Winners never quit…right?

John Kennedy Toole (1937–1969) was an American novelist whose novel A Confederacy of Dunces won the Pulitzer Prize for Fiction. When he initially wrote his book, he had sent it to dozens of publishers and was rejected across the board. One noted editor, Robery Gottlieb, told Toole that he has talent and potential, but A Confederacy of Dunces lacks a reason for existing. Gottlieb encouraged Toole to move onto writing other pieces, but Toole explained in an autobiographical letter to Gottlieb that he could not give up on the book because the characters were based on real people from his life; part of his soul is in that book. The rejections contributed to the development of his depression and paranoia, and he eventually committed suicide at age 31.

After two years of grieving at home, his mother became determined to have her son’s book published so that the world could see her son’s talent. Over the next 5 years, she sent it out to 7 publishers, and they all rejected it. One of the people she repeatedly contacted was the great author Walker Percy. In the eighth year, she managed to push her way into the Percy’s office with her son’s manuscript in hand. Percy did not have the heart to turn her away, so he decided to read a few pages. He was doubtful at first, but after reading a few pages, he realized the greatness of the work. Even with Percy’s support, the book still took 3 years to publish.

11 years after Toole’s death, his book was finally published. The first printing was only 2500 copies, but the book attracted much attention in the literary world. A year later, in 1981, Toole was awarded the Pulitzer Prize for Fiction. Since then, it has sold more than 1.5 million copes worldwide and has been translated into 18 languages.

Winners never quit…right?

Society, novels, and cinema tend to glamorize perseverance. They paint a story of a main character pursuing a big goal or dream, encountering obstacles, and coming out victorious on the other side. But real life is more complex. We all have goals, and we all encounter obstacles. In the last two posts, we looked at finding your passion and pursing it. Sounds simple, but one can definitely expect to encounter difficulties in execution. You’ll need patience and diligence to get past the obstacles. But should you always persevere when you hit roadblocks? Episode 254 of the Tim Ferriss Show, When to Quit — lessons from World-class Entrepreneurs, Investors, Authors, and More, delves into this question.

Often times, we have a big-picture goal and an envisioned path to reach that goal. But as we embark on our envisioned path, we encounter unforeseen obstacles. If we define success as achieving that big-picture goal, then the key driver of success is being flexible with the path. This means quitting at dead-ends and pivoting. When you do encounter obstacles, you should ask yourself three questions:

1. Do these obstacles make me doubt my big picture goal? Or are they merely getting me down?

2. Do I believe in the big-picture goal enough to pay the price and put in the time and effort required? Or is the price higher than what I’m willing to pay?

3. Is my effort resulting in progress?

Question 1: Is it a core issue or a temporary letdown?

Toole encountered many rejections (obstacles) for his book, A Confederacy of Dunces. However, he never lost faith in the book, as he truly felt his soul was in it. Therefore, he should not have given up. Similarly, if you are investing time and energy into what you think is your passion, and the obstacles do not make you doubt your convictions, then you should move on to question 2.

Question 2: Am I willing to pay the price?

Everything worthwhile in life has a high price tag. Rudyard Kipling once said, “If you don’t get what you want, it’s a sign either that you did not seriously want it, or that you tried to bargain over the price.” Many people casually say they want to write a book or run a marathon, but they do not put in the effort required. In other words, they are not willing to pay the price. Be honest with yourself. Spend some time reflecting. If you think what you are pursuing is truly your passion, or if your purpose is larger than yourself, then you will find the stamina to persevere. Then the question becomes, is your method correct, or should you pivot? That’s where question 3 comes in.

Question 3: Am I making progress?

In his book, The Dip, Seth Godin explains that most projects have a period of many difficulties, and he calls that period the dip. The dip is what makes that project worth doing in the first place because few people get past the dip, so once you come out of the other side, you can enjoy the rewards. For example, authors like Toole and J.K. Rowling faced the dip of multiple rejections, and many authors never get past this dip. But after getting past the dip, Toole and Rowling get to enjoy the rewards. However, obstacles can also mean you’re hitting a dead-end, so you must know how to distinguish between a dip and a dead-end. How?

You need to know the right metrics to evaluate if your efforts are reaping results. If you are a business, and your customer base is not growing, are you making progress? The intuitive answer would be to say probably not. But what if I told you other businesses similar to yours are losing customers. Now, it seems like you are doing something right. The key idea is that picking the right metric can be harder than it seems, and it requires careful thought. If you are making progress, you should keep persevering. If you are not making forward progress, then you should pivot.

Passionate about self-cultivation, happiness, and sharing wisdom.