Improvising Career Success

Anita Brick:

Hi, this is Anita Brick and welcome to Career Cast at Chicago Booth to help you advance in your career. Today we are meeting with Christopher Bishop. Actually, I am thrilled and delighted to be weeding with Chris. He is the author of Improvising Careers, a TEDx speaker, an ex I bmer, former touring rock musician, future workplace consultant, deep Tech mc Quantum podcast host and university guest lecturer on the future of work. While I have to take a breath, that is a lot. Chris, I can't wait for us to talk all about this.

Chris Bishop:

I'm delighted to be here.

Anita Brick:

I'm so glad a non-linear bimodal careerist. He has had eight careers so far. Based on his own atypical career path, Chris developed a lecture and workshop. It also includes a little concert along the way titled How to Succeed at Jobs That Don't Exist Yet. Designed to enable today's learners to successfully navigate the 21st century borderless workplace at prestigious universities, including N NYU U Stern School of Business, Georgetown, Columbia, and the London School of Economics, as well as in corporate settings, providing insight on the business and career implications of bleeding edge technologies, recasting his rock and roll persona. Chris performs the role of master of ceremonies and panel moderator at numerous events for the Economist as well as technology conferences worldwide. On the Quantum tech pod, he interviews C-suite executives at leading quantum companies. He's also, I don't know how you have time for all this, by the way, as an active member of the Quantum Economic Development Consortium, Chris plays a key role on the Workforce technology advisory committee, and he resides very happily I understand in Wilton Connecticut. Chris, thank you so much. I know you're very busy and with all these careers, and I'm sure you have like five more bubbling in your brain. I really appreciate your taking time for us.

Chris Bishop:

Well, a edit, really appreciate your interest and support. I love talking about how I navigated these multiple careers and then sharing my take on how today's learners, regardless of age, because we all are learners, can apply these tools that I developed and have a perspective on the cool stuff that they're going to do in the future.

Anita Brick:

And the book is both informative. I love the fact your story is there and also the tools, which are great. Okay, so let's start with an alum.

Chris Bishop:

Okay,

Anita Brick:

Chris, you're very optimistic about ai forward job markets, even for people with a lot of miles on their odometer. Like me, I'm struggling to see where my leverage is in all of this. If my human superpowers are the non automateable part of my career, how can you help me debug my thinking and find them?

Chris Bishop:

So they visibly have to take a step back and focus on the things that you do well and whatever discipline you've been working in. So certainly soft skills like communication, collaboration, team leadership, mentoring, even career guidance. Those are all skills that are tough for GPT or perplexity or grok to automate. The other thing I would say is look for areas where AI is being applied in the discipline, will you have expertise? The key is finding the right vertical setting. There's a famous quote in the Harvard Business Review, this is from several years ago, but apropos today that says, AI won't replace managers, but managers who use AI will replace the ones who don't. There's a lot of pattern matching, I think, of people being paranoid about technologies taking over jobs or requiring new skills. It's been going on for literally hundreds of years.

That's big picture perspective on ai, for example, and we're going to continue to see it. The example I use in my lecture, I mean there's several. One is in 1540, queen Elizabeth the first refused to issue a patent for mechanized knitting machines for fear. It would put her poor subjects out of work. So government intervention, trying to manipulate what kind of skills and what kind of industry, what kind of businesses were being run. Similarly, in 1910 when Henry Ford said a rolling model ts off his assembly on in Detroit, my contention is farriers and blacksmiths got really nervous. What are we going to do? We don't know how to apply the skills we have in this new setting, but the smart ones, the flexible, resilient, resourceful ones shifted gears. So certainly carriage makers learned how to manipulate an internal combustion engine. They knew how carriages work, but it's just the source of energy was not a horse, but a device, an engine. So I think that's a big picture thinking that you have skills that are transferable, that things that humans can do, but also being aware you're going to have to learn something new. There's always existing skills that are transferable and then net new skills that you're going to have to learn.

Anita Brick:

A couple of questions around this, but the first one is an MBA student said, you said that many of the jobs in our future don't exist yet. That's both exciting and terrifying as an MBA student, if I can't aim at a specific job title anymore, what's your playbook for getting me future ready now when everything is moving so fast and there's so much uncertainty?

Chris Bishop:

Thing to keep in mind, again at a meta level is that all future jobs are extrapolations of existing jobs, right? I would encourage you to use one of my tools, which is the antenna tool, and create a grid to track where conversations are going on in your area of interest. So as an MBA student, you may have to cut a broad swath. I think of if you get placed at a management consulting firm, they're going to expect you to learn a discipline or a vertical like on the fly, bringing what maybe based on what you study to where you have interest, but it's being resourceful and resilient and learning. These jobs in the future are evolving based on various factors including tech breakthroughs, shifting client expectations and demand, what's the market need, and as well as moves by innovative competitors and innovators at a meta level's general trending in the global market driven economy.

I would encourage you as an MBA student to track bleeding edge tech. That's sort of a mantra of mine, and they include areas like quantum information science, robotics, crypto, crypto assets, bio it, additive manufacturing, the space economy writ large. Aquaculture is a whole new area of focus. Sustainable energy solutions, applications of autonomy, and a range of transportation settings from cars to rechargeable personal drone taxis. So there's lots to do. Lots that's emerging, again, based on existing roles and jobs and technologies. So you need to be aware that this is happening and changing and be excited about it. It's going to let you do a lot of interesting things.

Anita Brick:

Okay, you talk about your way of tracking so that you can air, quote, predict the future a bit more. Another MBA student said, I love your idea of tracking trends like you were talking about in the bleeding edge technologies and beyond where investments are going, where the flows are, and patents. And I'd even add one more dimension, and that would be dissertations in my area of interest. I have a full job, a family and school. If you are brutally realistic, what is the minimally viable routine for staying future aware without burning out?

Chris Bishop:

So certainly given the setting, if you have full-time job, family and school doing real world stuff and not just having the luxury of being only a student, I would encourage you to use my antenna tool. Lemme describe what that is. So again, the toolkit I've put together, future career toolkit is voice antenna and mesh voice is finding your brand using triggers like what's your favorite TV show, movie, book, or game, and that's an exercise you can do quickly and easily. I can share a PDF of this as a workbook, actually Anita with you, and you could distribute it if people want to see it.

Anita Brick:

That's very generous of you.

Chris Bishop:

Okay, no, that would be great. So I would say thinking about what you're doing now if you have a full-time job, so that indicates you have skills in a certain discipline and probably in a vertical, I would go right to the antenna tool and start by finding two to three sources of conversations like where are these conversations going on around the business you're currently in? It doesn't have to be limited. It can be TikTok can be elite newspapers, but find where future aspects of your topic of interest are being discussed. Maybe find one source to check every day. Could be the Economist Espresso app on your phone. Could be the Wall Street Journal. Bloomberg Tech now on the BBC is a great TV show that goes, it's on once a week, maybe YouTube channels for maybe twice a month updates, but be diligent about putting together a pattern, a routine, and checking them, and that'll move you to the front of the conversation, if you will. You'll then have a sense of what's happening at the bleeding edge of the discipline I'm currently working in, and that will then position you to be successful as that whatever discipline that is is influenced by technology and global markets and competitors.

Anita Brick:

Okay. So along with that, you mentioned finding your genius, finding your brand. You talk about that a lot in the book. Here is a question that came through from another in tech and getting an MBA keep hearing that I need a sharper personal brand for impact and longevity. If we treat my career as a product in beta, how would you advise me to prototype and test personal brand that actually helps me not just for now, but in the future as well?

Chris Bishop:

Yeah, so it used to be that brands writ large were reserved for say, athletes or actors or maybe musicians, but nowadays everybody has a brand. We all have an individual sort of worldview and value prop that we bring to the workplace. In this case, take a step back again and realize that you've got to have a personal brand and that it's going to change and evolve over the course of your careers. That's plural. By the way. We all have a unique individual brand compelling value prop that we bring to the market. My general guidance is to exploit LinkedIn and I don't get paid. I'm not being compensated by them, but based on years of being in the business world, I've determined that LinkedIn is basically the lingua franca. It's the coin of the realm. That's where the global business community goes. That's where a hiring manager would go, where an executive might go to look for talent, where people follow thought leaders.

Certainly my experience in the quantum information science community is that there's lots of really interesting conversations that go on on LinkedIn around that topic, but they're wide ranging conversations in groups on that tool. Some specific guidance, I'd say be sure you write a compelling but personal summary on your page, on your LinkedIn profile, there's guidance you can look up on the web. LinkedIn has guidance. There's some other sources that'll give you a sense of what to say and how to say it. I would also encourage you to post anything and everything that represents your expertise. Perhaps you have a video of you speaking, maybe it's a blog post, maybe a white paper, a research note that you contributed to an article you wrote, pictures of you at an event, posing with thought leaders. You need to provide easy and clear access to deliverables and work products that demonstrate your passion as well as your expertise and make it a job to keep it updated. Add content as frequently is realistic, at least every couple of weeks would be my general guidance. Join groups on LinkedIn to see what like-minded people are discussing and certainly lurk, but then weigh in as appropriate. If you see somebody talking about a topic that you're interested in or that you have a perspective on, feel free to say something right. But that's my general guidance.

Anita Brick:

I like that. One of the things that came up that goes along with this, and this seems to be something I hear a lot more from alumni than students who are also listening.

Chris Bishop:

So

Anita Brick:

Here's an alum who said, I'm a self-identified generalist lately. I keep hearing specialize or you won't get hired. How would you design a career where I can build a sharp, measurable, marketable spike of expertise and keep my generalist mental agility as a benefit?

Chris Bishop:

So that's a good question. I would say I identify as a generalist as well. I mean, I have a degree in German literature, but you need to find settings as a generalist where you can apply your skills. I was in the jingle business in New York writing music for radio and TV commercials for many years, and it was fascinating. I mean, key was that there were the players varied. There might be a singer, a recording engineer, a copyist, a guitar player, but always a client and a budget and a deliverable. So when I became tired of the Jingle Biz, if you will, and decided that this new wacky technology called the Worldwide Webs was going to have global, social, cultural and business impact, and I wanted to get involved in that, I learned how to apply skills that I'd used in the Jingle Biz in the web biz.

Again, the actors were different. In the web business you have a graphic designer and a coder and someone writing scripts and a copywriter and someone testing the gear, testing the website to beat it up. But you have a client and a budget and deliverable similar to the Jingle Biz. So I learned what these actors were doing, the players in this setting, again as a generalist so that I could direct the team and create a deliverable based on what the objective was. So in this case, rather than a 32nd TV spot for CLA all shampoo, it might be a website for Johnson and Johnson, I actually led the team that built their first corporate website. But that's the way to think about this, right? That you have skills. I read books I learned at HT ML, I stayed up late surfing the web, looking at source code to figure out how these wacky website things work, right? And then had enough skill that I could run a team and say to the designer, well, that's not matching the hex code on the brand that we got from the client. Those colors need to be this. So again, being a generalist, learning big picture skills so you can be hired and run a team in different settings.

Anita Brick:

I love when you talk about cognitive disinhibition and you talk about loosening mental filters so that new ideas can connect. So a friend of career cast said, okay, most of us are trained to do exactly the opposite. What are a few safe practical experiments we could run in daily life to create more cognitive disinhibition without becoming a total chaotic mess,

Chris Bishop:

Really? So I would say cognitive disinhibition is important and it is a muscle you can flex and there are exercises you can do to explore that. My general guidance is explore topics that may be orthogonal to your area of training, for example, so are you a physicist? Maybe you take a course on medieval Irish literature, or are you a student of history reads, Stephen Hawkings, the theory of everything, or join a club or go to a meetup on a topic that you know nothing about but would provide sort of a loosening of the mental filters, if you will, and you'll meet people who are interested and who are expert probably, and also people who are curious and learning the same way you are. Maybe attend a conference on a net new topic, go to some event where people are talking about something that you're interested in but maybe not necessarily familiar with. That's a way to do it,

Anita Brick:

Right? And you can practice some of your questioning development

Chris Bishop:

That

Anita Brick:

We use in prompts today with ai, and we can also use those questions with humans and sit back and listen.

Chris Bishop:

And again, thinking sort of outside, I mean the cliche outside the proverbial box, looking for areas where you'll learn in a topic or discipline where you don't have say as much expertise or interest and depending on how brave you're feeling, how antithetical to what you know how to do. The topic might be jump in, go for it.

Anita Brick:

To go along with that, an MBA student said, you were talking about discomfort in the book, and the student said, do you deliberately seek out discomfort or does it find you? And what are one or two concrete habits that you would recommend to stay in the discomfort long enough for it to pay off without getting scared off?

Chris Bishop:

Simply put the discomfort kind of finds you. As I went through these various careers, for example, there were different factors that made me want to change what I did. I was a touring rock musician. I ended up, when the band broke up this band McHenry Spring, I had a tube route delivering newspapers in rural central New York. I was like, well, this is not going to be something I'm going to be want to be doing for a long

Anita Brick:

Time. I

Chris Bishop:

Figure something else out. So I said, well, let me move to New York and see if I can run with the big dogs. So I did, and it was challenging for sure. The idea is looking for new opportunities to explore different kinds of applications of skills and interests. No, that's going to change. Another example is I came off the road from some tour and said to my friends in New York, how do I sleep in my own bed at night? And they said, well, you've got to break into the jingle scene, man. You got to get into the studio scene. So I did. I, through sheer perseverance, I tracked down producers and artists and creative directors at agencies and copywriters and broke in and met people and introduced myself. And then I was a studio guy. I did a Miller genuine draft beer commercial for a producer at Backer Spielvogel, and then I was in crossed the threshold, if you will, I was legit as a New York studio musician.

Anita Brick:

It sounds like you have the style and personality to engage with people. Got lots of experiences that you share. Not everybody is extroverted or seemingly extroverted as you are. What about for the dorky introverts, which I'm sure myself included are on this listening to us right now?

Chris Bishop:

Again, it's finding what your voice is, what your brand is. We all have a brand, a value prop, a personal set of criteria or talents or expertise or perspective that are valuable that we need to focus on and bring them to the marketplace, and also knowing that they're going to change. It's a bit of self-reflection for sure. What is it that I do that no one else can do? The story in my book about being in the studio with Michael Brecker, Michael Brecker was a very famous tenor saxophone player. Part of the Brecker Brothers, his Randy, his brother Randy, played trumpet. They had a kind of jazz funk band in New York back in the eighties. Incredible musicians playing these really complex, really interesting kind of r and b funk, jazz tunes. Anyway, we're in the studio listening to Michael's solo coming back off the tape, and as it goes by, he reflects on, he is listening very intently to the playback. He goes, oh, that's phrasing that. Part of this improvised solo was inspired by John Coltrane, needless to say, legendary jazz Saxon player. The two inch tape goes by a little more and he's reflecting on it. He says, now that lick there and that kind of approach is based on Sam Rivers a bit of a more avant-garde kind of jazz saxophone player. And he pauses and the tape goes by a few more bars, and he looks at me and he says, and that's the stuff that I can do that nobody else can do.

Anita Brick:

Oh wow. I

Chris Bishop:

Was like, okay, Michael. Yeah, you're right. So he had sort of invented this way to play triads over chords that nobody had ever really done before. But the idea is he found a brand, he found an approach, he found something that he could do. And again, I encourage all your listeners to be aware that you have that as well. You have things that you do that nobody else can do, that you can bring to the market, to the workplace community, if you will. Be aware of that. Again, I encourage you to check out my tool, the risk of under Best Sell promotion.

Anita Brick:

Well, you're going to send it to me, so we're going to post it. Everybody can go use it, and it's good. It's good. But I don't think you answered my question. My question is how do you connect when it's uncomfortable to do so?

Chris Bishop:

My general guidance, and again, a risk of sounding crass is to connect with people who the market or the community or the world at large has rewarded and who are successful. Where are people in my community or in my environment that are going to reward me, that have already been rewarded, that are successful?

Anita Brick:

This is all true Chris or not. I mean, people have to draw their own boundaries of what they feel is right for them.

Chris Bishop:

But

Anita Brick:

How do you muster the courage actually reach out when it really is uncomfortable?

Chris Bishop:

Yeah. Well, you have to be motivated, right? By factors probably other than just wanting to get a new job or wanting to prune a new skill, think about what it is that's going to make you feel more centered, more successful, more comfortable, more fulfilled. What are the criteria and go to it. Trust your gut, make it work for you. To the degree can, it

Anita Brick:

Sounds like also you need to know why beyond your own ego.

Chris Bishop:

Yeah.

Anita Brick:

You talk about that a little bit too.

Chris Bishop:

Yeah, I mean, I sort of made a deal with the muse, if you will, whatever that means that I would continue to play the bass, but I wouldn't live at the level that it afforded me. But playing the bass afforded me. Okay,

Anita Brick:

Got it.

Chris Bishop:

That's partly what drove me to get into the jingle business and then to get into the web business, become a web producer. It's led me to various other technology based roles like Quantum, being an mc for the Economist at their commercializing quantum event. Factors and criteria that are sort of more meta around how you want to live, where you want to live, who you want to hang out with, who you want to be with, what kind of community you want to be part of. So being aware that those factors will influence how you live and ultimately what you do for a living or what you do to make earned income.

Anita Brick:

And it's okay to be a little uncomfortable. Here are a couple of questions, one about you. The first one is from an alum who said you help a lot of people see what's missing in their own careers. What's a blind spot you suspect you still have in your own career or life and what unconventional experiments, people you talk to, environments you enter, tools you use, have you considered to help smoke that out?

Chris Bishop:

Great question. My current focus is speaking and writing about the future of careers. So I'm certainly looking for opportunities, and this is like a net new space for me. This is really, I would describe it as career nine. As a published author. I'm kind of making it up as I go here. It's a bit of a blind spot. I've never really promoted myself as a published author. Where are these conversations going on? How do I get the book reviewed? How do I get someone to buy the book? How do I do author talks at libraries? How do I do lectures at universities? I dunno if it's necessarily a blind spot, but it's certainly a new area for me. I leverage my network and try to expand it and find settings where this message will resonate. So it's an ongoing thing for me. I'm still doing it my age now with a book.

Anita Brick:

I like it. Do you have time for a couple more questions?

Chris Bishop:

Yes, absolutely.

Anita Brick:

Okay. So this is one I particularly like, and this is from an MBA student. Hi Chris. Think of one major quote, wrong turn you made that not only worked out but became an unfair advantage. Looking back, what were some early signals that this apparent misfit might become a superpower, and how can you train us to notice those signals in real time rather than only in hindsight?

Chris Bishop:

So that's a great question and I want to share with you a personal story. And with the lessons that came out of it for me in 1999, I was working at IBM in corporate internet programs, and the frenzy around the.com bubble was remarkable. Companies were hiring and growing and people buying all kinds of hardware and servers and setting up businesses like chefs.com and pet food.com, and without any viable business models. They were heady times. It was exciting, somewhat similar to the AI rush today, although AI, I think has more real world advantages than the early days of the internet, if you will. So anyway, I was recruited by a bunch of different companies, including pwc. They flew me to London. I took some psychometric tests for them, but this company called pcom, it was a systems integrator basically, right? They worked with vendors, but they built some web-based tools for Wall Street, and they were hiring like crazy.

So they offered me as an ibm er, a 40% bump in salary, a director title and stock options, which were almost immediately underwater. So I was like, okay, well this looks really good on paper. This is certainly an opportunity I should take advantage of. So I took the job, I left IBM, and I went to look at proxy comm, and I knew the first day I'd made a mistake among other things. There was a culture of pre and post IPO. So the people who had built the company before they went public sort of resented all the new hires, and they're hiring people from IBM and from McKinsey and from Cisco. I mean, they were staffing up like crazy, but the people were kind of grumpy and not fun to be around and not very supportive, not very engaging. So I knew that was a mistake.

So the net lesson for me was trust your gut. I have to say that after about nine months, I got fired and I was so relieved, and I stayed in touch with friends at IBM and one of 'em said, we're still building out this team strategy and internet. Would you want to come back to IBM? And I said, absolutely. So I went back to IBM and worked there for another 13 years. And that net is, no matter how good it looks on paper, need to trust your gut, the stock options were underwater. I think January was year 2000. NASDAQ went south in February, so the stock options were underwater, and then there were sort of tumbleweeds in the office virtually because the Wall Street money had dried up. But what I did is I used it as a superpower to realize that I wanted to do things that were interesting and that even it looked good on paper. You had the culture and the vibe and the work that needed to be done were much more important than how it looked. So I went back to IBM and worked out well.

Anita Brick:

I'm glad it sounds like it was something you needed to do. I think you would've probably had regrets if you hadn't jumped on the.com bubble bandwagon, whatever image you want to use.

Chris Bishop:

Yeah, no, it was definitely a painful lesson, but a good one. Again,

Anita Brick:

We like to be really practical and actionable. So one of the questions I would have to bring everything together is what are three things you would advise someone to do to improvise and create a fun, exciting and enduring career?

Chris Bishop:

So I have three sort of meta points that I make again when I do this lecture. The first one is chase the maelstrom, find the chaos, go for the mayhem. So by that I mean go where they, in this case, the royal, they being existing business models don't know what's coming, where they're inventing something new. In fact, who's pushing the envelope? Who's at the front of the bleeding edge, chase the maelstrom, find where they don't know what it is yet. And that's where there's opportunity. That's where the sort of job Nebula is. That's where new careers are being created at that sort of outer perimeter, if you will. So that's one. Second is own the learning. The beauty of living in 2025 is that there are lots of ways to get information and acquire new skills. The hard part about living in 2025 is that there's lots of ways to get new skills and require information.

Managing the tsunami, if you will, is doing triage on the opportunities and the options is challenging, but exciting. And there are lots of ways to get new skills. Now that never existed before from formal settings like Coursera or edX. You can get courseware from MIT or Harvard companies, go to these vendors and ask them to create courseware based on their current needs in their business. We need people to how to do X. Can you put together a curriculum, a syllabus or whatever that'll teach them, and then we'll guarantee to take a look at the top 25% and maybe offer them jobs if it's appropriate. So that's exciting. And again, something you can manage. And the third point I would make is follow your passion. Back to my story about ProCon. Like go where it's interesting to you, trust your gut. Again, I was a touring musician, got tired of it, didn't want to be on the road.

Moved to New York, became a studio musician, got tired of that, wanted to write jingles and sleep in my own bed at night. Became intrigued by the web, became a workplace futurist, working at a company called Future Workplace. Anyway, know that it's going to change and trust it and follow it. Trust your interest. It's going to morph and modify us. Bureau of Labor Statistics, a few years ago put out a survey saying that today's learners are going to have eight to 10 jobs by the time they're 38. So the compelling part of that for me is this is a public sector agency with no agenda. It's not McKinsey or Accenture or Deloitte trying to hire you. They're like, here's what we found. Here's what we think. Use it to your advantage or not. And now standard mean deviation indicates some will have more, some will have less and sort of relax into it. Like take a deep breath and realize it's going to be interesting and you're going to have careers plural over the course of your time in the workplace.

Anita Brick:

I love it. Thank you so much. You are inspiring. You are wildly creative and yet very, very practical. Very, very practical. And you leave the breadcrumbs so that people can follow them, whether they're in college or they have decades of experience. I know this is me, this is very corny. Thank you for being you and honoring who you are, and thank you for sharing all of that with us.

Chris Bishop:

Well, thank you indeed. I really appreciate the opportunity to share my perspective and please contact me, connect with me on LinkedIn. I encourage all your listeners to connect with me on LinkedIn. Please, let's continue the conversation. Check out the book. I think you'll find it interesting. There's a memoir at the end which is titled the afterward, and it has my sort of set of careers so far with teachable moments that I think you'd find interesting at each transition describing what I learned, how I made the move. So thanks again for this opportunity. Indeed. I really appreciate it.

Anita Brick:

You're welcome. And the end of the book, your story, not for the rest of the book wasn't good, but I enjoyed that probably the most. So thanks for bucking the trend of what your publisher thought you should do and you included it. Anyway, I thought it was a great addition.

Chris Bishop:

Well, thank you.

Anita Brick:

Alright, thanks again.

Chris Bishop:

Yeah, thank you.

Anita Brick:

And thank you all for listening. This is Anita Brick with Career Cast at Chicago Booth. Keep advancing.