Build Your Portfolio Career

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Welcome to the HBR IdeaCast from Harvard Business Review. I'm Sarah Green Carmichael. The gig economy is one term for the way we're all supposed to work someday, juggling multiple jobs at the same time. Another word tossed around in media stories often is portfolio career, which sounds a little fancier and maybe a bit more positive, right? You have a diversified portfolio of investments and you can almost picture that leather portfolio carrying all your sheaves of paper under your arm. That is until you trip and they all go flying into the wind, juggling jobs and building them into a career. Maybe it sounds exhilarating to someone who's tired of the daily grind of the same old job, but can also sound really exhausting and scary. So today you're going to hear from someone who's living and thriving in his portfolio career. Kabir Siegel is an investment banker and a Grammy winning producer. He's also a best selling book author and a U.S. naval Reserve officer. In his free time he writes for HBR.org, which is how I came to know about his kaleidoscopic career. Kabir, thanks for talking with the HBR IdeaCast.

My pleasure. It's great to be here.

So what are some of the benefits of this kind of career? Why do this at all?

Well, I generally like to take on new projects because I'm interested in them. I'm genuinely interested in these projects. I love jazz music. Not that many people love jazz music, but I have such a passion about it and curiosity about it that I work night and day to produce these jazz records. I don't know how many investment bankers are creating jazz records, but I'm probably in a very small community and those records have been now recognized increasingly by the recording academy. All of a sudden I get a currency at work where I'm the one guy, I'm the one banker who's interested in the arts. And that now provides a common link to connect with people who also are interested in music. I think there's a benefit in exploring your passions because if you do so, you're going to work diligently and create sort of a separation from the pack.

So it's not only about kind of just selfishly pursuing your creativity and passion, although I hate to call it selfish. It's a nice thing to do, more people should do it. But it also sounds like there are professional benefits in your sort of day job, if you will, to doing that kind of thing as well.

Totally, totally. I was in India, actually, and I was with a client of mine who managed a multi billion dollar investment firm. And we were at the Taj Mahal. We were just talking. We had a very inspirational conversation. I said, what's on your bucket list? And he said, the number one thing on my bucket list is to go to Cuba. I said, why is that? He said, he's from Argentina and Che was from Argentina. So I called up my friend who was a great jazz musician, and I said, we're going to do the next project in Cuba. And soon after that, we had raised all the money to go to Cuba, which was a lot of money. And we arrived, we made an album. And the day after we arrived in Cuba, President Obama normalized relations with Cuba and we created this amazing album which was recognized with a Grammy and a Latin Grammy. And all my clients who came on the trip had a great time and it was a memorable time. And because of that, they introduced me to more investment, more Latin American investors, and I got introduced to more artists who wanted to work on Latin jazz projects. So bringing the worlds of high finance and music together provided mutual benefits for everyone.

What I find surprising about that story is that a lot of people have side hustles that aren't that different than their usual sort of day job. You know, if I'm a writer and an editor, I might do a little moonlighting writing and editing. You know, it's like. But it's the same thing whether I'm doing it in the morning or at night. But those two fields seem so different. It does surprise me that there would be some Venn diagram between them and some synergies that you could pull from that.

I think the synergy is a skill set of managing a project and getting it done. So I learned how to execute by executing deals at JP Morgan. We had a deal and we had to run it to the ground, call clients, do the ipo. And I take that same skill set to writing a book or producing an album. It's the same thing. You have to have a team. You have to recruit people to your projects, you have to do your research, you have to have a timeline, you have to have a budget. I don't do a lot of these projects alone either. I have great teams that work with me, and I generally am in a leadership position, especially on the recording projects, where I'm recruiting the team and working with them to execute a vision. So I hear you that Sometimes people work on a side hustle that's similar. But if you're bringing the skill set of how to get it done, you can work on almost anything.

Do you even consider it a side hustle? I mean, is that even a fair way to talk about it? It seems silly to be like, yeah, I worked on this little side project and it won a Grammy.

Well, I always say I feel a bit odd calling myself a music professional because I don't make money in music. And when you call it a side hustle, it feels like you're doing it just to make money. I know that's not always the case, but that's obviously another benefit for doing these quote, unquote, side hustles is you can make more money and diversify your income stream.

So some organizations have rules against any moonlighting, and some bosses, I think, are very skeptical. You know, they would say, you know, you seem to have all this time to do all this other stuff and do it at a really high level. Isn't that time you should be spending, you know, on your salary job that you're doing for us? Have you ever had a manager or a boss sort of approach you with that kind of skepticism?

Sure. I wrote five books while I was at JP Morgan over two years. I would write a project, and then I would present the project to the compliance people at JPMorgan and say, hey, this is fait accompli. The book's already done, and it was not anything controversial. I wrote a book on jazz music or the civil rights movement, and they were generally supportive. But had I gone to them at the beginning and said, I want to write a book, they're going to say, oh, you're going to spend all this time? I would have had that conversation. So I generally just squirreled away on the weekends and in my lunch hours writing and researching. When I wrote my book on money, it was like I was already reading all this research on economics. When I wrote my book Coins, it was sort of this thing where when I presented it to them, they thought it was a great thing. And by that time, by the time I wrote my fifth book of Jake and Morgan, they knew this is just sort of how I spend my free time. I like to write. So that's one way of accomplishing this thing, is just do the work, and then when it's done, you can just say, it's already done.

Yeah. Ask for forgiveness, not permission.

Exactly. Exactly.

Yeah. It seems like one of the key things to your ability to do all of this is that no one Notices, any performance drop, they're not like, huh, Kabir suddenly isn't bringing in any revenue. Then they find out you're writing a book. It seems like they don't even really notice. And then boom, there's a book.

Yeah. And I had a conversation with my manager when he got his job because I had deep client relationships and I said, look, I will help you get to know your clients better and I'll help you with your job, but I ask that you just judge me on results and please don't ask me where I am or what I'm doing. And he was cool with it, to his credit. I mean, I tried not to abuse it. And we had a few conversations to reel me in when I was really, really in the throes of my research for my last book. But you have to have sort of an adult conversation and say, if I bring in the bacon, can I do this? And I realized not every job is like that. I was working in a banking sales role and you know, if I was working a very analytical, research intensive job in my day job, I may not have had that free time to do it. So I totally get that. And sometimes it's a paradox. Sometimes your performance can go up as you're taking time off. I think that's probably true in many cases. If you're talking to your manager, I would just set up a schedule and say here instead of benchmark and say, you know, I'm going to do this over four weeks and let's see what my results are and start out with sort of a mini schedule to see if the program's working right.

So it's almost like a little experiment.

Exactly, yeah.

So what about, we sort of talked about how you've managed all this with your bosses. What about your peers? What's their kind of reaction to this?

Well, I should say when I was JP Morgan, it probably engendered some jealousy. People were like, why is Kabir rarely here? Or why is he never at the morning meeting? But because on Wall street we would have to come into work at like 6:30 in the morning and then listen to a phone call with people around the world talking about investment ideas. And then the idea was to go call your clients and tell them what was happening in the markets. But my clients, A, already got all the research through email and B, never picked up their phones. And so I was like, why am I getting in at 6:30 in the morning just to leave a voicemail? It's absurd. A lot of people agreed with me. But you know, When I said it aloud, people were, oh, you can't say that. Well, I'm not going to show up because it's just silly. And I'd rather spend my time actually with my clients once a week than, you know, talking to their voicemail five times a week. And so I think there was a generational divide. People who worked on the street since for 20 years were like, no, this is how you do it. But I think the younger generation was like, at least my peers, they realized that this is maybe a more sound way of conducting the job. I had to tread delicately over time as people realized that what I was doing outside work was actually benefiting me inside work. I was not only connecting with my clients, I was connecting with the senior ranks of JP Morgan through my outside activities. They saw, wow, this is a great professional networking opportunity too. In many cases. Some of my peers started emulating me and started joining civil society groups and starting charities. And I like to think it had a positive impact on my colleagues. But I'm sure there's probably a lot of snarky comments too.

So we've talked mostly so far about your writing and your music and how you sort of fit those in and around your daily day to day job. But your military service, how do you make that work? Is that sort of a different thing?

Yeah, it is. I mean, I was working in a bank. I wasn't being all that I could be. So I called a military recruiter and I joined the Navy Reserve. And then I started going to my reserve unit on the weekend. And we call it the two week job because you spend five days on your day job and then you spend two days as a reservist on the weekends and then you spend another five days your day job. So you're always sort of grinding. But if you look at any job or even in the military reserve, you're not working every single hour. There's downtime, that downtime. You can recharge, you can do other things, you can call your friends. How did I fit it in is your question? I just did it for several years on the weekends and then my annual two week drill, I would do that. And then last year I got deployed for much of the year and, and I had to. Thankfully, I worked at a company that was supportive of my military service. So I talked to my manager, I was like, hey, I need to do this. And to his credit, it was just, he was so supportive, you gotta do what you gotta do. And so I got deployed to the Middle east and I was using my skillset while I was deployed of financial analysis. And I came back and I was really proud of my service.

And I should mention there are sort of legal protections for people who do this. You know, employers are obligated to give you the time. But it is interesting to me, you still, as an individual, have to figure out how to, like, tie up your loose ends, leave, go to a completely different environment, then come back and be like, yep, here I am back in this cubicle or whatever. What was that like?

Well, I made sure while I was deployed to continue my work at my day job because I wanted people to realize that even though I was deployed, I was still on the ball. And it worked because I knew that when you leave, you give your employer an opportunity, especially if there's a performance bonus, not to maybe pay you as much or to figure out ways to shuffle the stock around so you don't get as much. I was trying to be as responsive as possible while I was deployed and come up with ideas. Today you can work from anywhere. I was constantly sending emails to clients to say, hey, what can I do to help? And calling. So there was a bit of that.

One of the things that sort of dawning on on me as we talk about this and you talk about sort of the way you write and the way you manage your time is just how inefficient a lot of big organizations are. I mean, morning meetings that seem to serve no purpose, voicemails that people probably just delete without listening.

Yeah, there's probably a paradox that the bigger the company, the more you can hide in some sense. Because if you're working in a big place that has a lot of bureaucracy, you might have more time to actually work on your side hustles, to work on your passions. If you're working in a small startup where you're more accountable for things, it's going to be a lot more difficult. I've only worked at relatively large institutions. That's what I've realized has worked for me. I appreciate the steady income and the salary and I try to do a really good job at the job, getting paid for it, but I try to find the pockets of inefficiency schedules. I realized when I was at JP Morgan. Even these top investment bankers, people say they work 10 hours a day, but if you go at a certain period of time, they're reading ESPN.com and just talking to each other. It's like, okay, that's two hours I could spend working on something else. If you were actually to map out how much time people actually work at their day job, you might be surprised that people aren't nearly as busy as they say they are or they think they are. If you actually converted those down hours into productive time, time where you can actually show something for your work, you might be startled with how much time there actually is to produce great content.

What about documenting your output? Because I think in a lot of industries it's all sort of squishy and hard to measure. It sounds like you've benefited from the ability to say, I've created this many deals or I've created this much revenue, which then is sort of reassuring to people who worry that you're sort of distracted from your main job.

Yeah, I think one of the most important things is being able to measure your impact and creating metrics that measure impact if you don't have them. So for example, in a revenue job, it's pretty easy. You can say, okay, this is how much money I made. But if you're not in a revenue creating job, you can create metrics that point your productivity. I was working in a non revenue job and I was trying to implement a customer satisfaction survey. Every week I would send an email out to my team, my colleagues, my managers. I would just say, this is my weekly productivity and I measured it by how many surveys went out. I also started putting there next to it all kinds of efficiency scores. Even though it wasn't making revenue, I could easily point to growth. I actually did this when I was deployed too. I would put a number next to everything that I was doing so that the more senior people who are watching me, I could say, hey, I was up 15% this week. I was down 3% that week. I think speaking of percentages is really helpful because you can convey things so quickly. When everyone else is giving qualitative, squishy feedback, you're boiling it down to a few things. The great thing is if you actually create the metrics for yourself, you can create a scorecard that you can thrive on. You're the one creating the metrics. Why not create things that you'll do well in? You might create a new system for your company to actually measure results.

Is this something that you have tried to convince other people to adopt and do? If not to push them to portfolio careers, then at least say, hey, this is how I'm super productive so that I can do these other things. Why don't you just try it and be more productive?

That's one way of doing it. I think a lot of big companies have these Create your three objectives for the year and that's one way of doing it, or they'll give you the three objectives for the year. But I find that if you actually imagine it and create your own metrics, you can start to shape the conversation with your manager and you can actually get their input and say, what do you think about these metrics? They may say yes, they may say no, but at least you're going to show them that you're thinking about the job in new ways and you're thinking about efficiency, about how to measure things. I think a lot of middle management, they speak one language, which is the language of spreadsheets and numbers. They're always trying to look at how to cut the numbers so that their pie of the organization is thriving and doing well. They want to be able to convey to their managers how other team is doing. That would be something I would say focus in on. What can you do? What are the three or four things that you can measure that can convey what you do in a succinct manner that make you look good?

What about from the manager's perspective? If the manager would like his or her employees to be a bit more aggressive on the productivity frontier and execution frontier, how can the manager use some of what you've learned to push that team forward?

Radical transparency, putting the productivity next to people's name. There's something to be said for healthy competition. I know in some industries it wouldn't work that well because people want to see more quality than quantity of productivity. But I think healthy competition is great. I had healthy competition when I was working at JP Morgan. A sheet would go out every morning of who did the most deal flow. The last day we would elbow each other and say, wait till we see what happens today. So there's a bit of that. If you want to unlock value from your team, get to know your team outside of work. If someone's really interested in some obscure area, can you bring in that passion somehow to their day job? Because the employees are going to be like, wow, my manager actually cares about me. And he's trying to figure out some way to bring. Maybe that's a good question to ask. If you could do a side hustle, what would it be? And incorporate elements of that into the main job.

So you clearly thrive on this kind of life. But do you think it's for everyone?

No, I don't. And the reason I say that is because if you don't love those other careers, you probably shouldn't be doing it. It's difficult for me to sit down and watch TV or binge watch Netflix, I just don't do it. And I know a lot of people aren't like that. My sister is like, what are you doing? Why can't you just watch a football game with us? And. And I was like, well, I have to be doing this. There's definitely downsides that maybe you don't live in the moment as much. You're always thinking about what you have to do next.

Are there any times when you think, gosh, this would just be easier if I just had one thing to do?

I think that a lot, and I struggle with that at times because people say, do one thing and do it well. There is a certain truth to that. You get good at something, you develop your craft, you get known for that. You may go higher up in the tower and you can see further along across your great land of your career. But I generally find it more interesting to find all the nooks and crannies of different jobs and see how they come together. It would have been great to be an amazing investment banker, the best investment banker on Wall street, but I would have missed the opportunity of working with so many talented musicians. But I do know that having written for HBR and having lived this life, I know there are a lot of people like me.

What would your advice be for people who think I would love to do more with my life, but I really just feel like I don't have the time.

I would take a look at, what are you doing today? What's your main job? And then I would try to measure out how much time you're actually spending at that day job, actually doing the job. Like, how much time do you actually spend talking to your colleagues or going to lunch, not doing the main job? I think you could probably find 30 minutes or an hour where, if you could take that and allocate it to something else. It's just got to be this thing where one of my friends has a daily email. He's trying to start a company on the side. And that daily email is how many clients did he talk to for a second company? He has to respond to that email every day. So you just got to create ways to carve out time to move the ball forward every single day. That would be the first thing. The second thing is realize the assets you have. If you have a primary job, one of your big assets is your paycheck, and one of your big assets is all the intangibles you've learned about how to do your job. You can bring those professional skills to people or areas that may not have that. And once you realize that you don't have to do everything, you can just work with teams of people, all of a sudden you can start to get more done than you may think.

Is there a particular type of job or organization you think is more conducive to a portfolio career?

Probably relationship management, sales jobs, especially institutional sales, because it becomes more of a maintenance thing where you're checking in with clients and you're trying to make sure that they're getting what they need. You don't have to spend that much time producing a product. If I was sitting there writing computer code and trying to hit a delivery schedule, it would be probably more difficult. I think the more relationship driven jobs where you're not spending a lot of time, analytical time, give you free time to do analytical work in your secondary jobs.

It also strikes me that we have this kind of stereotype of the waiter who is really an actor. But actually being a waiter is like a terrible way to support an acting career because the hours are like really difficult. And it's not like you're at your cube pretending to work on your real job while you actually work on this other thing.

And there's a great history of T.S. eliot. He was a banker. He was writing his poems and writing his stories while he was doing deals for clients.

My favorite thing about T.S. eliot is that he said he preferred working as a banker and doing poetry on the side. He felt he was more artistically free because he had the stability of that job.

That is totally right. And people ask me, you do so much, how do you do it all? And then when we have a conversation with that person, they have interest in just as many things as I do. They may not create content around it, but people are interested in many things. The question is, can you create work around it? Can you create pods around it? And I think a lot of us can. If you find those gaps of time and you start working towards it, how.

Important is the money?

It doesn't always have to be a revenue generating side project. I mean, if I were gardening, I'd probably figure out a way to make some money on the vegetable garden or something. But I think you can do it. I'm not saying you should work a second job to make money, although that's a good reason to do it. If you work another job, make sure you're doing that other job out of happiness.

Is there another passion project in the future you wish you could take on or are hoping to take on.

My man. He's pretty full right now. But I think my opera. So I'm working on an opera that's a financial crisis opera that's inspired by the European debt crisis. This basically takes what was happening while I was working in the markets and turning it into a jazz opera, an absurd jazz opera. And where you have the three tenors, not just Pavarotti, Carrera and Domingo, but my three tenors are Sarkozy, Papa Andrea and Berlusconi. Singing to the music of Nessem Dorma, but singing about fiscal austerity. But I'm excited to get that out because that's a great example of sort of interdisciplinary projects where you take, you know, that's the big thing. If you could take one thing that doesn't belong with something else and jam them together, you, when you put them together, you create a new genre, you create a new space. And I would have written a terrible opera on any other topic. And this may be a terrible opera, but I'm probably one of very few bankers that have written a jazz opera on the European debt crisis.

So based on your experience of writing this European debt crisis inspired jazz opera, I think that's the first time I've ever said that phrase out loud. Is there like a through line that kind of ties all your disparate activities together, or are you just sort of embracing the idea that one person can contain multitudes and you don't really worry about ever seeming, I don't know, maybe a little dilettante? Ish? Does this all make sense to you in some way or do you just embrace the kind of diversity of it?

Yeah, it doesn't make sense to me. I just do it. And I like that paraphrase. You know, Walt, woman says, do I contradict myself? Yes, I contain multitudes and some things are duds. Maybe most of the things I do are duds. But if you continually work on producing things and focus on the quantity of things, the quality will eventually take care of itself. And I know that might be heretical to say, but over time you're going to find out how to do things right and more efficiently and more effectively. That is the combo link. It doesn't matter if it's writing music or writing a book or creating a deal. It's all about the act of creativity and using your imagination. And that might sound broad, and I know it is, but that's what I. I believe.

Well, Kabir, thank you. And let us know when the jazz opera goes up.

I will.

That's Kabir Siegel this is where I would normally list where he works and what he does, but there are too many jobs to list, which is how he came to write the article why you should have at least two careers. You can read it at hbir.org thanks for listening to the HBR IdeaCast. I'm Sarah Greene Carmichael.