I’m seriously thinking about switching to contract work. I’ve heard it can pay really well and give you way more control over your schedule, but obviously it’s less stable than a W2. Part of me is excited by the freedom, but the other part is terrified of the gaps between contracts. If you were between jobs, would you take the leap into contracting?

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Take the leap. W2 security is mostly an illusion these days. At least with contracting, you’re in charge.

What does contracting look like? Does anyone know of very short term contracts <1 month? I like the idea of contracting as a side gig, but don’t want to take on something that feels like a second full time job.

Lack of stability and benefits is the biggest drawback for me. Have to keep track of your budget, what’s coming in, what you are charging, and allotting for taxes. Essentially, becoming self-employed. That does come with freedom, your scheduling, and you are the boss. I’ve done a few, upsides are there, but ultimately makes more sense for me to work for someone else.

Picking up contract gigs while between regular jobs makes a lot of sense. I'm not sure it's a good strategy to pursue as a permanent situation. You usually receive no benefits, and of course there's little security. But, it can let you have an income when you need it, so it does serve a valuable, if limited, purpose.

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