Budget for mistakes
A few months ago I received four to five identical notices from Arlington county saying I owed them thousands of dollars.
In Arlington, business owners have to register for a business license and if you make over $100,000, you pay a percentage of your revenue as tax (something like 0.35%).
I switched over from my first LLC, Davidson Consulting LLC, to my new one, Custom Analysis LLC, some time in 2016 or 2017.
But my wife started using the Davidson Consulting LLC for her own business and earned more than $100,000 for a few years.
It just didn't occur to me to keep paying the business license fee/tax.
This is not a lesson about being ultra diligent about administrative matters, but rather, accepting that it is a near 100% certainty that you will incur miscellaneous financial penalties if you work for yourself.
It's easy to get all worked up about it and for many, it means worrying about it so much that it prevents them from taking action at all.
But going 1099 means being a little entrepreneurial and accepting these types of things as the cost of doing business.
So be organized and stay on top of things, but just budget for these types of mistakes and move on. Set aside $200/month for mistakes and call it a day.
Ranting about bureacracy and taxes is also a good a strategy ;).