Ben Casnocha:

Now there’s this common misconception that successful careers are slow and steady, up and to the right. In fact, extraordinary careers benefit from what, Reid, we call in the book ‘breakout opportunities’—the singular opportunities that radically transform your career trajectory.

And to start, Reid, I figured I could just tell the story from our book The Startup of You of one man who experienced a breakout opportunity far away from the tech industry in Silicon Valley. Shall we do it?

Reid Hoffman:

Let’s do it.

Ben Casnocha:

So in 1982—this comes from the book—a young man from Kentucky named George Clooney moved to Hollywood like so many before him, with a dream of becoming a movie star.

He had a few things in his favor: good looks and natural talent, strong work ethic, and a couple of family connections. Yet after 12 years of auditioning, he had only landed occasional appearances on B-list television shows and C-list movies. Clooney was a long way away from fulfilling his career as an actor, never mind stardom.

But that all changed in 1994. Warner Brothers was producing an expensive, fast-paced, gritty medical drama called E.R., with “a script so exciting and fresh and unlike anything else on TV that assuming it actually made it to the airwaves, it had to either flame out or succeed spectacularly,” writes Kimberly Potts, who wrote a book about George Clooney.

And now, when one of George Clooney’s friends showed him a copy of the E.R. script, he knew right away it had the potential to be his breakout opportunity. And he didn’t wait for the E.R. producers to reach out to him. Instead, Clooney picked up the phone and called the executive producer to inform him that the actor wasn’t going to let anybody get the lead doctor role in the show. The producer laughed and invited him to the audition. Afterward, Clooney soon got a call back with good news, and he turned to a friend and said, “I just got a career.” Indeed, E.R. became a huge hit, and Clooney has never looked back.

Now, you might be wondering, “How did George Clooney know that E.R. would be the opportunity that would eventually take his career to new heights?” The answer is simple: he didn’t.

“You can never be certain,” we write in the book. Golden opportunities don’t come with a flashing neon sign. Killer job opportunities are rarely advertised on job boards; but in the absence of a crystal ball, there are usually hints that you can learn to recognize.

E.R. had some telling characteristics and Clooney picked up on them. The script was unique, risky and attention-getting. Moreover, the other people involved in the show were highly talented and had strong track records. And the reason Clooney was able to see these signs is because he had invested significant time and energy into learning the industry inside and out.

And another hint that this could have been the breakout opportunity was that Clooney hadn’t yet played a lead role in a major network drama. This would be a high visibility challenge. And sometimes when you feel overwhelmed by an opportunity, that’s precisely the sign that it might have major upside. A career move that makes you feel like you’re in over your head stretches you in new dimensions. So for George Clooney, E.R. was his breakout opportunity.

And the part that I always remember is that a friend of his handed him this script. And I think that underscores one of the most important things to know about breakout opportunities, which is: they don’t float in the sky like clouds. They’re always attached to people.

So we’re once again in this podcast coming back to the topic of network. If you’re looking for an opportunity that can change your life and change your career, what you’re really looking for is someone in your network who can tell you about that opportunity.

Reid Hoffman:

And all of the major inflection opportunities for me—in retrospect, breakout opportunities—came through people.

On my very first transition from coming back from saying, “Okay, I’m not going to be a philosopher, I’m not going to be an academic,” to, “What work should I be doing? I know I want to be working in the software and online stuff…” But it came through the freshman roommate of a good friend of mine to working at Apple and eWorld. And then similarly, you know, when I was doing my first startup, SocialNet, Peter Thiel came to me and said, “Well, we’re doing this thing called FieldLink (which later became known as PayPal). Would you join the board?”

Again, wasn’t like, “Oh my God, it’s going to be huge. It’s going to be PayPal.” It was, “Well, these are smart people. The first idea, which is encryption on—just encryption technology for mobile devices…total failure, not going to work. But, they’re going to iterate and try.”

And so you basically try to say, “Well, where could I stretch myself to get potentially breakout opportunities?” And those are where the kind of amazing things happen. And obviously it happens all the time with entrepreneurs, all the time with—whether it’s a financing, a realizational moment, a realization of a technology, a discovery of a co-founder. All these things always lead to some pretty amazing serendipitous recognition and then rapid movement towards a breakout opportunity.

And part of, of course, what we’re covering in The Startup of You is it isn’t just for entrepreneurs; everyone’s the entrepreneur of their own life, and that’s how careers work: to level up, to completely transform the next level of what you might be doing, what your potential might be, your economic potential might be, your autonomy potential might be your creative potential might be.

All of this plays into recognizing and then moving rapidly on breakout opportunities.

Ben Casnocha:

And it’s such an interesting idea, the connection between breakout opportunities and serendipity.

To state the obvious, when you go up to somebody in your network, you’re not going to tell them, “Hey, good to meet you. Do you have a breakout opportunity that could transform my life?”, right?

You’re building a relationship slowly over time. And as we talk about in the Network episode of this podcast, it’s  really important to take a long view to these relationships and to not be overly transactional. And so part of the benefit of building a long-term network is that these breakout opportunities can emerge very naturally or organically from the people you know, right?

When you met Peter Thiel in college, I don’t think in your first conversation you were talking about, “So in 15 years from now (or however long it was), you’re going to call me, right? And you’re going to call me with a life-changing opportunity. I’m going to say yes to that opportunity, right? And then ten years after that, we’re going to take that company public. Is that the plan for this friendship?”

You have to trust that serendipity can produce these sorts of breakout opportunities over time.

Reid Hoffman:

Exactly. And people can misgeneralize to saying, “Well, serendipity is just, ‘wait for it to happen’.” And actually, in fact, you can substantially change the course of your own luck. You can make it more likely you’ll be lucky. You can make it more likely you’ll find serendipity.

Prioritize, interact with smart, hard-driving, interesting people who are going and doing interesting things, possibly in the space that you would want to be doing them—possibly not in that space, but still potentially interesting. And to nourish those relationships as you aid and help each other—all breakout opportunities, as we say, are tied to people. Those can lead to those.

And like, for example, you know, even when Peter called me and said, “Hey, I’ve got this co-founder, Max Levchin. We’re doing encryption on mobile devices. What do you think of it as a business?” I was like, “Well, I think it’s a terrible business.” And it isn’t like, “Oh, maybe it’s going to be great.” This is terrible. Well, why do it? Because you’re going down the road with friends; they have a lot of potential; and usually you have to take some risks, you have to stretch yourself some. But those are what it’s worth doing.

And then—so one, you know, kind of the network of people, the network of intelligence as a way to doing it. And then begin to recognize, well, which things should you invest in? Which should you invest in heavily? Which risks you can take, which should you invest lightly in order to make it happen? And that’s part of the kind of the ability to suddenly find a breakout opportunity and then move very quickly and rapidly towards it.

Ben Casnocha:

You just hit on a couple of things there, Reid, in the Peter example that I think are worth explicating for folks.

So the first is that one opportunity will rarely knock at the perfectly convenient time for you in your life, right? Oftentimes, in fact, it’s just statistically likely that when you come upon a breakout opportunity, when you hear about a breakout opportunity, it will not be perfectly convenient. You will be annoyed. You will be—have just arrived in Paris for a three-week vacation and you will have been invited to an important dinner back home, and that could change your life, and you’re stuck in Paris. What to do?

Or you could have just started a company of your own and, you know, pledged down that path and then gotten the job offer of your dreams from the company you’ve always wanted to work for.

Or your manager might come up to you one Thursday afternoon and ask if you are around over the weekend to join him and a few of his colleagues on a boating trip. And getting closer to your manager could lead to a grand opportunity for you down the road, but you’re already booked that weekend. What to do, right?

So opportunity will knock at sometimes in inconvenient times. But the very nature of a breakout opportunity is that there’s a window of opportunity that’s closing, right? An opportunity that’s available to you today, next week, next month, next year, five years from now is probably not a breakout opportunity.

Usually a broken opportunity is something that’s perishable, right? It’s, “Do you want to come meet with me now? Do you want to work in this project next week? Do you want to work in this project this year with us in this team and build something? And if not, well, sorry, better luck next time.”

Reid Hoffman:

And I think part of that also is: breakout opportunities are the really interesting and almost never-sure things.

And you begin to learn what kinds of things to look for, like, oh, is it a major technological revolution? You see it early. Is it a team that’s forming around something that’s really compelling and you can join it early, or join it at all?

Is it something that, you know—kind of the being contrarian and right—something that you realize that the market may not and that you can go and do it before other people are, or before serious competition has set in, or before other folks have realized this opportunity?

And those always involve some risk. And while your network also gives you potentially amazing and privileged access, it can also help you assess whether or not this is something or not.

And so, for example, you know, one of the reasons recently I released some art with DALL-E and kind of NFTs and so forth. And as I realized that actually in fact there’s going to be pre- and post-OpenAI’s DALL-E on how we visually express ourselves.

Like if you say, you know, “A picture’s worth a thousand words; now I’m going to create a picture with ten words,” you’ve got a compounding effect, and what that’s going to mean in the whole world. So I realize that. So I put down other stuff I was doing and then worked really hard on kind of essays and images and, you know, saying what that is and creating NFTs around them and so forth, just to have kind of this early glimpse of how technology is changing things. Now, maybe I’m wrong, maybe it’s a risk, but it’s those kinds of things.

Ben Casnocha:

Yeah. For people who haven’t followed, you can check out Reid’s NFT collection of original art generated by DALL-E from OpenAI.

And, Reid, you launched this project at a very opportune time. There’s a window of opportunity for various reasons that made now a great time to launch this project. And it’s a great example of that opportunity; might not have been there six months from now.

And another thing you just mentioned, Reid, which I think is key, is risk. Any great opportunity will have risk associated with it. In the Risk episode on this podcast, I think we invoked or quoted Reed Hastings from Netflix—you know, the second most interesting Reid in the tech industry.

But Reed Hastings says that if you are not genuinely pained by the risk in your strategic plan, it’s not a very consequential plan. It’s not much of a strategy to talk about. If you’re not genuinely pained by the risk of a strategic plan, it’s not a strategic plan of consequence.

And so, similarly, when you’re evaluating different opportunities and you’re mulling to yourself whether a given opportunity might have breakout potential—potential like in the way that E.R. changed George Clooney’s career—could this opportunity change your career? You want to feel at least a little bit nervous about the risk you’re taking, right? It could be that you feel the risk is, “I don’t know if I’m qualified to do this job. I feel out of my element. I’m drowning in water. What if I fail like just from a competence perspective?”

It may be that you will have to postpone other plans that you had already made, and there’s a risk that those other plans might fall apart if you pursue this opportunity. It might be an opportunity that your friends or family or colleagues aren’t necessarily intuitively supportive of, right? And so you’re earning the disapproval of people who you respect to pursue this opportunity.

Whatever the risk might be, there’s going to be risk if it’s an opportunity of consequence.

Reid Hoffman:

Don’t try to avoid taking risk. Try to take smart risk where you understand the nature of the risk; you can mitigate it some; you can understand it’s a small risk for a large payoff; you understand you can pivot or change earlier on it. But actually taking risk can be part of the competitive differentiation, which then in turn can be part of the differentiation about realizing a breakout opportunity.

Ben Casnocha:

Now one of the concepts we introduce in the book is the idea of growth loops.

And growth loops is a concept that is prominent in our industry of venture capital and tech. But we wanted to introduce it in the book because we felt like it had broader application…that as people think about their careers and they think about breakout opportunities, if they can get involved in opportunities, that has a kind of compounding dynamic that entrenches their competitive edge, that has a sort of network effect associated with it, they’re going to be much better off as professionals.

And, you know, when I think about growth loops, you know, you’re the founder of LinkedIn, many of us use LinkedIn every day….LinkedIn is a great example of a company that has benefited from growth loops, right? Like, the more members there are on LinkedIn, the more useful that product is.

And I’m sure in the early days of LinkedIn, when there were only 100 members, people weren’t getting much value from the product. But today, what are we at now? 100, 600 million, 700 million members or something like that?

Reid Hoffman:

Over 700.

Ben Casnocha:

Now the network has just incredible value. And that growth loop of, “The more people on the product…it means the more valuable the product is to everybody, and thus the harder it is to disrupt….” That’s such a powerful dynamic in business and tech. It’s really interesting to think about how we can all cultivate that dynamic in our careers.

Reid Hoffman:

So, on the business tech front, part of the reason why when you look at a lot of the amazing fast-moving tech companies—also other companies too, but especially fast-moving tech companies—whether it was the distribution of browsers with Netscape; whether it was Yahoo; whether it is now Google and Microsoft or everything else is that they get a compounding growth loop.

The compounding growth loop can be—for example, on the LinkedIn thing, members—but it can also be engagement. It can be two loops interacting. So it could be, for example, the distribution of productivity software, together with the file formats within the OS, you know, kind of a classic Microsoft thing.

These loops are the things that can compound very rapidly at scale to very large volumes. The fact that the mobile world is primarily upon iOS and Android…this kind of thing creates these kind of compounding loops. And by the way, when you’re thinking about it as an adventure investor, you think about this as hugely valuable because part of where you get to the wisdom of folks like Warren Buffett and other things is: when you’re in something that’s compounding and it will continue to compound as it goes through scale, it is just awesome relative to impact on the world, relative to equity values, relative to number of jobs created…You know, all of this, the goodness of that business brings to our society.

Now, when you think about it, and you translate from this to individual lives, you’re thinking about like, “Well, life is, you know, work is a team sport, not just individual.”

You know, what is the compounding effect from the network that you end up building, which, you know, can create ties to breakout opportunities; can create enablement; can create network intelligence, all kinds of things.

You’ve got the kind of loops that play to when you learn something important, like, you know, for example, by having been early in the Web2 and resurgence…and not only created LinkedIn but also doing investing…then I became part of investing groups. I learned things from investing, I learned things from other entrepreneurs, I learned how to recognize really good investments, which is a rare capability. That’s one of the reasons why, you know, I think it was John Doerr who said, you know, it takes $50 million of failed deals to train the venture capitalist, and that was probably in old dollars; it’s probably substantially more expensive now.

Ben Casnocha:

We’ll check inflation rate later and update this episode.

Reid Hoffman:


And so—but you know, those kind of learnings for super important, very valuable skills…skills that can help society a lot; can help, you know, the allocation of capital to which kinds of efforts in which people should be ongoingly employed is very useful because…well, that business—not just for equity value, but it creates stable jobs and grows and creates the community around the people who have the paychecks and all this. So capital allocation to this kind of work can be super important.

And obviously within the fact that the new world will be constantly created by reinvention and entrepreneurship, both the entrepreneurs and the venture investors investing in them are part of how we create the industries of the future, the jobs of the future, the prosperity of the future. And so that becomes super important to our skill.

I kind of—again, breakout opportunities—learned it somewhat by accident, just because I was—had the theory that the consumer internet was not dead (as it was thought to be in 2002/2003), that it was going to have a massive resurgence.

And so I went around doing some angel investing. And by being—along with some of my friends like Mark Pincus and other folks—was doing this investment, that meant we were there at the beginning of this whole Web2, and meant that we learned these kind of key skills, which then creates the kind of compounding—this is kind of lengthy exposition of it—but creates the compounding that makes a huge difference in your career and what you can do in the world in economic results.

Ben Casnocha:

There is a ‘rich-get-richer effect’. And I don’t mean that just in terms of people getting richer in dollars, but just so many of these phenomenon—skills and access—compound upon itself now, and venture investing, for sure, founders want to take money from investors that have a track record of making great investments, and so certain investing brands can be entrenched for that reason.

And I think you mentioned, you know, network, Reid, and I think, you know, we keep coming back to network. I don’t know if our listeners are sick of hearing that word by now, but it’s at the center of this entire book, this entire framework, this entire way of thinking about your life in the world.

And network is really a compounding asset. And so when you’re thinking about a breakout opportunity, an opportunity that allows you to seriously magnify the size and strength of your network is really worth paying attention to.

And one of the ways that network compounds to connect to some other themes we’ve talked about, you know—in our network intelligence episode on this podcast, we talk about how to do reference checks. And your ability to successfully and effectively reference check is in some ways, in many ways affected by the size and strength of your existing network. Because when you do reference checks with people who you actually already know, you get much more honest feedback. More honest feedback leads to better decisioning on people to work with and collaborate with. Working with other people allows you to produce more projects and accomplishments in the world, which in turn grows your network, which in turns makes your network all the more valuable. The next time you’re doing a reference check to find the next collaborator and partner. And on and on we go.

That’s just one example of where the strength of a network can give people a leg up. As you’re evaluating a career opportunity, an opportunity that allows you or where you think it’s a plausible path to grow your network is key. And it also means that when you’re maybe negotiating a role with a manager or you’re evaluating sort of the specific scope of a role, adjusting the role so that it gives you the opportunity to grow your network would be a really wise thing to do.

So, for example, if you’re talking about a role at a company, and you have the choice of expressing a point of view that you would like to spend every Friday afternoon shadowing your boss as he or she goes and participates in a set of meetings—or you might ask for sort of a budget to go to a conference every month as part of professional element to meet people—you might get buy-in on the front end of your job opportunity, get buy-in from your manager, from your employer, that this is a soft asset you want to focus on. That this job becomes exciting to you if you can grow this specific part of your asset base…that would be something well worth negotiating for or codifying as you scope a tour of duty with your manager because it’s so valuable.

Reid Hoffman:

Success actually compounds. Part of the reason why they seek breakout opportunities early and success compounds is because you say, “Well, okay, let’s not just use ‘the rich get richer,’” because that’s usually, “Oh, you’re privileged and you’re born into wealth,” and so forth. But obviously there’s a lot of people—Elon to a huge number of other entrepreneurs—who basically had educated backgrounds, which was really helpful, and the ability to go take risks and make stuff happen, but did not start out rich at all. Started out middle class. You know, I, myself, am that way.

But the thing is, success does compound. So like one place we’ll look at it is like team sports. We say, you know, “Life works like a team sport.” Well, if you’re really, really good at playing basketball, then maybe you get inducted on to the Warriors and you get to play with Steph Curry and then you learn more from it. That’s part of the compounding.

So the same thing is true in like sports—the George Clooney thing. It’s like, well, once you get into a place where you’ve demonstrated a hit show, you’ve shown that you have market attraction and so forth—then a bunch of other opportunities come along. This is part of the reason why it’s so important to seek these breakout opportunities and work towards them, especially early in your career.

Ben Casnocha:

Beyond growth loops, there are some other attributes that tend to define breakout opportunities.

One of them is if you’re seeking or considering or have the opportunity to go pursue a job that allows you to build a set of skills that are highly transferable or have broad application—that can be really helpful. Especially early in your career where you’re not exactly sure what you want to do, you might be a little bit more experimental, you’re trying different things, you’re iterating through your Plan A, etc.

A job that—this is why so many people, I think, go into like management consulting and these sorts of things is because they can build a broad set of competencies, and that generally doesn’t necessarily predict a breakout opportunity, but it tends to be something that’s useful to optimize for first half of your career when you’re evaluating opportunities.

Another thing to look for when you’re evaluating the quality of an opportunity is an opportunity that will bring you into a white hot industry—an industry that is just rip-roaring with growth and energy.

We talk about in the book—and maybe we get to this in one of our episodes, Reid—about if you had the opportunity to be sort of a junior person in a really fast-moving market like the tech sector, the Internet economy right now, or a senior person at Kodak—much better for your career to pursue the less impressive title or the lower status opportunity in the fast moving industry.

And so any opportunity that can get you closer to the macro currents that are driving the world economy—driving human civilization—is an opportunity worth prioritizing.

Reid Hoffman:

If you think of this as kind of navigation—like Polynesian canoes upon the broad ocean—there’s navigation signs you can look for.

So one is like technology trends. If a new platform is opening up—mobile, A.I., cloud—any number of things…data as a new platform, video as a new platform—these can create enormous reshufflings and growth opportunities within industries. And then you could say, “Okay, it has that map to what I should do, which companies will be the ones growing or not.”

Sometimes, by the way, it’s like, “Oh, that’s a really talented team. That team I should go work with because they’ll figure it out.” I mean, that’s part of the ‘PayPal starts with just encryption for low CPO machines, turns into a global payment processor.’ That’s like, “Oh, this team I should work with,” could be another kind of recognition.

You know, there’s other things where you go, “Okay, well, actually, in fact, I think I know something big that the market doesn’t know.” So like when I was mentioning the OpenAI image generator, DALL-E-2, it’s like, well, most of the world doesn’t realize how this is going to transform kind of how visual design and work fits in all of our lives.

And people are saying, “Oh, well it’s going to replace graphic designers.” No, no, no. It’s going to be like Adobe. It’s going to be an essential tool for all kind of graphic designers.

And you say, “Well, I have a recognition. Well, what should I do? How do I build that?”

Now for me, I go and kind of like co-found an AI company called Inflection AI with Mustafa Suleyman. I help OpenAI, you know, do its various tasks. You know, I work at Greylock with a portfolio of companies, including Adept and others. That’s the way that I recognize and express it. This is one of the things where you have seasons of your career.

Like early in my career, it’s like, “Go find the right company to work at. Go find the right person to work with. Go choose the set of people that are in your network that you’re spending time with, having your interesting lunch fund, and going out and having lunch with to see what the signals are, and then to double down where the signals are really intelligent.”

And that’s why, you know, it’s not just, oh, you wait for serendipity, you really can change the nature of your own opportunities, your own serendipity, your own luck with some thought, with some energy, with some work.

Ben Casnocha:

Reid, you just mentioned in passing Polynesian canoes. Are those known to be the very best canoes?

Reid Hoffman:

Well, they were the early, kind of, just the canoe crossing the ocean.

And part of the reason I use that as a metaphor is if you think about being the entrepreneur of your own life in volatile and turbulent times, it’s an ability to cross oceans, to go do things…to not say, you know, “Look, I’m born in wherever town. All there really is here is a steel mill. And either I get a job at the steel mill or I don’t.”

It’s like, “No, no, no. You may have to cross oceans. You may have to be inventive,” because the ocean may not be simply moving from a town. That’s always a potentially good idea, but it could be the, “Oh, no, I’m going to start a new kind of business here.” Or, “My friend is going to start a new kind of business. I’m going to help them.” Or, “I’m going to recognize what business I could bring in the town from other places and bring that in as a way of operating.”

And so all of these are potentially ocean-cross things. And that’s the reason why the amazing success of the Polynesian navigators in a canoe crossing the ocean successfully and getting to another landmass—versus just dying at sea—was the reason I was using that colorful metaphor for the kinds of things we’re talking about in terms of navigating your career, navigating breakout opportunities.

Ben Casnocha:

I love that, and I love any metaphor with water. So I love the idea of canoeing across the ocean as an image for life. I think it’s totally apt.

And then just to amplify one other thing you said about tech trends, if you’re listening to this and you’re trying to understand what are some of these trends, what are some of the companies that are defining the future…A really easy thing to do is to go on to the websites of various venture capital firms; firms, for example, that we’re affiliated with like,, Entrepreneurs First,—a set of firms that do a lot of great investing in early stage tech businesses. Click on to their portfolio pages and look at the summaries of some of the early stage investments that these firms have made.

These are companies usually working on technologies that will not hit the mainstream for five or ten years. But it truly is kind of an early glimpse at the future. And generally speaking, where great technology venture capitalists are investing tends to be correlated with the sorts of trends and technologies that, you know, ten years from now, we say, “Wow, these are really shaping—these technologies are really shaping the world.”

It’s actually funny, I had a specific example of this today. I was reading an article about robots that were picking strawberries in agriculture. I saw someone tweeted out saying, “Oh my God, who knew, you know, robots could actually be replacing farmers in the fields picking strawberries. What a delicate task for a robot to be doing.”

Through the venture firm that I helped start, Village Global, we invested in a strawberry-picking robot company two-and-a-half years ago. And so you do really get this early glimpse and so track trends that way. Index off of VC activity.

Reid Hoffman:

Yeah, and it’s part of what we learn is how to get these signals because we talk a lot about network. But there’s other ways that with your network because…say compounding these two things, looking at the fact that all these VCs are are network nodes and assemblers of intelligence. They’re putting their money where their mouth is in terms of how they’re betting, so you can see.

Some of it is they’re doing podcasts and talking about it, so you can listen to it, but then you can also then cross-check that with your friends who say, “Hey, we both listened to The Startup of You podcast between Reid and Ben. What did you think? What did I think? Which part was really important? Which part was, ‘Ehh, no, no, I think something different’ or ‘They didn’t understand this opportunity that’s really possible.’” Then also—back to growth loops—leads to compounding.

Ben Casnocha:

Now, Reid, at the end of the Breakout Opportunities chapter in the book, we list a set of action items called ‘Invest in Yourself’. Any other action items on breakout opportunities you want to highlight for our listeners?

Reid Hoffman:

Well, one of the things that we were talking about in terms of compounding growth loops, which, you know, gave me a—just one more ways and our ‘Invest in Yourself’ opportunities that are meant to inspire and create new ones—not to be the only ones—is to say, “Well, where are the things where you might see breakout opportunities? What might be technological changes? Might be really interesting companies? What might be really interesting people?”

Write them—think about it—write them down for yourself, and then go talk to some of the other people you think have good network access, good judgment, good thoughts, good bold things, talk through them, make lists together, kind of come up with pluses and minuses for each of them.

And that might actually help you get a compounding opportunity because through your network, not only do you get access, but also an interesting judgment about what you pursue. And then that—adding that to the other kinds of things that we talk about in The Startup of You, like, well, that might lead to taking someone out to lunch that might be making a connection with the company that you hadn’t thought about just to see if there was any kind of interesting opportunity that you could possibly connect with there. And those kinds of things are part of how you cultivate serendipity that can lead to amazing breakout opportunities.

Ben Casnocha:

So just to recap and sort of summarize this conversation, you know, we began with the premise that the arc of a successful career is rarely slow and steady, up and to the right. Right? It’s actually punctuated by breakout opportunities.

If you talk to someone who’s really successful, someone you really admire who’s in their seventies or eighties, and you ask them to reflect on their career, they will probably point to a handful of these breakout opportunities that really defined their life and change the trajectory of their progress.

And then we talked a little bit about George Clooney and E.R. as one example, but we all can find an E.R. in our own careers. And just as Clooney came upon that opportunity from a friend, so many of the career- and life-changing opportunities that we find will come from people in our network.

So if you’re thinking about breakout opportunities that can change your career forever, you gotta think about your network. You gotta think about how you’re staying in touch with people you know; if you’re meeting new people on a regular cadence, how you’re staying in touch with those people; engaging with that network and leaning into the serendipity that can emerge from living a network life.

And then once you get some of those opportunities that emerge, we’ve talked on this episode about some of the things to look for that might predict breakout potential. We talked about the fact that breakout opportunities are often perishable, right? There’s often a window of opportunity that you have to seize.

Also, breakout opportunities tend to have some risk involved, right? If it seems easy, a no-brainer, don’t have to think hard about it—probably not a breakout opportunity.

And then we talked a lot about growth loops. The kinds of opportunities that can be game-changing are the opportunities that allow you to compound an asset that allows you to entrench more deeply in the industry that you work in. And so especially if that asset is your network, that can really give you a leg up over over others who you’re competing with.

Okay, Reid, so let’s talk about some of these questions that listeners have submitted over the last few weeks.

So here’s a really interesting one. The listener writes, “After listening to your episode on competitive advantage, I realized that my problem isn’t that my skills and passions don’t click with the market realities; my problem is that they do—too much. I have multiple skills and passions that can give me different careers, but I never lean in totally to any one position because I want them all. So I’ve changed frequently. Since I only have one life to live, and can’t have each and every career I would enjoy, what should I do?”

Reid Hoffman:

Great set of challenges and options to have.

Look, I think the macro thing is, kind of, what are your priorities? It’s always a question of tradeoffs. So some people, for example, encountering these set of circumstances say, “I really need to maximize learning. I want to transfer between things—a stable economic base or something compounds or ability to get to know more of a position of calling the shots is less important, and it’s more important to do the other.” Which tradeoff and risks are you going to take?

Now if it was me in this circumstance, I would kind of say, “Well, alright, I know that I have to have tradeoffs. I know that I can’t have it all. What it is is there are some concrete things that I really want to achieve.” So, for example, for me—when I was a young person—it was how to take these ideas that I have in my head about how we can really help, you know, individuals and groups and society through crafting new products, new services, a new medium in which we’re interacting together.

So, what would be the sequence in that? And then do those sequence, and some of the skills get traded out, and you have to really commit to a set of positions because if you’re kind of a little here and a little there and a little there, you’re very rarely the center of a project. The extreme edge of that is being an entrepreneur and a founder, because, generally speaking, when you’ve found a company, in a success case it’s 10+ years, sometimes even 20+ years in terms of what you’re doing, and that’s the focus of it.

But, you know, obviously that’s an extreme edge of that. And it could be the the question of, “Well, I’m doing five or six years here and then related, I do this next five or six years within this overall plan.” And, you know, you can have some evolution in doing that.

But I think it comes down a lot to what are your priorities and which risks are you willing to trade off in order to get there?

Ben Casnocha:

I think your point on sequencing is spot on. Obviously, you can’t do everything at once. It’s awesome that this listener has so many ambitions and ideas and visions for their future. So the question that I’m asking is, “How can you be strategic about the sequencing?” Like, is there a logic to do one thing now and a different sort of career path a little bit later?

One thing I’ve been thinking about in my career some is that—currently working full time in the tech industry, which is very biased in favor of younger people, right? There are a lot of young professionals. It’s not uncommon in my business to meet with 21-year-old entrepreneurs creating tech companies, raising tens of millions of dollars in venture capital.

You can be 21, you can be 31, you can be 41, you can be 51, and be very, very successful in the tech industry. There are some—but there’re not as many people—in their sixties, seventies and eighties creating tech businesses. By contrast, there are lots of people in their fifties, sixties, seventies, and eighties writing books, contributing deeply to other sorts of fields.

And so one way I’ve thought about this question for myself—because I really empathize with the listener’s multifaceted vision for themselves—is in the first half of my life, I’m going to focus on industries where my relative youthfulness can serve me, or at least not debilitate my ability to be successful, which right now is tech, entrepreneurship and investing.

And later in life, where it’s much more common to be writing books and other things that I’d like to do in my future (i.e. in my sixties, seventies and eighties), can be a fine time to write that novel that we have inside of us and actually be respected for having done that.

And so maybe focus on the things where there’s some external market reality that cause now to be the time to do one thing and perhaps later to be the time to do the other thing. Do you think there are other strategic lenses, Reid, that one could apply to figuring out the sequencing question?

Reid Hoffman:

Well, I mean, I think the sequencing of thinking about it is a serial thing in which things should go before others—and one lens to that is, you know, which tasks work, places where you can get a competitive edge, depending on which age you are, and kind of what the trade off between energy and drive and experience and skills are, which is kind of what you’re arching.

But I also think in that serial time, which things are important to do first, like which things might be either just the timeliness of opportunity now or which things might be, you can build on it.

Most often, I think part of the mistake that we’re trying to nudge against in this is to say, “Well, the most important thing is to follow your passions.” What we’re in part saying is, “Well, the most important thing is to be somewhat strategic while following your passions.”

So you say, well, for example, “But I really want to write the great American novel.” It’s like, “Well, that may not be the right thing to do to start out when you’re 21 or 25. There may be better ways of getting raw economics in some position within an industry and a workforce and then be able to build towards writing the great American—or the great whichever country—novel as a way of doing it.”

And that—being strategic about that is part of the reason why we do this. You know, what are the market realities. What are the competition? What are your assets? What is your drive in terms of where you’re going? And that strategic sequencing is very important.

Now, the reason I started with saying, “Well, what are your particular goals?” is strategy is towards a goal. And some people, you know, think, “Well, the goal should be maximum ability to retire early and comfortably.” Other people say, “Actually, in fact, I’m totally willing to risk that. The real question is who I’m working with. The real question is what I’m learning, or the real question is what I’m actually making in the world.” But each of these can be approached strategically with those goals, with a sequencing and a strategy in mind.

Ben Casnocha:

Yeah, for sure. And I think if somebody had clear conviction that one career path or one vision was definitely more compelling than another—if it was easy for them to rank order, then you should definitely try to do the thing that you care the most about as soon as possible, because life’s short and you never know what can happen and you don’t want to live too much of a deferred life.

So if there’s a clear winner for something that you just really want to do, assuming you can square it with the market realities and leverage your assets, you know, do that thing now, don’t wait.

But if you’re contemplating four or five different paths that you are equally interested in, and perhaps equally capable at, and equally have a thesis for how you could be successful, then I think applying some of these other prisms around, for example, age and demographics in the field that you’re interested in or what have you, or just being purely opportunistic about it.

I have friends that—they can’t decide between doing A, B or C, so they pursue all three kind of simultaneously until they figure out which one has the sort of most mojo that presents itself kind of randomly or serendipitously. Then they just pile into that plan and they do the other plan later, right? And so they can kind of be a little bit reactive. But it doesn’t matter. All plans are equally good and so they throw themselves into the one that happens to pick up the most energy.

One other comment, Reid. Not sure if you ever saw this commencement speech. It came out 10 or 15 years ago. It was called the ‘Centenarian Life Strategy’.

And the thesis of the speech, which was really novel, was—this is a neuroscientist who did the speech. He said the great problem in modern career strategy is that people still assume that lives are lived to be 70 or 80 years old and that careers end at 55 or 60. And a centenarian life strategy is a life strategy that assumes that you’ll live to 100 with an active fourth quarter, meaning you can actually do stuff in your last quarter. You won’t be relegated to a wheelchair watching TV. You can actually be very, very active in your later years.

And if you take that long view of life—which of course is probabilistic, anything can happen. But, you know, knock on wood. So if you take that long view, and you are excited by modern medicine and the ability to allow people to work late into their life if they so choose, you actually have a lot of decades to work with. You don’t have to do everything in your thirties, forties and fifties.

You could actually have an encore career, as a friend of mine likes to call them; an encore career in your sixties, seventies and eighties, and actually pursue an entirely different set of passions and vocations. And I think just remembering that and sort of reframing perhaps then the sense of urgency that you might feel to do all of your key passions right now can be really healthy.

What’s your kind of mental math in your head for—how old do you think you’ll live to just in general then do you think you’ll be working till the day you drop? Or do you have some vision of like, “Okay, I’m on the beach?”

Reid Hoffman:

Well, it’s definitely not a beach because beaches can be—you know, while relaxing—a little boring. I guess what I would say is that I tend to think that I’ll be fairly mentally competent and functional into at least my early eighties and so will be generating things.

I’ll probably be slowing down at some point, just from the prediction of looking at other people who have, you know, walked this path ahead of me. And, you know, if I’m really lucky, I maintain strong mental coherence into my nineties. And, you know, health is kind of a little bit of a function of rolling the dice on the various organ systems, whether it’s, you know, heart, liver, other things…you know, a little bit of the—you know, you don’t know when you’re, you know, playing that.

And I think that it’s worth having that thought even when you’re much younger and actually finally, you know, kind of thinking about the number of days that you have in front of you, like multiplying number of years and days, because that at least gives you a sense of no day is free. It’s a choice for what you’re doing and you should be somewhat strategic about it.

Ben Casnocha:

Okay. Well, thank you, Reid. It’s been a fantastic conversation.

Reid Hoffman:

Ben, awesome, as always. And thank you to our listeners.