The most important principle is that the tax tail should not wag the income dog. There is no such thing as a 100% tax rate in industrial world, so you'll always keep quite a bit of what you make. The best advise I was given by a tax accountant was: "Sell high. No matter what you do with your taxes, you can never beat selling high." I paid the guy $250 in 1995 to explain the AMT, and capital gains taxes to me and it's been worth every penny and saved me and some of my friends gobs of money. In fact, one day I ran into Niniane and one of her beaus and she introduced me as "the guy who saved her lots of money in taxes."
That said, it's surprisingly how little you can actually do to save on taxes:
- Join a pre-IPO company and exercise all your stock options. This usually involves substantial risk --- I've written off thousands of dollars in bad stock. But a college professor in Computer Science and I were comparing compensation and it turned out that he got paid about the same as I did, and the big difference was that I was able to convert most of my income into capital gains through this maneuver while he couldn't do so through his consulting business.
- Move to a low state tax. For me to give up California weather, that would be silly. I have friends who have done so, but if I wouldn't consider myself wealthy if I couldn't live some place with good weather. The folks I know who've done this don't consider an outdoor life important to them. If you're not a US citizen you can even move somewhere with zero capital gains taxes (like Singapore) and pay no capital gains on US stock. Pretty nice, huh? Except I've lived in Singapore and I moved away for very good reasons that are still valid.
- Use tax managed funds and indexed funds whenever possible for your taxable portfolio when investing
- Max out your 401(k) plans
- Buy a house (but not too much house that it destroys your finances). But frankly, buying a house is a consumption decision, not a tax decision. Do not let people talk you into owning a house because of tax savings! Someone I know had this happen to her and deeply regrets it. Fortunately, she won't be affected financially by this, if at all, but many others will not be as lucky!