In putting the finishing touches on the CollegeAppRoadMap program before its launch this Friday, I've found my favorite part of the whole thing. 

Each year, I have students do free-writing exercises to help brainstorm their essays. This time, though, we're doing it according to different themes. 

The first theme? Making Difficult Choices.

Download the handout here. I think it speaks for itself. But here's how the writing works:


  • Set aside 1 hour each week for writing time only (not including watching/listening/reading time). 
  • Break that hour into three 20-minute sessions. 
  • Get a designated notebook if you like writing by hand.
  • If you prefer to type, I recommend the Day One app, but a plain old document will do.
  • Always date your entries and keep them separate from each other.


  1. Sit down
  2. Set a timer for 20 minutes
  3. Open your notebook or document
  4. Take three deep breaths
  5. Start the timer
  6. Write as quickly as you can.

Do NOT delete, cross out, erase, go back, read, edit or stop until the timer has finished.
(If you get stuck, write “I can’t think of anything to write” over and over until a new thought comes.)

You can write about whatever is in the forefront of your mind that day. You could respond directly to the videos or podcasts, you could vent about a crappy day, or you could use one of the fun and interesting questions on the following pages as a springboard.


Let your mind wander—see where it wants to take you. 
The best college writings often come from the ideas that surprise you the most.