You will only go as far as your weaknesses. What are your limitations? Do you have the technical skill to do something, but not enough time to do it? Do you have more time than you know what to do, but not enough money to invest in something (school, investment properties, etc.)?
Your ceiling is determined by your capacities. Unless you can increase your capacities, you can only make it so far. The best businesses (large and small) realize this and put together programs to combat this.
How do you increase what you’re capable of doing? Either by outsourcing your weaknesses (hiring someone to do what you don’t like doing, aren’t good at doing, or don’t receive the best return on your time investment) or by working to improve your weaknesses (increasing your skill with more practice, talking with experts, reading, etc.).
In the beginning, it may make sense for you to try to improve upon your weaknesses to raise your ceiling. If you’re a business owner or a manager, you should have at least a basic understanding of what you will be asking someone else to do. The best way to gain that understanding is by doing it yourself. But over time, as your daily task list piles up, the best way to grow will be to delegate tasks to qualified, trusted individuals on your team.
How do you know when it’s right to hire someone new? Once you get to the point where your time is almost at capacity (say 80-90%), you need to hire someone to replace you and your weaknesses. Hiring too soon cuts into your profits (if the new hire is getting paid to work 40 hours a week, but really they’re only busy for 25-30 hours, you’re basically paying them to sit around). But hiring too late, when you’re already crunched on time, won’t allow you to properly train the new hire, leading to frustration and decreased productivity in your other tasks.
Before hiring someone though, make sure you develop an Operations Manual to hand to them on day one. This will be used as a reference guide, so they do not always have to ask you the same questions. It also gives them direction and lets them know what to expect, including daily tasks and what we feel are current best practices. It should be communicated to the new hire that the Operations Manual reflects the way we did things when we wrote it, but it should be viewed as a template that is a work in progress. You should always be open to changing specifics (tactics) as you find better ways to achieve your strategic goals.