When to Quit… and When to Persist

Overview

Winners never quit, is just bad advice. Winning requires quitting strategically those things that do not deliver on the targeted outcome and persisting relentlessly in becoming the best in world at the thing(s) that matters most or only those you can do. The question is, when should you quit and when should you persist? This is the ever-present question. Whether you are facing a challenge, enduring a setback or wanting to level-up an area in your life, this concept, based on The Dip, a short book by Seth Godin, will give you a framework for making that decision.

Watch This Before Reading Further…

This is a 5-minute summary of the concept and summary of Seth Godin’s book.

The Dip

The Dip is ubiquitous. You’re not the only one to experience it.
It’s the garage band playing to an empty room, or the infamous Decca Records rejection of The Beatles.
It’s the “seventh time you fall on your butt while learning to snowboard.” or the tenth failed attempt, in front of thousands on live television, to be the first in history to land The 900 on a skateboard.
It’s the “fifth job interview where they never even call you back” or the 1,000th failed experiment in building the light bulb.
It’s the fights between spouses that spiral out of control.
The Dip has many names. Steven Pressfield calls it “the resistance” in the War of Art. Geoffrey Moore calls it “the chasm.” Seneca, “the obstacle.” Dunning & Kruger call it “the valley of despair.” Others might call it a setback.

Why Dips Matter

Call it what you will, dips are difficult for three reasons:

1. ) They are painful (obviously);
2. ) It is difficult to know if you are in fact in a dip; and
3. ) If you know you are in one, the decision to stay or leave can be a difficult one.

To the first point. There is no denying that dips are painful, but there is an upside—quite literally. Dips create scarcity and scarcity creates value. They act as moats, separating the average choices from the best choices.
We don’t have the resources (time or money) to try every option available, neither do we want to. We want to consume the best and experience the best (at least in so far as we can afford). The dip weeds out the poorest performers (the products and the professionals) because when most people find themselves in the dip, they quit. “
Those that persevere through the dip, have a shot at being the best in the world—and the best in the world WIN BIG.

The Map

Let’s return to the second point. Seth says there are three curves in life:

1. The Dip
2. The Cul-De-Sac
3. The Clif

Before we discuss the dip, lets briefly define the others.
The cul-de-sac is just as it sounds, a dead end. Seth defines this as “a situation where you work and you work and you work and nothing much changes. It doesn’t get a lot better, it doesn’t get a lot worse. It just is.” The solution to this kind of trajectory should be fairly obvious, “get off it, fast… The opportunity cost of investing your life in something that’s not going to get better is just too high.”
The cliff, also self-explanatory, is “a situation where you can’t quit [or won’t] until you fall off, and the whole thing falls apart.” It’s the downside of an addiction or a willful blindness to the circumstances surrounding an area of your life—your business, your relationships, or your health. At the bottom of the cliff, you have no resources, and no where to go. The only thing left to do is reinvent yourself.
Now on to the dip…

Signs You May be in a Dip

In a perfect world, the journey to your destiny is smooth sailing—everything goes according to plan.

But reality is messy and as you set out to do anything— whether big or small, remarkable or mundane — anything meaningful— you will inevitably find yourself in the dip— “the long stretch between beginners luck and accomplishment… the long slog between starting and mastery.”
Meaningful pursuits begin with excitement—a big hairy audacious goal, a vision of possibilities, a hope for the future. You fall in love with the idea (whatever it may be). Success comes, validating your new identity and confirming your calling. You’re along for the ride as you are propelled into the future you envisioned.
And then, the plot twist. What was once easy, becomes difficult—the waves of rejections pour in, product launches fail, relationships grow strained, or you’re given a surprise diagnosis. Butterflies flutter in your stomach and psyche as you loose altitude, swiftly plunging from what feels like a cliff into a new unknown.
You don’t quit, so you tighten your grip and increase your effort, but progress per unit of effort is diminished. You begin to wonder if you are still on the right path. You weigh your options. You contemplate quitting… You wonder if you’re three feet from striking gold… You may be in the dip.

Diagnosing the Dip

The definition of these three curves are clear enough, but when you are among the trees of your circumstance, it is hard to see the forest.
There are three elements that when understood, diagnose the curve you are in and ultimately what to do about it:

• Your mission/ purpose and your commitment to it;
• The state of your psychology (fear or discomfort); and
• The trajectory of the endeavor you are engaged in and its relationship to the mission.

Reordered, these three elements answer, Am I in a dip? Is that dip worth sticking with? And do I have the guts to do so?
Mountains of books have been written about each of these elements, but a few simple questions can take you far in a short amount of time.

Your Mission

Ask your self, ‘Why am I doing this, really?’ The first answer you get may not lead you to a satisfied. You may have to answer your answer with a similar question, ‘Why do I want that?’. You may find that you need to repeat that sequence 5 – 7 times to get to ‘the truth.’ You may find that the reason you began in the first place isn’t the reason that will sustain you through a dip.
If you want to dive deeper, I recommend Simon Sinek’s work on finding your why. I think you’ll find this short exercise helpful.

Your Psychology

In many cases, the decision to quit is based on a reaction, so start with this question: Am I being reactive (panicking) or strategic? However, beware. Fear often couches itself in logic or strategy to give us a “rational” way out.
Ask: Am I quitting because this the best case scenario doesn’t align with me and my mission? Or am I quitting because where I am is uncomfortable and I don’t know that I have what it takes to get to the other side of the dip?
This fear setting exercise will help you working through these questions.

The Endeavor

I intentionally labeled this the endeavor and not your endeavor, because the endeavor is the vehicle (or the how) to your why. It is the means to an end, not the end itself. Conflating the two will only yield a very unhappy life.
The endeavor is best plotted across these intersecting axes: Progress, Permanence, Opportunity Alignment, Reward, Feedback, and Opportunity costs. Here is one question for each:

• Progress: Am I making measurable progress? Could I make progress if I improved my skills/ capabilities?
• Permanence: Is this obstacle temporary, or permanent?
• Alignment: Does this endeavor need what I have to contribute?
• Reward: Is there disproportionate rewards for making it through the dip? Or are rewards limited?
• Feedback: Do trusted experts tell me I am on the right path?
• Opportunity Cost: Even if this fails, does this vehicle move me closer to the person I want to become 5 years from now?

If you answered yes to the majority of these questions, congratulations, you are in a dip. If not, you are in a cul-de-sac.

Prescription for the Cul-De-Sac

If you’re going to quit, quit before you start. Derek Sivers, an author and entrepreneur, lives by this principle, “If it’s not [an emphatic] yes, then it’s a no.”
But if you have started, and found yourself heading down an unwanted Cul-De-Sac, quit.
It is easy to get married to a good or even great, idea, but if the results of your examination suggests a pivot, you must be willing to begin immediately.
I’ve asked many students if they’ve heard of the sunk cost fallacy, and I am consistently floored by how few are familiar with this concept. So out of duty, I will I will describe it here.
The sunk cost fallacy is “the irrational belief that prior investments must be recovered,” regardless of the probability of success. (EBSCO) This causes an escalation of commitment, where people to continue a doomed endeavor—like a failing business, bad relationship, or unenjoyable movie—simply because they have already invested time, money, or effort into it.
Cognitive psychologists Daniel Kahneman and Amos Tversky’s found that losses feel twice as painful as equivalent gains feel good. What this means is that your brain is wired to frame quitting as a loss — even when staying is the more expensive move.
Like a malignant cancer, sunk cost thinking will, by definition, send you uncontrollably toward a cliff.
To avoid these cognitive biases, ask this question: If I were starting fresh today, with full information, would I choose this path? If the answer is no, quit.

Prescription for the Dip

If you’ve wrestled with the questions above and you’ve emerged knowing: 1) you’re in a dip; 2) are in the pursuit of something worth doing, then the prescription is simple.
In an interview with Brian Rose, Seth says, “Once you see that the dip is there, you have two choices. Don’t start. Or if you’re going to start, be prepared to go to the other side.” Said differently, if you’re going through hell, keep going.
This is when the Vince Lombardi quote rings true, “Winners never quit, and quitters never win.” This is when commitment and perseverance become virtues.
The tactics that will get you to the other side of your dip are wholly unique to your context—the environment of the game in which you are engaged. And unfortunately, the best ones aren’t always obvious.
In next section, I’ll give a few strategies, but before you move on, watch this clip, in which Seth Godin describes the complexity of the dip in one of his businesses.

In Action

The best in the world are selective about which dips deserve their full contribution — and ruthless about everything else. They quit the wrong things and push through the right dips

1. Audit your endeavors. List your roles, responsibilities, projects, commitments. Determine which curve is present for each.
2. Set north star conditions. For your dips, define in advance what success looks like. A specific result. A measurable shift. A moment you’ll recognize. Likewise, define the conditions under which you will know that you are no longer in a dip, but a cul-de-sac and are willing to quit. Without these anchors, you’ll renegotiate your commitment every time it gets hard.
3. Quit fast or commit fully. Quit the wrong stuff. Stick with the right stuff. And have the guts to do one or the other. Because indecision… now that’s for losers.

In Closing

Being the best in the world is underrated. Those that cross the chasm, make it through the messy middle, master their craft, own their responsibilities, and dominate their market segment WIN at unimaginable levels. They create a world that elevates the human experience for all of us and are rewarded handsomely for it.
Each of us have something we can contribute and a purpose that is worth giving our lives to and for.
Whether it is a project, a venture, a relationship, a child, a cause, or a habit, find the things where winning would change everything. As Seth writes, “Go ahead, make something happen. We’re waiting!”

Additional Reading & Resources:

Books

There are more nuggets in this “little book.” I highly recommend it.

• The War of Art by Steven Pressfield. a must for anyone doing creative work.
• The Obstacle is the Way by Ryan Holiday – a must for anyone, full stop.

Videos

• Peterson x Tony Robbins – focuses on the idea that a strong enough why can overcome any how.