Novelty and risk and the unknown are what make experiences memorable. Neuroscientist David Eagleman believes that these kinds of experiences actually can lengthen our perception of time and life itself:

One of the seats of emotion and memory in the brain is the amygdala, he explained. When something threatens your life, this area seems to kick into overdrive, recording every last detail of the experience. The more detailed the memory, the longer the moment seems to last. “This explains why we think that time speeds up when we grow older,” Eagleman said—why childhood summers seem to go on forever, while old age slips by while we’re dozing. The more familiar the world becomes, the less information your brain writes down, and the more quickly time seems to pass.

– Source: “The Possibilian“, Burkhard, Bilger, The New Yorker, 2000

We don’t have to do something life-threatening to get that amygdala stimulation. Anytime we leave our comfort zones (leaving the known, well-trodden path), we’re going to get some amygdala action, whether we’re going blues dancing for the first time or riding a motorcycle through a new stretch of country.

But “remembering best” involves more than just distinctness of memory. The memory also has to be a healthy one – something that doesn’t cause us regret later on. What “best memory” means in a longer-term context – a full life-view – matters. The things we choose to do should be in accord with our values and self-interest, no matter how interesting they might otherwise be.

This is why we shouldn’t always do the riskiest or newest thing available to us at all times. Sometimes “doing what we’ll remember best” does mean doing something highly responsible to the wellbeing of our future selves.

So with all this in mind, we can rank our choices by “best-memorableness”. That won’t look the same for everyone.

Here again are our choices for the weekend:

  • Go home, eat gelato, and watch a few episodes of LOST 
  • Go snowboarding for the first time 
  • Go to a new restaurant with good friends 
  • Stay late and grind out a major work project with your colleagues until 1 AM 

For some of us, the best-memorable choice will be snowboarding for the first time. That’s something that will feel very new to you, and it will leave a deep impression on your brain. If you do it well, or at least with courage, it will also be a moment of personal development for you.

For some of us, the best-memorable choice will be forging relationships with certain (good) friends over a dinner. Maybe these friends are new to you. Maybe you’ll get to know old friends in new ways. And maybe this night is the one that you make the breakthrough or forge the relational bond that you’ll both remember and rely on into the future.

For some of us, the best-memorable choice will be working late, believe it or not. The work will stretch us. We’ll build camaraderie with our coworkers. The extreme pressure and risk-taking of a major project will make for deep memories. We may not always remember our day jobs, but we’ll remember exceptional moments like this one.

We shouldn’t underrate the importance of rest. It’s a precondition for doing all of the best-memorable things. But the best-memorable experiences will rarely ever be eating gelato and watching LOST, or any kind of lounging, repetition, comfort, or stagnation. And yet how often do we choose these ways of spending our time?

If you really have trouble choosing, just simplify. What makes for the best story? What makes for the life story you’ll be proud of? You are a player in a story, after all, and you get to choose the quality of your time on stage.

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James Walpole is a writer, startup marketer, intellectual explorer, and perpetual apprentice. He opted out of college to join the Praxis startup apprenticeship program and currently manages marketing and communications at bitcoin payment technology company BitPay. He writes daily at