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PodcastsMay 20, 2016

Podcast: Business in Boring #3 – The future of work with career guru Gary Bolles

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‘Business is Boring’ is a new weekly podcast series presented by The Spinoff in association with Callaghan Innovation. Host Simon Pound will speak with innovators and commentators focused on the future of New Zealand, with the interview available as both audio and text. This week: career specialist and eParachute co-founder Gary Bolles.

Failure. Disruption. Start-up. Portfolio. The gig economy. Before they became entries in a game of business-speak bingo these words all had meaning, and a lot of that meaning has come from a man named Gary Bolles. He’s been thinking about, talking about and defining a lot of what we understand about the new economy and the nature of work through his driving role in putting on and headlining the kind of conferences that the billionaires of San Francisco go to so they can work out what happens next.

He’s in town for Techweek, one of the many quite amazing speakers they’ve pulled down here. His talk could give you cirrhosis in a drinking game of business buzzwords, How to Thrive in Disruptive Times, but behind that line is meaning that’s been lost as these words have become cliches – the human impact of the changing world. Gary came to this field by way of starting the Internet’s first real newspaper, consulting on Google’s Zeitgeist and co-founding a site called eParachute, that helps people understand their best career options through what makes them most happy. It’s this marrying of the human and the macro that makes him such an influential and interesting speaker and writer.

Have a listen below, or download here on iTunes, or here on Stitcher – or read on for the transcript.

Simon Pound: Let’s start with failure. How do you become a failure expert and how do you define failure in this sense?

Gary Bolles: I’m a little nervous about being a “failure expert” because I would assume that to mean I’d have to have a tremendous amount of experience in that category. The word “failure” in a variety of cultures has a tremendous emotion coding. When I talk about the mentality that we try to encourage people as individuals, people as founders of start-ups, people with more mature businesses, to think about instead is: what is it that you’re really trying achieve? And what is your risk profile?

So really what ends up happening in a place like Silicon Valley is that you’ve got a process that people go through in trying to understand the best way possible to be innovative. First off, what’s your risk profile? If you have a very low profile, doing a start-up might not be the best thing. You have to think about yourself and the kinds of situations that you find yourself in. and if you’ve got the kinds of skills, the kind of mentality, the kind of personality traits that allow you to have a relatively high risk profile, that’s great. You should be throwing yourself into starting things, into doing new and interesting things, into taking those risks. And if you have a low risk profile, for instance if you have a family that you’ve got to feed or you have just been fired from a job and you’ve got to find a new one, that’s a completely different mentality. Therefore your ability to be able to put yourself into a position to have a failure, to make a pretty significant mistake, may be relatively low.

How does one change their risk profiles? I imagine if you have a fantastic idea for a world-changing app but you also have three children and a mortgage, you can’t just ditch one or the other, can you? How do you set the conditions so more people can have a high risk profile?

I tend to come at things from a macro standpoint, from the high level view, the 40,000ft view, and from the ground level. From the ground level it’s what do the individuals do, what are the right decisions to be making about their career. Let’s start from the ground level. As an individual in the past, and especially in the States, there was a fairly consistent mentality that you could go to work for a company and you could have that job for a good long period of time. So you could a really low-risk profile and still have this meaningful work opportunity, the nurturing environment. What’s happening as technology and globalisation partner together to disrupt industry after industry, and they change the dynamic of work, what’s happened is work is becoming “unbundled”. Work is being split apart. If you look at Uber and a variety of different work platforms, what they do is they have this sort of low friction entry point that makes it very easy to come in and do this kind of work but they don’t actually you to be able to grow and change. These aren’t companies that are committing to give you work for a long period of time and so on.

So in the past, having a low-risk profile meant hey, we’re gonna work for one company, I’ll be there for a long period of time. In this new era where change is absolutely guaranteed, in the United States for instance, the statistics that were just released by the Department of Labor, the average person’s going to change jobs once every 2.5 years and that’s accelerating. What that means is you’re going to continually be going into new work situations. Your previous work situation is not going to last. So people with low-risk profiles are actually going to be more and more uncomfortable in this constantly adapting world. What that means is, to actually answer the question you asked which is how do people change their risk profile, there’s a variety of different things you can do, starting with permission.

Many people, when they go to make career decisions, they feel they actually need to be given permission to be able to take risks. It’s not that they necessarily don’t have the internal makeup to be able to do it, although that can be a challenge for some, but it’s really going around and getting the support, the trust of the people that you trust to be able to say “yes you can go ahead and do this.” Sometimes it’s going to a spouse, sometimes it’s going to your parents, sometimes it’s going to your friends, former coworkers, even your existing boss, and trying to take small risks. Doing something more along the lines of the kinds of things that you love. Starting a business on the side. Doing a little bit of work part-time in something that could be a little risky, so that you practice those muscles and you get used to putting yourself in a position where you can take a little more risk. And where you can start making mistakes.

There’s a wonderful entrepreneur friend of mine, Esther Dyson, who is also invested in a variety of companies, and her tagline on her email is “Make new mistakes”. So the whole idea of developing a risk profile is to try out new things. But if you make mistakes, if you bump your head up against a wall, understand the lesson that you got from it and go try do something different. Pivot, adapt to new opportunity, but don’t make the same mistakes.

The areas that you’re talking about and the “how to thrive in a time of disruption” idea, it’s touching on the future of work, the change in the economy, the nature of business today. It’s a huge area to look at. Let’s take a step back and talk about how it is that you come to be talking about thriving in a time of disruption?

Probably the most useful framing for me, not to terrify people, is that if you look at what happened to Western economies when we all made this transition from agricultural to an industrial society. Obviously a country like New Zealand still has a tremendous agricultural component of its GDP but in the States, we basically shifted from an agrarian to an industrial society of a period of 80 to 85 years. It happened in about three or four phases. Went from about 70% of employment in the United States focused on agriculture to 60-70% focused on business and industry. There were a number of other seismic changes going on, a lot of technological changes and so on, but basically it happened over a really long period of time. Three or four generations. I believe that we’re going through as fundamental a change in the way that Western economies work as we did in that shift from agricultural to industrial, as we shift into what we can call the digital economy in a blindingly short period of time. Think of all the institutions that had to be reshaped by that period. We’re going through a lot of that same process but before our eyes. We’ve got this increasingly rapid pace of change.

If you look at the first businesses that were impacted by the combination of technology and globalisation, it was actually media business. So if you’re a student of history and you look back to Napstar, you look at the initial impact on media businesses. Because they were about content, and content being 100% bits, you could break the business apart and allow new companies to come in and take pole positions, take over, for instance, advertising. The reason that Google was able to basically take a big chunk of the value proposition from media companies is it said “I can create a more efficient marketplace for attention”, which is what a media company really is; you create content and people draw their attention to it then you try to market that attention. Google said “I can create a better marketplace for the combination of attention and advertisers.” As we reshape so many of these different industries and so many of our institutions, there’s a tremendous amount of disruption for the incumbents, but there’s a tremendous amount of opportunity for start-ups and new players.

You mentioned Google and advertising which is another part of this puzzle. In the past you had this institution that’s perhaps geographically bound so media companies were in a territory and they employed people in a territory and they paid tax in a territory. But we now, in New Zealand, are facing a very interesting situation where companies like Facebook and Google have dominated the digital advertising space but they repatriate their profits off to places like Ireland where they pay low tax and aren’t contributing back to an economy. So the disruption’s compounded in terms of civic institutions too.

Absolutely. If you want to be bored with understanding the nitty gritty of those dynamics, I’ve actually written a series of papers on If you just look at @gbolles on you’ll see I’ve written papers on “Unbundling Media” which comes from a concept held by a man named John Hagel at Deloitte. “Unbundling Higher Education” which I believe is one of the next major industries to be unbundled, and so on. “Unbundling the Middle Class” and “Unbundling Work”. But the basic premise is that as you recalibrate so many different industries – and media is a perfect example – there are a couple of dynamics that are absolutely inevitable.

The first is that these new platforms, and “platform” is an overused word but basically it’s a set of software capabilities that allow others to be able to build businesses on top of you. That’s an oversimplification but what ends up happening is it turns out if you pair technology and globalisation – which is absolutely critical. If it was all within the borders of one country it’s only a certain set of dynamics. The minute that you can start to expand beyond borders and, as you say, to be able to come in and take over this category of mobile access with social networks or mobile access to web pages. What you’ve done is you’ve essentially said the most efficient player is the one that’s going to win.

Another dynamic is that if you think of industries historically as being pyramids with large, dominant players at the top and small, niche players at the bottom and a nice, healthy middle in between. A variety of different industries, when the internet and globalisation hit them, it actually evaporates the middle. So what ends up happening is a tremendous number of studies have shown that increasing returns are aggregated to the player at the top. So that’s why there’s one Google, one Facebook, one Amazon. Because those players become extraordinarily efficient and they do so in a wide variety of markets. And unless you have some very, very unusual market dynamics where either it’s a very isolated economy or it’s an economy that puts a firewall around itself and doesn’t allow certain businesses in, it becomes global very rapidly because they’re the most efficient provider of that particular service.

And those global providers end up having an enormous effect back down at the person level, on the kind of work people do and the kind of businesses that are able to survive. You came to this from a job counsellor background in the very beginning; tell us about your father and the world’s bestselling career book.

I was never all that interested in college when I finally escaped high school and so I actually, I’m fond to say, was probably one of the worst possible students of my father’s work at the time. I basically had no clear career path. But I ended up working in the family business, being trained as a career counsellor when I was 19. One of the greatest learnings I wish every 19 year old on the planet could have is to talk to people who perceive themselves to have been in dead end jobs for 10, 20, 30 years and are complaining about the fact that they never made a change in their lives at the time they felt they should. The only takeaway you can have as a teenager when you hear that kind of input is that you should do what you love, you should do what fascinates you. So that’s actually the learning I took away and so I did a variety of odd jobs in my early 20s but I eventually found high tech.

What I realised is that is what I love. That was sort of the context of understanding because high tech tech changes very rapidly and I’ve got a high case of Adult Attention Deficit. There’s always new waves, new trends to be able to identify and as I started to realise I liked writing about those things, journalism gave me an opportunity to get a different perspective on it. Then ultimately that morphed into doing events and initiatives to be able to bring people together around world.

But to answer your question directly, I always think about first the impact on the individual and what it is that any individual can do to be able to adapt to the current challenges that they’re facing and how they can be the most proactive and resilient in dealing with whatever their goals are and being able to achieve them. So I’m highly biased towards the needs of the individual, having been a journalist and having seen a variety of cycles. I first came to Silicon Valley over 30 years ago which allows me to back up and say “Wait a minute, I’m hearing all of these patterns as I’m talking to people, now I’m starting to see how these patterns are actually affecting us at a macro level.” You’re talking about, for instance, the future of work. How we understand work today is going through the most fundamental change you can imagine, again, in a blindingly short period of time, because we’ve been living in a construct of what work means from the industrial age. We don’t even know it. So when you’re talking about my father’s work, What Color Is Your Parachute?, he’s a recovering minister and he wrote it when he was actually laid off from a church in San Francisco and he found that other ministers were also being laid of. So he wanted to write a pamphlet to help them and ended up writing a book. But one of his greatest insights after he wrote that book-

Bestselling career book ever. Twenty two million copies.

Ten million in print and then it’s got a pass along factor of about two to three, so we normally say you’re easily affecting 25 to 30 million people. My father also had another great insight which is that actually the arc of our lives is sort of blocked out into three chunks; education, work, and leisure. We come out of the womb and suddenly need to learn a lot of things. And what we did during the industrial age is we created institutions around education that actually were quite literally, in the United States, designed to teach students as if it was a production line. There’s a tremendous amount of writing by very influential educators around the turn of the 20th century that basically said this was the goal of a public education, so that they would be trained workers in factories.

So then you suddenly had this shift into this work box with absolutely no preparation whatsoever. Especially if you’re graduating from college, you’ve learned all the rules in that first box and then you are newborn child going into the work box. You have no idea how those roles work. The narrative is you work as long as possible, very little education, very little leisure. You come to the end of your relationship with work, we call it the period formerly known as retirement. This is a narrative that very beneficial to industry. “Why don’t you give us your best years and then the ‘golden years’ will be the time when you can actually do what you wanna do.” My father’s insight was why don’t we turn that on its side. Why not lifelong education, lifelong work, lifelong leisure. He wrote this book 30 years ago but if you play that out, the inevitable ramifications of that mentality, we have to unbundle work, we have to unbundle education. Because we’ve got this construct that said “well you’re gonna go work in a factory” and in the States at least, there’s a very small percentage of people working on a farm, very small percentage of people working in a factory anymore. Even with the resurgence of manufacturing in the States.

It was really interesting to hear you talk just before about the way that work has changes so that the average worker works 2.5 years for a place. I wonder if there isn’t more overlap. If new workers today aren’t working at 2.5 places at once for 2.5 years.

I’m going to offer another perspective that I’ve found helpful. When you look at labour statistics, for instance, which are typically used by countries to try to understand what’s going on with their workforce. So many of the labels and mentalities that we’ve used in the past are not going to be useful going forward. One of them is “job” as well as “career”. The old definition of career was you come out of college or you finish high school then you’re gonna pick a field and you’re probably going to be in that field for a really long time. If you’re trained as a doctor, if you’re trained as a lawyer, that’s your personal identity and that’s what you think you’re going to be doing for a long period of time. If you’re going to change jobs every 2.5 years, on average, one takeaway has got to be that the word “career” has got to be redefined. It’s going to be all of your relationships to the world of work until you stop having a relationship with the world of work. That can be a variety of different jobs, projects, activities, volunteer work and so on. That’s the first thing, we have to redefine the word “career”.

The second thing is we have to redefine “job”. One mentality that I find useful is a mathematician will tell you there’s two ways to look at the world in terms of sets. There’s set theory which is I’m either a member of something 100% or I’m not. Binary. Fuzzy-set theory says I have a degree of membership. I might be working at a job but I might also have a part time business and I might also be consulting and I might also be volunteering. So you have a relationship with work that’s actually a portfolio. And there’s a degree of involvement and that degree of involvement could change on a daily, a weekly, an annual basis. But that’s a portfolio in the same way an investor thinks about having a distributed set of things that they do. As you look at especially younger people, millennials, the way they think about work, they’re doing exactly what I’m talking about. They have a portfolio of work without anybody ever teaching them that that’s the way that they should be thinking about it.

Part of that is necessity. They’ve had to because of the change, and this is a macro change again, where a lot of the reasons why you had this idea of almost bondage. There’s even terms in academia like “tenure” where you’re absolutely fixed to something for life. But there was also the quid pro quo of that which was we’ll give you bereavement leave and sick pay and health insurance. There was a real patriarchal kind of relationship between work and workers. But now with casualisation of jobs and without those protections around workers, people kind of have to make up a mix to look after themselves, don’t they?

When you look at it from a macro standpoint, for any single individual, if they have this kind of mentality about being proactive and adaptive and resilient in the way that they are continually trying to find work then any single individual might be able to find meaningful work at reasonable compensation. When you back up and look at it from a macro standpoint, what freaks out a lot of people looking into the future is they see those dynamics and what they’re worried is that a workforce in total for a country is going to make less money. If you can compare the older model where you worked at a company and they gave you a living wage and you worked nine to five.

And one job and 40 hours could support a whole family. Now people have nine jobs and 60 hours to look after themselves.

So that’s the problem. Now you’ve got this new portfolio, you’re driving for Uber and you’re doing some Task Rabbit activity and you’re working as a barista at Starbucks, I’ve got a t-shirt so I must have a start-up. So the result is you have a portfolio of work and from a macro standpoint, at the end of the day, all that really matters, if you feel that that’s working for you and it’s meaningful and you’re enjoying what you’re doing, is that in comparison you could still make a living wage. What the challenge unfortunately is there’s two dynamics going on; one is that during the recession in the United States, there was a significant drop in the average percentage of the wages that were being paid. What you saw was this growing gap between the haves and the have-nots because there was tremendous downward pressure on wages.

The other problem that we’re talking about with the Ubers and the Task Rabbits of the world, they’re designed for wage compression. Because essentially they’re trying to be the most efficient marketplace possible for supply and demand. When you look at an Amazon or an equivalent, it’s basically what they’re doing. They’re trying to continually compress cost because we’re all very cost conscious and what it’s going to do inevitably is the producer has to get more and more efficient and producing for a lower amount of money. And same thing for you as a worker.

What that means especially in the examples you raised there, of Uber and Amazon, is the worker ends up being the most expensive thing that becomes removed by robots. This is a really interesting thing, I see you’ve been doing work with the Singularity University. The Singularity is the moment artificial intelligent becomes sentient, as a broad term. The people around the Singularity institute are looking to try to smooth this transition and that’s the work of the Singularity University. Where are robots in this future of work and what does that mean for people?

Singularity University is a marvellous think tank based in Mountainview, California, and probably the word that most embodies the way that they think is “exponential”. Technologically-driven change is actually at an inflection where it’s a hockey stick. It’s not this nice, smooth line, it’s actually accelerating very, very rapidly. Their mantra, which I think is actually quite accurate, is that because we’re going through these massively disruptive times, understanding how to adapt to change is the new skillset. It isn’t that you can accurately predict any future change in the economy or your business or a particular industry, although reading those tea leaves can be helpful, but it’s more building into your DNA of your business the ability to continually adapt and change. And back to the ground level, same thing for individuals. The question that is constantly asked in the States is “will robots and software eat our jobs?”

The answer is yes.

Right. So the answer is yes, inevitably it will eat some jobs but again, I tend to oversimplify these things. The question for you as an individual is will you be able to make a living wage with this portfolio of work compared to what you might have had if you’d have a full job. It’s the same question for an economy. Will there be enough new jobs created at the pay level that is commensurate enough with the people who were disrupted, and will you help the people who were disrupted to go and do those new jobs?

What you’ll find, and this happened in the shift from agricultural to industrial economy, is older workers are the ones who get left behind. The reason is because they came from a time where change was at a slower pace. It has to be. If change is going exponential and you just walk back a couple steps, just a generation or two, even though we had massive changes on the global landscape in terms of wars and disease and so on, the truth is technological change was not as rapid as it’s going to be. As it is now and as it’s going to be in the future. Younger people, they’re calling them the digital generation, they’re calling them the adaptive generation, they grew up in a time where change is going to happen. So they’re much more used to that. The older worker is the one who’s most at risk. And so we have to reshape a variety of our institutions, including higher education, so that we can more rapidly help that worker who is displaced to get these new jobs that are created.

We don’t know yet if there’ll enough new jobs created at scale to replace the ones – but the truth is, if you talk to a variety of manufacturers, what they’ll tell you is the reason that we’re starting to automate a lot of things is not because we want these workers to be displaced, it’s because we can’t find these high-value workers over here in the new jobs. And we can’t train people fast enough to be able to do them. We need data scientists, we need people who typically have a fairly long education path. So we need business to be more articulate about the skills they’re going to need in the near future and then we need our higher education institutions to rapidly provide those learning opportunities.

If you look, for instance, at start-ups like Udacity, which was founded by Sebastian Throne who used to be at GoogleX. What Sebastian says is “my whole mentality is figuring out what those businesses are going to need and then trying to create the information products that will get us there.” For instance they have this thing called nano degrees. AT&T has outlined several jobs that they need people for now. If you successfully complete a Udacity training and you basically hit a certain level of performance, AT&T will hire you. So we need far more of that dialogue where the connection between businesses and higher education institutions are rapidly, dynamically binding around the problem of exactly what skillset you need in these new jobs that are being created.

Does part of it come back to something that your father was very prescient on 30 years ago, that maybe we don’t have to have lives where it’s all about work and there can be more leisure. Does every job need to be replaced? Do humans need to be working 40 to 50 hours every week if robots can do the jobs? Where does that come from?

As a teenager I was always fascinated by science fiction. I’ve got 2000 paperbacks still sitting in my basement. So it was inevitable that science fiction authors back in the ‘50s and ‘60s would start to sort of play out the idea of if robots and technology was going to take more tasks, would we as a society still need to have people working  and being able to have the sustainable lifestyles that they want. If you can put together a portfolio of work that allows you to have the lifestyle that you want then more power to you. The increasing perspective in the United States, and one of the reasons you see this tremendous dynamic with the current presidential election, is that there’s a significant group of people that people disenfranchised. They feel that actually the rules have changed, I can’t make as much money. The job that I had before is not available and sure I can go drive for Uber if I live in a city but I’m not gonna be able to feed my family.

And that’s not a long term job as they talk about having autonomous cars.

Change is going to continue to increase rapidly so you as an individual, you’ve got to learn more and more to be adaptive. We talked about risk profile, you’ve to learn to be able to take more and more of those risks to do new things. Increasingly, you’re going to have to know more and more about yourself. The impetus for doing self-inventory (you were talking about my father’s work) is going through and understanding what makes you unique. Your skills, your values, your interests. We call that the “what”, the “what” of you. What makes you unique? What do you love? What are the skills and knowledge that you have that you’re absolutely dying to use or that you want to learn more about?

So there’s a strong impetus to being far more aware of those unique characteristics for you because in the past you could have just worked at a job, kept that for a good period of time. Didn’t really need to be constantly adapting to new opportunities. But now, if you’re going to continually be in a situation where more and more tasks are going to be automated, you’re going to have to be more proactive. So the problem, in a world where perhaps more and more tasks will be automated and there might an aggregate less need for work, is most Western societies have not yet said “that’s great. What we’ll do is we’ll just pick up the slack for all those people who don’t have enough work and we’ll pay for them.”

The universal income that’s being talked about in places like Norway. That is another criticism that has been levelled at this idea of failure which is hero’d in start-ups and technology businesses. It’s sometimes said that it’s something that only the privileged can afford so that if you’ve started a business with friends and family’s money and you don’t have access to capital and you don’t have that risk profile that allows you to fail, failure isn’t something you can celebrate because failure is actually something that results in bankruptcy and misery. So it’s kind of like a situation of privilege where if you have the resources to fail then you can.

Absolutely. When I talk to people as individuals, instead of talking about businesses and startups and that sort of thing, the first place to start is entrepreneurial thinking. Entrepreneurial thinking doesn’t require you to go and build a company. What it requires you to do is to have a passion for solving a problem. At the end of the day, employment, or starting a company or whatever, if you take it down to its absolute basic is there’s a set of problems that need to be solved for somebody. And you’re going to perform a series of tasks to be able to solve those problems and you have very specific skills to perform those tasks. So an employer hires you because you’re a problem solver. They’re not going to hire you because you’re a problem, they’re going to hire you because you’re going to make things better for them.

It’s the same thing with a customer. A customer hires you because they have a problem, they have a need, and you’re going to solve it for them. Entrepreneurial thinking simply puts you in the context of trying to figure out what it the set of problems that I’m passionate about solving? It doesn’t mean you have to go do a startup. What it can mean is you can more entrepreneurially approach an opportunity for work. For instance, if you’ve defined that you have a set of skills, the kinds of problems that you like to solve and the skills that you have to solve those problems are really good in terms of helping people to choose particular fashions to wear. That doesn’t mean you have to go do a startup focused on building an app so that people can choose fashion, but it might mean that you can approach fashion companies and say “I have a really good understanding of these issues and how people make these choices, let’s create a job where I can help you to build this app or I can help you to be able to be more responsive to the needs of your customer and what they want to wear.” If the job doesn’t already exist, you can help create it with an existing employer. So that’s very entrepreneurial but it’s not starting your own company.

So to the point about not everybody can have a failure, again back to your risk profile. Think about what you think you can accomplish and push yourself beyond that. Take a little bit more of the risk, put yourself in a position to be able to take a little bit more of that risk. But don’t put yourself hugely at risk unless you feel that you can actually have a reasonable outcome. If you’re going to mortgage your house and start a company, you’ve got to be okay with the ramifications of not achieving that.


Like any portfolio, you have certain parts of it that would be conservative and certain parts of it that would maybe be taking a higher risk with a higher potential for return. That’s such a great metaphor for what’s been called the “Gig Economy” or “Slashies”, where you’re a DJ slash photographer slash startup worker slash Uber driver and barista.


Thank you for talking Gary. If people were to find you online after this there’s eParachute, where you’re able to actually go through some of those exercise that you talked about to discover the “what” that you have. A lot of the talks I post I post on For good or bad I’m actually quite easily Googleable.

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