Accept the mess

by Dale Davidson March 18, 2026

If you're a logical thinker, you may think going 1099 is a straight forward exercise.

You get good at something, you get leverage, and then when the opportunity is right you rationally persuade a prime to take you on as a 1099 for a mutually agreeable rate that accounts for your risk and is still profitable for the prime.

While the basic outline is correct, it will of course be a lot messier than you anticipate.

A program manager may not like you, a contract falls through, someone wants to hire their goofy nephew instead, the sub-contract administrator went on vacation, etc.

Lots of things "get in the way" of you going 1099.

Conversely, you may benefit from the mess and have a 1099 project drop in your lap!

The mistake is to think it will work out linearly.

So focus on doing the right things, accept the mess, and trust that it will work out.

Want the full playbook? Check out Going 1099.