I'm an accidental timer.
I had both my Roth and my husband's Roth maxed out for 2015 and invested in our typical allocation of stocks/bonds on, like January 2nd last year. I do this every year, and I think nearly every year after I contribute there's a dip in the next day or two. It annoys me, but I don't really care because I know lump sum, the earlier the better, beats other choices.
This year I was ready to fund our IRAs ASAP, as usual. But I decided we should switch to traditional IRAs. So that required opening a new account.
I either missed a step, or Vanguard has some sort of policy about the money first going into a holding fund (money market) of sorts. I called as soon as I could that same day to find out how to move it. Easy peasy, just do it online.
Went to do it online, but then learned that I couldn't invest in Admiral shares because the minimums are based on that individual account, not your investments across vanguard. Figured I should call back and first do a roll-over that's been hanging out on my to-do list first, then I can invest the 2016 contributions in Admiral shares.
New traditional IRA still has $5,500 just sitting in the money market. I have tried calling Vanguard several times since then, and for some reason or another haven't been able to complete the rollover. (Call went on too long and I had a meeting I had to attend, so I had to cut it off. Called at 9:30 thinking they closed at 10. Called on a weekend and they weren't open. Called and then a kid needed me.)
Since this is taking me so long (we are going on a week now), and prices keep dropping, I'm like "hey, good thing I can't seem to get anything done! Hmm, maybe I should do that rollover and let the $5,500 sit for a while until it see it coming back just a bitty bit.." I know market timing is stupid, that's why I do things the way I do. But I'm suddenly finding it almost irresistible...