Considering a long term contract role. I’ve never worked as a contractor. What kind of things do I need to take into consideration? Self withholding taxes & 401k? Benefits? This is new territory for me.

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Most contractors do not get 401ks. Some get other benefits, depending on the employer. You'll want to plan to pay up to 35% in taxes all told, and look into IRAs. Potentially will need an independent health insurance plan. Lots of information out there on all these things; if you're willing to do the work the freedom is worth it imo - good luck!

I've done the contractor life, and I loved it. But I also had a spouse who was working a non-contract career, so I didn't have to worry about health insurance. Definitely an important consideration.

Same. It isn't great if you hae to pay for your own benefits. But I also had a spouse I got health insurance through so it worked out.

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