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There’s nothing earth shattering about that concept. The process is often done haphazardly or even against traders’ best interests. If tax consequences were not a factor you’d theoretically search for the weakest link in your current holdings and sell those shares to fund the new purchase.
Human nature often clouds that fairly easy goal and leads to bad decisions. Suppose you have one position [Stock #1] that was purchased for $10,000 and is now worth $20,000. You also have a different holding [Stock #2] that was bought for $30,000 and has declined to $20,000.
You feel great about the winner as it’s ahead by 100%. That bad position represents a 33.3% paper loss. That makes you feel like a chump, not a champ. Here’s a quick look at the possible actions you could take to get the cash for your newest exciting idea.
| Sell Winner | Sell Loser | Collect | Tax Implication | Inner Feeling | |
| Stock #1 | X | $20,000 | Owe Tax on $10,000 Gain | Winner’s Glow | |
| Stock # 2 | X | $20,000 | Save Tax on $10,000 Loss | Loser’s Remorse |
In either case you would free up $20,000 of cash to make the new investment. Selling the winner made you feel smart but adds a big tax liability. Exiting the losing position abandons all hope of a recovery by locking in a loss. Either action provides $20,000 for the new investment. It could cost $2,000 - $4,000 next April 15th to revel in your success. Any psychic damage from feeling dumb is offset by the hard cash tax savings.
Even knowing all the above doesn’t stop most people from taking the gain while continuing to ride with the underwater position, hoping to reach breakeven.
Before making your own choice, go back to your research. Evaluate each company based on all available information available right now. Figure a realistic target price for each. Unless the presently depressed stock has substantially better future potential than the winning stock does think about taking the loss and shifting the funds to the new, more promising shares.
The taxation angle gives that strategy a big statistical advantage.
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