You have to leap some time

You can only prepare so much.

You've done all the research. You have savings. You know you can get a back up job offer. You have great client relationships and technical skills.

At some point you're going to have make your move.

This might mean telling your boss you can only stay if they keep you on as a 1099.

It could mean asking a potential client if they'd like to work with you, and if so, ask for an introduction to the contractor program manager they work with.

It could mean turning down a great W2 job offer and only accepting a 1099 arrangement.

There's no amount of preparation that will de-risk the move 100%.

By not making the leap, you are actually choosing to stay.

So if you choose to go 1099, do as much as you can to prepare, but no more.

Just leap.

Want the full playbook? Check out Going 1099.