Hacker News Reader

I would suggest finding someone who's trusted in working with local small businesses - probably themselves a small local shop with a few accountants - ask your hardware store owner, coffee shop owner, etc. If you are within a taxing municipality it can be helpful to have someone who knows the local ins and outs.

Generally speaking, the tax implications of being a freelancer are less complicated than small scale retail (e.g. no inventory).

View on HN

But note that the tax implications of being a freelancer are way more complicated than those of being a W2 worker.

I learned this lesson the hard way several years ago.

I can't stress enough the importance of making sure wherever you go isn't a place that just rubber-stamps W2 returns.

I made the mistake of going to H&R Block during the year I was 1099'ing, and aside from the person doing my return having to go ask someone for guidance at every line item on the forms, I ended up getting a letter in the mail from the state saying that they'd calculated I overpaid by a few grand.

I can't even fathom how bad of a job they must have done, if the state was the one to inform me that I'd given them too much money.

Reply on news.ycombinator.com