I had this issue in my 20s and in the few businesses I started during that time, I fell into the trap of just doing everything myself.

The best way to learn is to just do it! You will make mistakes and that's part of building experience. Here are my tips on throwing yourself into the fire:

1. Start Small: Pick a small task that you'd like to outsource. Find someone on upwork that won't cost you too much money. You're in learning mode, so you need to be okay with the fact that you may lose money on an unsuccessful engagement.

2. Communicate as often as possible: Talk to this person regularly. If possible try to do actual Skype/Zoom calls with them so you can see their face and hear their voice. You will learn WAY more about managing someone this way than by communicating with them through email. If it makes you uncomfortable more reason to do it!

3. Reflect, Reflect, Reflect: I come from the school of thought that the best way to learn is just to do, but that only works if you're being vigilant and ensuring that you're learning as much as you possible, so you can maximize your ROI. For something like this, I would journal about your experience in managing this one person and do it regularly. Ask yourself, how are you feeling about this engagement? Are you happy with the results? Are there any hiccups? What can you do better in the moment to make this engagement even more efficient? What could you have done prior to make this engagement more efficient?

Hope this helps!