The Subtle Art of Not Discounting Yourself

Pricing isn't about defending your number; it's about owning it.

I still recall the first time someone said, “That’s higher than I expected,” after I sent them a proposal. My initial reaction was simple: panic, followed by asking myself a series of questions:

• Should I discount it?

• Explain every line item?

• Apologize for charging what I charge?

I didn’t do any of that, but the urge was strong. It was rooted in a sense of insecurity, a familiar feeling during these conversations. By recognizing and naming this emotion, I developed a better understanding of what drives those instincts. Such self-awareness has been a powerful tool, allowing me to pause and respond more effectively to these situations.

Here’s what I’ve learned since then: when someone says that, they’re not automatically saying no; they’re recalibrating.

Most people have no idea what thoughtful, strategic branded merchandise actually costs. They see the finished pieces on Facebook or Instagram and assume it just magically appears. They don’t see the strategy sessions, the sourcing, the back-and-forth, the revisions, the logistics, the supply chain coordination, the risk mitigation, or the “by the way, the gradient in your artwork won’t embroider the way you think it will” conversations.

They hear a number, and for a split second, their brain needs to adjust. Where I used to go wrong was treating that moment like a complete rejection. I’d get defensive, start justifying every penny, and over-explain, trying to smooth over their reluctance.

All it did was make things really awkward, which is why I could probably use a therapy session or two, but I digress.

Now, I take a deep breath and say something direct and simple: "I get that. I'm more than happy to walk you through what's included if that would be helpful." Then, I do something that is the most difficult thing for me to do in that situation: I shut up. After allowing a moment of strategic silence, I follow up with, "How can we make this work for you?" to reopen the dialogue on their terms.

Sometimes they say no, and that’s completely fine. Sometimes they ask questions, and we adjust the scope to make it work. A lot of times I’ll hear, “Let me think about it,” and they come back later to ask a few questions, or are ready to move forward.

The key lesson is that their reaction isn’t necessarily about you being too expensive; it’s about reference points. Pricing creative, strategic work is confusing, even for us in the industry. Knowing that, of course, it’s confusing for someone who doesn’t live and breathe it every day. Here’s the part that changed everything for me: the worst-case scenario isn’t that bad. If they genuinely can’t afford it, that’s not a failure at all.

Remember, you’re not trying to convince everyone, you’re trying to find the right client who values what you do and can invest in it. The real work is learning to sit in that uncomfortable silence after they react, rather than rushing to discount, scrambling to justify, or lowering the price to relieve your own tension.

It does get easier. Not what I would call comfortable, but easier. It’s also when you start pricing and selling, like a professional.