#1 Most Valuable Lesson I Learned at Harvard Business School: How to Avoid Regret

70% of people have career regret, which is just an astronomical number, and workers are quitting their jobs at a record pace. But it doesn't need to be that way. There's never been a better time to have a self-determined job process where you ultimately control the dimensions of the work you do. Information has never been more widely accessible in what used to be opaque industries like venture capital, nor your ability to get close to the best mentors and practitioners. Add in remote work, where jobs have been opened up to a global talent pool, and more and more platforms that make it easier to start your own business or side hustle, like a content business on YouTube. Add all of that together, and there's more options than ever to control your own destiny. But I think counterintuitively, that's part of the problem. Most people do better when they're faced with a limited set of choices. And it's almost like there's so many options these days, it's overwhelming and bound to leave people questioning whether they made the best choice. I've been through my own sideways journey for almost 10 years, going from Goldman Sachs Banking to McKinsey Consulting to Big Tech at Google. You know, I don't mean to obnoxiously name-drop, but it's to say I followed the crowd from one quote-unquote prestigious job to another, in part because I didn't know what else to do, and I was miserable for a lot of it. I ultimately went to business school because I wanted to broaden my aperture. And that's where I met a professor who wasn't just an academic, but had started eight tech companies in the past. And he shared a framework for what to solve for in your career to be happy and fulfilled. And since then, I've followed the advice and settled into the startup and venture capital world myself about 10 years ago. And it's been my dream job since. I've said many times I'm going to do this until I get fired or retire. Hopefully the latter. So in this video, I'm going to share that advice, which has changed my life, and hopefully will help you also find your career sweet spot and avoid being part of the 70% who have major career regrets. Before we get going, if you think you already know where your career sweet spot is and it's tech and startups, I've shared a tactical step-by-step process for recruiting and interviewing to get your foot in the door, which you can check out on my channel. I'll be posting more content on what's happening in the tech scene inside Silicon Valley and advice for ridiculously ambitious people. So please like and subscribe if you want to see more of that. Okay, so without further ado, here's the key to happiness in your career. They are, number one, be good at what you do. Number two, be recognized and rewarded for it. Number three, find meaningful challenge in your work. Number four, do it with people you like. Number five, believe in a bigger purpose for your work. If you have those five qualities for your job, you will be part of the happy minority. But even though it sounds straightforward, the path to getting there is really hard. On the first, finding your calling. How do you even know what you're going to be good at or even what different kinds of work are enjoyable to you when you're just starting? Some kinds of work you may end up doing in your career may not even exist yet. I think a lot of people believe they can figure this out through massive self-reflection. Maybe having some visions on a mountaintop somewhere to learn some deep secret about themselves. Really though, I think the only way to figure out what you're good at is to try working on it and see how fast you can progress. But what area do you try out first? In the early days, you're going to have to make an educated guess. It's okay if you're wrong as long as you can learn about yourself quickly. To complicate things, your taste may evolve over time but pay attention to what excites your curiosity over an extended period and what kinds of people in various fields you seem to be naturally drawn towards. Pay particular attention to the day-to-day minutia that seems to bore or repel other people that fascinates you. That's a really strong sign you're onto something. It's a common question to wonder how long should you try something before deciding it's not for you and moving on. You're not going to find out if it's for you unless you give it enough time and effort to see if you can get good at it. And you don't want to be one of these job hoppers going from role to role every 6 to 18 months that recruiters stop hiring. But at the same time, you don't want to waste years of your life in a dead-end job that just isn't for you. My advice here is to think about the right timeline that aligns to the feedback loop inherent in your job and commit to working as hard as you can for that period before you re-evaluate. This could vary a lot by industry but usually I've seen it be roughly two years or so. In product management or engineering, for example, you may want to work on a product all the way until launch and see the results of that through. And that may take a couple years. Good work isn't done overnight. Venture capital is unique in that a startup you invest in may take 10 to 15 years to IPO. So it may take a long time to figure out if you're any good. But that said, you probably have a good sense from the first couple years after you make an early investment when those companies are going to market trying to raise follow-on capital. If two years sounds like a lot to you, let me tell you it'll be over in the blink of an eye. Like I said, I spent 10 years in jobs that ultimately weren't for me just to find my ultimate sweet spot. Over time, there may be dips in your motivation and your affinity for that job day to day. So don't re-evaluate on a daily basis. Commit to this minimum learning time period and then do your re-evaluation in a more comprehensive, thoughtful way. One other thing, you may hear people talk about 5 or 10-year plans. I personally think these are overrated when you're young and you don't even know what you want to do. I was shocked when I heard from immensely successful people like John Doerr, the greatest venture capitalist of all time, how much serendipity played a role in their career paths. So instead, you should be maximizing the surface area for yourself to be lucky. And the way to do that is to be proactive and curious. Try lots of things, meet lots of people, learn a lot, ask a lot of questions. To the extent that long-term planning is helpful or maybe even required, I like to draw patterns from role models. Like if you're inspired by the CTO of OpenAI, then you can figure out what commonalities there are in the case you need to plan multiple steps to get to where you want to go. When in doubt, maximize for two things. Areas that are shifting very quickly, like AI, for example, where the tech stack seems to be changing on a daily basis. Those areas advantage fast learners rather than people who've built up a wealth of knowledge over decades. And then second, optimize for areas where you can work with great people you like. Fads like crypto may come and go, but great people will still be valuable to have learned from and have built relationships with. Even if you do all this and find a natural place for your talents, it's possible to do great work without being rewarded for it. Franz Kafka worked unhappily in insurance and died of tuberculosis without publishing any of his now famous writings. That's obviously an extreme example, but there are people who do great work buried in mountains of bureaucracy or deemed irrelevant due to big company politics. So you have to understand the organizational context in which you're joining. Naturally, it's easier if you're joining a small startup or company that has a very flat structure, where the work everyone done is obvious to everyone. But if you're joining a bigger company, you have to ask, how does the company work? What's their business model and how do they make money? And how central is the team that you're joining connected to that? Is your manager empowered at the company? How are they viewed by the leadership? Is the manager new or have they been there a while? Have they been promoted a bunch of times and they're clearly a high flyer? And how does your role fit into that team and the manager's work? This is really important because once you join, especially if you're a junior, there's just powers, company politics, etc. that's beyond your control. And it can sink you even if you do great work. These organizational factors are often a very overlooked blocker for many young people. Now, even if you're really good at your job and you're in a healthy environment where you can get rewarded for it, you can still easily hit that limit on learning curve and stagnate. The best work should get more interesting and in some ways more challenging as you sink your teeth into it. Ambitious people crave that challenge, not just clocking in time before going home. And it's just as well because becoming great at something usually involves spending what most people would think of as an unreasonable amount of time obsessing over that skill. The key is extended consistency over years. People who have great careers figure out how to get 1% better every day. That compounds such that you're several times better than others just in a year, much less a decade. But even for ambitious people who found something exciting to work on, there's still going to be times where you leap out of bed in the morning and times when you don't. You don't just put up your sail and get blown forward by inspiration every day. And yet there are techniques you can cultivate to bring your A-game. The hardest thing is just to start working. So you'll often have to trick yourself to get over that threshold. So it's okay to say to yourself, I'll just write the first paragraph of this memo or I'll just proofread my YouTube script. And then more often than not, you'll be in your flow five minutes later and off to the races. A lot of ambitious people who accomplish more than others have something in them pushing them further. Whether it's some desire to win, some narrative about their own manifest destiny, or some deep sense of obligation, or maybe even just some insecurity to prove others wrong. A lot of founders I know are keenly aware of their own psychology. Oftentimes it is a chip on their shoulder and they figured out how to manipulate it to push themselves to create and do productive work rather than self-pity. Now, even if your work is a bullseye, you have to love the people you do it with. Any ambitious career-driven person is going to spend more time with their co-workers than their own family. So you better respect and like who you're working with and critically feel that you've got something to learn from them. The way to ensure that is to find people with shared values and working styles, but complimentary zones of genius. Not just people who are exactly like you. Birds of a feather tend to flock together. So this requires a certain mental plasticity to appreciate people who bring something different than you to the table. Your ability to assess the quality of people you work with and find people who can complement your own blind spots is an unbelievable driver of your long-term career success. And it's a very rich topic that I'll explore more in a follow-up video. Fifth, this is maybe the most abstract and difficult criteria to sell for. So many young Gen Z folks in particular talk about being mission-oriented, but they're lost as to what that mission is in their early days. I think what a lot of people miss is that, yes, you may have some incoming biases, but especially when you don't have any experience, you have to create meaning over time through a job that connects with you on a foundational level. Meaning is often directly proportional to the blood, sweat, and tears you've poured into something. And that could be very much in your future rather than in your past. This, in my opinion, is the hidden secret to finding meaning. Rather than having some spiritual come-to-Jesus moment and have your purpose just revealed to you one day. I heard a powerful parable from the former VP of product at YouTube about how two women were laying bricks. When asked what they do, one said, I lay bricks side by side. And the other said, I build cathedrals. So that's to say meaning is self-constructed and deeply personal. It's not something that you stumble upon one day through sheer luck, but it's instead born out of an openness for self-discovery and an investment of time and effort that builds up gradually. Those are my tips for how you can find your own personal power alley in your career. And more broadly, how you aim to make a positive dent in the world. As I mentioned, after a period of being lost in the wilderness, I found my personal stride about a decade ago. My personal mission is to raise the collective level of empathy in the world. Today, I do this by investing in early stage startups that are breaking down the barriers to more connected, open, and educated society. I'm inspired by a world with no gatekeepers. And this YouTube channel is an emerging part of that. Hit like and subscribe if you want to follow along that journey as I post more content. Thanks so much. See you next time.