When is it worth it to hire someone to do it versus doing it yourself?

Help wanted sign (Photo credit: andjohan)

I have this conversation with myself every few months:

Gah! I’m in over my head. I need to hire some extra help.

That sounds like a good idea. It would free you up to do other things and maybe equal more money in the long run. And isn’t it worth it to spend a little money to take a little of the stress off you?

OK, let’s see. I could hire someone and for $x they could get this big chunk of work done.

$x? Eesh. Does it have to be that much?

I’ve done the research and that’s the lowest I’d be able to pay at the going rates. Though I guess I could try to offer lower and see if anyone is interested but then won’t I get a lower quality of worker?

Can you absolutely guarantee that you’ll make more than $x back with that work?

Most of the work I need done is background stuff, there’s no real way to judge the conversion rate exactly…

Well, unless you can guarantee you’ll make a profit on the work it’s not worth losing money.

But what about freeing me up to do other things? Equaling more money in the long run?

How long would that work take you? Just do it yourself and save the money of hiring someone.

B…but the whole point was that I was in over my head. That I needed to take some of the pressure off me…

Clearly, you just need to work more. Besides, think of how long it would take to rain someone to do things as well as you do.

Ugh, that would take forever. *dreads it*

And then they’d probably just screw it up anyway and you’d be paying them to do things half as well as you can do them yourself. Think of all the nightmare employees and contractors you’ve had in the past.

*shudders* You’re right. I can’t really trust anyone but myself to do things right… But, wait, isn’t that just me being a control freak?

Is it? Or is it you being right?

Gosh. I don’t know.

So, really, it’s a waste to hire anyone else. Forget all about it.

OK, I guess I could just try to work more. (time passes) Gah! I’m in over my head. I need to hire some extra help.

and so on, forever…

You know my thought process on this so I put this to you:

How do you break from this thought cycle and actually make a decision as to whether hiring help is right or wrong?
When you do you know it’s time to pull the trigger and delegate a project to a freelancer or take on a new employee versus time to just buckle down and do more work yourself?
What are your hang-ups when it comes to forking over more money for more help?