I’m a digital marketer and in the summer of 2011, I started my own Creative Ad Agency.

And as anybody who’s self employed knows, there’s this obligation we have to make quarterly estimated payments on our income.  Unfortunately accounting and managing my books was the last thing on my time.  I spent all my time on client acquisition and working on projects.  And when it came time to make my estimated payments, I was short.

But I didn’t worry too much.  I’ll pay whatever penalty and make sure I add it to the next payment.

Of course, when it came time to make the next payment, I was short again.  It seemed money would go out as fast as it came in.

This went on for years and I always told myself there would be time to catch up.  I even filed for filing extensions in April and then would not file in October.

Everything was always “someday”.

Until I started to receive letters from the IRS.