How to secure your stock positions without paying taxes?

[WannabeWealthy]

This year has been a tear so far for me in my investments.  I got really lucky and have only $80k left to go before I would have gained back all of the money I lost in my divorce.  I'm very worried however.  I've had to sell/buy stocks multiple times.  I would like to cement my gains to remove risk from my highly volatile stocks, but doing that will require selling some.  I don't know how much I'll owe in stocks but the ones I'd like to sell I haven't owned more than a few months.  It would be considered ordinary income.  Are there any ways of being able to move stocks into safer stocks/bonds, etc.. without paying tax on those withdrawals?

[CCL]

Off the top of my head, the only thing I can think of is to reduce some of your taxable income as an offset. Could you contribute to a deductible 401k or IRA?

[phil5185]

"""I'd like to sell I haven't owned more than a few months."""

You can move your 'sell' date by buying 'put' options.  When you own a 'put' your gain/loss is cancelled. Eg, if your stock goes down, your 'put' option goes up by a corresponding amount. Ie, your value is locked, doesn't go up or down. So you can stay in that neutral position until your gains switch from short-term to long-term (one year) and the tax rate drops to 15%.

Another way is to sell 'call' options against your stocks. If the stock price goes down, the option buyer has the option to buy (call) your shares at a predetermined price. (He buys your shares at the lower market price, and you are contracted to sell to him). 

But for the most part, you still pay the taxes, you just postpone them.  You can move some of your gains into the next year to lower the rates. 

Or, a more certain way is to let your heirs inherit them, the gains from inherited stocks are tax-free.

 

[MN-Investor]

Do you have any investments which you can sell for a loss to offset the stock gains?

[WannabeWealthy]

Jul 13, 2020 10:07:25 GMT -5 MN-Investor said:

Do you have any investments which you can sell for a loss to offset the stock gains?

Not really with everything going up so well.  I'm completely into tech stocks.

[Deleted]

One of my favorite stock market maxims: Nobody ever went broke taking profits. I know, the tax part of it stinks, especially for short-term gains.

You might want to just sell part of each holding, so you take some off the table but leave some to grow.

[Rukh O'Rorke]

Are you maxing 401k?

Seems like a way to balance the tax bite is to put more in 401k to offset the taxes.