Hey guys!

I traditionally sell some of my brokerage holdings to max my Roth on 1 Jan

How do you psychologically get over the hurdle of selling in a “down” market?

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  • My dude, you're buying stuff again immediately at a depressed price.  It actually is less tax liability from the sale of the market is down.

    Yeah it’s the best time to sell and invest in Roth.

    Just need to avoid a wash sale rule, right?

  • What down market?

    Don't you know being 1-2% off of an all time high that happened within the past few weeks is a recession?

    OP uses air quotes around down, still gets chatter. too funny.

    market has been flat for two months - it's ok to acknowledge that. nobody hurting anybody.

  • I mean... you're just going to invest it again immediately after putting in the IRA right?

    So you start with $X in securities, you temporarily have $X in cash, and then you end with $X in securities, the only difference being any movement in price during the few days you're holding cash. You haven't materially changed your position.

    Also, the market is only "down" over the last few days. Literally days. It's up massively over the last month, the last several months, year to date, and the past several years. Especially since this is your retirement money, keep your long-term perspective.

  • Think of it as a transfer

  • You're also buying in a down market. You don't lose anything.

  • fit more shares into roth, get to deduct against taxes? I'm throwing a party

  • if you're selling winners in a down market, you're still winning.

  • lol. Brother we are so far from a down market.

  • It’s literally more beneficial to max out your accounts in a down market. Assuming an eventual recovery, you are getting more value/shares for the same price.

  • You're just moving $ from one account to another. Also...the US market is up about 14% from the last time you did this, and international is up a lot more than that. So, what down market are you worried about exactly?

  • Because you are buying in a "down" market. also . . . the market isn't really down

  • Why wouldn't u just contribute enough throughout the year such that you don't have to dont this???????

  • I'm paying less taxes when the market is down

    I am diversifying my after tax money into different tax treatment accounts

  • My understanding is you also need to be careful with wash sales if you sell at a loss in a taxable account and buy immediately in a tax sheltered account.

  • The S&P is down from its all time high by about 1.5%. If that’s what you call a down market it will be interesting to see your reaction when the inevitable 40-50% drop happens.

  • Why do you have to sell some of your holdings to fund your Roth IRA?

    If your funds in the taxable brokerage account are with the same firm as your Roth IRA, why can't you just transfer securities?

    IRA contributions have to be made with cash.

    Quick question so I understand this: I know you’d sell securities from the brokerage to get the cash, then deposit the cash in the IRA. Would you later owe tax on that cash from the brokerage withdrawal?

    You can owe taxes on any gains realized from selling those securities.

    Oops! You are correct. I was thinking about the other side, distributions. In that case you don't need to distribute cash, you can take your withdrawal in kind, by transferring shares out of the IRA.

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