Hey, Anonymous. Great questions. I've enjoyed working as a 1099 or B2B contract on and off for a number of years with my consulting business. Here are some things I've learned along the way:
1. As a 1099 or on a B2B contract, you are a small business owner. You need to get some good people to help you ensure that you do it well (at minimum, I highly recommend a good accountant and an attorney-- both need experience working with self-employed, small business people regularly). Having a mentor in your industry helps too.
2. Your professional organization may have a deal to help you get decent insurance and related benefits (e.g., American society of journalists, Mystery Writers of America, National Association for the Self-Employed, etc.). If not, Dave Ramsey's team are all about cost effective strategies. (You can Google them easily.)
3. If you want to stay a 1099 for the long-term, you should talk to an estate planning attorney about how to meet your retirement goals with this new plan. Talk to someone who isn't paid on commission AND is a fiduciary (this means that they have a legal responsibility to act in YOUR best interest; not theirs, not their company's--yours.) Go ahead and ask them straight out if they're a fiduciary-- you're unlikely to be first to ask. If they don't knew what you're talking about, they aren't the person you need.
4. Ask your attorney and accountant (preferably in the same conference call, so everyone is on the same page), what entity you should incorporate as (e.g., LLC, LLP, S-Corp, etc.). Ask about:
A. professional liability (what happens if you do something or miss something and a client sues you) and
B. Tax liability (when do you pay taxes, how do you pay taxes, can the accountant send the check in for you, can the accountant do the payroll for you & your assistant, should you set up a separate account for tax money, would it benefit you to be taxed as an S-Corp if your an LLC, etc.).
5. As soon as you're able, get an assistant. Even if it's a part-time assistant, they can take administrative tasks off your plate, so you can focus on the things that make you money.
6. Entrepreneurs (AKA business owners) don't get paid time off from their customers/clients. As a 1099 small business owner, you're an entrepreneur. However, you can set up things so that your business continues to pay you/your bills when you take time off. One way is for your business to set up a bank account that is set aside to pay you when you need PTO. Talk to your accountant and attorney about how to set something like that up, and if it could be in a tax deferred account.
I've loved working for myself and with my clients. The freedom is addictive.
Best of luck!
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