The Important Question Is Always the Same
In your 20s, "how am I doing?" is about identity, finding your footing as an adult. This is the crucial foundation for everything that is to come. In adolescence you were too unformed to establish a firm core of identity. By your 30s, you either have a core of identity or you don't. So the essential question in your 20s should be, Am I dealing with my issues? People who reconcile their psychological issues in their 20s are the best equipped for the challenges of life as it unfolds. The vital thing to ask is, What kind of person am I becoming? The answer needs to fit your hopes, wishes and ideals, not what others expect of you.
In your 30s, "how am I doing?" shifts from identity to achievement. You know that you belong in the world; your adulthood feels secure. Now it's time to test your powers and see how far your aspirations reach. There's still a freshness of possibility, untarnished by too many setbacks and hardened realism. Reducing this to a vital question, it would be, Are my dreams coming true yet?
In your 40s, "how am I doing?" shifts to a wider arena. Responsibility to society becomes important because the idealism of youth now finds itself yoked to a position of power and influence. In your 40s, you can begin to speak with authority, and you know the rocky landscape of early adulthood well, which means that you can navigate between idealism and realism. Distilling this to one thought, it would be, Is this the world I want to live in?
In your 50s, another shift takes place, but defining it is murky because of changing expectations. Turning 50 used to mean that you had arrived, that you were feeling financially secure, expert at your job and feeling the advances of middle age. So living through your 50s was a pivot into old age. Most of this has changed for better and worse. People feel younger, far from ready to consider the prospect of old age, yet fewer people feel financially secure in their 50s. Personally, I feel that with a remaining 30, 40 or even 50 years of life expectancy unfolding after 50, this decade is about creating a second adulthood. With the knowledge and skill accumulated from the first 50 years, you can winnow out the bad and keep the good, establishing a foundation for a purposeful life that can rise from decade to decade. So the essential thought is, What will my new life look like?
In your 60s, you used to be retirement age, but that is now undefined. Some people feel that their best years are behind them, others that the future is as fresh as ever. Some minds are filled with regrets and nostalgia, others with higher aspirations and a drive to keep evolving. It's our choice which side of the divide we want to be on. Therefore, if you decide that your life should continue to be an upward arc, the vital thing to ask is, How can I keep growing?
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