Stage 3: Vision & Direction | The Rocking Chair

You're going to imagine yourself at 80 or 90 years old, sitting in a rocking chair and looking back at the life you have lived.

From that vantage point, you'll ask yourself a handful of questions. What are you grateful you did? What do you wish you'd done differently? What turned out to matter, and what turned out to be not as important as you thought back then?

The exercise works because the perspective of the end strips away social pressure. When you're imagining your 85-year-old self, you stop caring about what your peers think, what looks impressive on paper, or what you're "supposed" to want. Those layers fall away, and what's left is just what actually matters to you.

Interestingly, most people discover that what they actually want from their life is peace of mind. Knowing they lived on their own terms, cultivated deep, meaningful, and beautiful relationships that mattered, and that they didn't trade away decades for someone else's definition of success. The specifics differ from person to person, but the underlying feeling is remarkably consistent. Peace.

This is a short exercise. It shouldn't take more than 30 to 45 minutes, but do it somewhere you won't be interrupted.

Why this works

Three bodies of research point in the same direction here.

Bronnie Ware spent years working in palliative care, sitting with people in the last weeks of their lives. She recorded their most common regrets and published them in her 2012 book, The Top Five Regrets of the Dying. The top regret? "I wish I'd had the courage to live a life true to myself, not the life others expected of me." The others follow the same theme: working too hard, not expressing feelings, losing touch with friends, not allowing themselves to be happier. Every single regret is about authenticity and connection, not achievement.

Karl Pillemer, a gerontologist at Cornell, took a more systematic approach. His Cornell Legacy Project interviewed over 1,500 Americans aged 65 and older, asking them what they'd learned about living. The results became his 2011 book, 30 Lessons for Living. One of the clearest findings: older people almost universally say they wish they'd spent less time worrying. They describe worry as the single biggest waste of their lives. They also emphasise choosing work for meaning over money, investing in relationships early, and saying the things you need to say before it's too late.

Terror management theory (developed by Greenberg, Pyszczynski, and Solomon, building on Ernest Becker's work) studies what happens psychologically when people confront their own mortality. The research shows that mortality salience, simply being reminded that you'll die, shifts your values. People become more focused on what's really meaningful to them and less driven by external validation. The rocking chair exercise uses this effect on purpose. By imagining the end, you gain access to priorities your everyday mind tends to bury under obligations, deadlines, and other people's expectations.

All three sources converge on the same point: people at the end of life, or people confronting mortality, get remarkably clear about what matters. This exercise borrows that clarity and gives it to you now, while you still have time to act on it.

The exercise

Access your Notion workbook here.

Part 1: The visualisation

Read through the passage below. You can close your eyes after each paragraph and build the scene in your mind before continuing.

You are very old. Somewhere in your 80s, maybe your 90s. You're sitting in a comfortable chair on a porch or by a window. The light is warm, and everything feels quiet.

Your body has slowed down, but your mind is still sharp. You've lived a full life. Decades of choices, changes, relationships, losses, and joys are behind you now. There's nowhere left to rush to.

Now you're looking back. You can see the whole arc: the things you're proud of, the risks you took, and the ones you didn't. The relationships you had, the time you spent well, and the time you wasted.

From this chair, at this age, you can now see clearly what mattered and what didn't. The things that felt urgent at 30 or 40 look different from here. Maybe some of them turned out to be important, but many of them didn't.

You feel peaceful here, in this rocking chair at this very moment. Whatever happened, you're here now. And you have something to say to the younger version of yourself, the one still in the middle of it, still worrying, still figuring it out.

Part 2: The questions

From that place, answer these questions. Write in the first person, as your older self. Don't overthink it. The first answers that come are usually the right ones.

• What are 3 things you're most grateful for that you did?

• What is the one thing you wish you'd done differently?

• What relationship do you wish you'd invested more in?

• What did you spend too much time worrying about?

• What gave you the most peace of mind?

• What would you tell your younger self right now?

Part 3: A letter from your older self

Now write a short letter. It's from 80-year-old you to present-day you. Speak directly, be specific, and tell yourself what to pay attention to, what to let go of, and what to protect.

There's no format. Just write what comes. Start with:

Dear younger me,...

Reflection

Look at what you wrote and reflect on these questions:

• Which of your answers surprised you?

• Is there a gap between what your older self values and how you're spending your time right now?

• What's one thing you could start doing this week that your 80-year-old self would thank you for?

• What's one thing you could stop doing?

You don't need to act on everything at once. The point of this exercise is direction. If one answer keeps pulling at you, that's the one you should pay attention to most.

AI companion (optional)

How to use: Complete the exercise first. Then paste your answers into an AI assistant for a deeper conversation about the patterns in your responses.

Copy and paste the prompt below into Claude, ChatGPT, or any AI assistant:

I just completed a rocking chair exercise where I imagined myself at 80-90 years old looking back at my life. Here are my answers: [Paste your answers from the questions and/or your letter here]
Help me go deeper. Ask me follow-up questions about the patterns you see in my answers. I want to understand what my responses reveal about my current priorities versus the priorities of my older self. Where are the biggest gaps between how I'm living now and what my future self says mattered most?
Be direct and specific. Don't give me generic life advice.