The glamorous life of the freelancer

I am now two-and-a-half weeks into being self-employed. So far, the overriding feeling is that of an extended home vacation, but the reality of my situation has been slowly seeping in by dribs and drabs. This gig has many aspects; it's fun, fulfilling, mundane, and terrifying. In short, being a freelancer is the perfect combination of elements to keep my attention and motivate me to work. So far so good.

For your edification, the following is a list of the plus side of working from home:

• I get to make your own schedule
• Sleep in when necessary
• Go pants- and/or shirt-less whenever I want (no pants dance! no pants dance!)
  
• More time for cooking
  
• Save on gas since there's no daily commute and I loves me my bike
  
• Do the work I want/like to be doing
• Have more time to expand and find new venues for my work
  

Of course there are downsides as well, and we'd all do well not to forget:

• Far less stability / security; don't always know when your next paycheck will come
• If you're not good at scheduling yourself and sticking to it, you're screwed
• It can get lonely
• Health insurance? Pfft.
  
• Taxes. Goddamn taxes.

Apparently I made enough money freelancing last year for the IRS to demand a decent chunk of change from me when I sat down to work out my taxes the other day. No sweet refund for me this year. And even though I was just gonna blow it all on hookers and coke, I still take offense to being so put upon. I'm not sure how me paying 1/4 of an incredibly meager take is sensible, but thems the breaks.

Which brings me to the first major lesson of the freelancer: It's time to turn my ass into an LLC. Doing so will help me to avoid a major IRS smack down come next tax time. I'm in the process of making this happen now and will post about my experience as it unfolds. I'm hoping the story ends up being more encouraging than cautionary, but keep in mind that I'm no accountant (another good thing to look into, frankly). The odds are pretty even.

But becoming an LLC, and then opting to be treated as an S-Corp, will go a long way toward simplifying my life when it comes to dealing with taxes without paying out the wazoo. It's also important to then keep incredibly detailed track of all my work related expenses so that I can claim them as deductions and save cash that way, too. Plus then I'm ironclad if Uncle Sam comes sniffin'. I like being on the up-and-up, personally. I also like getting to (legally) hold on to as much of the little money I make as possible. It's all about balance, you see.

So once I've done the LLC thing, what's my next step? Buying a file cabinet. Ah, the glamorous life. I'll be sure to blast some Lady GaGa while I set up the thing. Y'know, for ambiance.