Death and Taxes…

I own a small business.

Interestingly, there are a lot of “small businesses” out there that from my stand point are huge! A manufacturing business that has less than 500 employees is considered “small.” From my “mom and pop” perspective – that is a really different universe with really different challenges, needs and opportunities.

But there’s one thing we all share – a deadline to file taxes on March 15.

What? Tax day is April 15, every one knows that!

On the contrary, certain types of corporations and trusts are required to file their taxes by the March 15 deadline rather than the April 15 one.

That gives me two weeks to file.

Am I ready? Have I started? Will I file an extension? 

Maybe. It depends.

img_1874On the one hand, of course I’ve started. I keep records all year and filing my taxes just requires my reviewing my records compared to the various bank statements, account statements, tax records and credit card statements I’ve been keeping all year, so once I’m done verifying everything it’s just a matter of confirming my records and submitting them to the IRS. Easy.

I started doing my own taxes the second year I owned my business…because my business is a micro-business without a lot of complicated tax needs. I’m able to do it myself for a couple of reasons:
1) My business if very small.
2) My business doesn’t have a lot of complex tax needs.
3) I have a background in mathematics and accounting, so I’m not totally unqualified to do this
4) I have a wonderful friend who is a reputable tax professional who I know can help me out if I find out that it’s more complicated than I realized.

Should you do your own taxes? I don’t know.

But I do think that filing your taxes is a useful time to get some information about your personal (or in my case business) financial picture that can help you manage your money and plan for the future more effectively.

That sounds positive. Why all the dread? 

Well, they are taxes. And if I’ve made a mistake or missed an important calculation last year, I might discover that I owe the IRS a whole bunch of money. Has that ever happened to you before? No. Are you still totally paranoid about it? Yes.

Filing the Extension

It’s tempting for me to go ahead and file a 6 month extension to file my tax return. That would give me until September 15 to get this taken care of.

But one of the things I’ve learned about myself is that I kind of need a deadline to get things done. It’s a characteristic of Obligers in Gretchen Rubin’s 4 Tendencies (if you don’t know what the means, you should check out Gretchen Rubin’s 4 Tendencies Quiz to see if you’re an upholder, obliger, questioner or rebel!). And if my deadline is September 15, I know myself well enough to know that I’m not going to do my taxes until September 15.

I also know from experience that it’s going to take 2 weeks whether I start on March 1st or September 1st and I’ll save myself a lot of pain and suffering if I just do it now.

Getting Started

Pieter Brughel the Younger, The tax collector’s office, 1640 (this painting may or may not, but definitely does, resemble my office during tax season.)

Over the past few weeks, I’ve begrudgingly taken the first steps to get my taxes ready. I’ve made file folders with my credit card, bank records and tax records from 2017.

Today I’m going to download my tax software. I like Turbo Tax because I’ve always used it, and it’s easy to transfer and update data from year to year if you keep using the same software. But H&R Block and other companies have pretty good software, too.

I’ll be back tomorrow to share some lessons from managing my business that have changed the way I manage my personal finances.

Wait, I’m here for the pelvic floor exercises!

Don’t worry! You can still find those here! I’ll be compiling my 7 Day Pelvic Floor Challenge into an easy to use PDF format that you can download for easy reference. I’m also going to take some of my other exercises and ideas and compile a short e-book that I hope will help you get started and continue on a journey to sneeze, laugh, jump and move with more confidence!!

In the mean time, we all have taxes to take care of!

Note: Just like I’m not a doctor, physical therapist or other health professional. I’m not a CPA, certified tax adviser or accountant. I’m sharing strategies I’ve learned and use as a small business owner that work for my (admittedly very small) business. Any advice or ideas I share here are my own. I’m not receiving any affiliate payments for sharing my ideas or linking to resources I find useful. If you want to try anything I’m suggesting, I’d love to hear your feedback and I recommend that you review any decisions you make with a qualified financial adviser that you know and trust.


  1. I took the quiz and I am also an obliger! But I’m also a chronic procrastinator. If I get the feeling that someone is watching to see how fast or how well I’ll respond to a request, I can get totally paralyzed by anxiety. And the feds are the scariest of all! Good thing my husband’s not terrified of filing our taxes!


    1. Gretchen says that obliger is the most common type of tendency, and there’s a lot of variation of the kind of outer accountability you respond to. I tend to tip towards a rebellious obliger (sometimes I suspect that I’m an obliging rebel…because I can have a hard time with expectations, so it’s really kind of good that I’m self-employed), if I feel like someone is pushing me too hard, I’ll have a really hard time doing something.

      You’re totally not alone in procrastinating. I get into that zone where things pile up and it all seems so important and urgent that I can’t do anything. More on that topic to follow!


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