How do I sell different parcels of the same shares, and calculate CGT?

Let's say I want to sell $2000 worth of a particular ETF to fund my retirement later on. Since I would have DCA'd throughout many years, how do I select which particular parcel to sell so that I can calculate the capital gains/loss for tax purposes? I am happy to go with the First In First Out method, which seems to be the most common, but how can I calculate this? I assume that we don't need accountants now during our accumulation phase, but do I have to keep all the CHESS paperwork so that I can calculate CGT decades later when I've finally FIRE'd and am ready to sell? This seems to be quite cumbersome (especially for someone like me who hates paperwork)! Can you please explain everything we need to know (and the paperwork we need to keep for filling out our tax return) to get us ready for when we start selling parcels of shares down the track? Thank you!

Clara Fu

Asked on 13 November 2023

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