Nothing ruins a good Spring like April 15th. 

I love Springtime, but I hate Taxtime.  Actually, my tax misery extends throughout most of the year.  Preparing taxes when you are self-employed is exponentially harder than preparing taxes as a regular W-2'd employee.   Most W-2'd people I know spend an evening, or maybe a Saturday preparing their taxes on Turbo Tax and then electronically filing, ensuring a speedy refund.  For them, the refund is like a bonus they can use to spend on vacations and furniture and yard stuff.

 My tax misery starts about the 2nd week in December.  This is when I start to update all the books for National Mortgage Brokers, Inc., and Matthew Prestwich Construction, Inc.  Now, I know your thinking "Matt, if you updated your books each month then it would make your year-end a lot easier," to which I respond "ha ha ha ha ha ha ...yeah right! like anybody really does that."  Actually, in all seriousness, I know I should update all my books each month but I just get so busy with everything that that job goes right to the back burner.  If my businesses were larger then this would be de riguer as it would be essential to know month by month and quarter by quarter where everything stands.  But, since my businesses are smaller, I simply check the bank statements two or three times a month and keep a running tally of everything else in my head ("Matt, I think we have identified your problem!")

The problem with doing the books in December is that there is still a bunch of year end stuff still to do.  So, my tax misery extends to about mid-March, when I can no longer put off finishing the updating for the previous year and preparing all the final stuff for the accountant.  Usually, it is about the 12th or 13th of April (today as a matter of fact) that I actually meet with my accountant (who has already dutifully filed extensions for my corporate returns) where we determine if I have (hopefully) paid enough salary and estimated tax that I do not have to pay any more additionally now.   Then, on the 15th (the 16th in the case of this tax year) I pay any additional amounts due and file an extension.   This gets me through to September, when my accountant actually starts working on my the corporate and personal tax returns.    At this point he calls me with a bunch of questions which, due to the 6 months that have passed since April, I cannot remember the answers to (so much for keeping a running tally in my head).  Finally, my accountant finishes my returns and I file them, usually on the last day for extensions (sometime in October, I think). 

 Then, just like in the movie Groundhog day December rolls around again and the misery starts all over.   Hopefully all of you entrepreneurs out there are much more organized than me.  I actually look forward to the day when I can hire a full time (or part time) bookkeeper to keep things up do date but that day seems a long way off.

 And as I am watching all of those W-2'd people serendipitously spending their tax refund I think to myself "I sure am lucky to be self-employed!"