How to drive your tax guy crazy!

In honor of tax day, I am going to list the top ten (or more) tax questions I’ve answered in the last year:

1. Why can’t I include the cost of my singing lessons as a business expense? (From a non-professional singer with no “business income”). Because hobby expenses can only be deducted to the extent there is actual INCOME!
2. Can I include the cost of my vet bills as medical expense? Unfortunately, our 4-legged friends are not considered dependents (and are thus ineligible for the medical expense deduction). Especially when the “vet bills” are actually for weekly shampoos.
3. I sold some land earlier in the year for $500,000 but I don’t know how much I paid for it. Can you just estimate that for me? Um…No.
4. Can’t I get the education credit for my daughter’s pre-school tuition? Nope – it’s higher learning only folks! And the same goes for high school private-school tuition, for piano lesson, for soccer league fees…you get the drift.
5. I think I got a 1099 for my investment accounts, but I threw it out. You should call my investment advisor and ask him for a copy. (And when I insist that they call first): Why can’t you do it? Because if he’s worth his salt, he’s not going to give information about your account to a total stranger! And if he did, I recommend getting a different advisor!. And hey, since you’re calling him anyways, tell him to fax me a copy and save me the phone call!
6. Can I deduct my “spiritual advisor’s” fees as medical expenses? Not unless they are licensed psycho-therapists as well!
7. I gave my nephew a $50 “donation” towards his schooling – why can’t I deduct that as a charitable contribution? Sorry – It’s got to be to an actual charity to be deductible! (Otherwise, I’m taking “donations” too!).
8. I had about $150 in income for some crafts I sold. And about $5000 in dining expenses. Why can’t I deduct ALL of my dining as business-related expense? Ummmm… I doubt all of your dining expenses (if any) were related to your craft business. Besides, see answer #1.
9. I started a new job and “had” to buy a whole new wardrobe, along with spending thousands on haircare and makeup. Isn’t this deductible as employee-related expense? Generally, if you can wear it outside the workplace and look normal, it’s not deductible. Now, if your wardrobe is made up of clown suits and you’ve been dying your hair red…maybe…
10. I just deposited $15,000 into a SEP-IRA that you’ll need to add to my return! (Coming from someone without self-employment income). Ummm…big problem. If you’re not self-employed, you can’t contribute to a SEP-IRA.
11. One client asked me to estimate their quarterly taxes and consistently ignored my advice and paid about 20% of my recommendation. Then, when the tax bill came due (along with penalties and interest) they asked, “Why is this so high? Shouldn’t we have paid this earlier?” Ugggh!
12. I needed a TON of psycho-therapy. Like every other day for months on end. I’m pretty messed up. Is it deductible? Yes! As long as it is from a licensed therapist. This one is included because of the emphasis on how much psycho-therapy was needed. (And because dealing with this particular person almost sent me to therapy!).

So there you have it. Hopefully you all have gleamed a bit of knowledge from these inspiring questions to help you in the coming year!

<Added note: Nothing in this post is to be construed as tax advice. It is for entertainment purposes only. Please contact your own tax advisor for particulars regarding your situation.>