How to Negotiate Like a Toddler (And Win Every Business Deal)

After 107 straight days of showing up—writing about surrender, deadlines, exhaustion, and the kind of magic that finds you when you least expect it—we've arrived at Day 108.

And this one feels like both a celebration and a quiet little mic drop.

Because if there's one thing this journey has shown me, it's this: sometimes the most powerful negotiation lessons don't come from books or strategies or experts.

Sometimes they come from learning how to negotiate like a toddler asking for the pink cup.

After running multiple businesses—and navigating everything from six-figure deals to partnerships that fell apart spectacularly—I've tested every negotiation framework out there. But the strategy that actually works? It showed up in my living room, courtesy of a two-year-old with zero business training and 100% effectiveness.

The Most Unexpected Negotiation Expert

I've been in the middle of a business negotiation recently for one of my companies. And if I'm being honest? It hasn't been going exceptionally well.

It's just one of those slow, slightly off conversations where you can feel someone testing your boundaries. Seeing if kindness equals pushover.

And for a split second, I questioned it.

I thought: Is this the problem? Is being kind making me weaker at the table?

For a long time, I believed that. I thought being thoughtful, being willing to meet people where they are, being compassionate somehow made me easier to move. Easier to discount. That people would see my kindness and take advantage. That they'd mistake it for weakness and walk right over me.

I've lost deals because of this belief. I've pre-discounted my rates. I've accepted terms I shouldn't have. I've walked away from negotiations feeling like I'd abandoned myself at the table.

But then something clicked.

Kindness isn't the problem. It's actually my superpower.

The problem is being a pushover. Worrying so much about hurting feelings or offending someone that you abandon your own ask.

And weirdly, the clearest example of how to negotiate like a toddler showed up in the smallest possible teacher: my two-year-old daughter.

What Toddlers Get Right About Negotiation (That We Completely Forget)

Toddlers are not strategic. They are not polished. They are not trying to "win the room."

And yet they are wildly, almost frustratingly effective at business negotiation.

They are clear, consistent, and completely unavailable for self-abandonment.

After studying negotiation tactics and applying them across industries—from tech partnerships to creative licensing deals—I can tell you this: toddlers intuitively understand principles that take most business owners years to learn.

Let me break down the exact negotiation strategies toddlers use naturally—and how you can apply them in your business deals.

They Know Exactly What They Want

When you negotiate like a toddler, you start with crystal clarity. Toddlers don't hint. They don't soften. They don't say, "I mean, if it works for you..."

They say: "I want the pink cup."

Or: "I want the blue cup with cars."

That's it. End of message.

In my experience building Karma Penguin and advising other entrepreneurs, I've watched people lose thousands of dollars simply because they walked into negotiations without clearly defined non-negotiables.

Somewhere along the way, we learned to dilute our asks so we'd be easier to receive. We hedge. We add disclaimers. We reword things mid-sentence to make the other person more comfortable.

But clarity is not confrontation. It's respect—for yourself and the other person.

Before you walk into any negotiation, you need to know your non-negotiables. Price, timing, scope—whatever it is. Write it down. Get clear. And then stay clear.

I've spent years circling back to this idea in my writing: healing begins with honesty. So does business negotiation. You can't advocate for what you haven't named.

They Repeat Without Shame

One of the most powerful ways to negotiate like a toddler? Persistent follow-up without apology.

If you don't respond? They ask again.

And again. And again.

My daughter asked me for something sixty-five million times yesterday. "Can I have it?" Not right now. "Can I have it?" First this, then that. "No." "Can I have it?"

She didn't interpret my silence as rejection. She didn't assume she was being annoying. She just kept asking.

Toddlers don't see repetition as pushy. They assume the conversation is still open.

Adults, on the other hand, send one email and spiral.

"Was that too much?"

"Should I have worded it differently?"

"Maybe I'll just leave it..."

No.

In my experience, most deals don't die from disagreement—they die from silence. The person who follows up (professionally, consistently) almost always has the advantage.

Follow-up is part of effective business negotiation. Persistence is staying present until there's a genuine reply.

Remember when I was too tired to micromanage my day and discovered the hotel room magically became available? Or when my neighbor won the Broadway lottery on her first try after she entered without attachment? Staying open—without the death grip—invites serendipity. You're not chasing. You're just... still there.

They Don't Over-Explain

If you want to negotiate like a toddler successfully, learn this: brevity equals power.

Toddlers don't build a case. They don't justify their needs. They don't prepare a five-paragraph argument for why the pink cup matters.

They just say it. And then they wait.

Here's the uncomfortable truth about business negotiation that I learned the hard way (and cost me real money): the more we over-explain, the less powerful we sound.

Confidence is often quiet. It's simple. It lands, and then it waits.

I try to write that way too. One sharp line—"Sometimes the most spiritual thing you can do is just drink your coffee and let the universe do its job"—and then I trust you to feel the rest.

Trust yourself to let the ask land without a dissertation. You don't need to convince anyone of your value before they've even responded.

They Don't Negotiate Against Themselves

This is the most critical lesson when you negotiate like a toddler: never pre-discount your position.

This one. This is where most people lose before the business negotiation even begins.

Toddlers don't say, "Actually never mind, whatever you want is fine."

Adults do this all the time.

I've done this. Multiple times. And I can tell you exactly what it cost me—both in revenue and in self-respect.

We soften. We pre-discount. We adjust our price, our timeline, our boundaries before anyone even asks us to.

This morning my daughter threw herself on the ground—full body, Oscar-worthy performance—over a spatula. A spatula she didn't need. Had never touched before. Didn't even know existed until thirty seconds earlier.

But in that moment? That spatula was everything.

She didn't reword her position to make me comfortable. She didn't add disclaimers or apologize for wanting it. She didn't back away from her ask just when I said no.

She stayed right there. Fully committed. Unapologetic.

Hold your position in any business negotiation. Let the other side respond before you start negotiating your own value down.

After advising dozens of entrepreneurs through Karma Penguin, I've seen people negotiate against themselves before the other party even responds—and it costs them real money. Sometimes five figures. Sometimes six.

Being kind doesn't require being a pushover. I built Karma Penguin around the belief that compassionate realness means feeling it all without apology. That applies to business negotiation too.

They Feel Everything—And Still Ask

To truly negotiate like a toddler, you must separate emotions from the ask itself.

Toddlers feel frustration. Disappointment. Big, overwhelming emotions.

But they never conclude: "I guess I shouldn't have asked."

They feel it all, and then they continue.

That's the part we've lost in business negotiation.

In business, we often interpret discomfort as a sign we've done something wrong. But discomfort is just part of the process.

After navigating countless high-stakes conversations—from terminating partnerships to renegotiating contracts mid-crisis—I can tell you: the discomfort doesn't mean you're doing it wrong. It means you're doing something that matters.

You can feel nervous and still make the ask. You can feel uncertain and still hold your ground. The emotion doesn't invalidate the need.

On Day 107, when I was running on two hours of sleep thanks to New Moon energy, I acknowledged deep exhaustion and still went ahead with my day. Recognize your emotions in any negotiation, but don't let them derail the ask.

They Expect an Answer

The final secret to negotiate like a toddler? Unapologetic expectation.

Toddlers assume you heard them. They assume you will respond. They don't shrink after expressing themselves.

And that expectation? It changes everything in business negotiation.

When you don't energetically disappear after making an ask, you leave space for the other person to actually meet you there.

Too often, adults make an ask and then energetically retreat. We assume silence means no. We start second-guessing. We back away before we've even gotten a response.

In my experience coaching entrepreneurs through difficult conversations, this is the single most common place people lose deals they could have won.

Stay in the conversation. Sometimes being "too tired to try" is what allows the universe to finally unlock a door. In business, staying present—without chasing—gives the other party room to meet you.

The Real Shift: Kindness Is Your Negotiation Superpower

I used to think being kind in business meant people would see me as weak. That they'd take advantage. That I'd get steamrolled at every negotiation table.

And honestly? I spent years trying to compensate for that. Trying to be harder. Sharper. More aggressive. Worried that if I showed up as myself—thoughtful, compassionate, willing to listen—I'd lose before I even started.

But here's what running multiple businesses taught me, and what learning to negotiate like a toddler confirmed:

Kindness is what allows me to stay grounded. Clarity is what allows me to be respected.

And the combination of both? That's where the power is in any business negotiation.

You don't need to become harder. You don't need to become louder. You just need to stop leaving yourself mid-conversation.

Karma Penguin exists to help spiritually curious, heart-led humans reset their energy, reconnect with themselves, and rise with soul. I've worked with hundreds of sensitive, strong-hearted entrepreneurs who were told their kindness was a liability. It's not. The core values—Radical Responsibility, Sacred Play, Compassionate Realness, Practical Magic, and Cosmic Alignment—invite truth-telling and fun in equal measure.

In business negotiation, kindness and firm advocacy aren't opposites. They're mutually reinforcing. You can be generous and clear about your worth at the same time.

The trick when you negotiate like a toddler is refusing to be a pushover. Refusing to soften your ask just to avoid making someone uncomfortable. Refusing to negotiate against yourself before they've even responded.

When Nothing Is Moving in Your Business Negotiation... Let Go

There's another layer to learning how to negotiate like a toddler. If you've been here the last few days, you've probably noticed a pattern.

Day 106: My neighbor stopped gripping, entered a Broadway lottery on a whim, and won on her first try.

Day 107: I was too tired to control the outcome—running on two hours of sleep and Nessie coffee—and the impossible hotel room magically became available.

And now this.

Here's what I'm starting to understand about business negotiation: not every deal is meant to be forced.

Sometimes the shift doesn't come from pushing harder. Sometimes it comes from releasing just enough control to let something new enter the room.

When negotiations feel stuck, there's wisdom in pausing, breathing, and allowing the conversation to rest.

Detachment isn't indifference. It's confidence that your worth isn't contingent on any single deal.

I've walked away from deals that would have compromised my values, and every single time, something better showed up within weeks.

Stop fighting it. Drink your coffee. Put on The Sound of Music. Do the next right thing in front of you.

Let the space do some of the work.

You might just be too tired to get in your own way. And that might be exactly when the magic happens in your business negotiation.

An Invitation to Negotiate Like a Toddler Starting Today

If you're in a moment right now—in business, in life, in anything—where you're being asked to hold your ground, here's what I want you to remember:

Stay.

Be clear. Be kind. Repeat yourself if needed. Don't over-explain. Don't negotiate yourself down before anyone has even countered.

And if nothing is moving in your business negotiation?

Take a breath.

Drink your coffee. Do the next right thing.

Trust that if this negotiation isn't the one, something better is coming.

You're not too sensitive. You're not asking for too much. You're just human.

And if a toddler can demand a spatula with that much conviction, you can ask for what you're worth in any business negotiation.

Open your hands. Enter the lottery. Trust that something good is trying to find you.

It might just be waiting for you to stop trying so hard and start learning to negotiate like a toddler.

About the Author | Day 108

I am a soul-led coach, entrepreneur, and recovering control enthusiast who just wrapped 108 straight days of showing up with stories about surrender, toddler tantrums, New Moon insomnia, and the kind of cosmic timing that makes you laugh out loud at your desk.

I work with overthinkers, over-explainers, people who've been white-knuckling their way through business negotiations and wondering why kindness keeps getting mistaken for weakness, and anyone who's ever sat on their kitchen floor wondering why doing everything right still isn't working.

I believe in the power of staying present (even when it's uncomfortable), trusting that your worth doesn't require a five-paragraph defense, and the undeniable magic that happens when you're too tired to resist what's trying to come through.

One clear ask, one spatula tantrum, one open hand at a time.