Quit Your Way to Win: Why Flexible Goal-Setting Beats “Never Give Up” Every Single Time

Hi there,

What’s the Story?

I hope you’re doing really well.

On my end, it’s been one of those seasons where the days blur together in a very specific cocktail of client work, creating, and trying to remember what I walked into the kitchen for.

We’re also wrapping a season of the podcast, which means a short hiatus before we return with something fresh. I am beyond excited about it!

This week’s edition is built around an idea that makes a lot of high performers squirm:

Sometimes the smartest move is to give up.

Not on yourself or your standards or what matters, but on the plan that’s quietly draining you while pretending it’s “character building.”

The framework I’m sharing is heavily inspired by Courtney Clark’s work, and if you want the full model, her book, The Short Cut, is on Amazon here.

I recently interviewed Courtney on the podcast, where we had a fantastic discussion. You can watch the episode here.

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Quit Your Way to Win: Why Flexible Goal-Setting Beats “Never Give Up” Every Single Time

Estimated reading time: 5 minutes 28 seconds

Courtney Clark has been through the mill. She has battled and beaten cancer on multiple occasions and today is a highly sought-after keynote speaker who speaks on resilience and how to handle the toughest challenges in the smartest ways.

Recently, we sat down for a podcast interview, and Courtney shared a radically different way of thinking about a critical concept in achieving success: grit.

You see, there’s a certain kind of pressure that only modern life can produce.

The kind where you’re expected to do more with less and faster. All while remaining calm, grateful, and “high vibe” about it. And when things start to wobble, we reach for the cultural comfort blanket:

Just keep going.
Push through.
Don’t quit.
Grit fixes everything.

It’s not that Courtney suggests that grit is the villain. It is useful. It’s saved plenty of people from bailing too early. But grit has a shadow side we don’t talk about enough:

When grit becomes your only tool, you become less adaptable.

In a world that keeps moving the goalposts, adaptability is the difference between progress and burnout.

Here are some lessons I took from our conversation:

Quitting feels like a character flaw.
Most of us aren’t logically evaluating whether a goal is still worth it.
We’re emotionally defending our identity.

Quitting feels like:

Failing publicly
Proving our inner critic right
Breaking a promise
Disappointing someone
Becoming “the kind of person” who gives up

So we stay.

We stay in strategies that stopped working months ago, or goals that no longer fit our lives, or we stay loyal to a plan that’s actively punishing us, and we call it “discipline.”

While sometimes it is, other times it’s just fear wearing a productivity costume.

Many “Goals” aren’t Goals

Many “goals” aren’t goals; they’re plans.

A goal should be the destination. A plan is the route.

But most people fuse the two and then wonder why they feel trapped.

Example: “I’m going to lose 20 pounds.”

That’s usually not a goal. That’s a single-route plan.

And it works… until life interrupts.

You get injured, or work ramps up, or sleep falls apart, and stress spikes, so your schedule collapses. Before you know it, you feel like you failed.

But what if the real failure isn’t “not losing 20 pounds”?

What if the failure is clinging to a plan that was never designed to survive reality?

Supersize the Goal

I loved this concept of supersizing the goal that Courtney shared. Ask yourself one question:

What’s the goal behind the goal?

If the surface goal is “lose 20 pounds,” the deeper goal might be:

To feel confident in your body again
To have energy after 3pm
To reduce health risks
To be fit enough to play with your kids (or grandkids)
To feel like you again

This is the difference between chasing a number and chasing a life. And once you find the deeper “why,” you learn that you can let go of a plan… without letting go of what it meant to you.

That’s the part most people miss.

They think quitting a strategy means quitting the dream. Instead, it just means you’re mature enough to stop worshipping one particular route.

Parallel Plans: How Resilient People Avoid the All-or-nothing Trap

When you identify the supersized goal, you stop relying on one fragile path.

You build parallel plans, multiple ways to reach the same outcome.

If your supersized goal is “feel strong and energized,” parallel plans could look like:

Walking daily instead of intense workouts
Improving sleep before changing diet
Strength training twice a week instead of seven days of punishment
Getting support/accountability
Managing stress like it’s part of the program (because it is)

Now, if one plan gets derailed, you pivot.

You build growth resilience: the ability to adapt without abandoning what matters.

Does the Math Still Math?

Another useful insight from Courtney was a checkpoint that saves people years of wasted effort:

Does the math still math?

If you’re halfway through the time window… but nowhere near halfway to the result… and you’re still doing the same thing…

That’s repeating a strategy out of pride. And pride is expensive. “Never give up” can become dangerous because it can keep you locked in even when the evidence is clear: your current approach isn’t paying off.

A lot of people stay the course because they’ve already invested so much. This is known as the Sunk Cost Fallacy.

Time. Money. Reputation. Effort. Identity.

You tell yourself:

“I can’t stop now; it would all be for nothing.”

But staying on the wrong train because you’ve been on it for a long time just takes you further away from where you want to go.

And the brutal truth is this:

The cost you’ve already paid is gone either way.

The only question is whether you keep paying.

“Stoptimism”: The Healthiest Kind of Quitting

There’s a version of stopping that’s not tragic or dramatic, or that ends in defeat.

It’s strategic.

Courtney calls this Stoptimism: the optimism that comes from freeing your resources (time, energy, money, attention) and redirecting them toward something that actually works.

Your calendar is limited.

Your nervous system is limited.

Your health is limited.

Your focus is limited.

So “staying the course” is often just irresponsible.

The Gut Feeling Problem (and why your instincts might be lying)

We’ve been told to “trust your gut,” your gut actually works best at recognizing patterns, which is great for safety, but terrible for change. When you try something new, a pivot, a reinvention, an uncomfortable conversation, a bold move, your gut often interprets unfamiliar as unsafe.

So it throws up an internal warning:

“This feels wrong.”

A useful practice here is a mental yellow flag: