Painful things on my to-do list, tasks I dread and loathe but that I know I’ll feel much better having completed:
- Renew my passport.
- File and pay my taxes.
- Buy a home of some sort.
All of these have one thing in common: paperwork. I absolutely hate paperwork. That’s why I hate filing taxes above all else: paying the taxes I owe (and I owe a lot) is a sting, but filling out the reams of paperwork is a real (prolonged!) kick between the legs. Naturally I use TurboTax to make the process somewhat less painful, but there’s still a ton of data entry involved. Last year, I actually exhausted an entire inkjet cartridge printing out my tax return! This year, I cleverly installed TurboTax on my laptop so I can just print it using the gargantuan laser printer at work.
Exercising, buying, and selling stock options generated a fair number of transactions, but I’m already done with those.
What’s really bugging me now is trying to find all transaction information for my Morgan Stanley ActiveAssets account. Because I have a substantial amount of money invested in a couple of managed asset accounts, each of which maintains a portfolio of around a hundred stocks each, I get a mountain of paper records from Morgan Stanley. In fact, some weeks I receive mail from them faster than I can open it; the envelopes pile up on my desk, two or three more each day. Eventually I get sick of staring it, so I open the envelopes, throw out any generic brochures not specifically tied to my account, and dump the rest into my filing cabinet.
Now I learn that some of the information I need for my tax return can only be found somewhere inside that filing cabinet… because apparently Morgan Stanley can’t just mail me a consolidated statement with all the information on one or two pieces of paper. Aargh!
The US tax system really sucks. Sure, taxes are lower than in Canada. (Slightly; CA has the highest taxes in the US, whereas Ontario has the lowest taxes in Canada, so the two almost meet.) But the system itself is poorly-designed, with obscure and arcane rules, non-standardized forms and schedules. In Canada all I had to do was basically copy the contents of each tax slip I received into correspondingly-labeled boxes on my tax return; no digging through heaps of paper, no using Excel to extrapolate information that doesn’t show up on any paper…
And don’t get me started about AMT. And estimated tax payments. Grrr…