Sell Stock and move the money to a 401(k) w/out paying taxes?

[sunshine77]

As an employee I was gifted company stock that vested over 10 years. It has all vested now and is free-and-clear with a value of about 50K.

Is there any way I can move this "value" into my 401(k) without paying capital gains? Do I have to pay regular income tax on it if I sell it as well? I feel like the government should WANT me to move this into retirement tax-free

 

[shepherdgirl]

@sunshine77 No. You must pay capital gains on the sale, regardless of what you do with the money afterwards.

If you aren't already maxing out your 401k, you can increase your paycheck contribution and then pay for your ordinary bills with the proceeds from the stock sale. This will have the effect of reducing your taxable income via greater 401k contributions.

 

[briantheguydude]

@sunshine77 Why would the government want to let you move all this profit into a retirement account tax free? They’re going to tax you as much as possible.

 

[sunshine77]

@briantheguydude Yeah I was kind of being sarcastic.