Times when I have large sums to invest are when markets are at all-time highs :/

[RioIndy]

Anyone else find this frustrating?

For the last several years, whenever I finally get access to large sums of money to add to my portfolio, the markets are at an all time high. Whereas many of the bigger dips, hence the best buying situations, are when I don't have much on hand. And I can't just hold all this liquid cash hoping that markets will drop, because a drop may never happen.

I assuming that markets are this way because that is simply the trend that most people find themselves with funds around the same time. Biggest trend I have been noticing is beginning of the the calender year.

Only thing I can do is try to dollar cost average my contributions over a few weeks, or perhaps a month or two at best.

 

[Mulligan]

I'm with you! Of course large sums is relative, but it is large to me. I have a nice pension that I live off of and continue saving from it and for awhile had a part time job. I reached my goal of accumulating safe money in CDs and IBonds, and now that I determined a while back I was going to fully invest my HSA and other dead money not allocated to the above, the market won't cut me any slack and drop so I can invest it. I did deposit my full yearly Roth contribution from last year at the low a few weeks ago, but I really thought it would go lower. I fully understand I cannot time the market, but then I start thinking this might be 1964 all over and I will be under water for the next 18 years. Yes, I confess, I am a loss aversion type, so I will just wait even if it's a year or two. I would even be fine if the market didn't drop as long as big oil did, and I would then just buy them and forget the money for 15 years.

 

[Options]

My ISP calls for a dose of self-flagellation if I attempt to time the markets. I invest regardless of what the market is doing. Buffet's latest annual letter addresses this.

 

[robnplunder]

Only thing I can do is try to dollar cost average my contributions over a few weeks, or perhaps a month or two at best.

Beats market timing over long run. I settled on moving a set amount once every month (every 15th of the month to be exact). I do the same when cashing out of equity. I take a fixed amount at a time to average it.

 

[Mulligan]

Rob, I use that exact day to have an automatic $500 deposited into my total stock fund. It's odd in my own peculiar ways, but since that is a small amount and I treat it like a bill with no intention of ever using the money and it has grown nicely for the past 5 years it doesn't concern me. But this big chunck I am sitting on would bother me if I lost any of it right off the bat, even though I plan on never accessing it either.

 

[SVHoper]

Yeah I feel your pain, but sorry no answers.

I had a bit of cash at the beginning of the year and made two schedules:

(1) Equal chunks for 12 month or

(2) Equal chunks for market drop 5%, 6.25%, 7.5%, 8.75% and 10%

I was planning to do (1), but if (2) happened I would put the bigger chunks in. Well I hit the 5% one which means at least I am ahead of the first schedule

If the dip happens late in the year (2011 when big VB drop happened in August) - I may be out of $ by then and of course I would have been better lumping.

Such is life.