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But one danger you should be aware of is the high flyer that becomes addictive. Shortly after I retired, I was granted family and friends IPO shares in a startup that spun technology from a research center I had directed. The price of the stock rose so fast and was so exciting, wife wife insisted in investing all of her Keough funds in it. After rising to nearly $200 a share it precipitiously collapsed along with so many dot.coms. It's as bad as Martinis or pot, but maybe I had just made too many visits to One Palo Alto Square and 3000 Sand Hill Road.

I'm very familiar with that - I worked for one of those high fliers, and saw the "value" of my ESPP and options go from $100+ to $3-. As my father used to say, "We get so soon old and so late smart". Fortunately, I cashed out of a good part of my stock and options near the top, so although we didn't do as well as we could have, we did better than many of my coworkers who held out for even greater returns.

I like the idea of the bucket approach. I did the NPV calculation using Excel, and if I treated the pension as FI, then with a 50/50 allocation all my pretax accounts would be in equities. This made me feel quite nervous, which is why I made the original post. I'm now thinking of CDs or short term cash instruments for 5 years of income needed to make the difference between pension and living expenses (remembering to allow for income tax and inflation), and then the rest in a diversified allocation of equities. I'll check out the discussions on the DCA approach.
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