You are pushing a boulder up a hill.

You have been pushing it for six months. Maybe a year. Your muscles ache. Your bank account is draining. You are exhausted.

But you keep pushing because you have read the biographies of the greats. You know that Steve Jobs faced rejection. You know that persistence is the key to success. You tell yourself that if you just push a little harder, if you just tweak the marketing copy one more time, the boulder will crest the hill and roll down the other side.

But what if there is no other side?

What if you are just pushing a rock up a mountain that goes on forever?

This is the most dangerous dilemma in business leadership. It is the tension between grit and delusion.

We celebrate the pivot in hindsight. We applaud the company that started as a podcast platform and became a groupon clone and then became Andrew Mason’s Groupon. We love the story of Slack starting as a video game company.

But in the moment, a pivot does not feel like a clever strategic move. It feels like a failure. It feels like admitting you were wrong. It feels like burning money.

So we wait.

We wait too long. We burn through our runway. We burn out our teams. We hold onto the original idea like a life raft, even as it drags us underwater.

We need to have a hard conversation about how to let go. We need to look at the mechanics of the pivot not as a moment of weakness, but as a necessary function of navigation.

The Sunk Cost Fallacy and Your Brain

Why is it so hard to stop?

The answer lies in a cognitive bias known as the Sunk Cost Fallacy. This is a glitch in the human operating system. It causes us to make decisions based on the resources we have already spent, rather than the future value we can gain.

Imagine you bought a ticket to a concert for two hundred dollars. On the night of the show, there is a blizzard. You are sick. You do not want to go. But you go anyway. You suffer through the drive. You are miserable at the show. Why?

Because you didn’t want to “waste” the money.

But the money was already gone. By going, you just added physical misery to financial loss.

In business, this manifests as “we have already built the code” or “we have already printed the brochures.”

Your brain is wired to avoid loss twice as much as it seeks gain. This is prospect theory. The pain of admitting that the last six months of work were a dead end is psychologically unbearable. So you invent a narrative that says you are just in a “dip.”

You convince yourself that the market just hasn’t “got it” yet.

To be a successful leader, you must become a ruthless accountant of the future. You must look at your resources today time, money, energy and ask: If I started this company today with a blank slate, would I invest these resources in this current strategy?

If the answer is no, you are in a trap.

The Difference Between a Dip and a Dead End

Seth Godin famously wrote about “The Dip.” It is the hard part in the middle of any project where the initial excitement fades and the real work begins. Pushing through the dip is necessary for success.

But there is a difference between a dip and a cul de sac.

A dip responds to effort. When you push, you see movement. It might be slow, but there is traction. You get a new customer. You get a piece of feedback that unlocks a feature. The data trends upward, even if the slope is gentle.

A dead end does not respond to effort. You push, and nothing happens. You spend ten thousand dollars on ads, and you get zero conversions. You launch a feature, and nobody clicks it. The feedback is not anger; it is apathy.

Silence is the loudest warning signal in business.

If you are pouring energy into a black hole and getting no radiation back, you are not in a dip. You are in a dead end.

You need to look for the signal of “Market Pull.”

Market pull feels like you are running downhill. Customers are asking for the product. They are complaining when it breaks. They are trying to give you money.

If you have to use all your energy just to convince people that they have a problem, you are pushing the boulder uphill. You might be right about the problem, but you are wrong about the timing or the solution.

Are you fighting the friction of execution? Or are you fighting the friction of reality?

The Three Signals That It Is Time to Turn

How do you know for sure? You can look for three specific indicators that suggest your current strategy is terminal.

1. The Customer Apathy Signal

We often fear negative feedback. But negative feedback is good. It means people care enough to be angry. It means you missed the mark, but there is a mark.

Apathy is fatal. If you launch a product and nobody cares enough to complain, you have built something nobody needs. If you cannot get people to use your product even when it is free, you do not have a pricing problem. You have a value proposition problem.

2. The Sales Velocity Signal

Look at your sales cycle. Is it getting shorter or longer? In a healthy business, as you get better at explaining your value, the sales cycle should accelerate. You should have case studies and social proof that grease the wheels.

If your sales cycle is getting longer, it means the market is resisting you. It means you are having to work harder for every inch of ground. This is a sign that your product market fit is slipping, not gripping.

3. The Team Morale Signal

Your employees know the truth before you do. They are on the front lines. They hear the customers saying “no.” They see the bugs that go unfixed because the architecture is flawed.

If your best people are checking out, or if there is a pervasive sense of cynicism in the office, it is not because they are lazy. It is because they have lost faith in the mission. They feel like they are rearranging deck chairs on the Titanic.

How to Pivot Without Panic

The word “pivot” scares people. It implies instability. It implies that the captain doesn’t know where the ship is going.

To execute a pivot successfully, you must frame it as an evolution, not a revolution.

Do not walk into the room and say, “Everything we did was wrong, we are starting over.”

Walk into the room and say, “We have learned something valuable.”

Use the scientific method as your shield. Frame the last six months not as a failure, but as an experiment that yielded data.

“We hypothesized that customers wanted X. The data shows they actually want Y. Because we are a data driven company, we are going to follow the evidence. We are shifting our resources to build Y.”

This validates the hard work your team did. It gives meaning to the struggle. It tells them that their effort wasn’t wasted; it was the price of admission to find the right path.

You must also be decisive. Once you decide to turn, turn hard.

The worst thing you can do is a “soft pivot.” This is where you try to do the new thing while still maintaining the old thing just in case. This splits your resources and ensures failure in both directions.

You have to burn the boats. You have to tell the team, “We are no longer doing A. We are doing B. If you are working on A, stop today.”

The Relief of Alignment

There is a strange thing that happens when you finally make the call.

You expect grief. You expect anger.

But usually, you get relief.

You get relief from your team, who have been waiting for you to see what they see. You get relief from your investors or partners, who were watching you struggle.

And most importantly, you get relief from yourself.

The energy that you were using to prop up a failing idea is suddenly released. You can direct it toward something that actually works. You feel the wind at your back again.

I want you to look at your business right now. Look at the initiatives you are funding. Look at the projects on your desk.

Is there one that feels heavy? Is there one that you are dreading?

Ask yourself the hard question.

Are you persisting because you believe in the destination? Or are you persisting because you are afraid of the cost of turning the car around?

Your job is not to be right. Your job is to find what is right.

Building a business is not about never getting lost. It is about realizing you are lost and having the courage to look at the map, admit your mistake, and choose a new road.

The destination is still there. You just need a different vehicle to get there.