How big is the team you're working with/in?

Excellent. It's a team of smart, talented people so we follow a commander's intent model [1] with minimal overhead. One meeting per week where we review the past week's progress then plan expectations for the coming week.

[1] i.e. rather than micromanaging the details of how people on the team operate, I coordinate with them on high-level goals, then they autonomously figure out the nitty gritty of how to reach those goals.

I hire freelancers for specific tasks and areas for which I do not have the time, or feel that I could find somebody who is better and, very important, simply faster than me. Ideally you are at least twice as fast as me, because then I'll feel like I made the right decision to outsource the work. :-)

For me this means:

• SEO & content creation: found somebody great and he is really taking lots of mental load of my shoulders
• design: I am not too shabby when it comes to design, but still miles away from a professional. Makes total sense to me to have somebody really good available when I need this
• frontend dev: my current hiring project. I need somebody to finish a small project (a few days) for me. I could do it, but it would take too long, and eventually I'll need somebody additional for frontend work any way.

I follow the rule of "hire slowly, fire quickly" and even only start looking for somebody when I really feel the pain.