Stoic #1: Use Prospective Retrospection to Minimize Future Regret

If what you care about most of all is that your life have a certain arc, then in travelling along that arc you are moving towards a point at which the arc is complete and your purpose is lost. If you are telling the story of your life, and you hope to avoid the midlife crisis, better not to tell a story of this kind.

In effect, I am urging a philoso

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Time horizons are the bases of our decisions – and of our regrets. Live as if you would die tomorrow, and you will regret not having pursued long-term engagements (such as fulfilling professional ambitions, building a family, and so on). But live as if you couldn’t die and you will regret not having done what you cannot do anymore. Getting the time

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The past wasn’t as good as you remember. The present isn’t as bad as you think. The future will be better than you anticipate.

In the beginning, the dissonance between the scale of your aspirations and the reality of your days will riddle you with anxiety. You will be tempted to strip the unknown of its surprises and travel to the future: What if my customers churn? What if a competitor introduces a better product? What if I run out of ideas? But spending your time wrestli... See more

The future will never provide the reassurance you seek from it. As the ancient Greek and Roman Stoics understood, much of our suffering arises from attempting to control what is not in our control. And the main thing we try but fail to control – the seasoned worriers among us, anyway – is the future.