This may sound like a n00b question, but I've never seen any guidance on exactly which shares to sell when wanting to convert some of my portfolio into cash to use for spending.

There are many online articles about re-balancing portfolios which sounds good in theory, but they simply advise you to sell a percentage of shares to get the overall portfolio share close to your target. All good, but *which* shares to sell?

To keep it really simple, my question is when selling shares in a portfolio (let's say for almost any reason, but if it matters my specific reason is because I'd like to use the proceeds for life expenses), do you generally:

1. **Sell shares that have *outperformed* the market.** The rationale here may be that you're "taking profits" from shares that have performed well, and that this is these shares' purpose - you're not meant to hold shares forever, and ones that have grown well over time are there for the purpose of "harvesting"
2. **Sell shares that have *underperformed* the market.** The rationale here may be that these shares may be duds anyway, so you're better off cutting your losses and removing poor performers from your portfolio. May as well convert them to cash to spend since they haven't performed well from an investment point of view

I *know* that past performance is no indicator of future returns - I'm not a finance or investing novice. But I've never seen this specific question answered and I feel certain that investment professionals generally choose between one or the other, all else being equal.

Even though I'm only looking for a general answer that may be a "rule of thumb" for practitioners, in case it makes a difference to the answer my situation is as follows:

* Significant capital in the market (let's call it an even million)
* I don't *need* the cash - I'd just like it to fund lifestyle choices like better travel etc.
* Purpose of investment is long term growth, but I also wish to draw down on the portfolio every year (sort of using the 4% rule, but not exactly) to fund my lifestyle and so that I don't have to work, or can work a lot less
* About 15 years away from retirement age
* Most of my funds are in shares, with a small percentage (let's say less than 10%) in debt-like instruments and cash. Not enough to care about for the purposes of this question
* Portfolio is directly invested in (i.e. not an index fund or similar)
* Country is Australia, but I also direct invest into global shares. However I'd suspect that this rationale should apply regardless of country

Note that this question and answers come close:

[I need cash. What funds or stocks should I sell?](https://money.stackexchange.com/questions/139515/i-need-cash-what-funds-or-stocks-should-i-sell)

but I'm not happy with the "sell bits of everything" answer as this seems like a massive PITA to me and not really in keeping with the spirit of the question. It doesn't seem the best approach to me to sell a few shares of *every* stock I own, rather than sell *all* of the stock of one company.

Thank you.