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How I Prepare to Meet My Accountant

Up until I got married to The Wife I did my own taxes as they were straightforward!  A W2, a few bank accounts, an investment account and my student loans.  Then I bought a house and got married…that’s when my tax world became more complicated.  The Wife is an independent contractor, and as an independent contractor she does not receive a W-2, nor does she have tax withheld every 2 weeks.  Instead The Wife gets a 1099 and has to pay quarterly estimates every year.  Since she is/was a 1099 independent contractor I decided it was one of those times when I should rely on a professional who does this a couple hundred times a year.  So every year I create an outline of my financial life for my accountant so we can work together an optimize my situation.

I figured why not share it with the readers of this blog.

Mapping my Financial Life for My Accountant

I am sure I don’t have to put this much work into my taxes considering I pay someone else to do it for me, but I figured the more organized I am decreases the chance of miscommunication with my accountant and thus a lower chance for an audit.  I am not a naturally organized person so this exercise took me a couple hours!  I think it was well worth it.


  • Wages

    • Evan’s W2
    • The Wife’s 1099
    • The Wife’s Bonus (should be in her 1099, but should be double checked)
  • Investment Income

    • Walt Disney 1099 – The Wife’s parents set her up a DRIP when she was younger and we get a check for $30 every year.  Literally Thirty dollars lol.
    • Fidelity Non-Qualified Accounts
    • The Wife’s Mutual Funds – From all gifts growing up
    • My Mutual Funds – Invested in 1996 when I made my dad use my money to buy a few…ignored since I was about 17.  Probably worth about a grand but I can’t liquidate and condense emotionally tied to the account.
    • Tradeking – Old home of dormant trading account before my work made me change brokers
    • Sharebuilder – Old home of Dividend Investment Portfolio account before my work made me change brokers
  • Online Ventures S-Corp

    • 1099-K – This is a brand new form CPA will have to look into it.
    • Misc Check Stubs
    • 1099s from other companies that are built into 1099-K
  • Misc. Income

    • 1099 Flex Offers (wasn’t moved to Online Ventures Yet)
    • 1099 Google (Has since been moved to Online Ventures)
    • Law Offices of Evan – Less than a few Grand this year as I have been focusing my energy on Online Ventures
  • Banking

    • Chase
    • Ing


  • Personal

    • Church Donations
    • Mortgage Interest Paid/Property Taxes
    • Student Loan (SAF)
    • 529 Contributions
    • Roth IRA
  • Business

    • Gas/Electricity
    • New Computer Purchase
    • Auto Payments
    • Hosting
    • Freelancers

Do you think I am missing anything?



  1. Oh I remember the simple days of living single and simple tax returns. Then came The Mrs and running a business. Now every year I look forward to just getting the taxes dones and over with. Though i have a great accountant I just hate being there and possibly forget something. And to think I may be incorporating several businesses so the list just grows.

    • I hear you! I am so anxious about getting my taxes done and it has nothing to do with being shady. Rather it has to do with just forgetting something.

      What projects are you working on?

  2. It should be interesting to merge incomes and taxes. I get married in May — it will definitely be different. I’m looking forward to it though. I’d rather have a wife then my independent taxes. 🙂

  3. I was an independent contractor for 8 years, I miss working on my taxes! Anyways, I would always say the “clock was running” as soon as I awoke everyday. Pretty much everything I spent money on could be counted on as a business expense (car/food/entertainment/cell). I had a home office so a portion of my utilities were deductible. The best thing I did was keep a notebook (yes I know, old school) of every expense I had that day then transfer it to a spreadsheet every month. Taxes were actually pretty easy then.

    • Today I have to sign into 14 different accounts and create a spreadsheet of EVERYTHING. Its not easier or harder than the notebook just more time consuming I think.

    • No she does have a “boss” it is just that when you are an independent contractor that boss is not supposed to control your day to day activities. It is a tax distinction in the eyes of the IRS and the Court (for liability purposes).

      • She doesn’t really have a boss. If nobody controls what you do (that would be nice) then it’s not really a boss. Maybe a…I don’t know what you’d call it.

        I wish I could do what I wanted at work. Like take breaks when I feel overwhelmed.

        • More like a manager. And you can have that – go into sales. There are PLENTY of sales jobs out there.

          Just remember – If she doesn’t produce we don’t have income. Freedom comes at a very heavy price.

          • Technically my boss IS a manager (store manager, assistant manager and customer service manager are all my bosses), so a different kind of manager, I guess.

  4. I meet with my accountant each and every year and there are a few things that I always forget. Since I use Quicken, he always wants my P/L sheet as well as a file saved to a USB drive. If you have that, be sure to bring that along as well 🙂

    This is a great checklist and what I have is something similar to yours and I will check off each w-2, etc when I receive it.

  5. Our taxes were pretty easy this year with the W-2’s and rental income and the mortgage stuff. The GPS on Turbotax walked us right through it without any problems. I dont have all the nuances that you do but with blogging now hopefully I will in the future! I worked on the taxes on the SuperBowl and got them back on Valentine’s Day. I know taxes on Superbowl Sunda, talk about big nerd! Great post!


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