The article's description of the way in which I got into this position sounds right though -- you start out resourceful, people rely on you, and that makes you reluctant to rely on others.
I've just noticed that clients of all ages have trouble bringing themselves to get the right help they need when they need it. Coming into your own in business and in your career is not a linear progression, so people learn different things at different stages. You're lucky to have learned this early. :)
For example: if you're bootstrapping it makes sense to use a second-hand photocopier yourself; at some future point, all things going to plan, your business will need a more reliable machine being operated by your secretary. Most business owners make that decision reactively - they wait until the old copier dies or they're too stressed out and need admin support.
Great business owners put in a little bit of time to capacity planning, so they have the milestones (eg, when I hit $X revenue per month for 3 consecutive months) for adding resource to maintain profitability and sustainable growth. As a spreadsheet-literate business geek, helping them do that planning is one of the more fun elements of my career.
Of course, my career would be more profitable is more business owners read Jesse's blog, and made that first step.
Maybe this is holding me back in some way that I don't realize?
