14 writing prompts for your daily journaling

I journal nearly daily using Day One on my iPad. Occasionally, I go old school and write with a pen in a notebook. But mostly on my iPad. With a mechanical keyboard that goes clickily-clack when I type. Yes, all my colleagues love me. Why do you ask?

Day One has the advantage of allowing users to create templates for reuse as they see fit. I have one that asks if I have meditated, exercised, what I have read, what my mood was, and so on.

But I have a few more with a single question each. They help me reflect. To reflect is to know thyself. Probably Shakespeare.

I try to answer a different prompt every day; hence, why they are 14. Here they are:

  • What is the worst that could happen today? (Premeditatio Malorum, stolen from the Stoics)
  • What is the best that could happen today? (Premeditatio... Bonorum? My Latin is inexistent!)
  • How did past decisions evolve contrary to what I expected? Where can I adjust for the future? (Second-order thinking but reversed)
  • Do I enjoy what I am doing daily? If not, how long has the answer been no? (Stolen from Steve Jobs)
  • What was my biggest win last week?
  • What am I grateful for? Name five things. (Stolen from gratitude meditation)
  • What are the three big things that I learned today? This week?
  • How could today have been better?
  • What did I say no to today? What should I have said no to?
  • What were my blind spots this week? My biases?
  • How can I slow down today?
  • Have I asked for help this week?
  • Have I done something that made me uncomfortable?
  • What do I spend a lot of money on? What are my money dials? (Stolen from Ramit Sethi)

There you go. You're welcome. If you have other questions, please share them with me.