{ "media_type": "text", "post_content": "I am considering transitioning from being a W2 employee to a independent contractor/1099. What are some important questions I should ask before making a decision? \n\nFor context, I have been with my litigation firm for just over 3 years and have been barred for 4. I am doing fine, but I dislike the job and would like to reduce my hours (and get rid of some of the non billable work I have to take on). Ideally, I would transition to a job that I love, but I’m not sure what that is yet. Cont. below.", "post_id": "60f5ade19cbb8a0020dbb539", "reply_count": 7, "vote_count": 3, "bowl_id": "552d1d24dc1c586b09d2d052", "bowl_name": "Law" }

I am considering transitioning from being a W2 employee to a independent contractor/1099. What are some important questions I should ask before making a decision? For context, I have been with my litigation firm for just over 3 years and have been barred for 4. I am doing fine, but I dislike the job and would like to reduce my hours (and get rid of some of the non billable work I have to take on). Ideally, I would transition to a job that I love, but I’m not sure what that is yet. Cont. below.

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I’d be worried about malpractice insurance, which may not extend to contractors. Benefits may also be an issue. Why not just become a part time employee.

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Thank you!

Save, save, save for your taxes. If you under-estimate what you will owe and underpay throughout the quarters then the taxes can be a shock the first year because you are paying the whole amount. Whereas an employer does deductions for you and also direct pays a portion of your taxes. Also, be really clear on the malpractice insurance. Ask to read their policy if they say it will cover you. Consider getting your own malpractice insurance too just in case. The easiest way to not pay a claim is to say it doesn’t fit within the parameters of what is insured. Finally, scan all of your receipts for business expenses. You and your CPA will thank you for doing that come tax time. Bonus points if you track your expenses on a spreadsheet as you pay them.

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Better than a spreadsheet: QuickBooks. Your CPA can import your QB file into their tax prep software, which should save you money when you have your taxes done.

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I am working remotely from a small town where there are very few opportunities (here because of my husband). Plus I’m not barred in the state we are living in—so I’m quite limited. We plan to go back to where we are from, where there are many more opportunities, but that won’t be for another few years. I know others at the firm who have gone 1099 successfully. Wondering if it is the right option for me, but not sure of everything I need to consider. Any insight is appreciated!

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