The Dip is where dreams go to die.

March 30, 2025•5 min read

A client asked me a tough question recently:

“Do you think I can actually make this work?”

He wasn’t being dramatic. He was in the middle of building something new—testing a service model, taking it to market, and feeling that classic mix of excitement and exhaustion. And he was starting to hit that point where the friction makes you second-guess everything.

My answer was simple:

“Absolutely—100%. But only if you stick with it and keep iterating. If you treat this like a science experiment and stay in the game long enough to learn what works, success is inevitable. But it’s going to be f***ing hard.”

And that’s not just true for him. It’s true for any entrepreneur chasing outsized results.

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Every High-Leverage Move Comes With Resistance

Whether it’s:

Hiring your first salesperson
Standing up paid ads
Launching cold outbound
Building content systems
Creating a new offer or service line
Starting an organic content strategy

Every meaningful initiative—anything with the potential to actually move the needle—comes with a degree of difficulty most people aren’t ready for.

It’s not just logistically hard. It’s emotionally and strategically hard.

It stretches your patience, tests your resilience, and puts pressure on the weakest points in your business and mindset.

That’s why so many people quit halfway through.

They hit resistance and assume they made the wrong move.

But in reality?

The resistance is the path.

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The Dip No One Warned You About

Seth Godin calls this early struggle The Dip—the space between beginner’s luck and meaningful results.

It’s the part where the excitement wears off, the real work begins, and all the friction that was hiding under the surface shows up at once:

The SDR you hired flames out after four weeks.
Your paid ads start spending money but don’t produce real leads.
Your cold emails get ignored—or worse, marked as spam.
The systems you hoped would save you time just add more complexity.

That’s when people start pivoting.

They say, “Well, that didn’t work. Let’s try something else.”

But what they don’t realize is:

They were right in the middle of the dip. And that’s where most people bail—often just before they would’ve started to see traction.

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The Emotional Cycle No One Talks About

Godin’s concept of The Dip is actually rooted in a framework called the Emotional Cycle of Change, originally developed by Don Kelley and Daryl Conner in the mid-1970s.

It outlines the emotional stages people go through anytime they pursue meaningful change of any kind:

Uninformed Optimism — “This is going to work!”
Informed Pessimism — “This is harder than I thought.”
Valley of Despair — “Maybe I’m not cut out for this.”
Informed Optimism — “Okay, I see what’s not working. I’m learning.”
Success — “It’s working. I’m glad I stuck with it.”

Most people give up somewhere between steps two and three.

They hit a wall, mistake it for a dead end, and start over—again and again.

But if you stay in the game long enough to push through that cycle—and keep testing, adjusting, and learning—the breakthrough usually comes right after that darkest stretch.

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Why You Keep Starting Over

I’ve seen it (and done it) too many times to count.

You try outbound. It’s harder than expected.
So you pivot to paid ads.

Then you realize the leads don’t convert.
So you launch a content strategy. Or rebuild your offer. Or hire a new agency.

Each time, you’re starting something new—which also means you’re starting back at the beginning of a new dip.

What most people don’t realize is that every viable strategy works—if you stick with it long enough to figure out how it works for you.

But instead of treating the friction as a necessary part of the process, they treat it as a sign they made the wrong decision.

So they keep changing strategies—chasing the next “easier” thing—without realizing that easy doesn’t get you where you want to go.

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Should You Ever Quit?

Absolutely.

The “winners never quit” mantra is bullshit. Winners quit all the time.

They just quit the right things—and stay committed to the things that matter most.

So how do you know which is which?

Godin talks about two types of hard:

The Dip — hard, but leads somewhere
The Cul-de-Sac — hard, and leads nowhere

To figure out which one you’re in, ask yourself:

Am I panicking?

You’ve invested money, made big decisions, and now things aren’t working as fast as you hoped. That’s stressful—but it’s not the time to reverse course. Pause. Step back. Evaluate the situation when your head’s clear.
Who am I trying to influence?

If it’s one gatekeeper who’s saying no on a big deal, maybe it’s time to pivot. But if you’re trying to influence a market and the message isn’t landing yet, the opportunity is probably still there. You just haven’t cracked the code.
What progress am I making?

Big wins are often just small wins that compounded. Look for progress—even if it’s slower than you’d like. Just make sure you’re moving forward, not just staying busy.

Here’s my rule of thumb:

Quit tools, techniques, talent, and tactics—but not strategies.

Outbound as a strategy? It works.
You just need the right tools, techniques, talent, and tactics.

Hiring an SDR to run outbound and maximize inbound?
It’ll work—if you’ve got the right structure around them.

This applies to almost every growth initiative you can think of.

The strategy can work.
The problem is usually the execution.

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