A Silicon Valley billionaire's 30-year business review: All the goals I pursued in the past were foolish

Author: Deep Thinking Circle

Have you ever thought that those goals you are desperately pursuing might actually be the very things preventing you from success? Promotions, raises, titles, social status—these seemingly natural milestones in life—may actually be trapping you in a carefully designed trap. Recently, I watched a video where Chamath Palihapitiya, an early Facebook executive and well-known investor, summarized his 30 years of business experience in 13 minutes. One sentence he said completely shook me: “It took me 30 years to realize that all the goals I once desperately chased were foolish.” This is not some motivational cliché, but a profound reflection from a billionaire after experiencing countless successes and failures.

Chamath’s background alone is legendary. He was a core member of Facebook’s growth team and later founded Social Capital, a venture capital firm that invested in numerous successful tech companies. When someone like him tells you that most of what he pursued over the past 30 years was wrong, what would you think? When I first heard this view, I was resistant internally because it completely overturned the success principles we were taught from childhood. We were educated to set goals, make plans, and steadily achieve milestone after milestone. But Chamath tells us that this way of thinking is fundamentally flawed.

Why Goals Can Become Your Enemy

The first core point Chamath raised made me think deeply: you can never stop. It sounds strange, but he explained that most people frame life as a series of goals. The problem with goals is that once you achieve enough of them, you think, “I’ve succeeded; I can stop now.” This mindset causes a loss of motivation at some point, losing the reason to keep moving forward.

I deeply understand this feeling. At a certain stage in my career, after reaching some of my set goals, I did feel a sense of emptiness. That “what’s next” confusion made me unsure of what to do next. Chamath observed that many people he once admired stopped around their 50s. They no longer stay active in the industry, no longer challenge themselves, no longer learn new things. As he put it, “They are no longer in the arena.”

In contrast, he cited Warren Buffett as an example. Buffett is still working at 95 and only recently started stepping back. Charlie Munger, essentially working until he passed away. What do these people have in common? They are not committed to achieving a series of goals but are dedicated to continuous learning, taking risks, and associating with interesting people. It is this mindset that keeps them sharp and energetic.

This perspective made me reevaluate my own career planning. I used to set many specific goals: reaching a certain position by a certain age, earning a certain amount of income, achieving financial freedom to some degree. But now I realize these goals themselves can be harmful because once achieved, they can sap your motivation to move forward. If you focus on the process—continuous learning, growth, challenging yourself—you will never truly stop.

Chamath said that if someone had told him this earlier, he would have made very different decisions. He would have reduced his focus on money, taken more risks—even more than when he was younger. This is especially interesting because it reveals an counterintuitive truth: true success is not achieved by optimizing short-term goals but by persistently focusing on the long-term process.

Three Boundary Conditions: How to Live in the Process

If you want to abandon goal-oriented living and embrace process-oriented living, Chamath believes you need to set some very good boundary conditions. These are not goals but principles—bottom lines you must never violate regardless of circumstances. He proposed three specific boundary conditions, each of which resonated deeply with me.

The first boundary condition is: No debt. It sounds simple, but Chamath explained that debt is something that will make you stop. It causes you to cease learning, stop taking risks, and start pursuing short-term goals, most obviously money. All these short-term optimizations will have a huge impact on your life 20, 30, or 40 years down the line.

I completely agree. Debt is not just a financial burden but also a psychological shackles. When you carry debt, your decisions are distorted. You might give up an interesting but low-paying opportunity and choose a boring but high-salary job just to pay off debt. You might stay longer at a company you dislike because you need stable cash flow. Debt robs you of the freedom to choose, and freedom of choice is the most important prerequisite for living in the process.

Chamath specifically mentioned a phenomenon that is especially dangerous for the younger generation: spending a lot of time on social media, watching people who are essentially lying to you about their fake lives. Too many are deceived by this false life, thinking it’s real, and start pursuing the same lifestyle. All of this revolves around money. No one is praised by society for lifelong dedication to the process. Kobe Bryant might be an exception, but unfortunately, he is no longer with us.

This made me think of the wealth flaunted on social media—designer bags, luxury cars, extravagant trips. These constantly stimulate young people’s desire to consume. To live such a lifestyle, many go into debt, overdrawing their future. But in reality, many of those showing off luxury lives are themselves heavily in debt, or their lives are far from as glamorous as they appear. Pursuing this fake lifestyle ultimately traps you in debt, preventing you from focusing on what truly matters.

The second boundary condition is: Manage your life with humility. Chamath said this was a lesson he took a long time to learn. What does humility mean? It means being brutally honest about your current reality because only then can you see things clearly and share the truth with others, creating genuine resonance.

This resonated with me. Humility is not self-deprecation but honest assessment of your abilities and limitations. In entrepreneurship and work, I’ve seen too many failures caused by a lack of humility. Some are overconfident and refuse to admit mistakes, leading them down a wrong path. Others are afraid to reveal weaknesses and try to project a perfect image, losing opportunities for sincere connection. True humility is admitting “I don’t know,” being willing to learn, and daring to say “I was wrong.”

The third boundary condition is: Surround yourself with people younger than you. Chamath said that young people see the world completely differently. Their biases are different, their mental frameworks are different. Although he sometimes feels he has learned enough and doesn’t need to be told he’s wrong, the truth is quite the opposite. The more time he spends with young people, the more he realizes that everything he knows is stuck at a certain point in time.

This is a very profound insight. Our knowledge and experience are always time-sensitive. What is correct today might be outdated tomorrow. The methods effective today might fail tomorrow. Young people are like early warning systems for the future—they help you see how the world is changing. Chamath said that at some point, how he thought things should work is completely opposite to how they actually work. Recognizing this requires courage because it means admitting your knowledge is becoming outdated.

I’ve had similar experiences. When I communicate with people 10 years younger than me, I am often shocked by their perspectives. Their understanding of technology, use of social media, acceptance of new business models—far beyond my expectations. If I cling to my own cognition and refuse to listen to young people, I will quickly become rigid and outdated.

Those Foolish Goals

Chamath candidly listed the “foolish goals” he pursued in the past. When he was a director, he wanted to become a vice president. When he was a vice president, he wanted to become a senior vice president. When he was a senior VP, he aimed to be a principal (leader) at a venture capital firm, then a general partner. At Facebook, as part of the management team, he wanted more equity. These were all foolish goals.

This confession shocked me because these goals don’t seem foolish at all. They are what most professionals dream of—moving from director to VP, from employee to partner, from management to ownership. But Chamath said these foolish goals kept him away from his true self 100%. They turned him into a cartoon version of himself, exaggerating certain small aspects to represent a bigger self. Not only for himself but also for those around him.

I understand what he means. When you pursue external goals, you unconsciously adjust your behavior to meet the expectations of that role. You might suppress certain traits and amplify others because you think that will help you achieve your goals. But in this process, you gradually lose yourself. You become a distorted version of yourself, aiming for goals rather than being your most authentic, complete self.

Chamath admits that these lessons can only be learned over time. Everyone in their 40s or 50s who hears him speak nods in agreement. But every person in their 20s or 30s thinks, “This doesn’t apply to me.” So you have two choices: the easy way or the hard way. The easy way is to do these simple things now. The hard way is to spend 30 years learning these lessons yourself.

This reminded me of a classic paradox: when young, we have time and energy but lack wisdom and experience; when older, we have wisdom and experience but have lost time and energy. If we could understand these principles early in life, how much time and effort could we save? But the truth is, some lessons only become clear through personal experience. Listening to others isn’t enough.

Optionality: Keep the Freedom to Choose

One of Chamath’s most important principles is: preserve optionality at all costs. He said he strives to maintain optionality in business negotiations. Finding win-win situations is very powerful and has helped him greatly.

What does optionality mean? It’s about keeping your options open, not trapping yourself in a single path. When you have options, you can adapt flexibly to changing circumstances. When an opportunity isn’t right, you can say no. When a better opportunity arises, you can seize it immediately. When you lose your optionality, you’re trapped. You have to accept the current options, even if they’re not ideal.

Chamath explained that maintaining optionality helps protect relationships, others’ self-esteem, and their emotions. It forces him to be more restrained, listen more, speak less. It’s proven that many people self-destruct by doing foolish things. For him, this framework helps him avoid that as much as possible.

I deeply agree. In my career, decisions made with preserved optionality always lead to better results. For example, I once rejected a high-paying job that required a long-term contract, choosing a more flexible but lower-paying opportunity. Months later, a better opportunity appeared because I wasn’t bound by a contract and could jump on it. Those who accepted the long-term contract watched opportunities pass by.

Debt is the biggest enemy of optionality. When you carry debt, you must make monthly payments, which means you need stable income. This requirement limits your choices. You might have to accept a job you dislike just for stability. Without debt, you have the freedom to explore, take risks, and pursue opportunities that may not pay off immediately but are more valuable long-term.

Chamath also shared a philosophical thought: if we truly live in a simulated world, there might be a layer of the game that shows you these secrets and gives you a chance. Now nearing 50, he finds these secrets unfolding before him. He said, “Wow, this is incredible. I didn’t know these when I was young, and even if someone told me, I would ignore it.” So he offers this advice, knowing most people will ignore it, but everyone will eventually go through this process.

This metaphor is interesting. Life is like a game, with some secrets only unlocked at certain levels. But ironically, by the time you understand these secrets, it might be too late to use them effectively. That’s why listening to elders’ advice is so important, even if you don’t fully grasp it at the time.

Complete Honesty in Relationships

When discussing relationships, Chamath shared the most important lesson he learned: marrying someone who fully supports you is crucial. The only way to gain such support is through complete honesty.

He admits honesty is very difficult for many people. He himself doesn’t know how to be fully honest. He shares most things but not everything. This is part of his way of life learned in his family. But if you don’t learn this lesson, it will come back to bite you.

Chamath said that having your partner, your co-founder, by your side is very important. He went through a divorce, which he said was almost like losing a family member. What was missing in his first marriage? Complete raw, unfiltered, pure honesty. When things are good, you celebrate together. When things are bad, you point them out and call them out. They didn’t do that. His second marriage is completely different; he says finding such a relationship is a blessing.

This made me think of many marriage or partnership issues. Many believe that keeping secrets or glossing over truths is necessary to protect the other or maintain peace. But Chamath’s experience shows the opposite. Lack of complete honesty is like a ticking time bomb in a relationship. Small issues, if not addressed promptly, grow into big problems. Misunderstandings, if not clarified, ferment into resentment.

What does complete honesty mean? It means speaking up when you’re dissatisfied, admitting mistakes, being open about fears. It requires great courage because honesty makes you vulnerable. But only through vulnerability can you build truly deep connections. Only when your partner knows the real you—including your weaknesses and fears—can they truly support you.

The same applies in business relationships. The most successful partnerships are often built on complete honesty. When you can openly discuss disagreements, admit mistakes, share concerns with your partners, you can face challenges together and make the best decisions.

Advice for Young Professionals

Chamath offered very specific advice to ambitious young people. The first and most important is: you must go to Broadway.

He explained that depending on what you want to do, if you want to enter politics, you need to go to Washington D.C. It might take one or two turns to get there; perhaps you need to start at a state capital but begin there and then move to D.C. If you want to do finance, you need to go to New York or London. If you want to do crypto, maybe you need to go to Abu Dhabi. If you want to do tech, simply put, you need to go to Silicon Valley. There are no shortcuts for these decisions.

This advice seems simple but requires courage to execute. It means you might have to leave your hometown, step out of your comfort zone, and start anew in a strange city. But Chamath’s view is that you must go where the fish are. If you want to catch big fish, you can’t stay in a small pond.

I strongly agree. Geography has a far greater impact on career development than most realize. Being in the right place means meeting the right people, accessing the right opportunities, learning the right things. In Silicon Valley, you’re surrounded by entrepreneurs and investors; you naturally absorb that startup culture. In New York, you’re exposed to finance and media elites. If you stay somewhere unrelated to your career goals, you’ll miss many opportunities.

Chamath’s second piece of advice is: don’t optimize for salary. That’s why you need to live humbly. You should optimize for opportunity. When a chance to work with someone smarter than you appears—and it feels like a rocket ship—you jump on it. If you don’t, and instead prioritize other trivial factors, you will fail, and looking back, it will hurt. That’s because you let all those foolish indirect factors block your way.

This advice is the opposite of what we were taught growing up. We were told to fight for the best salary, to negotiate for our worth. But Chamath says that early in your career, learning and growth opportunities are far more important. A low-paying job that helps you grow quickly is more valuable in the long run than a high-paying job that keeps you stagnant.

Chamath also mentioned that young people often talk about work-life balance. He said he doesn’t even understand what that means. When you’re in a vibe state or flow state, it means you’re working in a way that gives you purpose, living in a way that gives you purpose, blending work and life seamlessly. That’s what you want. You’re in a continuous process, constantly adding things that make your life better.

This view might be controversial, but I understand what he means. True work-life balance isn’t about strictly separating work and life—working 8 hours and then completely disconnecting. It’s about finding a way to work that makes your work a meaningful part of your life. When you love what you do, when it aligns with your values, and when it gives you a sense of achievement, the boundaries between work and life become blurred—but that’s not a bad thing.

The Mouse and Water Experiment

Chamath shared a shocking experiment. Scientists placed mice in a large tank filled with water, measuring how long they take to drown. On average, about 4.5 minutes. Then they repeated the experiment, but when the mouse was about to drown, roughly 30 seconds before, they pulled it out. They dried it, comforted it, and then put it back in the water. This time, the same mouse survived an average of 60 hours.

What’s the difference between a mouse that drowns in 4 minutes and one that survives 60 hours? Aside from what we can infer, no one knows—except the brain. It’s the brain that unlocks the mouse’s resilience and survival ability. That’s what everyone should find: a place that allows you to go deep into your mind and unlock levels you thought were impossible.

This experiment moved me deeply. What does the second mouse know? It knows someone will come to rescue it. It has hope. And hope increased its survival capacity by nearly 800 times. What does this tell us? It tells us human potential is far beyond our imagination. When we believe it’s possible, when we have hope, we can do what we thought was impossible.

Chamath said Navy SEALs talk about this, athletes talk about this. But in business, the great thing is—we have no expiration date. Unlike Navy SEALs or athletes with a 10-15 year physical shelf life, we can keep playing this game forever. So you must find a place that makes you like that mouse struggling in water for 60 hours because it profoundly changes you in a way only experience can teach. Then you look at others and wonder why no one else understands this.

This speaks to the common trait of truly successful people—they have all faced some form of trial, some experience that pushed them beyond their perceived limits. It might be a challenging project, a comeback after failure, or completing seemingly impossible tasks under extreme pressure. These experiences transformed them, made them realize their potential is far greater than they imagined.

And the beauty of business is that, unlike sports, there’s no age limit—you can pursue these breakthroughs at any age. People in their 60s can still start businesses, those in their 70s can learn new skills, and even in their 80s, they can still contribute. Buffett and Munger are perfect examples. This endless potential makes business a perfect stage for lifelong learning and growth.

Status as a Trap

Chamath’s view on status might be the most disruptive in the entire video. He said that the most important thing about status is: it’s entirely man-made and completely irrelevant. It’s something people use to deceive others and waste valuable time. If you understand this, one of the most powerful things you can do is ignore all the ways society tries to give you status.

Why? Because society is essentially placing a small hook on you to pull you back. If you start believing in these things—things validated externally by others—you open yourself to judgment, small or large. When you chase enough of these, enough status, you become completely controlled by those who don’t care about your best interests.

Chamath said he learned this the hard way because he wanted many things, thinking they were important. Making the list, joining the club, being invited to events. But all these things are meaningless because they are entirely artificial. You distort yourself, sometimes bending your expectations and behaviors to fit in or be recognized, and in doing so, you become less whole.

This made me reflect deeply. Our society is filled with symbols of status—degrees from prestigious schools, titles at big companies, luxury offices, expensive cars, memberships in exclusive clubs. We are taught to pursue these because they represent success. But Chamath tells us these are traps.

Why? Because once you start caring about these symbols, you adjust your behavior accordingly. You do things that boost your status, even if they’re not what you truly want. You avoid doing things that might harm your status, even if they are the right choices. You care about how others see you, about your ranking in various lists. This obsession binds you and robs you of freedom.

Chamath said that status is a completely man-made, corrosive thing society uses to keep you in check. The more you can detach from it, the more of a superpower you have. This might sound radical, but think about those who truly change the world—they often don’t care about traditional symbols of status. They follow their curiosity, do what they believe is important, not what society deems important.

I am also working to let go of my obsession with status. I find that when I stop caring about how others view my choices, I feel freer. I can pursue what genuinely interests me, even if it doesn’t bring me the traditional markers of success. I can connect with anyone I find interesting, regardless of their social standing. This freedom is priceless.

My Reflection

After watching Chamath’s sharing, I spent a long time digesting these ideas. They challenge many assumptions I’ve held for years. I used to think setting clear goals was the key to success, but now I realize that obsessing over goals can cause me to miss what’s truly important—the ongoing process of growth.

I’ve also started to reevaluate my definition of success. In the past, I might have used titles, income, or social standing as benchmarks. But now I ask myself: Am I continuously learning? Am I challenging myself? Am I doing something meaningful? If the answer is yes, then I am successful, regardless of my title or bank balance.

Chamath’s experience also made me think about the value of time. He said it took him 30 years to learn these lessons. If I could understand and apply these principles now in my 30s, how much time and energy could I save? But I also realize that some lessons only become clear through personal experience. Listening to others is helpful, but it’s not enough.

Finally, I want to say that Chamath’s insights are not about everyone becoming billionaires or building great companies. It’s about living more fully, more authentically, more meaningfully. No matter what your career goals are, these principles apply: focus on the process, stay humble and eager to learn, protect your freedom of choice, be honest in relationships, and ignore society’s artificial symbols of status.

I believe that if more people understand and practice these principles, we will see a different world—a world where people work not for external validation but for internal growth; where they don’t climb someone else’s ladder of success but walk their own unique path. It may be a harder choice, but it is definitely a more meaningful one.