Positioning beats negotiation skills
Negotiations in the movies are dramatic. They involve clever maneuvers, witty retorts, and small pieces of papers with numbers written on them.
Real life negotiations are not like that (at least in the solo 1099 world). I have done most of my negotiations over e-mail with minimal back and forth.
But negotiating skill probably only accounts for 10% of the final outcome when negotiating a solo 1099 deal.
What matters most is your position when you enter negotiations.
Your position is the cumulative state of your desires, your skills, and your business environment.
If you're in a position where you want a 1099 gig but don't need it, have valuable skills, and are in a hot job market or growing industry, it will be very easy for you to negotiate a favorable outcome.
If you have weak skills and desperately need to get out of your current job and no backup opportunities, you are in a position of weakness and negotiation skills will only help you so much.
So instead of spending the majority of your effort trying to build a good poker face and practicing banging your fists on the table, I recommend building your client and program manager relationships, developing in-demand skills, and researching and defining your realistic and ambitious billable rate numbers.
If you do that, you'll likely succeed even if you are a horrible negotiator.
Want the full playbook? Check out Going 1099.