When Should You Quit?
The business world loves persistence.
The keynote speaker at a recent conference I attended was Angela Duckworth, who popularized the concept of grit as a key driver in achieving long-term goals.
We celebrate the founder who refuses to give up, the executive who keeps pushing through obstacles, and the employee who works harder when things get difficult.
At the end of the day, persistence matters. However, there is a point at which persistence stops being determination and starts becoming a detriment.
Annie Duke makes this point in a Knowledge at Wharton article about knowing when to quit—Duke argues that the goals we set can actually make it harder to recognize when we should change course. Once we've committed to an outcome, we can become psychologically attached to achieving it, even when the circumstances that made the goal worthwhile have changed.
For leaders, this is a particularly important problem. Sometimes, after you have invested months or years of time, money, energy, and reputation into someting, the most responsible thing you can do is to stop. And, that is hard.
Persistence Isn't Always the Same as Progress
Imagine that a leadership team sets a goal: "We need to grow revenue by 30% this year."
Six months later, revenue is up 8%.
The team responds by working harder—more meetings, more sales calls, more marketing, and more pressure.
But, what if the market has changed?
What if the original assumptions about customer demand were wrong?
What if the product isn't generating the expected margins?
What if the team has discovered a more profitable opportunity elsewhere?
What if the goal was reasonable six months ago but no longer reflects what the organization actually needs?
Once we set a goal, an achievement-oriented individual’s natural response is often: "We just need to try harder."
In reality, we may need to reassess to ensure we are not confusing commitment to the goal or KPI with commitment to the outcome that we actually want.
Your Goal Is a Tool, Not a Contract
Goals are useful because they give organizations direction. However, goals should not become a contract that leadership is obligated to fulfill regardless of what happens around them.
Markets change.
Customers change.
Employees leave.
New information emerges.
Budgets change.
Priorities change.
Yet we often continue operating as though the assumptions we made six months—or six years—ago are still true.
A leader might say:
"We've already invested too much to stop now."
"We can't change direction after telling everyone this was the plan."
"We're almost there."
"We've come this far."
"We just need to give it another quarter."
“The Board is expecting us to do this.”
The leader might be right, but there is an important distinction here—those statements are about past investments, and not future value.
The Sunk-Cost Trap Shows Up Everywhere
I studied economics and pride myself on understanding the concept of sunk costs. However, I have come to appreciate that understanding the concept and making decisions that disregard sunk costs are two different things.
I have seen managers crippled by an inability to abandon sunk costs both in strategic initiatives and in everyday operations:
We keep an employee in a role because we have invested heavily in training them.
We continue using a software system that doesn’t work because implementation took a year.
We keep a program alive because the organization has always offered it.
We continue pursuing a customer because we have already spent months trying to close the deal.
We continue forcing a strategy to “work” because admitting it isn't working feels like admitting we were wrong.
Unfortunately, leadership isn't about proving that yesterday's decision was correct—leadership is about making the best decision with the information you have today.
Build Reassessment Into the Goal
One of the most useful ideas from Duke's framework is deceptively simple: don't wait until something is obviously failing to reassess it.
When you establish a major goal, establish the checkpoints at the same time.
Don't just say: "We are going to launch this program."
Instead, ask: "When will we stop and evaluate whether this is still the right program?"
Don't just say: "We're going to hire five people."
Instead, ask: "What will tell us that this hiring plan is—or isn't—working?"
Don't just say: "We're going to expand into this market."
Instead, ask: "What evidence would tell us to continue, modify, or stop?"
Reassessment shouldn't be an emergency meeting after something goes wrong—it should be part of the original plan.
Give Yourself Permission to Quit Before You Start
At first, this statement might sound counterintuitive. However, one of the best ways to make better decisions is to define your exit criteria before you are emotionally attached to the outcome.
Duke describes these as "kill criteria"—specific conditions that tell you when continuing no longer makes sense.
For example:
Instead of: "We'll continue investing in this product until it succeeds."
Try:
"We'll continue investing in this product unless we fail to reach X customers, Y revenue, or Z margin by June."
"We'll continue recruiting for this position unless we cannot find a qualified candidate within three months, at which point we'll reassess the role."
"We'll continue pursuing this partnership unless the partner cannot meet these three requirements."
This reframe separates changing your mind from failing. You are not quitting because something got difficult; you are shifting priorities and following a path you established when you were thinking objectively.
Don't Make Everything Pass or Fail
There is another leadership trap worth avoiding: treating a goal as either a success or a failure.
Maybe you failed to launch an initative, failed to hire a new VP, or failed to enter a market.
At the same time, maybe the initiative uncovered a customer need you didn't know existed, your failed hire revealed that your job description was wrong, and market research showed you exactly where you shouldn't invest.
In a world where we spend time crafting KPIs and chasing metrics, we need to remember that progress doesn’t always look like reaching the original destination. Sometimes, progress involves discovering that we need to drive in a different direction.
What This Looks Like in an Organization
If you're leading an organization, here are a few ways to make this practical:
1. Put a review date on every major goal
Don't just establish the goal; establish the date when you're going to ask: "Knowing what we know now, would we make the same decision again?"
2. Define your warning signs
Before starting a major project, identify the things that would concern you.
Ask:
What would tell us this isn't working?
What assumptions are we making?
Which assumptions are most likely to be wrong?
What data would change our decision?
What would cause us to pause?
What would cause us to stop?
3. Separate effort from results
Working harder doesn't automatically make a strategy better. Track outcomes—not just activity.
Instead of:
Number of meetings
Number of hours worked
Number of initiatives launched
Also track:
Revenue
Customer retention
Employee retention
Time saved
Quality
Margin
Customer satisfaction
Progress toward the actual business objective
Activity tell you whether people are busy, but outcomes tell you whether you are progressing.
4. Create a culture where changing course is not considered a failure
If leaders penalize people for abandoning bad ideas, employees will keep pursuing bad ideas.
Your team should be able to say: "We tried this—here is what we learned. Here is why we think we should change direction, and this is the direction we should go."
Appreciate organizational learning and the courage, data, and improvements it uncovers.
5. Ask what you would choose today
This is one of the simplest ways to challenge sunk-cost thinking.
Ask: "If we hadn't already invested in this, would we choose to invest in it today?"
If the answer is no, get curious.
While it does not automatically mean you should quit, it does mean you should understand why you are continuing.
Sometimes the Goal Needs to Change
There's another possibility that's easy to overlook—you don't have to choose between continuing or abandoning ship. Sometimes, the right answer is to change the goal.
Maybe growing from $5 million to $10 million isn't actually what the organization needs or isn’t possible—maybe the real goal is profitability.
Maybe hiring 20 people isn't necessary if the organization can redesign its processes and serve the same customers with 12.
Maybe opening five locations isn't the answer when one highly successful location would accomplish the strategic objective.
Maybe the goal wasn't wrong—maybe it was simply too rigid.
Good leaders aren't afraid to adjust the destination when they learn more about where they actually want to go.
A Simple Exercise for Your Next Leadership Meeting
Pick one major initiative your organization is currently pursuing and ask your leadership team:
If we were making this decision today, would we still make it?
What have we learned since we started?
What evidence would cause us to change or stop?
What value have we created even if we don't reach the original goal?
When should we formally reassess this decision?
You may discover that the initiative is exactly where it needs to be.
You may discover that it needs to change.
Or you may discover that it's time to let it go.
All three can be good leadership decisions.
The important thing is that you're making the decision deliberately—not simply because you're already invested.
