Becoming A Boss

What is the cost to you doing it? What is the cost of you delegating? What are the risks? What is the opportunity cost? (The opportunity cost is not your sleep, or your time away from your business. The opportunity cost is you having to delegate something else. The business will expand to the time you let it, anyway.)

As a boss, your goal is to become a multiplier. What can the team get done with your guidance as opposed to what it could get done alone, with you as a line worker?

But when all else fails, err on the side of delegation, because your first instinct will be to do it yourself. :)

Basically, some people have a knack for managing, others have a knack for creating. Put a creator in a management position, and they will suck. Put a manager in a creator position, and they will suck. The trick is to put the right people in the right roles, and to make sure you're hiring both types of people. Managers prefer hiring other manager-type people, and creators prefer hiring other creator-type people. Often you have companies that are either heavy manager based (where nothing gets done), or are highly creator based (where the office environment is miserable due to conflicts and ego). Both companies are bound to fail.

Apart from these, there are certainly other ways to organize, if efficiency is not the key thing. If the bottleneck is "try out lots of cool things, and see which one sticks", such as a research department, then it could be organized more like a cooperative with individual makers. There would probably need to be some selection of things to include in a next release if it is a manufactured product, but on the web, that might not even be necessary. Sure, integration would be a mess, but in some cases, that is not so important.