Tax Time 2020

Been dragging my feet for months on this now.   I'd finished them about two months ago, but waited until the last day possible to file. Can't file an extension since I owe this year.  Back in 2006 I had a painful year.  I'd cashed out Stock Options, bought a convertible Corvette .. and bought momma a top end Lexus SUV.  I was loving life, feeling like I'd won the lottery.. until tax time.  Ouch!

Well... today was the day.  I'd wrote about what led up to this.  Late last spring I started investing in stocks heavily, buying and selling most mornings.  Became a full time job of sorts for me.   When the smoke cleared and the stock market had pretty much recovered, I was patting myself on the back. Lets just say ... I did well.  Really well.  Not what I haven't done.. and I'm not going to (might be too painful to realize) is compare ...   what if I had just done a buy and hold strategy on say .. my first dozen stocks that I'd bought?   Had I done that I'd be sitting with all my gains (or losses or zero growth) .. but..   not owe any taxes on their short term gains.  

The mauling began in Apr 2020, in red above. A month into the mess, I got proactive and moved in with additional funds and began the 'day trading', shown in Green, with two diff deposits. The graph shows the success, but ...... more than one way to skin a cat? Did I mention I hate taxes?

So today, I finally hit the SEND button on my tax app and gave Uncle Sam my routing info to take my hard earned money.  There's a lesson learned in here somewhere ...   maybe I should do a quick comparison ... or maybe after the next 'crash' or 'correction'  I simply buy in on a chunk ... I'll pick my dozen stocks and hold on for the ride to see how it plays out.   Because this shit today was ... PAINFUL!

 

Is she smirking?

So here I am .. short period of time later and I get "....... your federal return was rejected by the IRS. Don't worry, we'll help you fix the problem. Check your email for more information." in a text message.  I'm thinking WTF?  But...I look up in the SMS message an there are previous ones... .. same thing happened in 2020 .. and in 2016.  Hmmmm.....   Well.. I'm checking my email, where's it at?   Hmmmm... the previous years AGI ..   they adjusted my refund last year .. is that the issue?  We shall see. As I type this later on afterwards, guessing I'll be doing an extension and manually printing all the crap :(

Before pulling the plug that night...  headed to IRS.GOV, logged in under my account and .. paid the tab.  Automatic extension until this October.