gosmund wrote:I have a few individual stocks and a bunch of cash. Instead of jumping in with two feet at an all time high are there any suggestions on how to get into a well-planned, diversified, index fund portfolio?
My allocation is well research but I do not know if I should dollar cost average over several months or what?
Welcome to the Bogleheads forum!
Your most important decision is to decide on your overall stock/bond/cash decision. Vanguard has this tool to help you:https://personal.vanguard.com/us/funds/tools/recommendation
Once you've made your decision, consider the Three-Fund Portfolio:viewtopic.php?f=10&t=88005
With a suitable stock/bond allocation, I prefer to invest all at once to the desired portfolio. However, if a subsequent and immediate market decline would discourage you from staying-the-course, it is better to invest over a period of time.
If your individual stocks are down; sell and get the tax benefit (and use diversified mutual funds).