[USER]

Have a stock account value about $1.6 million. Mostly individual stocks. Apple, tesla, att, travel stocks. Account has grown well this year and over history.

Retiring early this year and would like to have more safety with indexes, etfs, maybe bonds and dividend stocks.

Is there a way to sell off most of what we have and buy the others and not be taxed?

Or any options to make the tax less expensive?

[Jenn]

If this is all in a 401k or Ira, the answer is no. You’ll pay the gains.

Now with that said, you don’t have to pay the gains right now.

You’ll have until 4/15/26 to cut the check.

[Rawee]

When you don’t have the diversity of a index or concentrated sector-based ETF, you need to become a hybrid portfolio manager and analyst if you plan to hold individual stocks as you re-balance, as some are still in growth-mode while others plateau (e.g. analyst ratings of buy, hold or sell based on price targets).

Most of those stocks you listed are consumer discretionary, and if there’s a recession into the period before you re-balance, you’ll be completely exposed.

Even in a sector ETFs: the Vanguard Consumer Discretionary VCR ETF has 18% exposure into TSLA, which I completely disagree with based on their EV-only product-line offering.

[Luciano]

What type of account is it? You didn’t mention that. If it is a retirement account ira, roth ira, 401k then you can sell and buy tax free as long as you don’t take the money from them.

Ira & 401k you will be taxed and possibly pay 10% penalties if you are not at least 59.5 years of age

[Paul]

For those stocks in the portfolio that pay dividends, you may want to turn off reinvestment, so you can invest those proceeds elsewhere.

You will pay taxes on those distributions regardless, so that’s one gradual way to channel some of the funds elsewhere.

[Jonathan]

I would get rid of or downsize AAPL. Either it topped in Dec and will reject in the 250-255 area or 1 more high to 270 and down down down for some time….

Do you own DD of course

[Nam]

Wait until you retire to sell but you’re going to get a tax hit regardless.

It might be less of a hit if your overall income is less.

[Kurt]

There is a way to convert low basis stocks into an etf deferring taxes until you sell that etf. Do you have an advisor?

Please ask him or her about it.

It’s important that it’s done correctly in order to defer all the tax at conversion and allow diversification.

[George]

* Sell stocks with minimal capital gain
* Stop auto reinvest on dividend

* Donating/gifting stocks instead of cash
There’s really not much you can do to avoid the tax.

[Author]

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