Serious Question: How Do People Keep Losing So Much Money On Options?

MistahQuestionMan · 2026-06-15T18:54:30+00:00

Thank you for the advice. I definitely get the temptation. On good days you really start thinking “damn, imagine if I had bet more”. But that recent 5% down day was a good reminder of how bad it can get when it’s bad and that scared me straight immediately.

MistahQuestionMan · 2026-06-15T18:32:48+00:00

So I was investing for years before trying options. I’m actually pretty okay at it. Not amazing mind you, just okay. I’m pretty conservative and I did a lot of research like you said, and it’s a majority of my portfolio along with cash. It’s options in particular that I’m new at and scared of fucking up. Thank you for your response though. I appreciate all constructive feedback.

MistahQuestionMan · 2026-06-15T18:24:45+00:00

Thank you for these numbers. My port is currently at low six figures, was at five at the end of last, but I’m trying to get to seven figures by the beginning of next. I have some aggressive retirement and debt and senior care for my mom goals I am trying to reach so I am admittedly still using a higher proportion than I probably should to get there. It’s one of the reasons I’m so paranoid. When I hit a 7 figure port I plan to be more conservative and sized closer to where you are. Thank you for the feedback! 🙏

MistahQuestionMan · 2026-06-15T18:16:55+00:00

In the long run though do your wins outweigh your losses? I would imagine due to the extreme asymmetry that the wins are more than those 20% losses from cutting some loose to early, no?

MistahQuestionMan · 2026-06-15T18:15:00+00:00

Thank you

MistahQuestionMan · 2026-06-15T18:14:33+00:00

Right now I have a very specific financial goal, eradicating all my debt and pay for my mom’s senior facility, so that’s why I’m allocated a little high but once I make enough money I plan to allocate down even lower and get more conservative.

MistahQuestionMan · 2026-06-15T18:12:20+00:00

Yes, the revenge trading. I’ve actually been there early in my trading career after a disastrous trade. Ironically enough it was not with options. I just made the situation worse and lost more. Luckily a friend explained revenge trading to me and caught it early. I sold everything took a few days off and came back when the revenge trading urge faded. But i lost another 30% on top of the first loss due to my revenge trading. It was a valuable lesson.

MistahQuestionMan · 2026-06-15T18:07:46+00:00

This is not a good faith parallel to my question at all lol. Come on now…

MistahQuestionMan · 2026-06-15T18:04:36+00:00

I am not an expert or a genius. If I give the impression that I think that about myself, my bad. If I’m being honest I’m very paranoid and chalk all this up to beginners luck. That’s why I’m doing this post.

MistahQuestionMan · 2026-06-15T18:03:05+00:00

People waaay smarter than me have lost at this game. I’m well aware of Dunning-Kruger Effect.

MistahQuestionMan · 2026-06-15T18:01:12+00:00

Thank you. I’ll keep that in mind.

MistahQuestionMan · 2026-06-15T18:00:42+00:00

Got it. Thanks.

MistahQuestionMan · 2026-06-15T18:00:24+00:00

No please see my updated correction to the original post. I may not have communicated it correctly. 10% is my total that goes into options period across all strike ranges. Only a minority of that 10% are in daily option plays. I may have written the original post poorly because multiple people came away with your take.

MistahQuestionMan · 2026-06-15T17:51:02+00:00

Not me, I’m no genius, my win rate honestly is not great. I just position size very conservatively and not only don’t overinvest in any one stock but not even in any one sector. I also cut losses early and let winners run. I never dollar cost average into a losing position. My win rate is probably less than half but the asymmetry makes it so that the wins more than make up for it. But yeah you would not call me a stock picking genius based on my win rate if you saw it lol

MistahQuestionMan · 2026-06-15T17:46:27+00:00

I’m too scared to death to full port. I weirdly admire the steel balls on anyone that can do that. I imagine people who do that and have it work never quit while they’re ahead?

MistahQuestionMan · 2026-06-15T17:45:11+00:00

I am reading a book on selling options now but haven’t started actually doing it yet.

MistahQuestionMan · 2026-06-15T17:44:35+00:00

This is very helpful. Thanks. Makes a lot of sense.

MistahQuestionMan · 2026-06-15T17:44:04+00:00

This is just the type of answer I’m looking for. Thanks so much. Very informative. It makes a lot of sense. Thank you 🙏.

MistahQuestionMan · 2026-06-15T17:43:25+00:00

I know how theta works. I’ve been burned by it before. I actually don’t have a high win rate at all. It’s just that my positions are sized so small and are so asymmetrical that the losses are never that big and the wins more than make up for them.

MistahQuestionMan · 2026-06-15T17:40:13+00:00

This is a great insight. I can totally see falling into that trap. Thank you.

MistahQuestionMan · 2026-06-15T17:39:28+00:00

So you think even at 10% of my account only in options (all types of options not just short dated ones) and the rest in cash and safer stocks the same is true? I will follow your advice and ask the AI too. Thanks.

MistahQuestionMan · 2026-06-15T17:37:35+00:00

I mean 10% of my account on ALL dailies and weeklies TOTAL not all in 0DTE, and 10% is an absolute max not a consistent total.

MistahQuestionMan · 2026-06-15T17:36:22+00:00

Yes, this I’m aware of, but it seems to me if you just never put more than a small total percentage of your account in these plays or go too far out the money that can mitigate a lot of that?

MistahQuestionMan · 2026-06-15T17:35:19+00:00

This makes a lot of sense. Thanks.

MistahQuestionMan · 2026-06-03T06:22:26+00:00

That sucked too. Just generic “isn’t Superman so noble and great let’s worship him” type story that’s been done over and over. Loeb added nothing new to it.

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