Do it yourself first
37signals.com
37signals.com
But, I'm (finally) beginning to learn that there are simply some things that I will never do well. And some things that, even if I can do them, it makes me ill to do them because of how repetitive they are (like bookkeeping, filing, accounting, etc.), or how much practice it takes me to get to proficiency (like web design), or how my natural and very strong introversion fights against success in the area (like cold calling, or LinkedIn "warm calling", for market research and business development). I'm also beginning to realize that by focusing on these tasks, which can be very time consuming, I'm missing out on other opportunities to grow our business. So, I'm interviewing bookkeepers this week (craigslist is awesome for job postings, by the way...I've been amazed at the results: 200+ applicants for a part-time bookkeeping/filing office management position), and I hired a friend to do some light business development and market research for us.
The thing is, when I add up the numbers (for example, $400/month for a bookkeeper), I realize how stupid it was for me to try to do this work for so long. There is certainly value in knowing the position well enough to hire well. I can choose someone based on their intelligence and enthusiasm rather than purely on the resume and experience, since I can train them in the specifics, if needed. But, I think I waited too long to hire this position. It's one of the aspects of the company that has been weighing on my mind for a while, and keeping me from being as enthusiastic about getting to work each day.
So, as with most things DHH says, I agree...but with caveats. Don't take it to extremes.
Opportunity cost is such a stealthy killer. Like you, I've spent a lot my time doing things like car repair, painting, moving...even simple (but time-consuming) things like taking stuff to the dump. The immediate reasoning is always something like: "why in the world would I PAY someone three times as much to fix my brakes, as it would cost me to do myself?", and it usually made sense at the time. But then I realized that I was far less productive at the things that I wanted to do, because I was spending so much time on the cruft.
I've learned a lot by doing things myself, but this habit has also left me with a less free time to do the things I wanted to do, or to excel at the important things. So now I try to pay people to take the uninteresting things off my plate. Still...that's a hard thing to do when you're the type of person who is inclined to find nearly everything interesting, so it usually boils down to setting firm priorities.
So I'll code, design, sysadmin, and all this other stuff. I'd be a genius if I weren't so average at all of them. The problem becomes, though, that since I've been doing all this stuff for so long I'm very reluctant to actually let someone replace me. What if they're incompetent? What if they're really smart but lazy? How do I manage them when I can't even reliably manage myself? What do I do about the fact that I've become so used to being in complete control of everything?
I think there's something to be said about just finding someone smart and talented to do something you have no idea how to do. I definitely take this approach with all business matters as they are forever deferred to Dan; I have no desire to gain more than a cursory understanding of how that stuff works. Sometimes I'll want to learn a bit more about what caused the financial crisis or what some business term is and I'll ask, but it's only out of curiosity, not because I want to actually use that knowledge for anything.
A prerequisite to buying a microwave isn't knowing how it works, at least for me. I only care whether or not it heats shit up.
Also, if you want to do everything yourself first, I hope you're not in much of a rush to get your overall project finished. There are a lot of things that you can easily understand and appreciate without having actually done them yourself.
If you need to do everything yourself first, you're probably not going to be a great manager or boss. A good manager should have a good sense of what his/her employees are doing and be able to get them to communicate the most important parts of the job without actually having to do the job. Sure, you'll have a better sense if you do it yourself, but that doesn't mean that's a good trade-off in terms of how to spend your time. There are a lot of tasks that you can intelligently analyze without actually doing them. Are there a lot of crappy managers out there who have no sense of the jobs their reports are doing? Sure. But they can put some effort into understanding them without actually doing them. It's more of a communication issue, not an execution issue.
Finally, I'm assuming the post is in the context of getting a project finished, not running a company. But if it's the latter, then I think it's especially bad advice: taxes, legal, accounting, etc. should NEVER be done by anyone other than an expert unless it's at an EXTREMELY basic level (and even then it's still usually a bad idea). I'm sure founders with limited financial resources fall into this trap sometimes, but it can really bite you in the ass down the road.
A bit I wrote down from Growing a Business:
"Be a hands-on learner, and get involved with all aspects of your business, so that you know exactly how they work down to the details."
http://www.squeezedbooks.com/book/show/4/growing-a-business
Which is a good book - it's like "getting real", but an actual, real, published book with an ISBN number, rather than a "let's see how many pdf's we can sell to our followers before we release it for free" type of deal.