Exercise 16 of 20 from the Playing With Purpose Student Edition
From Book 8: The Leap (Exercises in Shipping)
The Parable
A painter was terrified of sending her work to galleries. She was about to give up completely. Then a friend asked her to do something strange. Write a letter from yourself five years in the future. She sat down and wrote. The future her talked about what it cost to take the risk. She lost some time and made some bad work along the way. But she also talked about what it produced. A body of work she was proud of. A career she loved. Connections with other artists. The letter also answered a question. Was it worth it? Future her said yes, without hesitation. When present her read the letter, something shifted. She could see past the fear to what lay on the other side.
You need to see what’s on the other side of the fear.
The Exercise
Close your eyes. Imagine yourself five years from now. You took the creative risk. Write a letter from that future self to your present self.
The letter should answer these questions: What did the risk cost me? Was it time? Money? Reputation? What did taking it produce? Did it lead somewhere?
Most importantly, future you answers: Was it worth it? Why or why not?
Write it as a real letter. Not a list. A warm letter from someone who lived it.
Now reread the letter. You just heard from someone who survived the risk.
Reflection Questions
1. What did the letter say it would cost you to take the risk?
2. What did it say you would gain?
3. Did the answer to ‘Was it worth it?’ surprise you?
4. Does knowing how future you feels about the decision change how you feel about it now?
What We Were Trying to Do
Many people believe that fear is a reliable guide. They think if they’re scared, they shouldn’t do it. But the misconception treats present fear as future truth. You’re scared now because you can’t see the other side. But the other side exists. Your fear is about the unknown, not about what will actually happen.
When you ask your future self instead of your scared self, you get different answers.
Why It Matters
This exercise collapses time. It pulls the future into the present so you can see what’s actually there instead of imagining disasters. Most fears are disasters we make up, not disasters that actually happen.
Your five-year future self is wiser than your present self. That wisdom is real. You have access to it.
References & Further Reading
Daniel Kahneman, Thinking, Fast and Slow, Farrar Straus Giroux, 2011, Chapter 10: Overconfidence
Jonathan Haidt, The Happiness Hypothesis, Basic Books, 2006, Chapter 3: What Makes Life Meaningful
Mihaly Csikszentmihalyi, Flow, Harper Perennial, 1990, Chapter 4: Flow and the Quality of Life
Going Further
This letter is just for you. No one else needs to see it. That freedom means you can be honest about the costs and the rewards.
This exercise is from the Playing With Purpose Student Edition by Greg Williams. The complete series of 650 exercises across 10 books is planned for publication in summer 2026.
This is practice. Nobody will grade this.
