If I Knew Then What I know Now (PROMPT)

“If I Knew Then What I Know Now” 

(Advice to Your Former Self) 


Life brings regrets — it’s inevitable. Even the most conscientious person can’t avoid mistakes or bad outcomes. And a lot of the time the negative outcome wasn’t even foreseeable, because you didn’t know enough to realize something bad was lurking around the corner. For this experience, you’re going to write to your past self and tell that past self something you know now that you wish you knew then. 


Your audience is literally you in an earlier time and space. But you should also presume that your circumstances are not entirely unique and are likely shared by others. 


  1. Identify a bad outcome that could have been avoided. Remember, it’s not a matter of making a better choice when the not-so-smart choice led to a predictably bad result. We don’t want you to tell us about the stupid choice you made (we’ve all had those). We’re looking for a situation where you lacked information, not a lack of judgement, to make the correct choice.  
  2. Draft a letter to your past self:  Be kind to the person you were. Tell them what you know now that you wish you’d known then, while also telling them how to act upon this new information. Emphasize the benefits of taking a different path. Your past self may need some convincing. 
  3. Revise, edit, and polish: You’ll want your past self to be impressed with the writer you’ve become. 


Are there times when you’ve escaped a negative outcome in this kind of situation, even though it easily could’ve turned out differently? What happened?

Remix (to your future self)

Write a letter to your future self, reminding that future self of something you’d like to remember about how you looked at the world when you were younger. Getting older doesn’t necessarily mean we’re improving ourselves every step of the way. What’s something you’d like to hold on to twenty or thirty years from now?