Hi Emily-- I enjoyed and took inspiration from your previous post on your pivot journey. This inquiry on freelancing and atomization of tasks is a smart follow up. 

As an experienced grantmaking generalist currently working for an non-EA foundation, I think there is a useful distinction between generalist tasks that can be projectized vs longer-term functions that are harder to separate from deep-seated organizational context.

Tasks that lend themselves well to freelance work have a clear end state and a well defined standard of quality:

• creative-forward projects like web design (traditionally left to freelancers given lack of continuity)
• clearly scoped writing projects like research memos, due diligence, landscape scans, or grant applications (assuming the org has heavily documented their own priorities and context)
• one-time database hygiene checks, workflow documentation, template creation
• bounded process analysis and automation projects (when the org knows how to define its desired end state-- difficult / not a given!)
• surge capacity for proposal review, event logistics, heavy reporting

All of this scoping and documentation that (I feel) is required to hire a freelancer responsibly requires significant internal capacity to spin up. If those conditions are missing, the freelancer may be set up to fail. 

It is also common for any of the above tasks to overflow their clean deliverable scoping and brush at deeper matters of prioritization judgment, internal inconsistencies, informal or unwritten context, org chart tensions, etc. One piece of the value of a full-time generalist is their ability to notice and take initiative to address these kinds of problems, which may require deep, long-term, and emotionally aware engagement. They can be especially prevalent for orgs with a startup culture or those that scale rapidly. Freelancers may notice these deep issues but tend not to be in a good position to address them out of fear of overstepping or creating relational friction that a full-time employee is far more incentivized to tackle.

I've also observed that EA orgs are extremely picky about their hires, and rationally so. Freelancers occupy an awkward position where it is not cost-effective to conduct a similar vetting process given short project timelines and expected turnover, but the risk surface for the org is still fairly high if this person turns out to deliver subpar work: the deficiency needs to be identified, the contract reassigned, and the work repeated.

This very cost-benefit tension is the kind of issue that a high-level, embedded operations person could identify and solve. When do we take on the risk of a freelancer to power through something urgent in the short-term, and when is it more sustainable to take time to solve the underlying capacity issue?

I do love the idea of a freelance generalist directory. It may benefit from some scaffolding: tips on turning organizational pain points into scoped projects and perhaps some sort of pre-vetting process. Either way, I'd love to support!

It's certainly an exciting time to be looking into a pivot into direct work! Thanks for this analysis, Sam.