Selling Yourself

A transcription of Merlin Mann discussing being self-employed, on the excellent Back To Work podcast:

What can be awesome, or awful, about being on your own is having to resell yourself, constantly. You’ve constantly got to show the value of what you do to people who are in a position to potentially pay you.

If you had to go in and re-interview for your own job - with ‘The Bobs’ - every day, that sucks. I’ve gotten to the point, though, that I’ve realised if I have to convince someone that what I’m doing is valuable, it’s never going to work out. […] If I have to educate you on the value of what I do, I’ve already lost my position of strength and it’s already told me we’re a bad match and that you’re not familiar enough with what I do; that I would have to tell you why that’s a good idea.

This resonated with me. I experienced it early in my career, as a freelancer, and more recently as a contractor. It’s something all small independent businesses face eventually.

If you can’t easily convince someone of the value of your proposition, then will that person be a good customer for you? And will your offering be good for them?