If I were in your shoes, the very first thing I'd do is make a list of every repetitive, low-value task you do each week and hire someone in the Philippines for just one. So many people get paralyzed by trying to outsource their whole business at once, and it rarely works. You need to learn the ropes of remote team management with a low-stakes task first.
In week one, I'd pick something you could explain in a simple document. As Nathan Hirsch mentioned on The My Wife Quit Her Job Podcast, it's smart to outsource customer service first. That's a great starting point. Your other option could be something like data entry or basic product research, a topic Jim Cockrum revisits often. Write a one-page operating procedure for that single task with clear steps. Then, I'd post a very specific job description on a platform like OnlineJobs.ph. The founder, John Jonas, gives great advice on this, emphasizing a unique interview process to find the right person.
In month one, your only goal is to build a working rhythm and relationship with your new hire. Don't expect perfection. Expect to give feedback, refine your instructions, and answer questions. It's not about the task's output yet; it's about learning how to communicate effectively across time zones and cultures. This is where you put in the work to build trust, which is the foundation of a successful long-term relationship, as John Jonas points out.
I'd completely ignore the idea of finding a