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Thorns in my Self Employed Side

It’s been a..unique experience so far in my meddling with self employment. For one, I’ve been cranking away with pitches and resumes to bring on more freelance work, and while there’s been plenty of rejection, there’s a number of hits as well. I’ve been slowly but surely building up my income to that of my old salary, which will feel good when and if I get there. Until that point it tends to feel more like an uphill climb. I can see the top, I’m working towards it, but the last stretch seems the longest, and the most difficult to obtain.

There are also two issues that I haven’t quite figured out yet, taxes and health care. My brother has been looking to break out of his cubicle once and for all and go the way of the entrepreneur as well, but he can’t seem to find proper coverage. He’s not that old, and fairly healthy, but getting individual benefits has proven to be…

  • Expensive: I’m appalled at how much benefits cost for the average person, even someone young, with a high deductible, will likely get bent over. No wonder people work at UPS and Trader Joe’s just for the health benefits!
  • Coverage is “meh”:  Even the policies I could get aren’t as good or comprehensive as what I currently pay for through COBRA, and nearly as expensive.

Health care is a hot topic on the political block, but all I’ve seen so far is a lot of hot air. Help and reform may be on the way for those of us who don’t want to be forever bound to their employer for benefits, but it’ll likely be awhile before we see any progress on that front.

The other issue I’m running into is taxes. I do a lot of one time deals where I write a few articles, get paid, and that’s it. I’ve been keeping track of said payments and squirreling away portions into a specified ING account for the tax man, but I’ve been having trouble figuring out how the average freelancer reports his income. So far I’ve seen “get an accountant” but if possible I’d like to do this on my own, since hey, I’m not exactly rolling in dough right now! Any ideas?

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