Though I love it when the checks roll in, I detest invoicing. Always have.

Turns out I’m not alone.

Over the last couple weeks, I made a point of asking my freelance friends how they felt about sending invoices, and surprise — nobody loves the experience.

Most of them hated it.

Which means there’s probably more at work here than a simple aversion to bookkeeping; several of the freelancers I asked copped to actually feeling uncomfortable “asking” for money, even though they’d already earned it.

To delve deeper is to get wrapped up in concepts like self-worth and value in a chaotic marketplace, but I will admit I regularly underpriced myself when I started freelancing — even in the booming tech market.

Fortunately, the same salesman who taught me the basics of negotiation immediately put his finger on my problem.

“When you’re crafting a proposal, do you imagine your client reacting negatively to your estimate?”

Which, naturally enough, I had been doing.

“Well, stop that.”

Good advice (and simple too).

A common negotiating tactic is the Wince, where one negotiator actually flinches when they first see the proposal, hoping to goad the other side into making an uncompensated concession.

It works a surprising amount of the time;  I was essentially self-administering it before the client even saw the proposal.

Thankfully, that nasty little habit is almost two decades behind me, but over the years, I’ve had to eradicate a handful of other money-related bad habits, including:

  • Failing to raise prices on long-term (years), recurring projects (your clients are probably getting cost-of-living raises, and you’re getting better at what you do)
  • Comparing myself to less-experienced, less-able competitors when setting pricing
  • Not making strong value statements about my work or expertise

Any of these look familiar? Any others popping into your mind?

Pricing yourself in a fast-changing, oversupplied market is already hard; why complicate it by practicing self-destructive behaviors around money?