Gyroscopic Investing

Does it make sense to sell some of my stocks or bonds in my taxable account, for instance, and buy those same assets in my IRA?  Especially  considering assets that I would be selling at a loss.

"It depends."

What are you going to replace the assets with in your taxable accounts?

craigr wrote: "It depends."

What are you going to replace the assets with in your taxable accounts?

Nothing. I'm out of money. Should I sell to max my ROTH each year?

I would definitely keep some money outside a tax deferred account for emergencies. Having it all locked up in an IRA could be a problem if you need to access it.