Talk To Tomorrow

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We all wonder what it would be like to sit across from our 90-year-old self, someone who has lived through the outcomes of our choices, watched our patterns repeat, and finally learned what mattered. That version of you wouldn’t speak in motivational quotes. They’d speak with clarity: what you protected that paid off, what you wasted time on, what you should’ve taken more seriously, and what you should’ve enjoyed more. With AI, you can actually simulate that conversation. Not as fortune-telling, but as a way to borrow perspective, so you can make better decisions while they still matter.

To do it well, you have to give the AI the raw ingredients of you. Tell it your age and current life situation, the traits you’re proud of, the habits you know hold you back, and the kind of person you’re trying to become. Then be clear about what you want: ask it to respond as your 90-year-old self—warm, honest, and specific—calling out what your strengths can build, what your weaknesses can cost, and what you’re most likely to regret if you don’t change course. This practice is useful because it cuts through noise. It helps you zoom out, see your life as a whole, and choose what “ages well”—health, relationships, integrity, meaningful work, over what simply feels urgent today.

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