Best time to sell shares

I’m planning to open my 2021-2022 ISA with FT. I currently have a GIA with them and I know I can’t just transfer my shares from my GIA to the new ISA, I would instead have to sell them first and rebuy in my ISA.

My overall portfolio is in a loss at the moment, as the majority of my stocks are at a loss. Would it be best to sell them all today and rebuy tomorrow in the new tax year. Or I was thinking funding my ISA tomorrow with some of my savings and then sell my GIA stocks when they’re in a profit. Although I know this will eat into my capital gains allowance. I’m not expecting to hit this allowance but I guess you never what will happen especially with crypto!

I just wanted to check what the best strategy would be, any opinions grateful!

This is your own decision to make. I realise it’s not a fun answer to hear, but only professionals should give you advice relating to investments and tax implications. It’s your decision and you need to be able to live with whatever loss or gain you make. Thus, I think it’s best to make this decision without input from others.

I agree with the above this needs to be your decision.
I don’t think there is a best answer just one that you are most comfortable with, but it has to be your decision.

I’m aware it is my decision to make and I will be comfortable with whatever decision it is. I was just curious if anyone had been in a similar position

Why not do it bit by bit? Dollar cost average it in? That way if the stocks take off you won’t get caught out.
You could do 5% a day.

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If you can be totally logical about it, ask yourself this: if you owned no stocks at all right now, would you buy that set of stocks today at their current prices because you think they are likely to increase in value more than any alternatives available to you? Do you think they have good business prospects and are fairly valued? If so, then buy them. If not, then maybe there are other investments with better prospects that you should look into.

It’s really hard to be completely dispassionate about investments. Most people have a tendency to cling on to the investments they already own in preference for considering alternatives. But a completely logical investor should, in principle, be ready to drop a stock without hesitation if there is some other investment with better prospects. (But don’t forget your risk tolerance and tax implications!)

Figuring out which investment genuinely has the best prospects, though, that’s even harder!

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The other question is whether it’s even worth bothering to move at all. If you’ve not already done it today, unless you’re 100% sure you won’t be able to use your ISA allowance next year, you might be better leaving the shares where they are for the time being. You’ll save stamp duty / FX fees if they’re applicable.

Obviously if the value of the shares rises a lot to the point where CGT might become a consideration, then you might want to sell them and move them to an ISA before you hit the threshold. And then at the end of the next tax year, if you still have ISA allowance left and no money to put in it, then it might make sense to sell them from the GIA and re-buy in the ISA to take you up to the limit.

But if you can, I’d say you’re probably better leaving them where you are and just using your ISA allowance to buy more shares either in this or something else.

At the end of the day though, only you know your situation and what makes the best sense for you.

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Thanks everyone! I think I’ll leave them as it is and move the ones I want to keep long term into my ISA gradually and the others I don’t plan to keep long term I’ll continue to hold in my GIA and sell them when the time is right