If you were near Pacific Beach in the early 1990s on a Thursday night, you would have noticed an oversized crowd gathering outside the struggling Inner Change Coffeehouse. The room was small and unremarkable, but week after week, people lined up down the sidewalk. They were there to hear a young singer-songwriter named Jewel. Most people know her now as one of the defining pop artists of the 1990s. But at Inner Change, she was an unknown teenager, nervous, and living out of her car.
Jewel grew up traveling and singing with her parents, performing wherever they could, but after her parents divorced, she lived a quiet, isolated life with her father in Homer, Alaska. Eventually, through a series of fortunate breaks, she earned a scholarship to attend Interlochen Arts Academy in Traverse City, Michigan, where she received professional vocal training and began experimenting seriously with songwriting.
Unable to afford flights home during holidays, Jewel hitchhiked with her guitar, playing wherever she could—coffee shops, open mics, street corners, and after her time at school ended, she wandered to San Diego to live with her mother. When her mom lost the house, Jewel moved into her car and parked near Pacific Beach. That’s when she noticed the Inner Change Coffeehouse.
The venue was struggling, and Jewel convinced the owner to let her play regularly on Thursday nights. She had no following and no promotion, so she did everything herself. She passed out flyers. She stopped strangers on the street. She begged people to come listen. At first, the crowds were tiny. But Jewel treated every performance like a classroom. She paid attention. She tested songs. She learned which lyrics connected and which ones fell flat. The more honest and vulnerable her music became, the more the room filled. That’s when the Record label executives began showing up. Soon she was being flown to meetings in fancy offices, and a bidding war began, leading to a million-dollar offer. It was what she did next that makes her story remarkable—she turned it down. This nineteen-year-old homeless girl turned down a million dollars. Why would she do that?
At the time, Jewel didn’t have a manager or a lawyer. So she went to the public library and checked out a book titled All You Need to Know About the Music Business. As she read, she learned that a signing bonus is a loan that artists have to payback from their earnings. The more she took upfront, the more pressure she would feel to produce hits, and that’s not easy for a folk singer.
So she made a strategic decision. She reasoned that if she didn’t cost the label money, they would be more patient. And if they were patient, she would have time to get better. It was a smart decision because her debut album, Pieces of You, was released in 1995 and went unnoticed. Radio wasn’t excited about a folk singer. But because Jewel hadn’t cost the label much, they weren’t concerned.
So she went on the road. No tour bus. No band. No entourage. She drove herself in a rental car, played college campuses and small venues, and kept learning night after night. Her philosophy was simple: keep costs down and get better.
Months later, her first single, “Who Will Save Your Soul,” began creeping onto the charts. Then came a second single, “You Were Meant for Me,” accompanied by a sultry music video that introduced her to the world. The rest is history.
Her album went from selling a few thousand copies in its first year to selling millions each month. In her words, “A tiny snowball in hell had caught enough momentum to create a tide change.”
Competence Comes First
In your Green Phase, it’s easy to fixate on income. You want to earn more and climb faster. That’s not wrong, it’s just out of order. The money will come in time, but first, you need to learn—you need to get better. Right now, your job isn’t to get rich. It’s to get ready.
When you’re just getting started, you mostly have theories. You think you know what will work. You’ve played it out in your head a thousand times, but you don’t know. I remember watching the NBA playoffs in 2018. After the Celtics won a playoff series, reporters asked a young Jayson Tatum how he planned to guard LeBron James in the next round. Instead of posturing, his answer was remarkably refreshing. He said, “I’m a rookie. I don’t know. This is my first year.” There are just some things you don’t know yet. How could you?
Contrast Jewel’s story with so many one-hit wonders who cashed in on a hit song and went nowhere. It’s not an exact science, but her strategy was brilliant and is a lesson for everyone in the green phase: keep expenses down and get better.
By now, you’ve probably heard of the famous 10,000-Hour Rule, popularized by Malcolm Gladwell. The idea is simple: if you put in roughly 10,000 hours of practice, you can become world-class at just about anything. It’s a principle that has been quoted endlessly to emphasize the importance of consistent effort over time. But here’s the part most people miss: the 10,000-Hour Rule only works if those hours are spent in deliberate, focused practice. Mastery doesn’t come from just “putting in the time.” You can spend ten thousand hours doing something poorly, and all you’ll master is bad habits. So take the time. Learn how to do it the right way. I know you’d rather be earning, but you need to be learning.
My first sales job was a doozy. A friend ran a label manufacturing company and offered me the opportunity to sell keg rings to restaurant owners. The job was easy. I would meet with brewers and bar owners and convince them to use my company to label their product. I accepted the job and hit the ground running with blind enthusiasm and unreasonable expectations. After 100 days of mediocre results, I threw in the towel, with little commission to show for my efforts. Looking back, I’m grateful I failed. That job taught me that success requires more than personality.
My first mistake was a lack of knowledge. I didn’t know the first thing about keg rings, or label printing, for that matter. I had enthusiasm, charisma, and a few clever one-liners to get my foot in the door, but the moment the client had a question, I had to try to fool my way through an answer, and I wasn’t fooling anyone. I learned a valuable lesson: you can’t fake true knowledge. Later, when I decided to pursue a career in insurance, the first and most important step I took was to learn everything I could about the insurance industry and the various products in my portfolio. I committed to knowing my product better than anyone else. But you have more to learn than just your product. You have to learn your craft, too. By craft, I mean judgment, timing, reading people, handling objections, and knowing when to push or pull. That kind of learning only happens through practice.
Play The Long Game
There’s an old Zen parable about a warrior named Banzo who sought wisdom quickly. He went to a Zen master and asked to be taught the way to enlightenment.
The master asked Banzo how long he thought it would take him to learn.
Banzo replied, “Ten years.”
The master said, “It will take twenty.”
Surprised, Banzo said, “But I will work very hard. I will give all my effort. How long then?”
The master replied, “Thirty years.”
Frustrated, Banzo asked why his willingness to work harder increased the time.
The master answered, “When you have one eye on the goal, you have only one eye on the path.”
The lesson is not that you shouldn’t work hard or desire to succeed, it’s that a student in a hurry learns the slowest. People who don’t have time to learn the first time have to make time to learn it again.
We live in a culture addicted to speed. Slow is how we describe bad service at a restaurant, bad movies, and people with a low IQ, but some things take time. Do you know what we call something that grows too large too quickly? Cancer. Success has a slow fuse. And if you don’t learn how to wait well, you’ll burn out long before you ever enjoy your ripe season. The most dangerous trap in the green phase is not failure—it’s frustration. Frustration tempts you to quit before the breakthrough comes. I’ve watched so many people quit because they couldn’t wait. So if you’re in the green phase right now, hear me: don’t rush it. Don’t despise it. Trust the process.
Patience doesn’t mean passivity. It’s not sitting on your hands waiting for life to come to you. While you’re waiting, let me encourage you to make yourself useful, make mistakes, and find a mentor. Let’s look at each of these.
Make Yourself Useful
In the mid-1970s, during a national financial crisis, Bill Belichick was an unemployed 23-year-old obsessed with football. He wrote hundreds of letters to college and professional teams, asking for any opportunity to work in the sport he loved, but almost no one responded. One opportunity finally came from the Baltimore Colts. It was unglamorous and unpaid. He would handle the work no one else wanted: breaking down film.
At the time, before all the digital tools we have today, film study was tedious and time-consuming. Most young coaches would have viewed it as a dead end, but Belichick leaned into the work. He wanted to become exceptional at it. Coaches from those days talk about how relentless he was. He listened constantly. He absorbed everything. When given an assignment, he vanished into a room until he figured it out, and then asked for more. It worked. One reason is that Bellicheck is a once-in-a-generation football mind, but it also worked for a more practical reason: he made his bosses look good. Never underestimate what making someone else look good can do for your career. What looked like grunt work from the outside turned out to be the path to football’s Mount Rushmore for one of the greatest coaches in history.
When you’re starting at the bottom, you want to be noticed. There’s nothing wrong with that. But the mistake many make in the green phase is wanting visibility when you should be aiming for value. Author Ryan Holiday calls this approach The Canvas Strategy. Early in his career, working as a personal assistant in Hollywood and later as a marketing executive and research assistant, Holiday learned a counterintuitive lesson: the best way to become indispensable is to help other people succeed—especially the people you report to.
The Canvas Strategy is the idea that instead of obsessing over credit, titles, or recognition, you find “canvases” for other people to paint on. You look for opportunities to make their work easier, better, and more effective. You condense information. You solve problems. You remove friction. Holiday’s career advice is, “completely ignore getting credit, getting ahead, even throw out what your job is supposed to be on paper. Instead, focus all your energy on finding, presenting, and facilitating opportunities that help other people inside the company succeed.”
That’s exactly what Belichick did, too. He spent countless hours studying to condense the important information for the coaches above him, and then, most importantly, let them take the credit and look good for the information he found for them—and he did it for almost no money. Most people don’t have the patience or humility to play the long game like that.
There’s a lot of debate today about unpaid internships and spec work. And rightly so—people deserve fair compensation. But it’s also true that many successful people got their start precisely because they were willing to do the work others avoided, for little or no money. Is it a privilege to be able to do that? Yes. Not everyone can. But if you can, it can become an advantage. But it’s usually not the lack of money that stops someone from a life-changing opportunity—it’s usually pride. It’s easy to be bitter, to hate even the thought of letting someone else take the credit for your work. You tell yourself that every second spent not doing your work is a waste of your gift. You feel noble and righteous, but it’s shortsighted. When you have no name or track record, the fastest way to get where you want to go is to help someone else get there first.
When I teach this concept to young professionals, I explain it like this: In life and business, there are trucks, and there are trailers. A truck has horsepower. It wants to go somewhere. A trailer doesn’t have power, but it has capacity—it carries the load. Without a trailer, a truck is limited. Without a truck, a trailer goes nowhere. It takes both. Most young professionals want to be the truck. I get it. I did too. But early on, you usually start as a trailer. You help carry the weight. You make progress possible for someone else. And if you hitch yourself to the right truck, you’ll go farther than you could on your own. So don’t ask for credit. Ask for more responsibility. Be useful. Build trust. Because trust opens doors.
Make Mistakes
When you’re just getting started, the pressure to get everything right can feel overwhelming. You’re new. You don’t want to look foolish. You don’t want to waste time, lose money, or damage your reputation. So you research. You listen to podcasts, read books, and watch videos. Preparation is good, but at some point, you have to act.
Too much study without enough doing will make you knowledgeable but naive. You’ll have theories but no experience. There is a certain type of learning that only happens in the field. Sure, you know the offer, but you don’t know how people respond to the offer. You’ve spent a lot of time thinking about it, but you haven’t had to think on your feet. That’s the difference between information and knowledge—knowledge comes from experience. At some point, you have to be in the room. In the field. Across the table from another human being.
Hank Aaron is remembered as one of the greatest hitters in baseball history. In 1974, he broke Babe Ruth’s career home run record, finishing his career with 755 home runs, a record that stood for more than three decades. What’s forgotten is how often Aaron failed at the plate. When Aaron retired in 1976, he also held the Major League Baseball record for career strikeouts, with 1,383. Both records have since been surpassed, but at the end of his career, no player had struck out more often or hit more home runs than Hank Aaron. Here’s the lesson: If you want to hit home runs, you’re going to swing and miss sometimes. Even the greats fail more often than they succeed. A .300 batting average, which gets you into the Hall of Fame, still means you fail seven out of ten times. Growing up playing Little League Baseball, I remember my dad always telling me, “You gotta swing the bat!” He didn’t mind if I struckout swinging, but it wasn’t ok to strikeout “looking.” The same is true in business. You’re going to swing and miss. It’s ok!
I know you’re afraid of failing. Afraid of looking stupid. Afraid of being the person who “didn’t have it figured out.” But here’s the truth: years from now, no one will remember the small mistakes you made early on. And if they do, it will probably be as a story told with laughter about the “good old days.” Actors make bad movies. Artists release bad songs. Entrepreneurs file bankruptcy. It happens.
I recently read that nearly half of men ages 18–25 have never asked someone on a date. There are plenty of explanations floating around, but here’s my theory: we’ve removed friction from early life, and in doing so, we’ve made failure feel catastrophic. When you grow up overprotected, you’re terrified of embarrassment. But failure is good for you. First, it teaches you that you’ll survive. The world doesn’t end. You recover. Second, it gives you feedback. It tells you what didn’t work so you can adjust your strategy and try again, but smarter this time.
Of course, the key is learning from your mistakes. Everyone makes them, but not everyone learns from them. That part is up to you. In the green phase, mistakes aren’t an indictment— they’re proof that you’re actually in the game. They’re the tuition you pay for the school of life. So don’t wait until you feel ready. Get your reps in. Swing the bat. Don’t watch another opportunity pass by.
Find a Mentor
There are two primary ways to learn in life: mistakes and mentors. Smart people learn from their mistakes, but wise people learn from other people’s mistakes. In the green stage, you have information, but you lack perspective. That’s why you need a mentor—someone who’s been where you’re trying to go.
The word mentor comes from one of the oldest stories ever written, The Odyssey. Before Odysseus leaves to fight in the Trojan War, he entrusts his young son, Telemachus, to a trusted friend named Mentor. His role was to look after Telemachus until he was ready to step into adulthood and leadership himself. Over time, the name Mentor became synonymous with someone who offers guidance.
Of course, having a teacher requires you to be a student. It’s impossible to learn what you think you already know. There is nothing more frustrating than trying to teach someone who believes they have all the answers. Especially if they’re unproven. That’s why the humility to learn is so attractive in the green phase. Leaders are looking for sponges who want to soak up every ounce of knowledge they can learn. Are you willing to change? Change your mind? Change your plan? Change your method? It’s ok to be wrong. Everyone is wrong at times. But being stubborn—being confident and proud of your ignorance—that’s immaturity. We all have blind spots and biases. We need another set of eyes, someone who can watch and notice what we’re too close to see. That’s why the best performers in the world still surround themselves with coaches. In almost every case, the athlete is more talented than the coach—but that’s not the point. They want another set of eyes. Someone who’s sees what they can’t see. So who do you listen to? Who has permission to tell you you’re wrong, or that there’s a better way?
While studying at the University of Nebraska in his early twenties, legendary investor Warren Buffett stumbled upon a book that would change his life: The Intelligent Investor, by Benjamin Graham. In it, Graham outlined a patient, disciplined approach to investing known as “value investing.” Buffett devoured the book later, saying, “It’s by far the best book on investing ever written.”
He was so impressed that he decided to study directly under its author. In 1950, Buffett applied to Columbia Business School solely because Graham taught there. After graduation, Buffett wanted nothing more than to work for his mentor. He wrote to Graham offering to work for free—just for the chance to learn. Graham initially declined, explaining that he wasn’t hiring and that Buffett would do better by gaining experience elsewhere. But Buffett kept in touch, sending letters and sharing ideas, and a year later, in 1954, when a position opened at Graham’s firm, Buffett finally got the call.
Buffett moved from Omaha to New York and began working for $12,000 a year—hardly glamorous, even then. But those two years under Graham’s guidance became the foundation for Buffett’s billion-dollar fortune. He didn’t just watch what he bought; he watched how Graham thought. He learned that sound investing had more to do with temperament than intelligence, how to find undervalued companies, and how to keep emotions out of financial decisions.
In 1956, Graham retired and closed his firm. Buffett returned to Omaha to start his own partnership, applying the lessons his mentor had taught him. Within a decade, he was running one of the most successful investment funds in the country. Today, Buffett still credits those early years of apprenticeship as the best investment he ever made—not in the stock market, but in himself. He often tells young leaders, “The best investment you can make is an investment in yourself… the more you learn, the more you’ll earn.”
In sports, it’s called a coaching tree. In horse racing, it’s called a bloodline. And in business, we call it a downline. As I watched the Kentucky Derby last year, I heard the announcers give a remarkable fact: Every single horse in the 2025 Kentucky Derby was a descendant of Secretariat. All of them. Secretariat won the Triple Crown in 1973 by a record-shattering 31 lengths at the Belmont Stakes, and 52 years later, the best horses in the sport came from his pedigree.
Bloodlines in racing are like downlines in business. You show me anyone successful, and I can almost guarantee they have a pedigree. They had people who opened doors, and shared wisdom. In business, pedigree isn’t about where you come from—it’s about who you learn from. Now more than ever, you need someone to help you make that first connection. Someone to correct you when you’re careless. Someone who believes in you when you don’t believe in yourself.
You’re Not Behind
I’m going to let you in on a little secret: most people don’t have nearly as much money as they act like they do.
It doesn’t feel that way, of course. With constant self-promotion, it’s easy to assume everyone else is crushing it. But much of what you see is performance, not reality. That private jet on Instagram is often a rented studio. The mansion backdrop? A short-term rental used to film a few hours of content. A recent report found that the average content creator online earns around $15,000 per year. Only a small fraction make six figures. But the illusion works. Everyone looks rich. Everyone looks like they’ve figured it out. They haven’t.
One of the quiet pressures of the Green Phase is the feeling that you’re falling behind while everyone else is pulling ahead. You’re still learning. Still trying things. Still wondering if you’re even on the right path. That pressure can be exhausting and dangerous. It can tempt you to quit too early or cut corners just to feel like you’re keeping up. But you’re not behind. Let me use another horse-racing lesson I learned living in Kentucky: the horse leading at the first turn almost never wins.
I was 35 when I made my first million, so I was ahead of schedule, but I had already worked for 3 companies before starting my own. I learned under other leaders. I failed in early roles. I made mistakes that felt embarrassing at the time but turned out to be invaluable later. It doesn’t matter how old you are—it matters how many years you’ve put into learning your craft. So what’s your business age? How many years have you been doing this—really doing it? Learning the craft. Developing judgment. Gaining perspective. You have time. Breathe. This is the season where you learn before you earn. Fruit eaten too early is bitter anyway. As the saying goes, “don’t despise small beginnings.” They’re necessary.
So if your life feels small right now, that doesn’t mean it’s insignificant. If your income hasn’t caught up to your effort yet, that doesn’t mean you’re failing. If your progress feels slow, that doesn’t mean you’re stuck. It just means you’re green.
