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Getting Ready for Tax Time

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The longer you wait, the more difficult the job.

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Editor's Note: This is the latest from Jessie Smith, who has been sharing her journey from deep debt to financial freedom weekly in Going for Broke ... and Back.


I'm not looking forward to April 15 this year. I'm dreading the thought of having to get the paper tiger in my office in order before I can head to the accountant's office.

I mentioned a couple of months ago that I'd purchased QuickBooks to get my finances in order. I was successful in getting it loaded on my computer. I was successful in receiving the data from my last bookkeeper so my chart of accounts would be set up. And, that's about as far as I've gotten.

I'm completely intimidated by the sheer amount of paper that's sitting in huge piles in my office. I haven't done filing in ages -- and it's all gathering dust for lack of attention. However, it's worse than that.

So much of 2009 was spent in sheer financial distress, that the thought of going through all of that again is enough to send me back to bed, hiding my head under the covers. Not to mention the abysmal amount of time I foresee all of this taking. Pile up on that the fear that some stray, unpaid bill will rear its ugly head and demand payment -- it's enough to make me want to click my heels and wish for HOME (wherever that may be).

Just to make things worse, I'm contemplating another move -- soon. So the thought of packing up all of that stuff to move it to a yet-undisclosed location to deal with it later...ugh, quick -- someone pass the Tums. Or the Jack Daniels.

I realize that the longer I put this off, the worse it becomes. And it definitely casts a shadow on all of my sunny plans for 2010. Anyone know an accounting student looking for class credit in an internship?

When my rational mind comes back into focus, I know some things will help me with this task. I'm now reaching deep into the way-back machine for some wisdom I learned from my business coach years ago:

1. Chunk down. Take a massive project and break it down into smaller chunks (almost like separate projects). So in this case, maybe I can break this project down into the following:

  • Personal expenses

    • Electronic downloads from accounts to QuickBooks

    • Pile and file (circular file especially)

  • Business expenses

    • Ditto personal expenses

    • Look for tax write offs -- make notes

  • Income

    • Accounts receivable (where are those checks I received from clients?)

    • 1099s from vendors


2. Set a deadline and schedule the time to do the tasks (the biggest problem I have with this is I have no reference for how long it takes to do this stuff -- my bookkeeper did everything for me. I'm so grateful for the time that I had her).

3. Lower my expectation. (Huh? I don't think I've ever done that, but it's possible that I need to strive for progress, not perfection.)

4. Look for help in affordable places. To you do-it-yourselfers: If you make $100/hour (or even $25), what kind of sense does it make for you to be doing $15/hour work (or less, if you find someone willing to work for less)? If this project takes up all my time, I'll end up losing money instead of making it. And, consider this logic even if you work for someone else Monday through Friday: Do you really want to be spending your nights and weekends away from loved ones, family, friends, or taking away from your own "recharge" time?

Anyway, wish me luck. I know I cannot continue to procrastinate on this issue -- but so far it's worked for me: Hey -- it's only Jan 14! (Just kidding).

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