What would I do differently?

When my parents introduced me to mutual funds with a Roth IRA, I thought the idea of dividend reinvesting was so novel! I did nothing and yet my fund kept growing and growing with more and more shares. I continued this practice, except in a normal taxable account. This is one thing I wish I did differently.

I keep having to pay taxes each year on my mutual funds that I have outside of a 401k or IRA account. In the future I plan to segregate all dividend-paying stocks and mutual funds into my 401k or IRA accounts, and hold stocks in both retirement and taxable accounts. Of course, I wasn't as patient an investor nor as wise as I am today, so if I had been in more stocks back in 1999, I probably would have gotten trashed during the dotcom bust and left the stock market forever discouraged.

I probably should have bought a home back in 2003, when the interest rates were among the lowest ever, and a townhome in Santa Clara still cost $400,000. I would have gotten a 30 year fixed mortgage, and I would be diligently paying it down to this day. With my rent now at $2500/month, I think I'd be paying the same for my mortgage today. It's difficult to say how that would have affected my thinking, as I have switched jobs twice in the past 5 years, to higher position and salary. Perhaps I might have been more conservative and less likely to look for jobs while I had a mortgage.

Also, there are now very inexpensive online brokerages that let you nibble on small stock purchases with low commissions like Sharebuilder, Tradeking, Zecco. These brokerages offer much lower commissions than Datek (now Ameritrade), E*Trade, Ameritrade back in the early 2000 years. I have Scottrade and Zecco accounts, as well as direct accounts with several mutual funds.

I use the Scottrade account for their free real-time java applet, and Zecco for their free 10 trades / month. Since I'm investing for the long term, I want to just buy and hold for at least a year. Sometimes I sell losing stock at the end of the year for capital loss deductions on my tax return, and then buy it after 31 days to prevent a wash sale.