Ran into this problem again with my daughter’s return. Yes, we trade stock options on her account. SMILE. Come on. It is like printing money. Why wouldn’t you trade, if you can.
I will readily admit that NEGATIVE ‘Total Proceeds’ is esoteric & unusual BUT it happens as I have been moaning about for the last 4 years. Yes, it is counter-intuitive. I will readily grant you that. Yes, it basically says you sold some investment instruments at a negative value. So, how does that happen. This mostly happens with option trading. When you option loses money & then it expires or is bought at a loss.
I confess, often, to being addicted to option trading. That the proceeds are NEGATIVE does NOT mean we are losing money. SMILE. SMILE again. Most times getting a negative return is good — you make some money & get a tax break. SMILE. What can I say. It is all legal.
Free File Fillable Forms might not work for you. Be careful.
I have been using FFFF for close onto a decade. It is NOT perfect. But, it does what I want. There has been a few years, like last year (methinks), that I could NOT use it to eFile because it has issues dealing with NEGATIVE NUMBERS in ‘Schedule D‘ — i.e., Capital Gains. Even if it refuses to do eFile, I still use it (beforehand) to do my taxes. I like it, I am used to it.
I, for very good reasons, DON’T trust ANY tax software! Period. I know — & I have been proven right multiple times — that my data will be COMPROMISED, EXPLOITED & SHARED. I don’t want anyone, BUT anyone, other than the IRS knowing about my taxes. I am a very private person.
Yes, I do my TAXES by HAND!
I know how to do taxes by hand. You should too. Useful skill.
Yes, I was trained by one of THE BEST over a period of 16-years.
Now I know how to do it by hand, I am NEVER going to lose that skill.
FFFF saves me from having to do in on paper — in pencil. SMILE.
FFFF still can’t handle NEGATIVE PROCEEDS in terms of Capital Gains/Loses in Schedule D. Luckily I didn’t have any such negative proceeds. So, I was OK. Not so one of my daughters. Had to file using PAPER!
I, for very good reasons, DON’T trust ANY tax software! Period. I know — & I have been proven right multiple times — that my date will be COMPROMISED, EXPLOITED & SHARED. I don’t want anyone, BUT anyone, other than the IRS knowing about my taxes. I am a very private person.
I have been using FFFF for close onto a decade. It is NOT perfect. But, it does what I want.
Yes, I do my TAXES by HAND!
I know how to do taxes by hand. You should too. Useful skill.
Yes, I was trained by one of THE BEST over a period of 16-years.
Now I know how to do it by hand, I am NEVER going to lose that skill.
FFFF saves me from having to do in on paper — in pencil. SMILE.
I saw the above yesterday. IT is very dramatic in that it CLEARLY shows a $0.00 Cost Basis!
It is basically saying you incurred a $2,000 loss without buying anything. Isn’t that cool.
NO, no it isn’t my 1099. Mine has MORE DIGITS. Smile. Yes, mine, IF I am lucky can have NEGATIVE signs too, but, ALAS, not for the last 2 years. {NOT SMILING} But, if I am really careful & canny I might be able to get back to negative numbers this year. SMILE.
I just wanted to SHOW you this because many wouldn’t believe me IF I told them of the counter-intuitive 1099s us option traders get.
Click to ENLARGE. From ‘Fidelity’. YES, you can have a NEGATIVE ‘Total Proceeds’. This is PROOF.
I will readily admit that NEGATIVE ‘Total Proceeds’ is esoteric & unusual BUT it happens as I have been moaning about for the last 3 years. Yes, it is counter-intuitive. I will readily grant you that. Yes, it basically says you sold some investment instruments at a negative value. So, how does that happen. This mostly happens with option trading. When you option looses money & then it expires or is bought at a loss.
I confess, often, to being addicted to option trading. Other than red wine, sex & walking it is my ONLY addiction. As addictions go, this is NOT bad. The option trading HANDILY covers the red wine & more. SMILE. That the proceeds are NEGATIVE does NOT mean I am losing money. SMILE. SMILE again. Most times getting a negative return is good — you make some money & get a tax break. SMILE. What can I say. It is all legal. Some may say it is complicated, but it is second nature to I. I average at least one option trade a day — on the days the markets are open. SMILE. What can I say. I said I was addicted. It also pays for my red wine & … & … & … SMILE.
Well, it is true that most people in my situation do NOT bother with the FREE File Fillable Forms. They will use an account or a paid service.
The paid services, i.e., TurboTax, H&R Block etc., are a pain to use! They ask so, so, so many questions.
Yes, as with options I know my way around IRS forms. SMILE.
I don’t need handholding. I know where to put what. IF it can do some sums for me, so much the better.
That is why I used to like Free File Fillable Forms.
However, I have not been able to use it for the last 3 years.
Like I said, I do know my way around & I have access to both Excel & a calculator. What more do I need.
This year, I fashioned an Excel spreadsheet to work out my Capital Gains taxes. I first did it by hand & then used the spreadsheet to check my math. Glad I did so. Found one mistake smile.
So, just a HEADS UP.
Free File Fillable Forms might not work for you. Be careful.
