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
Skills &
Education
Advice for getting started
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.
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.
Defining Moments
Experiences and challenges that shaped me
I wasn't a very good student in high school and barely graduated. I've never gone to college and had to figure out ways to navigate my career without a degree.
I switched careers a lot in my early 20s. I've done over 27 different types of jobs. I discovered that having a wide knowledge set and adaptable skills have allowed me to be flexible in my career and find what I am truly passionate about.