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Gary Bolles
Gary Bolles

Gary Bolles

Singularity University

San Francisco, CA USA

"You only need permission from yourself to do new things. You’re not going to get approval from society...The challenges we face all come down to mindset. Nobody is going to solve your problems, but we can all learn to have agency."

Career Roadmap

Gary's work combines: Technology, Education, and Teaching / Mentoring

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Day In The Life

Chair for the Future Of Work

I am an internationally-recognized expert on the future of work and the future of learning.

My Day to Day

My main focus is on the strategies for helping individuals, organizations, communities, and countries to thrive in the transition to a digital work economy. At Singularity University, I lead the organization’s efforts to empower a global community with the mindset, skillset, and network to create an abundant future of work and learning.

Skills & Education

Here's the path I took:

  • High School

Life & Career Milestones

I've taken a lot of twists and turns

  • 1.

    I struggled in school and barely graduated from high school.

  • 2.

    Decided that I didn’t want to pursue college and immediately began working—spent my early 20s working over 27 different jobs, trying to figure out what I wanted to do.

  • 3.

    Fell into the family business, where I trained as a career counselor and started working alongside my father, helping people in their 40s and 50s find work.

  • 4.

    Through working as a career counselor, I learned the value of pursuing work that you love—I decided to follow my interest in technology and moved to Silicon Valley.

  • 5.

    I’ve worked as the editorial director for six technology publications, including Interactive Week, Yahoo! Internet Life, and Network Computing.

  • 6.

    Spent a few years working as the Chief Operating Officer for Evolve Software, as the VP of Marketing for Network Products Corporation, and as a consulting producer for strategic events.

  • 7.

    In 2012, I took a role as a consulting partner at Charrette LLC and founded eParachute, an online resource for job-seekers, career changers, and entrepreneurs going through life or work transitions.

  • 8.

    I am now the Chair for the Future of Work at Singularity University, leading efforts to enable an abundant future of work and learning through the empowerment of the global community.