Top-Level Grit, Low-Level Quit
Early in her career, Angela Duckworth taught in public schools, working with students from disadvantaged backgrounds. She noticed that the students who excelled and rose above their circumstances weren’t necessarily the smartest or most talented. Intrigued, she left teaching to pursue a PhD in psychology, determined to uncover the true drivers of achievement. For more than a decade, she immersed herself in all kinds of challenging environments, including military academies, high-stakes business settings, and competitive sports teams. She published her findings in her book Grit, which became a mega-bestseller and sparked widespread interest in the trait Duckworth’s research found consistently linked to success: “grit,” the ability to stick to a long-term goal, despite setbacks, competing interests, the lack of visible progress, the lure of more lucrative or prestigious paths, and all the other reasons to give up. With its popularity, however, the book also sparked some misconceptions. Many readers interpreted “grit” as a fixed trait—something you either have or don’t, in every situation. But Duckworth’s work pointed to a more nuanced idea: “grit” isn’t a static character trait. Instead, it’s a dynamic interaction between a person and their “top-level goal,” Duckworth explains, “which is something that might span years or even a lifetime, but which one believes is worth pursuing at the cost of other paths or opportunities.” She contrasts these top-level goals with “low-level goals”—specific, tactical actions, like practicing an instrument or working on a laptop, which serve to support one’s broader, long-term aspirations. “The common mistake,” she said, “is to think that ‘grit’ is about being tenacious about the specific, tactical things…It’s really about being tenacious at the top level of your goal hierarchy. And then, being flexible and able to shift or give up easily on lower-level things.”
Being tenacious about some things but not about others—that’s the theme of this SIX at 6…
Take The Pebble Out of Your Shoe
Ross Edgley was the first person in history to swim 1,780 miles all the way around Great Britain. While towed to a 3,100-lb Mini Cooper, he ran a marathon, pulling the car all 26.2 miles. He climbed a rope the height of Everest. Most recently, he swam the Yukon River—317 miles (510 kilometers)—in over 62 hours, without stopping, without sleep, and without touching land or a boat. The author of The Art of Resilience, Ross defines resilience as suffering strategically managed. “What I mean by that,” he elaborated, “if we were running a marathon and you had a pebble in your shoe—resilience isn’t continuing to run, grinding the pebble into the ground. No, you stop and take the pebble out of your shoe and then continue on.”
The “Things I Like To Do” Hierarchy
When Duckworth explained her “goal hierarchy” to the economist Steven Levitt, he replied, “I don’t have goals exactly. I have things that I like to do.” At the top of his “things I like to do” hierarchy is that “I love to play with ideas. I love it when there’s a difficult problem and it seems like it can’t be solved, and then, with a twist of the wrist that allows you to see the problem differently, a solution emerges.” So, Levitt tenaciously pursued an academic career, earning a BA in economics from Harvard and a PhD from MIT before joining the faculty at The University of Chicago. He published extensively in journals like the Quarterly Journal of Economics and the American Economic Review. “But then,” Levitt said, “I just got tired of academics.” As Levitt explored new ways to do the thing at the top of his “things I like to do” hierarchy, The New York Times Magazine commissioned the writer Stephen Dubner to profile him just after he won the John Bates Clark Medal, awarded every two years to the nation’s most outstanding economist under 40. The profile, “The Probability That a Real-Estate Agent Is Cheating You (and Other Riddles of Modern Life),” was a hit, prompting publishers to suggest Levitt write a book. He wasn’t much of a writer, so he said he wasn’t interested in writing a book—“unless,” he proposed, “maybe Dubner and I could do it together.” The two coauthored Freakonomics: A Rogue Economist Explores the Hidden Side of Everything, a bestseller that led to their popular blog and podcast. The success of Freakonomics, Levitt told Duckworth, revealed that far more people shared his interest in ideas than he’d ever imagined. “I thought, ‘What am I doing trying to publish these papers that get 25 citations when I can be on the Freakonomics podcast and talk to millions of people?’ The academic world no longer made any sense to me.” “Freakonomics and everything that followed,” Duckworth replied, “was just doing what you most like to do but in a different context. It’s tactical shifting, not a complete change in the destination.” It’s top-level grit, lower-level flexibility.
Look At The People Ahead Of You
Early in his career, Ryan Holiday left a job in Hollywood and shifted to a seemingly less lucrative career path, starting as a research assistant for his favorite author. When I first met him, I asked about that decision. He told me he looked around at the people five and ten years ahead of him in Hollywood. He realized they spent most of their time doing things he didn’t want to spend most of his time doing. He then tried to call the author. As he knew it would, it went straight to voicemail. The author is writing, reading, researching, or thinking, he said. “And I knew I wanted my typical day to be filled with those things too.” It’s easy to take whatever job pays the most, he said, but most of your time is spent doing the work the job requires of you. When you look at the people five and ten years ahead of you in whatever career you’re considering, if they mostly do things you wouldn’t want to do all day, that’s not good. Because if your typical day is filled doing things that make you miserably, money can’t really fix that. “So ultimately,” Ryan told me, “the work has to be the win. You have to try to get to a place where doing the work is the win and everything else is extra.” You have to be tenacious about the things at the top of your “things I like to do” hierarchy and flexible about everything else.
Who Will Save Your Soul
At 15, Jewel Kilcher ran away from home, eventually landing in San Diego. She lived in her car and worked in a coffee shop but developed kidney issues, which sent her into a vicious cycle: getting sick, missing work, being fired, recovering just enough to start over, only to fall ill again. This relentless pattern trapped her in poverty.
Her health worsened—one day, she developed symptoms of sepsis, a life-threatening condition caused by the body’s extreme response to infection. She went to the ER but was turned away due to lack of insurance. Later that night, a doctor leaving his shift found her in the parking lot, covered in vomit and sitting in her car. He administered antibiotics on the spot, saving her life. For the next year, he continued to treat her for free while she remained homeless and jobless.
She began shoplifting, stealing small items like food and toiletries to survive. The thrill of stealing provided a brief escape from her harsh reality, and she found herself increasingly drawn to it—it became an addictive distraction from her precarious existence. The act felt oddly empowering, offering a brief sense of control in a life where everything else was out of her hands. But one day, as she stuffed a dress down her pants in a dressing room, Kilcher caught her reflection in the mirror. The image staring back at her—a homeless kid, stealing to survive—was not exactly a symbol of power or control. She realized then that stealing was just another force ruling her life, that the temporary sense of power was an illusion.
There in the dressing room, she recalled a Buddhist quote she’d heard as a kid, “Happiness doesn’t depend on what you have or who you are, it solely depends on what you think.” And then, she said, “I was like, ‘This is your moment, Kilcher. This is your moment—will you turn your life around, one thought at a time?’” Determined to reclaim control, she ran a two-week experiment, writing down every thought she had each day. At the end, she combed through the pages, hoping to spot patterns—recurring fears, triggers for panic attacks, moments of peace, or signs of hope. She didn’t really know what she was looking for—she just hoped to find some thread she could follow to reclaim control over her life.
As she flipped through the journal, it slowly dawned on her that the answer wasn’t hidden in the pages but in the experimental act itself. “I realized I had not had a panic attack in two weeks,” she explains. “That was a wild side effect of this experiment. I’d later come to understand that what I had stumbled on was mindfulness.” So she kept using her journal, writing poems, short stories, and lyrics—whatever came out.
Eventually, driven by both the desire to share some of what she’d written and to make a little money, she started going around San Diego, looking for places where she could sing. But this was the early 1990s, when San Diego’s music scene was launching bands like Blink-182, Slightly Stoopid, and Stone Temple Pilots, so local venues required artists to pay to play, offering them a shot at “getting discovered.” Jewel didn’t have any money, but one day she noticed a “going out of business” sign at The Inner Change coffee shop. She walked in and asked the owner, Nancy, “Can you stay open for two more months?” When Nancy asked why, Jewel proposed to try to attract a crowd in exchange for keeping the door money—a $3 cover charge for her performances. Nancy agreed, saying she might be able to stretch her budget to last two months. Jewel set to work, singing along the San Diego shoreline and inviting people to hear her perform at The Inner Change Coffee Shop that Thursday night at eight.
At her first Thursday night performance, two people showed up. She played a five-hour set, later saying, “I thought that’s what you did—I was an idiot.” She poured her heart into it, singing her most emotional, vulnerable, brutally honest songs. Those two people who wandered in ended up staying through the entire five-hour performance. “We were all crying by the end of it,” Jewel said.
She found her top-level goal: to make brutally honest music, even if connected with only one or two people.
The next Thursday, those two guys came back—this time, bringing two friends. Within weeks, the audience grew to seven, then twenty. Within six months, The Inner Change was packed to capacity every Thursday night, buzzing with people eager to hear Jewel perform. The once-struggling coffee shop transformed into a lively hotspot.
Word spread, and one Thursday, when Jewel arrived to set up for the night, there was an old marquee sign out front:
When Jewel asked about the sign, Nancy said, “Someone from Atlantic Records called—they’re coming to see you perform tonight.”
And then it was Sony and then it was RCA, Arista, Warner Bros., Columbia, Capitol, Geffen—and soon, every major record label was in a bidding war to sign Jewel. They flew her around the country, treated her to exclusive dinners, and promised they had the connections and vision to make her a star. After all the wining and dining, Atlantic Records made the biggest offer—a record deal with terms that included significant investment in promotion and a $1 million signing bonus. A million dollars is a lot for anyone, but for someone living in a car, it could solve almost every problem.
Jewel, however, saw it differently. She knew that everything comes with a price. Every opportunity, paycheck, and project has hidden costs. The price of a high-paying job might be long hours doing things towards the bottom of your “things I like to do” hierarchy. A raise brings more responsibility and expectations, often at the cost of sleep, increased stress, and strained relationships. Committing to a big project means saying “no”—to other people, other priorities, and other opportunities. Even a “bonus” isn’t a true windfall.
“I knew nobody was handing out a million dollars without costs,” Jewel said. “What were they?” To find out, she went to the library and borrowed All You Need to Know About the Music Business by Donald Passman. “The million-dollar signing bonus wasn’t a solution to all of my problems,” she said. “It would actually be another problem I would have to solve. That’s what the book taught me—that the cost was very high: I owed that money back.” The signing bonus was essentially a loan that Jewel would have to pay back through record sales. “I could do the math on how many records I had to sell to break even,” she said. “It was a very high number of records.”
It was a number of records that would be hard for an artist like Jewel to sell. At the time, the music industry was dominated by alternative rock, grunge, and pop. Jewel’s raw and acoustic style wasn’t mainstream, so selling enough albums to repay a million-dollar advance could take years, if it happened at all. That debt, she realized, would hang over her, creating the pressure to bend and conform to meet the demands of repaying it.
The real cost, then, was really that top-level goal: to make brutally honest music, even if connected with only one or two people.
As she considered the terms of Atlantic’s offer, Jewel created “a hierarchical decision tree, what I call my ‘North Star decision making process.’” Essentially, she identified the top-level things that most mattered, the mid-level things that supported them, and the low-level things that matter only if they align with the higher levels.
At the top of her hierarchy, Jewel said, “I wanted to be happy…I was just learning how to be happy. I was just starting to feel in control of my thoughts and actions. So I didn’t want a career at the cost of being happy and in control. That wasn’t a price I was willing to pay.” Next to being happy, she wanted to be an artist. “I wanted to be an artist, not a celebrity,” she said. “I wanted a long, 60-year career.” This meant she, one, wasn’t in a rush to cash in, and two, was wary of anything that would push her to prioritize commercial demands. “And so I made all my decisions based on that hierarchy,” she said. “It started right away—it started with turning the money down.”
Tenaciously committed to her hierarchy, Jewel turned down the $1 million dollar signing bonus and negotiated a unique back-end deal. Instead of a large upfront payment, she’d earn more from each album sold. The deal was set up so that her royalty rate would increase by one percent for every million albums sold, meaning her earnings would grow with her fan base. This structure was perfectly aligned with her top-level, long-term goals, giving her the freedom to create music on her terms, with a financial structure that rewarded sustained success rather than quick, fleeting hits.
Jewel’s debut album, Pieces of You, mostly recorded live at The Inner Change, was released on February 28, 1995, when she was 21. Her first single, “Who Will Save Your Soul,” came out on May 14, 1996. The song, about the compromises people make for success, became her first hit, reaching number 11 on the charts. Soon after, “You Were Meant for Me,” was released as the album’s second single, and it too became a massive hit.
With the two singles reaching listeners around the world, Pieces of You gained momentum and became one of the best-selling albums of all time. By 2006, it was certified 12-times platinum by the RIAA, marking over 12 million copies sold in the U.S. alone. Beyond its commercial success, the album received critical acclaim for Jewel’s distinctive voice and brutally honest lyrics. In 2007, it was recognized as one of the greatest albums of all time, ranking number 64 on the Rock and Roll Hall of Fame’s “Definitive 200” list.
Be Tenacious At The Right Level of Your Hierarchy
Angela Duckworth’s top-level goal is to increase psychological literacy. “If someone told me I couldn’t open my laptop at a specific time every day,” she said, “I might be disappointed, but I wouldn’t spend too much time and effort fighting it. On the other hand, if someone told me I couldn’t pursue my top-level goal of increasing psychological literacy, that’s where I’m going to push back. That’s the level where I’m committed to persevering, no matter what…So I think the secret of applying grit correctly is to be tenacious at the right level of your goal hierarchy.”