Tax loss harvesting and indecision

[sophie]

With bonds dropping like a rock, I have a nice opportunity to harvest losses, and in the process move the money into a Roth.

The only trouble is that I'm in sort of an analysis paralysis situation.  I just can't be the PP Zen master about the timing of when to sell.  The portfolio will be unbalanced during the 30 day waiting period.  If bonds go back up, it's likely that stocks and/or gold will have gone down, so the portfolio could take a significant hit and make me kick myself repeatedly.

Anyone else planning to tax loss harvest?

[sophie]

With bonds dropping like a rock, I have a nice opportunity to harvest losses, and in the process move the money into a Roth.

The only trouble is that I'm in sort of an analysis paralysis situation.  I just can't be the PP Zen master about the timing of when to sell.  The portfolio will be unbalanced during the 30 day waiting period.  If bonds go back up, it's likely that stocks and/or gold will have gone down, so the portfolio could take a significant hit and make me kick myself repeatedly.

Anyone else planning to tax loss harvest?

I just commented on your post in another thread here. No wash sale rules would apply in this case, so you don't need to wait.

Are you sure???  That would be great, but I thought it didn't matter if you buy the new assets in a different account.

EDIT:  The wash sale rule applies.  http://www.irs.gov/pub/irs-drop/rr-08-05.pdf

[buddtholomew]

With bonds dropping like a rock, I have a nice opportunity to harvest losses, and in the process move the money into a Roth.

The only trouble is that I'm in sort of an analysis paralysis situation.  I just can't be the PP Zen master about the timing of when to sell.  The portfolio will be unbalanced during the 30 day waiting period.  If bonds go back up, it's likely that stocks and/or gold will have gone down, so the portfolio could take a significant hit and make me kick myself repeatedly.

Anyone else planning to tax loss harvest?

Although I have not reached a rebalancing point, the plan is to only harvest losses in an asset when I have gains to offset those losses in another one. This should in theory restore balance to the portfolio. How this approach impacts the return of the portfolio is anothe question.