Re: I hate buying high...convince me otherwise
The best example of why it's sometimes okay to buy high is a (possibly true) story I heard. It happened when Buffett took over Berkshire Hathaway, it was trading around $15. Later it hit $100. One of his acquaintances decided to wait till it went back down before buying any. It never did, and he never bought. It's trading at $107,000 today, of course it's almost 40 years later.
In your case, I'm assuming you want to maximize your returns over the long run, since it's an IRA. Don't worry too much about the indexes setting records, for two reasons. First is the record setting indexes are just catching up to where they were 6 years ago (meaning you are buying something that's increased in value for 6 years, for the same price), and the Nasdaq is still less than half it's high.
Second is that you are investing for the long run, and you are only putting in a limited amount this year. Your IRA will be "dollar cost averaging" for the next 30 years. Google it. If the market collapses next year, your average price after your second year will be much closer to the market's low, than the high, because you get many more shares when the market is low. Just max out each year and don't worry.
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