It would be interesting to see an investment model that assumes a basket of historical companies to approximate someone's unrealized compensation over a random period of historical data.
Over 40+ years, consider not just a few current strong companies like Apple and MS, but also many others that have gone through many business cycles or perhaps have ended. IBM, Oracle, Sun, DEC, SGI, Cray, HP, Intel, AMD, ATI, NVIDIA, Maxtor, Seagate, Dell, Gateway... Or, consider other baskets to suit your employer basket: IBM, EDS, CA (tech consulting)... PWC, Arthur Andersen (audit/services)... Sears, Montgomery Wards, JC Penney (mail-order/logistics/merchants)...
I think many people make the mistake of "this time it's different" or "I'm different". My cohort saw many people go through the dot-com bubble and it sure seemed random as to which ones won a lottery and which ones got only a t-shirt in the end.
In my view, the only rational strategy would be to continually convert your employer compensation and reinvest into the diversified portfolio you would otherwise consider prudent if you weren't in that particular job. Anything less than that, and you are making an implicit gamble to time the market while perhaps telling yourself it is a tax optimization.
Over 40+ years, consider not just a few current strong companies like Apple and MS, but also many others that have gone through many business cycles or perhaps have ended. IBM, Oracle, Sun, DEC, SGI, Cray, HP, Intel, AMD, ATI, NVIDIA, Maxtor, Seagate, Dell, Gateway... Or, consider other baskets to suit your employer basket: IBM, EDS, CA (tech consulting)... PWC, Arthur Andersen (audit/services)... Sears, Montgomery Wards, JC Penney (mail-order/logistics/merchants)...
I think many people make the mistake of "this time it's different" or "I'm different". My cohort saw many people go through the dot-com bubble and it sure seemed random as to which ones won a lottery and which ones got only a t-shirt in the end.
In my view, the only rational strategy would be to continually convert your employer compensation and reinvest into the diversified portfolio you would otherwise consider prudent if you weren't in that particular job. Anything less than that, and you are making an implicit gamble to time the market while perhaps telling yourself it is a tax optimization.