Okay, Reid, in this episode, we’re going to talk about portfolio careers.
No, not stock portfolios or VC portfolios of startups that VC’s invest in. We’re going to talk about portfolio career s.
Now, this is a concept that’s gone by different names over the years. My friend, Marci Alba, her—wrote a book about “slash” careers, people who have a “slash” in their professional identity. There are solo entrepreneurs; there are these creators that call themselves “multi-hyphenate professionals”.
And we know who these people are, right? These are the foodie influencers/radio producer/translator. This is the person driving Uber, delivering food for DoorDash, and writing the Great American novel. This is sometimes really accomplished investors who write books on the side.
So sometimes there’s a side hustle involved. Sometimes it’s actually meaningfully two or three jobs happening in parallel; you know, 20 hours a week to one thing, 25 hours a week to another thing. And the rise of this phenomenon—the career landscape—comes from many different factors, right: the distributed workforce, globalization, the rise of the creator economy, the rise of the gig economy…
And some estimates put that in the American workplace, half of all Americans are actually independent contractors today. So for all the time that people spend talking about W2 employees, half of Americans are 1099 independent contractors cobbling together multiple streams of income to make their career work.
And so if you are one of these people—or you’re thinking about becoming one of these people—we want to spend some time in this episode talking about the ways you can make a portfolio career work.
And, Reid, today, you arguably have a very portfolio-y career. You are dividing your time and attention across, oh, just a couple of different pursuits in parallel. But it hasn’t always been this way for you. You’ve had chapters or seasons of life where you’ve been more or less hyper-focused. And then you’ve had seasons of life where you have been much more diversified in your portfolio.
How do you think about that and how has this concept sort of manifest in your life over the years?
You know, mine—and I think, you know, other folks like me—as I’ve gotten kind of more established in, you know, kind of my network and what I do, is obviously started by being really focused versus an employee…kind of working as a user experience designer and a product manager, and doing some stuff on the side to learn—like talking to people, like what’s going on in technology, what’s going on in different places, how to think about the jobs, how to do these better, what are the things that large companies do better, what are the things that small companies do better—all the stuff I was doing very early.
That then of course led to being an entrepreneur, which is when you are super focused ’cause, you’ve jumped off a cliff, here’s someone on an airplane on the way down, and you really don’t want to hit the ground.
And so you’re turning a ton of things into that. Now, even that, I’d say I started learning some things within kind of what you would think of as a portfolio career ‘cause I said, “Well, as I’m doing that—giving a little bit of advice, doing a little bit of angel investing—just some to get a breadth of perspective,” which also helped me on the thing I was focusing on.
So, for example, when I had founded LinkedIn, I was also doing some angel investing, ‘cause I thought that “Okay, here’s—”
Web 2.0 was coming, and there’s a whole bunch of things. And by meeting some entrepreneurs—that was almost always early Sunday afternoon ‘cause it was like a very limited time slot and I want to make it happen and that gave you something of a portfolio.
And then that has grown somewhat strategically and somewhat serendipitously and somewhat accidentally to now a broader thing where I do some things in a 501(c)(3) world. I do some things in investing, some things for society—I’ve just gotten back from a set of conferences in Aspen about how does technology play into the kind of things that make the country better, and make work-life paths matter, and make the world work in a better way.
Well, it is interesting that earlier in your career, when you’re CEO of LinkedIn, you ran a very focused life. And even people today who famously run portfolios—like Richard Branson or Elon Musk—there was a time in their careers when they ran very focused lives, right?
There was a time when Elon was not CEO of four companies at once and trying to buy Twitter and all the rest. He was focused on X.com, and so for you, Reid, you were an employee at Fujitsu and Apple. Then you were co-founder, CEO of two companies, totally focused.
And even then as you began to broaden your aperture—like running a tech company and doing tech angel investing on the side is a very synergistic activity. Like, it’s portfolio-ish, but it’s highly integrated to your main thing.
And then all the way, fast forward into the present: your current portfolio as I perceive it is really diverse. It’s not actually as synergistic as it could be, but that’s because this is the life that you want to run, and you have a lot of different interests, which is fine.
But you’ve built a track record and a level of success that allows you to actually do a set of seemingly unrelated things, from national politics, to philanthropy, to tech venture investing, to tech entrepreneurship, to other public intellectual pursuits, and writing books and all the rest.
And so in the same way that Elon and Richard Branson today run a really diversified set of portfolios—and you do, too—I think it’s worth underscoring that earlier in all of your careers—and I think in most successful people’s careers—they actually had to apply real focus to establish that credibility.
I think that’s totally right. I think even now there’s maybe more method to the madness than might seem from the outside, which is: what’s the way that it composes? How are you being strategic about? What’s the true line?
So, for example, I don’t go and do any piece of—I mean, look, obviously I’ll try to help for society as where and when I can—but I try to apply to where I have some highly unique differential assets. Might be in entrepreneurship; might be in technology; might be in how AI is going to affect a lot of different systems.
And so I try to do much more of that in everything that I’m doing, you know, and kind of have clear lines where there is an application of kind of some compounding leverage or synergy, or the fact that the things that I’m learning or doing are uniquely well-applied here.
In the book The Startup of You, we propose a framework for thinking about the continuum of focus to portfolio, because there are gradations here.
So in one of the—spectrum we talk about ‘laser careers’. These are people who are maniacally devoted to one job or skill. All of your eggs are in one proverbial basket. You’re all in on your job.
Then there’s what we call the ‘main thing career’. These are people who have their Plan A, right? They have an existing implementation of a competitive advantage. But they might have a side hustle or two, right? This is the person that works an intense job, but on the weekends they’re trying to write a book. Or on the weekends, they’re driving Uber, or whatever might be. But there’s some significant, singular side thing. That means they have a main thing and they also have a side thing.
The final end of the continuum is the true portfolio career which is, you know, 15% of your time to this thing, 23% of your time to another thing, and it’s the full portfolio. Any part of that continuum can work. It’s worth, as always, in The Startup of You framework to be sort of intentional and thoughtful about where you want to be on that continuum and what best suits you.
There are some people who are so sort of ADD at a macro level—they have so many different interests—that they love and thrive on the portfolio life. But again, just to make the point about Elon and Richard Branson—and even, Reid, your career, I’d argue—a lot of really successful people in the first half of their career lead rather focused lives. They tend to specialize, they tend to get good at one or two things, they tend to throw their all into that thing.
And to run a high-end portfolio life—and I say high-end to distinguish from less renumerative gig economy jobs, which nothing wrong with that, but I think most people who are driving Uber or DoorDash, they aspire to get out of those side gigs eventually.
To run a high-end portfolio career does require some track record of success. It’s kind of a privileged place to be. And so if you’re in the first half of your career and you aspire to do six different things at once, we might encourage you to start with focusing on just the one thing in that portfolio that has the most promise; get really, really good at that; develop what we call in the book—quoting another author—“career capital”; accumulate that career capital to earn the privilege of being able to, say, Reid, live your life as you have it today.
Well, and I think part of that is we’re recommending to be strategic in the way that entrepreneur is strategic. And frequently, by the way, being very focused—and getting the thing you’re doing to get you to a different level; to a different set of potential; a different network; a different set of soft and hard assets that can make you, enable you to do other things, is that—like really key. And focus is frequently a really important part of that.
Now, sometimes you might say, “Well, I’ll choose a portfolio life because I’m spreading out my energy some for different optionality or opportunity.”
And an example of—for me for that was, “Alright. I’m starting SocialNet. I’m doing that, making it happen. I’m intensely focused. It’s, you know, 80-100 hours a week.”
But then, you know, when my friend Peter Thiel comes along, and, you know, says, “Hey, I’m going to go and—I’m thinking of going and starting this company,” it’s like, “Okay, I’ll start as an advisor. I’ll spend some time helping you with this because it gives you [me] some”—and, you know, eventually joining the board of PayPal—“this gives you some breadth of learning, which helps you some breadth of optionality,” ’cause, you know, I ended up, you know, being part of the founding team.
And then stepping off the board and joining the company as a senior executive, and these kinds of things as some selective portfolio…that’s also in the theory about how one year, three years, five years from now, your position for what you want to accomplish is much stronger. Sometimes there’s some selective portfolio, which is that breadth of learning, that breadth of optionality, and that being important. And by the way, that’s still within an intense area of focus.
One challenge people sometimes have with the portfolio career is about their identity. Right?
They don’t really know how to describe what they do when they’re doing six different things at once. It’s kind of funny actually. It’s a common critique, Reid, I’m not sure if you’ve heard it about LinkedIn, the product.
And this is, I think, a little dated now ’cause I think the LinkedIn profile has evolved a bit and what it can accommodate. But there are people who run these portfolio careers and they say, “I don’t have just one job. What am I supposed to list on my LinkedIn profile?”
It’s a common attack vector that startups who are trying to compete with LinkedIn go after as they try to serve—I see it right now among creatives and the creator economy. Like, “Hey, how can you display your portfolio of work and profile the six different parts of your skill set?” And they’re trying to build a product to enable folks to do that.
I think the LinkedIn profile has evolved to allow people to post information about a diversity of skills and feature their portfolio of creative output if they’re in that kind of work.
But I do think there is this essential question, which is: how do I pithily express what I do every day if I’m doing so many different things at once? And it strikes me that a lot of the traditional career advice does presume a singular j-o-b, and makes it difficult for these people.
And, you know, again, I come back to, Reid, your headline on LinkedIn. We’ve talked about this before, but remind me; it’s “Entrepreneur. Product Strategist. Investor. Podcaster.” Is that the four?
Okay. So you have at least a multilayered identity that you just lay out in very close terms: “That’s who I am kind of in a nutshell in this moment.”
And I think that’s actually kind of best practice. I don’t think we need to overthink this like the—if you’re running the portfolio career, you don’t have to figure out like the one adjective or something that captures your essence. You can just tick off the three or four things you do.
But what do you think, Reid?
Well, I think—obviously we’ve worked on this a lot together, and I think everything that you have said is right.
I do think the important thing is to have, as it were, a strategic plan. What is the thing you’re doing? Sometimes that’s being 95, 99, 100 percent focused.
But even if it’s multiple things, don’t do the multiple things ’cause it’s like, “Well, I kind of like this a little bit. I like this a little bit. I like this a little bit.” Be thinking about where you’re moving to; where you’re going to be in one year, three years, five years…It doesn’t have to be exactly here because staying open for serendipity, and learning and discovering new things about yourself for the path you’re on can be really great. But you need to be thinking about that and even in a portfolio-like circumstance.
And so, too often people can say, “Well, I’m paying the bills. And I make it happen because I’m doing all these different things.” But if you’re not thinking about like, “Where does this leave me in the next phases of what I’m doing?”, then you may have a serious problem.
One thing in the laser career/main thing career portfolio that I think is interesting is there are certain career paths where you can apply laser focus to that job, but the job is itself inherently a portfolio.
So venture capital is one example here, Reid, that you and I know well, which is: for a VC to be hyperfocused on their venture portfolio is to be involved in a broad portfolio of companies and things. And that’s one way that I’ve personally tried to wrestle with this because I think if I could wave a wand, I’d love to have a portfolio of six different things going in parallel. Sounds great, right? We all have lots of interests. “Oh, it would be super fun to have breakfast with this kind of person, lunch with a different person in the afternoon, work on something different.”
And so part of what appealed to me about the venture business is the fact that you invest in lots of different sorts of companies, you can meet different sorts of entrepreneurs all around the world, different sectors focusing on different problems.
And so it produces, kind of, some of the emotional effect of a portfolio even though I think of myself as living a very laser-focused life on just this one stream of work.
And I think journalist also is another example of an industry where this is true, where you can be all in on journalism, be completely focused on being the absolute best journalist in the world you can, and what are you doing as a journalist? Well, not always, but oftentimes you’re canvassing a broad set of topics and subjects.
And so if you’re the kind of person who has a lot of interest or a lot of curiosities, but you’re also the sort of person who perhaps thinks that focus is called for at this point in your career—again, if you’re earlier in your career, we’d advise more focus rather than less—think about picking jobs or professions where the focus job is itself a set of really diverse activities.
And I think one of the things to really be thinking about is, like, what are the things where you accomplish where—like if you use a journeying thing—what’s the hill you can climb where you’re suddenly in a much better vantage point? You can see the world in a better way, you’ve got some elevation on the problems. Maybe you’ve climbed to a village and you have some colleagues and friends that have gone on the journey, or you’ve met there as part of it…
Thinking through those are the kinds of things you’re doing and frequently—you know, as you’re saying, Ben—you have to be very focused in order to do that. Usually if you’re like climbing Everest—super challenging, you have to be really focused on doing it—but also even when you think about what are the kind of the breadth or other options, or experimenting with different paths or everything else…you still have an overall thought and plan for where you may be going and what you may be doing.
Yeah, and I think one of the things to keep in mind at a practical level: if you’re running the portfolio career, you’re working on lots of different things. Think about how you can organize your efforts in some sort of coherent way to minimize context-switching and allow you to sort of chunkify the efforts.
You know, when I think about it, a friend of mine who’s—is trying to write a book on the side, to write a novel. She works in finance by day; she’s trying to write a novel by night. She does the novel-writing on the weekends.
Now, this might seem obvious. But, there is something to batching work. Again, we’re all different, know yourself; some people love doing an hour a day, and no matter what.
But if you have multiple activities—you have a main thing and a side thing, or you’re running a full portfolio—see if you can get logical about how that gets organized. Context switching every hour of the day between all of the different parts of your portfolio is more likely to exhaust you, less likely to produce success.
Yes, and—for example, again, it’s like: what are the things that are the key things to do and make sure you stay focused on them with whatever else you’re doing. And I think—and a little bit of our discussion is kind of emphasizing because it’s so easy to get distracted by a number of things of being focused.
Sometimes, by the way, you may be too focused, and you may miss out on opportunities. Focus is extremely important, but also, you know, if you look at the other side, it’s again this kind of balance of: how are you approaching the path that you’re on, such that, you know, one year, three years, five years…by being strategic and thoughtful and by putting in some risk, and putting in some work, and putting in some energy, and putting in some focus—but also some looking around—you can, you know, have an amazing career.
Yeah, I love that. And it’s sort of returning that spigot of serendipity and randomness. And so if you’re in a laser-focused career right now, and you’re all in, and that’s the one thing you’re doing, think about the weeks and the months and the years when you should open up the spigot a little bit, and pick your head up, and introduce some diversity or serendipity in your life.
When I think about the topic of portfolio careers, I do think—you know, when I reflect to myself and how I’ve struggled sometimes with this over the years—it’s so tempting to want to do portfolio because it maximizes optionality—or so you think, right?
Oftentimes when we struggle to decide, we say, “Well, I’ll just do everything.” And for anyone who’s been—as I have been—where you’ve debated, “Gosh, am I more passionate about X or Y? Am I better suited to do X or Y? Is the market opportunity more at A or B?”, it can be hard to make a decision.
And sometimes the easy way out is to say, “I’ll do both,” or, “I’ll do all three,” or, “I’ll do all four.” But sometimes maximizing optionality in the short term is the very thing that minimizes optionality in the long term. Sometimes, laser focus on something in the short term is what produces 10 different options, so you can run the Reid Hoffman-style portfolio in your fifties.
And so, I often find younger people—when they think about their careers—who are running versions of a portfolio, they do so not out of great strategic insight, but more a inability or an unwillingness to make a hard decision to accept the short term trade-offs that choosing entails, and I think that’s very shortsighted. I do think they’re limiting their ability to have a really epic portfolio later in life.
Yes. That reminds me of something you’ve heard from me before, which is one of the best pieces of advice my father gave me, which is: the difficulty of making decisions in the short term is you’re reducing current optionality. And people have—legitimately—concerns and difficulties about doing that.
But if you don’t do that, you’re then going to reduce long-term optionality, long-term opportunity. So part of making a decision now—and making a decision, focusing on it—is what gives you that amazing opportunities and optionalities in the future. And so you deliberately need to push yourself at least mildly to do this and have the discipline of making decisions.
And some would say—some cultural critics that would look at our sort of secular society today, and ascribe much of its ill to an unwillingness of young people today to make any commitment at all—to a spouse, to a family, to a community…it’s kind of…optionality is as hot as it’s ever been, and I think a lot of people who think that they have it all right now are the very people who are hesitating to commit to anybody, any community, any career.
And they’re sort of living the four-hour workweek, global nomad life. And there’s a lot to like about that life, at least in certain stages of your career in life. But don’t delude yourself that that doesn’t come with tradeoffs. And sometimes making a commitment and reducing the number of people who you can be in a relationship with; the number of jobs you can do in parallel; the number of cities you live in at any one time…sometimes the more boring configuration of those things is what creates the stability—especially economic stability—that allows you over time to really have a super compelling career portfolio.
You know, the parallels between some aspects of romantic life and work life are serious, and part of having an in-depth relationship that grows and compounds over time…it could be people you partner with and work with—there are people I’ve worked with at SocialNet, then PayPal, then LinkedIn, like my cofounders, Jean-Luc Vaillant and Allen Blue.
When you have those in-depth kind of relationships, it makes the whole journey—makes more successful, makes it more fun, makes it more meaningful…And so those kinds of commitments—not just to yourself in the path that you’re on, but also the people you’re going on the journey with—can lead to absolute epiphanies and delights.
It’s a great point. That really, the deep, deep alliances that you build in your career are likely built when you’re in a focused mode because the number and depth of those activities with those people are going to be, by definition, super focused, super intense, right?
So all the—the relationship you just mentioned, Reid, is a great example of that.
So, okay, Reid, this has been a great conversation. Just to recap for the listeners, portfolio careers is a modern career phenomenon. In the book, we talk about the difference between laser careers—being hyper-focused on just one job; main thing careers—which is you have a main thing, and you have a side thing, a side hustle, backend work; and true portfolio careers—a career in which the income that you generate in your identity is split across many different facets.
And there’s no one right path for you. It just depends on what you’re trying to do, where you are in your career. And it’s okay to evolve from laser to portfolio, back to laser, maybe to a main thing career.
So be aware of this as a phenomenon. As our advice, be intentional about which sort of mode you’re in, and be ready to accept the trade-offs that come with all of these paths.
Laser career paths sometimes can be a bit boring if you’re just thinking about one thing for years on end. The flip side of that is you can develop incredible specialized skills and incredibly deep network, incredible credibility in the thing you’re working on, and more likely to achieve success and impact in that thing.
By contrast, a portfolio career can be incredibly stimulating, invigorating, allow you to try and do lots of different things at once. Can also be less economically stable at times depending; more confusing in terms of your identity; likely shallow relationships with a wider number of people in your network.
Pros and cons to each of these paths, but be prepared to be part of all three of these strategies, or to implement all three of these strategies to different points of your life. Certainly, Reid and I have over the course of our careers, and it won’t surprise me that looking forward, we might become more or less focused at different points depending on the opportunities and how we’re changing and how the world is changing.
Question from a listener.
They say, “This is kind of a generational question. I’m not trying to reignite the tensions between boomers and millennials. But, as a millennial,” the listener writes, “it is frustrating to me to see some older people in positions of power who refuse to pass the baton to younger generations who are full of energy with new visions for the future. I know they know things that I don’t know, but it also feels like they hoard control. How can cross generational collaboration work better?”
And I wonder if this question should be addressed to our leaders in Congress, who know a thing or two about hoarding control among people in their eighties.
But, Reid, what’s your sense from the millennials out there? How do they connect with their older coworkers and not offend them, but also lightly nudge them to pass the baton when appropriate?
Look, it can of course be frustrating. And it’s of course frustrating ’cause all of us—including us, you know, old fogies—were once upon a time young Turks facing a similar kind of thing.
And so it starts with kind of an understanding of compassion or what the kind of circumstances are because the older generation talking to you is someone who’s put in decades, who’s paid dues, who’s generated a bunch of experience…to whom their meaning of life may be very well doing this work right now, and even then you go, “Look, I’m young, and I’m aggressive. I’m capable of it right now.” It’s in your interest more than theirs for them to hand that over, unless they think that’s the right thing for them to succeed in the mission that they’re doing.
I’d say there’s a couple of things. One is, generally speaking, picking your manager, picking the people you work with is, I think, a really central thing for happiness development skills. And so, pick people who want to see you grow, who want to give you that chance to do something amazing and to grow really fast.
‘Cause there are also a lot of folks who go, “Hey, if you can accomplish all these amazing things, that’ll be great for me too. And that’s what I want.” And so, pick to work with folks like that. If you don’t have that opportunity to fully pick, then, you know, kind of prove yourself. Put the energy in. Do the things that usually you have to go, you know, 10 extra miles in order to do that.
But that 10 extra miles is part of how you make progress, and you learn, and you do amazing things within your career. When I was just starting in my job at Apple, I would volunteer to write project requirement documents, I would do other kinds of things, as a way to kind of go, “Look here, I’m dedicated, and I’m energetic, and I’m really working on this stuff,” and that’s another one.
And then realize that while you don’t have to be patient and wait your turn, as it were, you want some balance of working and proving and paying your dues, and, you know, kind of demonstrating that you can do amazing things as you’re given more autonomy and authority to do so.
Do you think age and wisdom are correlated strongly?
Well, it depends. I think one of the things we put in the book was, “Do you have 10 years of learning or do you have 10 one-years of learning?”
Yeah, “One year of learning repeated 10 times.”
Yes, exactly. So, age can be correlated with wisdom if a person’s been learning a whole bunch. And I do think that one of the things you generally have to think about when you’re younger—I certainly had this experience, looking back—is when I was 22, I probably thought I knew everything, and actually in fact I didn’t.
And you—always be interested in: what are the things that I don’t know yet? What are the unknown unknowns? How do I learn them? You know, now at 55, I’m still doing that, right? Like, what are the things that I need to learn here?
And so I think there’s a kind of a wise mindset, a permanent beta: always be learning. Different people have different levels of speed at which they learn wisdom. But, you know, when you have a bunch of experience that you have in fact learned a bunch of new things from…that can add to your wisdom store, and so can be lightly correlated with age in selective instances.
And I wonder if there are types of wisdom that’s hard to articulate. Like, I suppose the most optimistic story—that if you’re young and frustrated at the workplace because the old fogies are hoarding control and you think you’re better than them…I mean there’re a bunch of things you can do, but if you need to stay in your current environment, and figure out how to work collaboratively and respectfully with those coworkers, one story you could tell yourself—and I think it’s a story that happens to be true, at least in some circumstances—is that sometimes the wisdom that comes with age is hard to articulate super crisply.
And I’ve learned this myself as I’ve gotten older and now I’m working with people who are 21, 22, 23, 24—very common in the tech industry—and there are things that I am intuiting that I know are just wrong or right or whatever. Maybe I’m just not taking the time to fully articulate it. I think it’s the wisdom that came with a set of experiences that I had that they don’t have, and that imbues me with some sense of superiority in those circumstances. And I look back and say, “Oh, I don’t think when I was 21 or 22, I had an appreciation for that.”
But I’m—and I’m sure as I was talking to some folks who were two, three, four times my age, they were probably having the same thought process that I now have. Now, of course there are tons of circumstances where it’s not correlated at all; that actually the fresh thinking, the beginner’s mind or whatever, is much more valuable. So I don’t mean to say that if you’re 25 and frustrated at work, you should just shut up and take it from your 55-year-old manager.
But, there are some circumstances and some forms of wisdom that are hard to articulate.
Yeah, and I think the other thing to always ask yourself as a question is: what can I learn from this person, right?
And to actually ask that, not as a skeptical question—“What can I learn from this person?!” It’s the: one of the things, you know, this person—you know, that you’re working with—has been going through life, chose an an industry, may have had some success. What are the key things that they have learned, that you can learn? And that’s, generally speaking, a very good approach.
Like, for example, almost everyone that I interact with—as you know, Ben, since we’ve done this a lot—is I have questions, that I have a theory that they may actually really be able to add something to how I understand the world by asking those questions.
And so even when I’m kind of being driven around by a college student, I will start asking questions like, “You know, so how do you think about what’s going on in society today,” and “How do you find universities today?”, and, “And when you use a mobile phone, what do you think is you use the mobile phone that you think is different than the way that I use the mobile phone? What is the way that you think about your friends or your peers differently because of using, you know, App X, Y, or Z?”
And, you know, having those questions—and learning from them—and so if you can’t imagine what questions you could possibly ask that you would learn something—’cause that’s a little way of doing it—then there may be something where you’re not leaning in and learning enough and being intellectually curious.
Because, you know, almost for everyone—I’ll share a kind of a small example that I thought was kind of funny is: I ended up late one night coming back from an international flight where I had to be waiting with a customs officer. And if you’d ever told me I’m gonna be waiting with the customs officer, I would been, “Uhh.” You know, I try to get through as quickly as possible, get on the rest of my life, and so forth.
So I’m sitting there, and I go, “Okay, well, what’s a kind of standard question I would ask?” I say, “Well, what’s some of the most weird stuff you’ve seen come through?”
And I got this whole like 30 minutes of really cool stories: anything from like monkey’s hands, to fake currency that was for weddings for burning and all that, and what the interactions were like, and so forth. And it gave me some snapshot to what the most unusual experiences of being a customs officer with people from various cultures coming through was.
And that was something I learned and I never even expected it. I just—I sat there and said, “Okay, what questions could I ask you that would be really interesting for something to learn?” and that plays to how you interface with everybody in your life.
I love that, and it’s useful for everyone to have in their back pocket—perhaps some questions that they can apply in those circumstances. So some other concrete tips along those lines, Reid, ’cause I love the story: you could ask somebody, “What do people frequently misunderstand about you and who you are in life? What do people misunderstand about your profession? What do people think the customs officer does all day, and they just get it wrong?”
You could ask them how they get better at their job. I’ve always loved the question—I think it came from Daniel Gross and Tyler Cowen—they say like a pianist practices scales to get better at playing the piano, what do you do to get better at your job? Like understand sort of the practice methodology.
But having a handful of those sorts of questions that you can ask somebody will automatically put you in the learning mindset, which is really key as you say.
Here’s a question from a listener. I’m not sure we’re the best people answer it, but let’s address it: “Can you have massive success and healthy work life balance? I’m guessing the answer is just no, but are there techniques for getting closer to having both?”
Yeah. I—you know, I don’t think work life balance is one of the things that someone would accuse either of us of.
Yeah. Not world experts at.
But you know the Jeff Bezos—his little one-liner on this is, “It’s not work-life balance; it’s work-life integration,” which I think is a good line. I’m not sure exactly what the next 4 paragraphs of thinking is there, but it’s definitely a good line.
My hot take on this—I’m curious how you think about it, Reid— but I read a book some years ago called The Power of Full Engagement, which talks about managing energy, not time, so that—his thesis of the book is like: time management’s overrated, it’s all about energy, because certain hours of the day drain or fill you up in energy more than other hours. So not every hour is the same. So look at the activities that drain you, look at the activities that fill you up, and manage accordingly.
One of the lines in that book is they advise that you think of your life as a series of sprints, not an endless marathon. But it actually occurs to me that I’ve seen both structures work.
I’ve seen people that feel like they really are running one long marathon; they have a mission in life, and they’re totally dedicated to it. I know people who run a series of sprints and they take time off, and what that can manifest—at a very practical level—is I know people that will work really, really hard for two-and-a-half years, basically never taking a break, and then they really disconnect and unplug, and sort of reset.
And then I also know people that do work-life balance by taking, you know, Sabbath every Saturday. They just disconnect every single week, right? And that works for them.
So there are a lot of different frameworks that I’ve seen work. Curious, what have you seen among your friends, Reid—or yourself—who have been been really successful?
So I think everything you say is really important. It’s, again, being strategic about it, and not realizing it’s only one or the other, but what you prioritize and what you put there.
I mean, one of the things that I think I personally have done is say, “Well, okay, I’m really prioritizing what I’m building and making a huge difference in the world. And so what do you do vis-á-vis work-life balance?”
So what I kind of made sure is that I never got burned out. So I would have: what are the most efficient ways that I can rest, or get some kind of emotional spiritual recharge like having a dinner with my friends? So it’s like, “Okay, I’m really, really working hard, but I make sure I have the occasional dinner with my friends. I’m really, really working hard, but I actually also make sure that I, on the weekends, don’t set an alarm clock for when I wake up. So as I, you know, kind of get enough sleep and recharge to be able to do that.”
As opposed to like saying, “Okay, well what I have to do is I have to plan, you know, a 1-2 week vacation to an exotic location.” Or I go, “No, no. Actually in fact what I really try to do is make sure that every so often I have a three-day weekend where I do something that’s kind of quickly recharging because that’s all emphasizing the success path, the journey path I’m on, but making sure that I stay balanced, poised, energized, making good decisions, happy enough as I work through them.”
And so I think that’s the, you know, set of things for me, which could also work for other people, but it has to be one of the things that kind of work for you because a little bit of can—the short term and the long term is, you know, you should be thinking about it as a marathon of sprints and you have to be able to sprint well and you have to be able to do the marathon.
And so what’s the way that that works for you?
I mean some people have careers that are really just a 9-5 job, and that can be fine for them and—depending on how they want to configure their life.
I think you and I, and a lot of people we know in the tech industry, the life and career thing is so integrated where they’re kind of working all the time. I think the work-life balance discussion, where it gets sort of dangerous is where we get into the world of naivete, or we deny sort of difficult truths.
And one I think sort of politically-incorrect truth is that every entrepreneur in the conventional sense of the word (i.e., someone starting a tech business that has done really well) has worked a phenomenal number of hours every week. I mean, there’s no tech entrepreneur in Silicon Valley that’s built a significant business that’s worked 40 hours a week. Just doesn’t happen. Almost everybody I know doing early-stage venture capital is doing meetings and calls most weekends, like it’s not uncommon for that to happen.
And I think if you love your work, that’s awesome, right? If you hate your work, that sounds like you don’t have work-life balance. But I do think—and it’s not just tech, I’m sure…although, I’m not as personally familiar with entertainment world or politics or whatever. But I assume in these other industries, people who love what they do tend to work a lot of hours, and the people that are at the top of their fields tend to work a lot of hours. They would not pass the traditional work-life balance sniff test as run by, you know, U.S. News and World Report. But if they’re happy, and they’re having huge impact, it kind of works out.
But don’t fool yourself into thinking that if you want to do something great in a really competitive field—like tech or law or politics or manufacturing or whatever the field is—you’re going to have to put in a lot of hours and you’re probably going to have to sacrifice some things along the way to get to the top of that field.
And you’re probably going to have to take some risks, some of which won’t work out. You have to do some recovery and persistence from that, all of which I think is personally, you know, very good to do.
But as a small instance: Ben, here you and I are at 7PM on a Sunday recording a podcast, partially because we love the work and are trying to share what little gleanings we have with other folks. But you have to do it in order to accomplish interesting things.
I’ll never forget when we were working on the first edition of the book, Reid—10 years ago, the book Startup of You—I was over at your house for a 2:00 to 3:30PM manuscript review meeting on a Saturday or Sunday.
We only met on the weekends, of course—I don’t think I saw you during the week for about three years—but you were going from 9:00AM to 6:00PM. All day Saturday, back-to-back, people were ahead of me, people were behind me. The next day, people were ahead of me, people were behind me. It was pretty astounding. All day Saturday, all day Sunday, just so many projects.
And, of course, your prodigious output and productivity and impact is for all to see. And I think you have figured out a way to make it work, and you love so many things that you do that I think it’s—you’re acting with agency, and autonomy, and building a life that you want to build.
But, if you want to have this sort of career that you’ve had, have the impact that you’ve had, it’s very unlikely to happen if you work at 9-5, Monday through Friday.
1000%. And, you know, part of it again—the little hack, the making sure that I was kind of being capable of a marathon is I’d also try to relegate things to the weekend that would be a little bit more—stuff you have to do in work you just don’t like doing, but you have to do—well, that was a Monday through Friday thing.
On the weekends, I tried to make sure I was only doing the things that, sure, they were work, there’s strain, and work, and, you know, cried and some stuff. But it was also the kind of thing that picked you up, right? ‘Cause like kicking around ideas with you and going, “Is this idea good enough? Is this an idea that’s something we should share, or is this have flaws with it?” That was fun.
Question from a listener: “Everyone says finding a mentor can be transformative for your career, but I’m in my early thirties, and I just can’t seem to find one. I’m not sure if they don’t see talent in me that’s worth investing in, or if I just don’t know how to broach the subject. Do you have advice on how to find a mentor?”
This is a question that we get a lot. It’s very common in the career space, and I think it’s really important—we write this in the book, I think—don’t go up to people and ask them to be your mentor. Going up to someone and asking them to be your mentor is like going up to someone at a bar and asking them to marry you before you’ve even gone on a first date. You need to build a relationship slowly, iteratively, over time, all sorts of relationships. And your professional life should be built slowly, iteratively, and over time.
So find a friendly first, find an acquaintance, find an ally, build that relationship, and later that relationship can turn into a mentor relationship. But if you’re looking for a mentor off the bat, you’re doing it wrong.
Yeah, and also, part of it is—I mean, a little bit like your analogy, which I agree with—“Be my mentor,” is like, “Engage in this really, like, committed, long relationship from the beginning.”
A great way to do it is just, “Hey, I’m working on this thing. Can I ask you some questions about how I’m trying to do it, or what you learned on the path that you were doing on this?”
And if both of you find that that’s a useful, fruitful, interesting conversation, then the next conversation is all the easier. And then all of a sudden on the tenth interaction, you’re finding that both of you want to be spending your time together, and the mentor relationship has persisted.
It’s one of those things where I think it’s also like friendship. Like, you say, you walk up to someone you don’t know at a bar and say, “Will you be my friend?” And—most people will be like, “Whoa, that’s weird,” right? Like something’s wrong here. You know, alarm bells are going off.
Whereas you show up and say, “Hey, the news of today has kind of made me feel a little, like, strange. You want to talk about today?” Right? You know? “Oh, okay, let’s talk about today.”
Or, you know, you’re in college and you say, “Oh, well, the sports team did X,” or, you know, “Oh, you—we were in class together. You know, I was fascinated by this lecture. Here were three questions that occurred to me. Would you mind talking about those?” And then you kind of get into the relationship, and eventually—when the dynamic and the dance is going well—it builds.
And that’s the—I think—one of the really key things to think about mentors. Don’t think about mentors is like, “Oh, look, check the box. Person X is now in my mentor.” It’s the work on building the relationships, and relationships always start with interesting and mutually beneficial interactions.
And the weird challenge with the word ‘mentor’ is that it does imply kind of a one-way street, a value exchange from mentor to mentee. And as we write in The Startup of You, and we talk about in our episode on building a professional network, it’s really critical to think about every professional network in your career as bidirectional—you helping them, them helping you, and these sort of volleys of exchange of value. That is what creates the trust that builds deep alliances over time.
And so if you meet somebody who you think could be a mentor to you, that’s great. And, of course, soak up their wisdom, their learning, all that. But don’t just be in the recipient chair. Think about how you can help them. And sometimes the word ‘mentor’ traps people where they think they should just be asking all the questions and sort of extracting information and learning, when really you should always be trying to make sure the values are flowing both ways.
At the very minimum, you know, one of the things that a number of people who play the role of mentors plus teachers, like, is: you’re going out and accomplishing things. And so sharing with them what you’ve accomplished—sharing your appreciation of how the person helped you accomplish these things—that can frequently be a bunch of the joy, and the sharing of that journey, which is part of what motivates these people to be mentors, teachers, etc.
Reid, thanks so much for the conversation about portfolio careers. This is great.
Ben, as always.
And thank you to our listeners.