Is There a 'Best' Time to File Your Taxes? by Julia Glum Ever since elementary school, I’ve suffered from chronic overachiever syndrome. I used to thrive as the teacher’s pet, clapping erasers and asking “Are you going to collect the homework?” whenever they forgot. I finished tests early so I could write stories on my AlphaSmart typewriter for kids. I once broke my arm playing kickball because I kicked the ball *too* enthusiastically. (I wish I was kidding.