Gary Bolles: “A Portfolio of Work”

A Portfolio of Work. Workers will increasingly have a constantly shifting landscape of traditional work, project-based work, and entrepreneurial activity. Parents ask me all the time, “Why won’t my kid get a real job?” A portfolio of work is a hedge strategy against an unpredictable future of exponential change. There have been major disruptions in […]

Thrive Global invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive Global or its employees. More information on our Community guidelines is available here.

A Portfolio of Work. Workers will increasingly have a constantly shifting landscape of traditional work, project-based work, and entrepreneurial activity. Parents ask me all the time, “Why won’t my kid get a real job?” A portfolio of work is a hedge strategy against an unpredictable future of exponential change.


There have been major disruptions in recent years that promise to change the very nature of work. From the ongoing shifts caused by the COVID19 pandemic, the impacts caused by automation, and other possible disruptions to the status quo, many wonder what the future holds in terms of employment. For example, a report by the McKinsey Global Institute that estimated automation will eliminate 73 million jobs by 2030.

To address this open question, we reached out to successful leaders in business, government, and labor, as well as thought leaders about the future of work to glean their insights and predictions on the future of work and the workplace.

As a part of this interview series called “Preparing For The Future Of Work”, we had the pleasure to interview Gary Bolles.

Gary A. Bolles is based in San Francisco and is the Chair for the Future of Work with Singularity University and a partner in strategy consulting firm Charette, LLC. A globally recognized expert on the future of work, he consults with C-suite leaders of global companies, labor and education leaders from Brazil to Canada, and global non-profits. He is the co-founder of eParachute.com, inspired by his father’s bestselling book What Color Is Your Parachute?, and visiting lecturer to a variety of school systems, including Isha Vidhya in India, and a regular guest lecturer for Gartner.


Thank you so much for joining us in this interview series! Our readers like to get an idea of who you are and where you came from. Can you tell us a bit about your background? Where do you come from? What are the life experiences that most shaped your current self?

I had very little interest in college when I was growing up in San Francisco. My father was a recovering minister who ended up writing what became the world’s career manual, What Color Is Your Parachute? As one of a series of gig jobs after high school, I fell into the family business, and was trained as a career counselor at the age of 19. After you’ve counseled dozens of people in their 40’s and 50’s hoping to pivot from dead-end jobs, there can be only one insight: Do what you love. For me, that was (eventually) moving to Silicon Valley, finding a gig job in hi-tech, and beginning what became a decades-long fascination with technology and impact for individuals, organizations, communities, and countries.

What do you expect to be the major disruptions for employers in the next 10–15 years? How should employers pivot to adapt to these disruptions?

The greatest drivers of work-related disruption are likely to continue to be seismic shifts in global events, the introduction of exponential technologies, rapidly changing customer behavior, and disruptive competitor business models. But the greatest impacts of disruptions are from the pace and scale of change. The “great reset” of the global pandemic showed us how rapid and how widespread that change can be. Employing organizations can better prepare to continually adapt by embracing a growth mindset, developing 21st-century skillset, and leveraging a toolset of “next” technologies and techniques.

The choice as to whether or not a young person should pursue a college degree was once a “no-brainer”. But with the existence of many high profile millionaires (and billionaires) who did not earn degrees, as well as the fact that many graduates are saddled with crushing student loan debt and unable to find jobs it has become a much more complex question. What advice would you give to young adults considering whether or not to go to college?

As someone without enough formal post-secondary learning experience to stuff into a thimble, I have no moral authority to counsel others on college choice. Yet since I’ve written and lectured extensively on “unbundling higher education,” and I have nearly 900,000 learners for my courses on LinkedIn Learning, I do have a number of suggestions. First, in a world of exponential change, it’s important to dial down the common anxiety about college decisions, since it will likely be one of several periods of learning throughout an increasingly longer life and extended career. Second, decades of insights from Parachute that tell us successful career choice comes from the combination of deep self-knowledge about your own best-loved skills and other unique attributes, and effective research about work opportunities that you can either find or create, by talking with people in the fields that fascinate you. So, do your homework, on yourself and your fields of interest. Third, the shelf-life of information in many industries is rapidly decaying, so make sure you are an intelligent consumer of any learning experience, so you can decide if you think the college investment is worth it. If you add all of these decisions together, and you determine that your near-term path is two, four, or more years of college, that’s great. Just make sure you believe that “future you” will be content with the decision you make today. But if you’re concerned that might not be true, then explore alternative routes that allow you to experience work in your chosen arena more rapidly, such as apprenticeships and project work, and then — if you find it’s a good fit for you — then you can invest in ongoing learning to develop mastery. (But I wouldn’t point to the experience of any Elon, Jeff or Bill as a signpost for your own decisions.)

Despite the doom and gloom predictions, there are, and likely still will be, jobs available. How do you see job seekers having to change their approaches to finding not only employment, but employment that fits their talents and interests?

The headlines of January 2020 predicted 73 million tech-destroyed jobs in 10 years. And then, along came a virus, and in America alone, 45 million people lost their jobs — in 12 weeks. The real impact of automation and globalization is the changing nature of the skills required in jobs, and what a hirer will pay for those skills. If workers become continuous lifelong learners, and organizations invest in the continuous development of human skills, we won’t experience the seismic work-market mismatch that so many researchers have predicted. To maintain your relevance in the world of work, the same basics of career choice apply: Do your homework on your own best-loved skills and other attributes, determine what kind of problems you can solve for an organization or a customer, and either find or create that work — even if it’s in the organization you’re already working for.

The statistics of artificial intelligence and automation eliminating millions of jobs, appears frightening to some. For example, Walmart aims to eliminate cashiers altogether and Dominos is instituting pizza delivery via driverless vehicles. How should people plan their careers such that they can hedge their bets against being replaced by automation or robots?

Automation has always made traditional work less common, and at the same time created new work opportunities. But robots and software don’t destroy jobs: They simply automate tasks. It’s a human’s decision to fire a “freed-up” worker — and we can make different decisions. To maintain your relevance, continually develop your “flex” skills — skills that you can use in a range of situations. I point to four critical skills: Problem-solving, Adapting, Creativity, and Empathy — PACE. If you continually present yourself to a hirer as a creative problem-solver who is continually adapting, and who has empathy for customers and other stakeholders, you will stay well ahead of the robots and software.

Technological advances and pandemic restrictions hastened the move to working from home. Do you see this trend continuing? Why or why not?

Where the pandemic subsides, traditional organizations will inevitably “bungee-cord” back to traditional workplace operations, hierarchies, and work roles. But “next” organizations will empower workers to continuously align with their teams to determine where they can most effectively work at any given time. Organizations with that nimble and responsive mindset will have a tremendous competitive advantage for hiring and retaining talented workers.

What societal changes do you foresee as necessary to support the fundamental changes to work?

Within the organization, we have to change the role of the manager to “the team guide,” focused on four “next rules”: Empower effectiveness, enable growth, ensure involvement, and encourage alignment. For economies, a more human future of work is dependent on stakeholder-centric business models shaped by inclusive capitalism, a more balanced power dynamic between those who lead organizations and workers, and inclusive policies that encourage reliable, well-paid, stable work.

What changes do you think will be the most difficult for employers to accept? What changes do you think will be the most difficult for employees to accept?

Those who lead in traditional organizations will have the greatest challenge in giving up the positional power that comes from the old rules of work — ”management by surveillance,” corporate hierarchies, and skyrocketing executive pay. And those workers who have a “fixed” mindset (as author Carol Dweck calls it) will have the greatest challenges in continually growing and adapting.

The COVID-19 pandemic helped highlight the inadequate social safety net that many workers at all pay levels have. Is this something that you think should be addressed? In your opinion how should this be addressed?

U.S. unemployment increased 10% from March to April 2020, while German unemployment increased 0.8% in the same period. That’s largely because the power dynamic between hirers and workers in the U.S. is out of balance. The ideal solution rewards hirers with the incentives to maintain employment and invest in continuous worker training, rewards workers for having the agency to continually remain relevant to the work market, removes systemic barriers of access to work and education, and provides a safety platform that ensures no citizen goes to bed at night hungry or without a roof over their head. Our mantra must be: No human left behind.

Despite all that we have said earlier, what is your greatest source of optimism about the future of work?

I believe that every single challenge related to work, learning, and creating inclusive economies has an existing or definable solution. But those solutions aren’t widely known, easily transferable, sustainable, or easily scalable — or all the above. We need radical collaboration by “coalitions of the willing” to develop scalable, transferable, sustainable, widely-known solutions.

Historically, major disruptions to the status quo in employment, particularly disruptions that result in fewer jobs, are temporary with new jobs replacing the jobs lost. Unfortunately, there has often been a gap between the job losses and the growth of new jobs. What do you think we can do to reduce the length of this gap?

History shows that these work market asymmetries are actually functions of intentionally-designed systems. They’re not bugs: They’re features. We have mired ourselves in industrial-era education, work, and capital systems that guarantee regular mismatches between worker capacity and work role demand — colleges that charge for degrees with no future work guarantees, mass worker layoffs with no penalties, and venture capital-fueled “innovation” that inevitably automates human tasks. These mechanisms guarantee that those who have already benefited from the system will continue to do so. Change the incentives, so that every player is rewarded for empowering market-relevant workers, and penalized for former “negative externalities” like massive college debt and long-term unemployment, and the system will fix itself.

Okay, wonderful. Here is the main question of our interview. What are your “Top 5 Trends To Watch In the Future of Work?” (Please share a story or example for each.)

1) A Portfolio of Work. Workers will increasingly have a constantly shifting landscape of traditional work, project-based work, and entrepreneurial activity. Parents ask me all the time, “Why won’t my kid get a real job?” A portfolio of work is a hedge strategy against an unpredictable future of exponential change.

2) The Fluid Workplace. Organizations that can empower workers to have more control over the six W’s — What work they do, Where they work, When they work, Who they work with, Why they work, and hoW they work — will be far better able to attract and retain the talented workers they need. It will take a completely new mindset, skillset, and toolset for many organizations to support such a constantly changing landscape of workplace options.

3) Worknets. “Next” organizations will embrace a flexible landscape of human skills that can dynamically bind around problems for the organization’s stakeholders — not a workforce, but a worknet. While the traditional job will remain as one “use case for work,” organizations will develop increasingly “soft walls,” using project work, apprenticeships, mentorships, and other flexible work contexts to leverage a never-ending flow of talent.

4) Global Talent Pools and Global Competition for Talent. The good news: Pandemic-triggered flexible work means you can hire talent wherever someone wants to be. The bad news: So can everyone else. Become a purpose-driven organization, and you’ll find yourself to be far more competitive.

5) An Exponential Toolset. Digital natives will continually leverage a constantly changing toolset of techniques and technologies. I frequently begin lectures by talking about a young worker 20 years from now using mind-blowing technologies — each of which turns out to exist today. As sci-fi author Bruce Sterling is quoted as saying, “The future is already here. It’s just not very evenly distributed.” Mindset and skillset matter most — but we will each need to have a basic familiarity with a tech-fueled toolset that will never stop changing.

Can you please give us your favorite “Life Lesson Quote”? Can you share how this quote has shaped your perspective?

In a YouTube video interview series my wife produced for Google Science Fair, the inventor Dean Kamen imparted wisdom his artist father gave when Dean was young: “Do what you love — but get so good at it that people want to pay you for it.” I use this sniff test all the time in my own work.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

That’s an easy answer: The Dalai Lama. To me, work spiritually is the process of channeling human energy. Nobody on the planet understands the most authentic ways to channel human energy as His Holiness. I was involved in the early development of his U.S. foundation, but I have never had the privilege of an audience with him. Yet.

Our readers often like to follow our interview subjects’ careers. How can they further follow your work online?

I post regularly on LinkedIn, and the links to my activities and writing are at gbolles.com.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.


Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Shampaigne Graves Of Bold Babes Companies: “Training and Team Development needs will increase with automation”

by Phil La Duke
Community//

Shahid Hanif of Shufti Pro: “Time Flexibility”

by Phil La Duke
Community//

Dr. Nisha Talagala: “Rising above the automation”

by Phil La Duke
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.