Had a 100k gain last year and didn’t set enough aside for taxes.
u/I-am-Jacksmirking ·
Reddit — r/wallstreetbets
· April 14, 2026 at 15:48
· ⬆ 420 pts
· 💬 140 comments
| View on Reddit ↗
AI Summary
Summary
A trader failed to set aside taxes on $100k in gains from the prior year, creating a $30k tax bill due immediately.
In a stressed, degenerate move, they deposited their remaining $10k cash into their brokerage and attempted to trade (via options) to generate the $20k shortfall, successfully making $15k before being forced to sell by pressure.
Quality assessment: This is noise/anecdote. It is a personal story with no fundamental analysis, research, or specific ticker mentions. It highlights the psychological stress of trading under capital constraints.
Score420
Comments140
Upvote %91%
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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.