How do you hope to have lived?

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Illustration by Jon Graeff
Hero image
Illustration by Jon Graeff

Over the past two years I’ve had the privilege of interviewing dozens of creative people — asking them about their thoughts, practices, processes, beliefs, and approaches to living.

Of the 100’s of questions I’ve asked during that time, two stand out as particularly illuminating.

As I share them, consider your own answers.

1. What are your ambitions?

Photo by Simon King on Unsplash
Photo by Simon King on Unsplash

2. How would you like to be remembered?

While the answers to each question individually are interesting, they become even more so when I think of them as a pair.

Because — essentially — they’re two ways of looking at the same thing: the imagined outcomes of a life’s activity.

Despite their common focus, my experience tells me (and perhaps you see it in your responses, too), that the twist in direction of thought — from projection to reflection — leads to very different answers from the same people.

Most often, the question concerning ambition results in answers about tangible things or events. These are objectives to be achieved, obtained or checked off — a goal that will be met or missed, concluded or incomplete, passed or failed. They tend to put the individual at the center and, in line with the question, describe what people hope to do or make happen in their life.

Contrastingly, answers to the question about looking back take the form of more intangible human qualities and values. Qualities like being kind, a good person, or a generous friend, being independent, free, dedicated, content or immersed in a rewarding passion — ideas focused on how people will have lived.

This is not to say that the pairs of answers are all mutually exclusive or incompatible — but very rarely do I discover deliberate and intentional relationships between the two, or a conscious appreciation of which is more important. Clearly whats and hows co-exist in all lives, but only one can be the true driver.

Our life always expresses the result of our dominant thoughts.
Søren Kierkegaard

Looking forward to what should be achieved and back towards what should be left behind provoke people to describe lives with different priorities and measures of success. Considering we only have one life to live, choosing the right lens seems pretty damn important.

If we want the result of our life to be something meaningful, something we’re proud of, something free of regret, we should know what’s important to us — we should understand the dominant thoughts on which to focus and orient our decisions.

As I think about how we might form and hold the right thoughts for a meaningful and rewarding life, I reflect on the answers I’ve heard and the demeanor of those answering.

Thinking about ambitions and future plans often seems tense, difficult, loaded, and filled with expectation. It’s understandable. While thinking this way gives us direction and tangible goals on which to focus, it also asks us to imagine what we can gain, have, keep, achieve or control in a future that’s full of chaos and unknowns.

People’s thoughts about how they’d like to be remembered, on the other hand, are regularly accompanied by relieved smiles, exhales, and surrendering shrugs. In fact, the answers flow out so easily that they’re frequently dismissed as being somehow too simple, obvious or generic to really count as valid.

That reaction, I think, is a mistake.

It’s easy to dismiss what comes easily in favor of what takes more careful consideration — but what if we welcome the ease with which these answers flow? What if we marvel at their simplicity and embrace their apparent obviousness as a sign of their validity and virtue? What if we cherish their focus on the how of how we live — and trust that the things we’re meant to do or achieve along the way will naturally fall out of the process?

When we’re imaginarily dead and looking back over our imaginary life we get a moment of priceless perspective—a perspective free from the expectations, pressures, ideas and desires that cloud our judgement in the present. We need only think about how we hope to have navigated the chaos and uncertainty of life, not what we want to have taken from it. We get to name what we really matters to us — what, in the end, we value above all else.

Holding onto this is important, because, as much as those answers are easy to conjure, they’re just as easy to misplace. The problem is not that we don’t know what we value, but that we forget to remember. We look forward from our current vantage point and allow ourselves to be distracted and dragged off course by what we think we want to happen — we focus on what we want to do rather than how we want to have done it.

While it might feel egotistical to think about being remembered, my experience is that that the effect is actually opposite — people’s desires tend to become more benevolent, simple, timeless and fulfilling.

Consider how different the futures we’re creating for ourselves and others might be if we start at the end — if we can look forward by looking back. If we can hold how we want to be remembered as the point from which we chart our goals, markers and ambitions, and if we can confidently dismiss anything that doesn’t serve the cause. If we can think about, in all aspects of life, how we’ll leave a situation, rather than what we can get from it. If we can wake up each day to appreciate accomplishments that are the bi-product of remembering how we hope to have lived.

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