Self Employment Help Needed

Does anyone know what all is involved in being self-employed? I am particularly interested in the tax aspects. It seems that a self-employed person has to send checks to the IRS multiple times in a year. Is that true?

Another important issue is health insurance. How can one get individual health insurance? Are there many hoops one has to jump through? Is it much more expensive than employer-offered plans? What are the tax implications for a self-employed person? Any recommendations of good insurance companies and plans?

I have poked around the web (and the IRS website) but I am still a little hazy on the concepts. So any help, direct or a link, would be appreciated.

By Zack

Dad, gadget guy, bookworm, political animal, global nomad, cyclist, hiker, tennis player, photographer

3 comments

  1. I’ve been through the tax aspects of this. You do have to pay estimated tax, usually quarterly. (Penalties only kick in at a certain level, but if you’re asking about health insurance you’re probably above it.) Drop me an e-mail and I’ll see if I can find the answers on old forms and instruction booklets.

  2. In my previous life I had been a partner in an IT Consulting firm. Its a royal pain! Managing taxes, payables/receivables, etc is a pain!! All i wanted was to do technical stuff. It was feast or famine for about 5 years. To me it wasnt worth it…tho I built some solid relationships.

    Health insurance is a whole another issue…its expensive!!!!! Thankfully NY State has a good plan for SMB’s called HEALTHY NY.

    Regards,

    – Ali

  3. Healthy ny, is the most competitive option available to the New York self employed, small business owner and individuals that arent offered health benefits on the job. You must be living in NY state and actively working in order to particiapte.

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