So basically my situation is I made over $500,000 on stocks in 2025, my agi was $553k, however in 2026 I pretty much lost it and I am down to $150k as of right now. I can’t afford to pay any taxes right now or even estimated quarterly taxes.
Now I think if I give it til January 2027 I can be back to $500,000 and be able to pay these taxes but my best bet is to take the fees interest and pentalties until then because if I pay anything now, I won’t have enough to pay the full amount and I’ll be left with absolutely 0 dollars.
Now I’m expecting to only make $80,000 this year because I sold some stocks for that much profit but I’m not selling anything else til 2027 so I can owe A LOT LESS than 2025 so I don’t screw myself up again.
I owe $167,000 to the federal, $34,000 to the state and $47,000 a quarter in quarterly estimates. How much fees, interest and pentalties can I look at all together when I file next year. I really need urgent help on this as I am very stressed but it’s my best bet other than bankruptcy which I do not want to do it will mess my life up. However I trust that I can make back + more what I have to owe this year but I just have to wait until 2027 to do this.
Need help! Drowning in tax debt but got a plan
byu/Confident_Dot_7240 intax
Posted by Confident_Dot_7240
8 Comments
Remember the 4 rules of planning:
Make the plan,
Execute the plan,
Expect the plan to go off the rails,
Throw away the plan.
So what you’re saying is that you’re a trust fund baby without a job and you want to do is take a HUGE gamble that you’ll be able to invest wisely and make enough money to set things right + all the additional money you’re going to owe from waiting.
Yeah, don’t do that. Set up a payment plan… It doesn’t even have to be that much per month. And get a part time job to pay it so you can leave you investment money alone.
If you truly plan to have 0 income this year from the selling of more stocks, then you don’t need to make $47k quarterly tax payments. Safe harbor is 100% of the taxes you owed for the prior year, or 90% of the taxes you owe for the CURRENT year… so if you make nothing, and you make no quarterlies, you’re fine.
So you made a bunch of money gambling in the stock market, burnt through $500k without a thought, and are now finding out how it sucks to owe money. Seems like you made poor life choices, mate.
You need to consult with a CPA or Attorney. Not Reddit.
Lowkey sounding cooked bro. Best of luck…
Have you seen a tax professional? If not, start there
So in 2025 you made $500k trading stocks, and in 2026 you already lost $350k trading stocks? Am I understanding that correctly?
