I sold some mutual funds I have had invested in for about 25 years in my taxable non retirement brokerage account and acquired about $274K in realized gains. The reason I sold off was that I’m 62 and retired and just didn’t want that much still invested in the market. I created myself a big tax bill and was just wondering if there was something else I could have done to prevent that large tax bill while selling off some of the mutual funds. I always paid taxes each year on those funds but never realized once you sold them that it could be costly. Clark has told us how to save but not really how to take it out. Thanks.
Well, just off the top of my head:
- If you normally make charitable gifts, you could have donated appreciated stock
- You could have opened a DAF and contributed appreciated stock
- You could have gradually sold the stock over the next couple of years.
- You could have offset the gains with capital losses, if you have any
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In addition to butler’s comments, maybe you could have transferred the money to CD’s (laddering the maturity dates). I don’t know if it’s possible to transfer mutual funds to CD’s without selling the mutual funds and then buying the CD’s. Just thought I’d throw that out there… 
I may be wrong here, but in addition to all the other suggestions, you could have stepped up your basis by adding back all the capital gains on which you paid taxes in all the previous years, if you reinvested the funds and didn’t take as cash. This would be a daunting task to go back over all of your previous 1099s, but it could save a lot on your current tax, because your basis will have grown.
I worry that mine has been tabulated because, for instance, my original brokerage house, TD Waterhouse, merged with Ameritrade, and is now Schwab. I then moved it all to Vanguard.
I did the same but in my retirement accounts where their were no tax consequences.
I pay close attention to Mark Hulbert’s market valuation metrics. Overall , the US stock market is off the charts in terms of high valuations.