In the Trenches: Tax Season Approaches

The arrival of my first 1099 the other day is a sober reminder that tax season is just about here. That makes a lot of people sweat, especially people with new businesses who haven’t done this before. I would be one of those people, too… if I hadn’t hired an accountant.

It’s certainly tempting to do my own taxes for the business. Until last year, I did my own taxes and I think the results came out right. At least, I assume they did because I didn’t get a guy in a black suit knocking at my door asking why I had written off this or that. Of course, I always played it conservatively to make sure that didn’t happen — so I could have left money on the table, too.

But by last year, things had changed. My business had grown to a point where I had multiple income sources and a lot more expenses to sift through. Fortunately, I had started using Quickbooks to manage my business but I was still apprehensive to do the taxes myself. I went for an accountant.

I hired an accountant who had done work for my family before, so I felt comfortable that he knew what he was doing. Sure enough, he had questions lined up and was able to get everything squared away very easily. The amount of time I saved was worth a lot more than his going rate. (Don’t tell him that.)

This year, it gets even more complex. I have to issue 1099s for my contractors, and that alone makes me break out in a sweat. If I make a mistake, I could end up paying big time for an honest mistake. At least, I have a vision in those men in suits crashing through the windows to take me to task.

So for me, when it comes to taxes, it’s back to the accountant once again. It’s just not worth the stress of doing it alone.

About Brett Snyder

Brett is the Founder and President of Cranky Concierge air travel assistance. He also writes the consumer air travel blog, The Cranky Flier.
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2 comments
Nicholas Barnard
Nicholas Barnard

You've been watching Brazil far far too much. They don't crash through windows anymore, they simply unlock the front door with their master key.

luy
luy

So just hire an accountant?I would love to see a post that includes tips either on interfacing w/ the accountants more effectively (questions to ask etc) or relating to doing it yourself.

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