Smartest (in no particular order)1. Maxed out my 401K contributions every year they were offered. (Had an IRA too)2. About seven years before retirement, I redid my mortgage as a 15 year instead of a 30. Then, over seven years I made extra principle payments and paid the mortgage off in seven years, not 15 so I retired debt free.3. Married someone with a retirement health insurance plan.4. Reduced my stock market exposure as retirement approached. Basically got out of stocks in 1999. That year was tough; the S & P 500 was up 21% and I made less than 10%. One of my accounts made only 1.31%! But in 2000 through 2002, when the S&P lost 40% and Nasdaq did a lot worse, I actually made money, and I upped my equity allocation to 45% in March of 2003. I missed the crash entirely.5. Took a lump sum pension instead of the income.Five Dumbest:1. Have been underinvested in bonds the last 5 years.2. Should have been looking more at real estate as an investment.3. There are some things around the house I wish I would have gotten done before I retired, like a new kitchen; stuff it's easier to bite the bullet and do when you are working.4. Wish I had put every cent I own in Euros in about 2001. For that matter, I wish I would have bought an appartment in Paris or a farm in Tuscany at that time. Someone who worked it so they have their hard assets in Euros and their liabilities in dollars at U.S. interest rates could have gotten sort of rich without really trying in the last 5 years and had a lot of fun doing it.5. As John Meynard Keynes said on his death bed "I wish I had drunk more champagne".
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