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Talk to at least 3 accountants and get each of their advice (all 3 told me different things). I ended up doing an S Corp, which was great for awhile. Most of my work was W2 this year, so I’m considering switching to LLC.
Spending money on a good accountant is a thing. Get a good one, be transparent about what expectations are and you’ll be good. It’s totally worth the $$$. You will not regret it.
Chat them up and run from anything that makes you uncomfortable. All I’m saying is that I pay a decent amount for a guy who set me up as an s-corp small business and I couldn’t be more psyched with the tax savings and peace of mind that it’s being handled over the past almost four years.
And would I want someone local (Chicagoland) or remote to have more options?
Yes and yes. I S-Corped when I started to see freelancing as permanent, I pay for business insurance, my accountant writes off literally everything (he specializes in creative freelancers) I push clients to do 1099 with these credentials (insurance + EIN) whenever I can and sometimes it works to get out of the W2 bubble. Not always with a larger holding company but sometimes.
can you explain the W2 bubble please?
Interesting findings...if you can find a knowledgeable company secretary that can handle this, I would love to find someone to launch digitalcompanysecretary.com with.