Analytical vs. Holistic
In the book The WEIRDEst People in the World, Joseph Henrich points that out that WEIRD people think very analytically, while non-WEIRD people tend to think more holistically.
"The key distinction is between focusing on “individuals” or their “relationships.” When thinking analytically, people zoom in on and isolate objects, or component parts, and assign properties to those objects or parts to explain actions. They look for strict rules or conditions that permit them to place individuals, including animals or people, into discrete categories with no overlap. They explain things by coming up with “types” (what type of person is she?) and then assign properties to those types. When thinking about trends, analytic thinkers tend to “see” straight lines and assume things will continue in their current direction unless something happens. In contrast, holistic thinkers focus not on the parts but on the whole, and specifically on the relationships between the parts or on how they fit together. And, as part of a larger web of complex relationships, they expect time trends to be nonlinear or even cyclical by default."
In my book, I provide some concrete methods and steps you can take to get your 1099 gigs. I broke down my process that I used to get 1099 gigs, and wrote them as a set of series instructions.
This is the WEIRD, analytical approach. A leads to B which leads to C which leads to 1099.
In reality, life is a lot messier.
Oh you tried to convert your job to a 1099 but your boss tuned you down even though it makes perfect sense?
Perhaps your boss has another friend he wants to help get a job and your position would be perfect for it. Your boss might want to let you quit to help his buddy.
Or maybe you networked your way to a meeting with a PM with a bunch of open spots to fill that you'd be great for (and available).
He turns you down because to maintain his positive relationship with his other sub-contractors, he has to give them some time first to fill it. If the spots are still empty in six months, he may become more receptive.
In the book, I didn't capture the holistic picture of everything that may impact your ability to go 1099. That book would be a billion pages and leave you unproductively overwhelmed. The analysis and experience based steps work and there is no need to get distracted.
But you should be aware that there are lots of dynamics that are not visible to you that will definitely impact you, both positively and negatively.
The trick is to accept them, become better at paying attention to those holistic forces, and keep taking action.
Want the full playbook? Check out Going 1099.