As someone who places great emphasis on developing quality, long-term relationships with my clients and network contacts, I recently have faced the hard-nosed question of where to draw the line. These past few months, the majority of my clients have failed to pay me, bounced checks, made promises, and seemingly ignored invoices, yet all with an apologetic, sometimes melancholy, response. Then, when I do receive payment, they come with low eyes, a monotone voice, and a frustrated look, gripping the check with white knuckles. This leaves me feeling guilty that I’m asking for compensation for the services I provided. (What, Jaylyn?!?)

Yeah, after collecting a two-month old payment yesterday, I spent the following three hours feeling as though I’d done something wrong. Did I not go the extra mile for this person? Didn’t I allow him to spread out the payments, only to have them bounce in my account, and charging me for the fee? Didn’t I do work and cut my prices? What else could I have done?

My goal is to support my customers as much as possible to 1. Keep a working relationship, and 2. Maintain the established friendship. But is this possible when difficult situations regarding money come into play? How much are you to sacrifice your well being for that of your clients?