You're Probably Screwing Yourself Out of Thousands...

Earners,

Negotiating is an art form and a beautiful one at that—and for me, it’s one of the biggest thrills of my day to day.

Few things compare to the back-and-forth dance of finding common ground while pushing for your best possible outcome. Over the years, I’ve shared a ton about negotiation, written countless newsletters on it, and applied what I’ve learned to real-world deals.

Recently, I said something during a conversation that struck me as a good way to see if you’re on the right track. Here’s the test:

If you send over an offer and you don’t feel queasy (even just a bit), baby, you’re not asking for enough.

Pushing the Boundaries

Whether you’re negotiating a raise, a new job, or a big business deal, you have to push the upper limits. It’s not about arrogance or being difficult; it’s about being disciplined. The confidence to hang in their isn’t just about knowing your worth—it’s about being willing to ask for it, even if it makes you uncomfortable and staying in that discomfort for as long as possible.

This discomfort is your growth zone. If you send an offer and feel completely calm, chances are you’ve under-asked. Negotiation is about holding firm when the silence drags on, when doubts creep in, and when the urge to backpedal becomes almost unbearable. You’ll rarely get irrational deals if you aren’t willing to throw out irrational offers (what seems irrational to you may be just fine for them - you just don’t know until you get it out there).

The key is polite persistence:

Follow up when needed. (“Hey, just checking in—where are we on this?”)

Stay curious. Ask questions like, “How can we work this out?” or “What’s driving your hesitation?”

Let them speak. The more information they reveal, the stronger your position.

But—and this is critical—don’t double back on your offer out of fear. The fear of losing a deal, damaging goodwill, or appearing “too much” are lies we tell ourselves. Instead, lean into the discomfort. That’s where the magic happens.

Chris Voss’ Playbook: Tactical Empathy

Chris Voss, the author of Never Split the Difference, pioneered the concept of tactical empathy—the art of understanding your counterpart’s feelings and perspective while maintaining your own objectives. His methods have been foundational in my own approach. Here are the top strategies I’ve adopted:

1. Mirroring: Repeat the last few words your counterpart says. It encourages them to expand, giving you more insight.

   Example: If they say, “We don’t have the budget,” respond with, “The budget is tight?” This often leads to them explaining further.

2. Labeling: Identify and name their emotions.

   Example: “It sounds like you’re concerned about cost overruns.” Acknowledging their feelings diffuses tension and builds trust.

3. The Open-Ended ‘How’ or ‘What’ Questions: These are your secret weapon.

   “How can we make this work?” or “What would need to happen for us to get closer?” Open-ended questions uncover their priorities without making them defensive.

4. The Accusation Audit: Preempt their objections.

   Example: “You are going to think I’m asking for too much, crazy even - but here’s why this number works for both of us.” By addressing concerns before they voice them, you disarm them. This is probably one of the best tactics I’ve ever come across - because it makes the process that much more smooth as you show that your understand the other side and their concerns.

5. The Silent Pause: Once you’ve made your ask, stop talking. Let the silence do the heavy lifting. Most people rush to fill awkward gaps, and in doing so, they reveal their position.

Confidence Isn’t Loud—It’s Steady

When you send your number, send it with conviction. A strong offer doesn’t need over-explaining. Simply say, “Based on X, this is what I’m looking for.” If they want more details, they’ll ask. But don’t undersell yourself.

Negotiation is about information asymmetry—you know what you’re worth, but they don’t. Your job is to maintain leverage by staying calm, focused, and strategic.

And yes, there will be people who think you’re crazy for asking what you’re asking. But for every person who balks, there’s someone who sees your confidence and matches it. The worst feeling for me isn’t losing a deal because I asked for too much; it’s realizing I could have asked for more and didn’t.

The Nerves Are Good

That queasy feeling? It’s your gut telling you you’re stretching yourself—and that’s a good thing. If you don’t feel a little uncomfortable, you’re leaving money on the table.

The trick is to keep recalibrating. As you hit your goals, push higher. Every deal is an opportunity to refine your craft.

Negotiating isn’t about winning every time; it’s about playing the long game, building confidence, and consistently raising your ceiling.

Earn more,

Nate