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I have hired a lot of contractors over the years, and I must say that if one of them pitched this to me I would likely walk away.

I thought this at first, as well. However, after reading the advice about only using "long-time customers" for this approach.

1) Only applies to a long time (happy) customer...and:

2) Said project should be appropriate for this sort of billing method. And will often vary, but I think he got it right. It should be a project that is important to the business where quoting and billing is difficult to nail down.

An example from my past: I used to do network config/wiring/support work for a small firm. They found out that I also wrote software and asked for my assistance on a small, very important, project in an area that was not my expertise (an EDI system). They didn't ask me for an up-front quote due to our previous business relationship. They did, however, gave me a short, hard deadline.

I billed them two hours instead of the twenty or so it took me to figure out the problem because I was inexperienced in the technologies they used. They volunteered a $1000 bonus to me on its completion.

I learned later that the short deadline was to give them enough time to pass the work off to a well known company that could easily get it done, but had quoted them north of $10,000.

I'm not complaining. This company and a few others that I did regular odd jobs for made my college years reasonable.

Really, all you're doing here is leveraging the relationship you have with a customer and the circumstances of the job are largely going to determine whether or not it would work or, as you put it, come of as naive and lacking confidence.

This customer knew from my past work that I was a little less expensive than most of their other options and yet I did quality work. They also knew I was going to school and -- like an employee of their company -- had to give me incentive to take on more work when it was necessary. I needed them, they needed me. In the case of this small assignment outside of my area of expertise, they saw underpaying me as more to their disadvantage.

I was shocked to receive the unsolicited bonus, but I'm willing to bet it would have been more than $1000 if I had just said "I don't know how to bill this. Pay me what you think it's worth" to this particular customer.




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