My 'checkpoint' occurs every birthday. I don't celebrate my birthday. Instead, it's a quiet day for me to reflect on where I am, where I came from, and where I'm headed. This is usually the time where I'll reminisce and become nostalgic about some things in my past. By in large, I use the time to look at the goals that I've achieved, what I fell short on, and what my next steps are going to be.