A 2-Part Framework for Knowing When to Quit (And When to Stick)

The difference between strategic quitting and failure

Hey everyone,

It’s been a minute. I hope you’ve been well since we last connected in August.

Today, I want to share a story from 2022, a time when a single article didn’t just make me think, it made me act.

And more recently, a tiny book I read in one day has added a profound new layer to that story.

Together, they form a powerful two-part framework for making one of life’s hardest decisions. This is about moving past the fear of quitting by learning to do it strategically.

The article that forced a decision

Back when I was preparing to leave Nigeria, I was working as a consultant for a company.

My work was comfortable, the pay was steady, but a quiet feeling of misalignment was starting to grow.

One night, someone shared a link with me. I can’t even remember who that was.

The title was provocative: “How to waste your career, one comfortable year at a time.”

It was an article by one Apoorva Govind, and as I read it, I felt a sense of profound recognition.

Apoorva wrote about the danger of complacency, the misplaced sense of loyalty that keeps us in roles past their expiration date, and the critical need to be deliberate about our careers.

But unlike most people who might read an article like that, feel a momentary spark, and move on, I decided to turn those insights into a system. I was a management consultant, for God’s sake.

I needed a tool, not just an idea.

Less than two weeks after creating and repeatedly revisiting that system, it was time to quit, I submitted my resignation

My goal with this newsletter today, isn’t to push the hustle-culture fantasy of quitting your job to jump into the deep end without a lifeline.

Instead, I want to give you a framework to honestly assess where you are right now, with your work, your life, and those brilliant product ideas you’ve been endlessly ideating but never launching.

That framework, which I’ll share in a moment, was powerful.

But I now realise it was only half the equation.

Earlier this year, I picked up Seth Godin’s short, brilliant book, “The Dip.”

I devoured it in one day, and it challenged my entire understanding of quitting.

The book’s core message is simple but seismic:

Winners quit all the time. They just quit the right stuff at the right time.

My system helped me figure out the “right time.” Godin’s book explains how to identify the “right stuff.”

The System vs. The Strategy

First, the system.

In that article, Apoorva lays out five key areas to evaluate your job every quarter.

I had been at the company for seven months at that time, so I decided to score my work quarterly.

The five metrics are:

1. Accomplishment: Have I done anything noteworthy?

2. Impact: Is the work I’m doing resume-worthy?

3. Growth/Future Alignment: Am I acquiring valuable skills that align with my future goals?

4. Challenge: Am I genuinely engrossed and challenged by the problems I’m solving?

5. Community: Am I excited to work with my team? Do I believe in the mission, vision, and leadership?

That last one, Community, was where the cracks first appeared for me.

I believed in the mission and vision because I had helped the company develop them years earlier.

I knew the market they were playing in, the industry was a booming one, and yes, I saw the huge potential.

But I did not believe the leaders had what it took to deliver on that promise.

I was already seeing gaps in their leadership, and an anxious “management said...” sentiment was spreading through the team.

I picked my journal for 2021 to 2022, as I was writing this newsletter, and reading through the pages that relate to my time in the company, I can now see the signs were there all along.

That single “No” was a major red flag.

After seven months, my assessment table looked like this:

Am I growing complacent currently? This data says… well

My score had dropped from a passable 80% to a glaring 40%.

For six months, I had been working on things that offered no personal growth, no meaningful impact, and no real challenge.

In Seth Godin’s language, I wasn’t in a Dip, a temporary period of struggle that leads to mastery.

I was in a Cul-de-Sac - a dead end that would never get better, no matter how hard I tried. And hey, I did try.

But… The data made it undeniable. I was on a road to nowhere.

Apoorva mentioned in her article that anytime she scores 40% or under, she stops to evaluate. That became my rule, too.

The system worked. It gave me the clarity to make a strategic exit.

The most challenging question you can ask

Reading Seth Godin’s “The Dip” early this year didn’t just give me a new idea; it gave me the language for a struggle I was already in. It connected all the dots.

Godin’s core argument is that quitting isn’t a sign of failure.

Strategic quitting is a conscious choice you make to free up your resources for a battle you can actually win.

As he puts it, “Quitting is better than coping because quitting frees you up to excel at something else.”

This hit me hard. His words forced me to hold up a mirror to my own commitments.

One framework in the book lays out three ways to approach any new project. You can do:

1. The Brave Thing: This is the decision to commit fully, push through the incredibly difficult Dip, and come out on the other side. This is the path for those aiming to be #1, knowing the struggle will be immense but the rewards of scarcity (being one of the few who make it) are worth it.

2. The Mature Thing: This is the decision not to even start. An informed person might look at a potential project, realistically assess the depth of the coming Dip, and conclude that they don’t have the resources, passion, or grit to make it through. So, they wisely save their energy for a battle they are better equipped to win.

3. The Stupid Thing: This is the most common and most damaging path. It’s the choice to start a project with enthusiasm, invest significant time, money, and energy, and then quit right in the middle of the Dip. This is the worst of all options because you’ve wasted all your resources but gain none of the rewards of being “brave” or the preserved energy of being “mature.”

Reading this, I immediately thought of a long-running project (since 2013), and a note I scribbled in the margin says it all: “This is speaking to me about Audacity2Lead... am I being brave, mature, or stupid?”

It’s a brutally honest question about whether my perseverance is strategic courage or just costly indecision.

But the questions didn’t stop there. They hit much closer to home.

Let me be honest with you. My role at my current job has been through significant upheavals.

I mean periods of reduced income and increased responsibility as the company navigated tough financial waters.

Applying Godin’s ideas, I had to ask myself: “Is this just a Dip before a breakthrough, or have I hit a dead end?”

To be clear, this isn’t a story with a neat ending yet.

It’s a question I am actively grappling with.

The stakes are intensely high and personal, with my family’s visa status tied to the role, making the calculus far more complex than just career choice.

Quitting felt less like a strategic choice and more like a stupid, personal risk.

But in the middle of weighing all this, the financial strain, the mission of the company I believe in, the pressure of my visa, a powerful piece of self-reflection from my own journal quietly resurfaced: “Remember: I joined this company because I wanted to take us from 0 to 1. Whatever you do from there is no longer my core mission.”

This is a stark reminder that I had, in essence, defined my own terms for this role from the beginning.

The challenge now is to honestly assess if those terms are still being met.

The framework isn’t giving me an easy answer, but it is giving me the right questions.

And through wrestling with this, I’ve landed on the most powerful, most challenging idea of all, and the one I want to leave with you:

Decide when you’re going to quit before you even start.

Instead of waiting until you’re in the messy, emotional middle of a product or project, define your quitting conditions from day one.

Write down the circumstances under which you will walk away.

This single act transforms quitting from a moment of failure into an act of profound strategy.

Your turn: Two Challenges for you

Again, my goal with this newsletter today is not about promoting a culture of quitting.

It’s more about promoting a culture of intention.

About ensuring that your precious time and energy are invested in projects and products where you can survive the Dip and become the absolute best in the world for solving the problems you say you’re solving.

Nothing less.

So, I have two challenges for you this week.

Challenge #1: Assess Your Present (The System)

Look at your current major commitment (your job, a key project).

Ask yourself the five questions. Are you in a Dip or a Cul-de-Sac?

• ✅ Accomplishment: Have I done anything noteworthy in the last three months?

• 💥 Impact: Is this work resume-worthy?

• 🌱 Growth: Am I learning skills aligned with my future goals?

• 🧠 Challenge: Am I genuinely engrossed in the problems?

• 🤝 Community: Do I believe in the mission, vision, and leadership?

Challenge #2: Define Your Future (The Strategy)

Look at the next project you’re about to start.

That new product, that YouTube channel, that course.

Before you begin, take out a piece of paper and answer this:

“I will quit this project if _______________.”

(e.g., “...if it’s not generating $100/month in 6 months,” or “...if I’m not in a state of flow at least once a week,” or “...if it requires me to sacrifice my family dinner time.”)

Average is for losers.

Coping is a dead end.

The world doesn’t reward the well-rounded; it rewards those who obsess over the right things and have the guts to quit the wrong ones.

Live courageously,

Dayo Samuel 💯

P.S. Interestingly, I recorded a podcast on this very topic back in 2015. It’s wild how some themes are timeless. You can listen to that old reflection here on YouTube

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