the endless paperwork trail.

Running your own show comes with some very real timesinks - specifically the annual and/or quarterly dance with the IRS and hungry local government.  There's a certain paradise of ignorance that you can float on for awhile.  Get your data into Quickbooks and renew your business license and pay your taxes once a year.  Accountant strongly recommended but not required.  Relatively simple.

The contract gig I've been doing came with some new-to-me caveats, particularly the fact that they are paying me through my company, adding an ever-widening complexity vortex that absorbs space and time and sanity.  The moment I became on the payroll radar was the same moment the alarms and alerts began.  Harassing-ish messages started landing on my voicemail, of missed due dates and threats of possible subpoena.  And here I stand wondering why exactly I'm paying unemployment tax on myself.  And how exactly am I supposed to file future unemployment claims against myself?  Relatively absurd.

A helpful hint for everyone visiting from Google - in Washington state you do not need to pay Unemployment Tax if you own your own company and have zero employees outside of yourself.  I was told this will probably change in 2014, but I can't wait to get back under this quasi-hostile government radar.

However, if you own your own business (specifically a S-Corporation) you are expected to pay yourself a reasonable salary so that the Federal government can get some of that sweet, sweet income tax.  Which is never an issue when you continually dump all of your resources into the ever-emptying coffers of zero-profit-meaning-zero-salary.  But I'm suddenly in a world where I'm taxed on both ends, where I'm paying taxes on expenses, and my reasonable hourly rate is suddenly not-that-reasonable.  And losing hours of research time among the weeds of conflicting legalese, the pinnacle of which is the ever-terrifying word "optional".

(Why would I ever optionally pay out anything?  Optional-as-required is far worse than required-as-required.)

In summary: don't ever try to invoice side gigs via your business, unless invoicing business is your business.  Let them do the work, carry the burden, and hire you on as a standard contractor.  Dream of running your own show?  Expect a good 5% of your waking time spent chasing down windmills like these.