My tax bill is gonna be close to 30k I only have 10k in my bank account so guess what my brilliant degenerate idea was. Put it into my brokerage and try to trade my way to 30k. Holy shit, I thought options trading was stressful in itself. It’s a whole other level when you gotta pay taxes due in a day lol. I actually made 15k. Could’ve made a lot more if I held, but once I saw that much my body pretty much forced me to press sell. I can come up with the other 5k, but damn I have definitely learned my lesson on setting aside enough for taxes. But I’m a degen so I say I learned a lesson when truly I never do, but that is the life we live.

    Had a 100k gain last year and didn’t set enough aside for taxes.
    byu/I-am-Jacksmirking inwallstreetbets



    Posted by I-am-Jacksmirking

    27 Comments

    1. theykeepbanningmebro on

      Good thinking regard. If you make 200% return on a bet you pay your taxes, if you mess up you go to $0 and probably get a levy on your assets

    2. youreaditfirst on

      Thats why I always yolo in December so I can lose it all and not pay any taxes

    3. Do you have enough to cover the taxes on what you just made?

      Its always a safe assumption to set aside 30% of all non-W2 income

    4. SubjectBubbly9072 on

      Atleast this year your not going to have 1 million in gambling winnings and 1 million in gambling losses and have to pay taxes on 100k of money you lost

    5. Deeznutzsgotcha on

      Offer in Compromise. There are options out there. Next time plan ahead or stack some Ls for an offset. Or don’t work a job and just trade for maximum tax breaks.

    6. Good-Factor-4927 on

      A few years ago a guy posted an annual profit of $300k. He lost all of it in January without paying any taxes on it.

    7. West-Childhood788 on

      Do what I did, have a massive loss and the just carry it forward to cover taxes on future gains.

    8. my exact problem for last year, owed about 23k. so painful to see it go. these are good problems to have after all lol

    9. You do know you can file an extension, right? The penalty and interest is not that high if you don’t wait too long to pay.

    10. Dry-Dependent-993 on

      lmao you actually pulled it off though, most people would be posting loss porn after trying to trade their way out of tax debt

    11. WorkingHorror99 on

      Your gain should cover your taxes unless you splurge on it..where did the 100k go? 

    12. Ordinary_Basis_1599 on

      $5K? That’s ALL you owe? The IRS will let you set up a payment plan so pay $250 a month or whatever you can afford. Also – congrats you made $100K investing. tldr: buy calls.

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