Future of Work Report: Progress and Potential

August 11, 2023



Future of Work Report: Progress and Potential

Future of Work Report: Progress and Potential

Gary A. Bolles is Chair for the Future of Work at Singularity University, co-founder of eParachute.com, and Author of “The Next Rules of Work: The Mindset, Skillset and Toolset to Lead Your Organization through Uncertainty”. After a first interview in April 2020, Gary returns to the show to report on how he sees the Future of Work progressing and our ongoing adjustments for it. He shares insights about important work trends, mindsets, behaviors, and balance. Gary describes how concurrent waves of old work rules, transitional models, and the next rules of work are impacting leaders and our multigenerational workforce with its shifting weighting of employees and non-employees.


[02:20] Revisiting our first podcast discussion at the beginning of the pandemic in 2020, Gary recalls his article about the Great Reset.

[03:54] The helpful visual of multiple waves to understand the evolution of work.

[05:10] Some leaders have bungeed back to old rules of work while others have embraced new rules and operating systems.

[07:02] The effect of perceived incentives and disincentives on changing habits and rules.

[08:05] How to benefit from pandemic learnings and accept the messiness of adapting new practices.

[10:50] Zooming out to shift your mindset about how to solve problems across your ecosystem.

[11:36] Imagining leading without ego and with trust in order to alter leaders’ approaches.

[14:53] How media’s mischaracterizations don’t help as three waves of work try to co-exist.

[15:32] The inevitable trend of continuous co-creation which young people especially seem to embrace.

[16:30] The power dynamic had tilted towards employers which flexible work is rebalancing to some degree.

[18:29] Picture ourselves as icebergs. We employ entire people, not just the tip of the iceberg which we recruit.

[19:32] In the new era of work, leaders are responsible for workers, their lives, and communities.

[21:43] Sophie anticipates smaller core employee groups and more non-employee workers in future.

[22:50] Future employee “agency” achieved through a “worknet” - a flexible flow of talent with varying degrees of organization membership.

[24:05] How to help increase degrees of membership in your company, enable people to feel connected, co-create effectively, and be rewarded.

[25:00] Cybersecurity provides a similar framework for the worknet model.

[27:00] Using words and concepts that reflect people’s sentiments and realities helps us reach balanced understanding and outcomes.

[29:10] Aren’t young employees manifesting the Future of Work rather than disrupting work norms?

[30:15] How young people are responding to new market signals as new work practices endure.

[32:09] Why older leaders are bereft at Gen Z’s behaviors and miss the opportunity of co-creation.

[33:23] Why aren’t younger employees’ deciding their careers now, and other related outcomes?

[34:45] How the precarity of the world is driving youth to hedge their bets with a portfolio strategy.

[35:32] Looking at the three stages of life horizontally not vertically (sequentially) as proposed by Gary’s father who wrote “What Color is Your Parachute?”

[36:47] Parents ask “Why won’t my kid get a real job?” It’s a hedge strategy. It’s ensuring optionality.

[39:00] How culture can be a journey, defined by a mindset and behaviors that are reinforced.

[41:30] What is the process and ongoing actions that empower agency and co-creation?

[43:46] Gary defines empathy as lived experiences. He focuses on caring for coworkers.

[47:19] The sea change ahead as more capable tools come online.

[48:08] Work involving synthesis is greatly enhanced by AI-boosted tools.

[49:46] Leaders need to focus on helping workers be upskilled and utilize the tools to solve current problems.

[51:18] Starting with a growth (vs fixed) mindset and focusing on flex (or soft) skills for today’s business needs.

[52:15] Companies must invest in training employees as education systems are still biased towards teaching bodies of knowledge, not flexible skills that augment interactions and social situations.

[55:40] IMMEDIATE ACTION TIP: Reframe managers and supervisors as team guides. Rethink the process, what their role is, and how you can help them to guide teams throughout your organization, “un-boss” meetings, and be there to remove roadblocks so team members can co-create solutions.


“We’re pattern recognizers, we’re general-purpose problem-solving machines.”

“I think that’s actually a failure on our part, wasting a perfectly good pandemic. We showed that we can trust. We showed that we can imbue teams with the power to be able to decide when and where and with whom and how they work. And then we took it away from them.”

“We’re going to find that once you’ve given people agency and some level of autonomy, they don’t want to give it back. And I think that’s a perfectly reasonable request.”

“Along comes a pandemic, and suddenly you and I are looking into each other’s homes on Zoom calls. And we realize: that’s a whole person and if I’m an employer I have to be responsible for their physical health, their mental health, their emotional health, the whole person. And that’s not what I signed up for in the old rules of work!”

“I don’t hear a lot of workers complain to me that they’re not engaged. That’s not the way that a worker would say it. A worker would typically say ‘I want to feel motivated by my work’, ‘I want to feel like I have meaning in my work’, ‘I want to feel well compensated’, ‘I want to feel recognized.’”

“Gen Z was born around 9/11. They were children through the global recession and young adults in a global pandemic, on a planet on fire. There aren’t a lot of other generations that have had that sequence of precarity.”

“In a world of almost complete uncertainty, there are no safe jobs.”

“Why are you waiting to enjoy life until retirement? Does that make any sense in a world on fire? No. We’re going to do it now.”

“We keep thinking “Just shove more bodies of knowledge into those little heads”. And that’s not the way the world is working. The shelf life of that information, of those skills, is decaying so rapidly. We have to explicitly teach these much more flexible skills and then employers have to demand them.”