Gary Bolles

Gary Bolles

Chair for the Future Of Work

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.


By Roadtrip Nation

Gary Bolles

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My Career PathInterview Excerpt


My road in life has taken me all over.
I struggled in school and barely graduated from high school.
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.
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.
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.
I’ve worked as the editorial director for six technology publications, including Interactive Week, Yahoo! Internet Life, and Network Computing.
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.
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.
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.
Keep following my journey


High School


Chair for the Future Of Work

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

Career Roadmap

My work combines:
My work combines:
Teaching / Mentoring

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 & Qualities Beyond School

Learn how to be an effective problem-solver. Be able to identify what is wrong and iterate quickly in order to test out solutions. Work-life balance is really important. Know what is important to you in your everyday life and your work life and find what works best for your lifestyle. Gain a wide variety of knowledge and pursue things that you are curious about. Specializing in something is not really needed for the majority of jobs. Have adaptable knowledge.

Advice for Getting Started

Here's the first step for everyone

Do what you love. Find your passion and go for it! Give yourself permission to pursue your dreams! Make mistakes and learn from them. If you don't have a college degree, take the time to reflect on your skills and think from the mindset of an employer. Figure out how your skills and qualities can help them mitigate their hiring risks in picking you and how you can uniquely solve their problems. Do some self-inventory and figure out what makes you unique. Network and build up your contacts.


Challenges I Overcame

School Stress
Career Change

Interviewed By



Future of Work Roadtrip