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Rebooting Work: Transform How You Work in the Age of Entrepreneurship

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From Silicon Valley leader Maynard Webb, how we can leverage technology to change how we workMaynard Webb has always been the go-to guy when Silicon Valley companies have thorny problems. Whether revamping eBay's crashing servers (transforming their technology weaknesses into a competitive strength) or investing in emerging technology start-ups, Webb brings strategic and operational savvy to every issue and venture. In his first book, Webb brings this same focus to tackle outdated models of work, created a century ago, which no longer sync up with either individual or employers' needs.

Through a unique framework, Webb identifies 4 different mindsets around work (the company man, CEO of your own destiny, disenchanted employee, and the aspiring entrepreneur). It organizes those who are self-motivated versus those who are waiting to be discovered and aims to give readers the tools to become more self-actualized, happier, and ultimately more fulfilled in their careers. In identifying a paradigm shift that is already under way, Webb demonstrates clearly how to harness technology to embrace our own personal happiness, allowing people to become more productive at work and also spend more time with their families.Contains a framework that demonstrates how we can leverage technology to create better job opportunities and foster more balanced livesWritten by Maynard Webb, chairman of LiveOps, former COO of e-Bay, founder of Webb Investment Network (WIN), and board member of Yahoo! and salesforce.comIncludes personalized worksheets and empowering action-oriented advice

"Rebooting Work" reveals how anyone can take control of his or her own future, finding greater fulfillment, productivity, and happiness.

224 pages, Kindle Edition

First published January 17, 2013

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Maynard Webb

6 books7 followers

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Displaying 1 - 15 of 15 reviews
Profile Image for Ian.
139 reviews
May 12, 2013
I like his objective approach to work and career. Its up to each of us to make the work we want. Some good ideas, like building your own community of work, outside work.
Profile Image for Danielius Goriunovas.
Author 1 book261 followers
May 28, 2019
Great ideas, but writing style isn't easy to read and the topics don't really go into any depth. It's an okay-ish book on modern freelancing but not really anything more.
Profile Image for Jonathan Crabb.
Author 1 book13 followers
May 29, 2013
Important analysis of the current work culture, especially the last couple chapters.
Profile Image for Tim.
151 reviews
December 19, 2017
The four frames discussed in the book were interesting. I found myself thinking back to previous jobs (as well as thinking about my position currently) and determining which frame best represented my situation. I liked the thoughts on how to escape certain undesirable frames and land in the ones designed to give the employee more happiness and satisfaction in his job. While this book could be valuable for many different types of employees, I found it slanted heavily toward the entrepreneurial type (which I'm not).
1 review
December 6, 2015
Very shallow coverage

The book was not up to my expectations, particularly considering the high credentials of the author. It presents a very shallow treatment of the topic. It actually seems more like a book advocating work from home or remote working models than anything more 'strategic'.
2 reviews
September 13, 2013
Doesn't really break any new ground, but useful enough information to hear again, with a few (though inconsistently used) examples sprinkled in. Main issue is that it has the content of a nice newspaper article or blog, stretched out into a book.
Profile Image for Bojan Tunguz.
407 reviews198 followers
May 6, 2013
I have to admit: when I first got this book I thought it was yet another vanity book project by a powerful egomaniacal Silicon Valley bigshot promising to solve all of the World’s problems by recasting them in the mold of his own special insight. I’ve read several such books and have even bought into the hype of some of them. They were full of grand proclamations and even grander visions of the future, but most of them left any crucial nitty-gritty steps out and did not really connect with the majority of the ordinary workers hoping to further their own careers. However, I was in for a big pleasant surprise. “Rebooting Work” is a succinct and to-the-point case for the emerging world of entrepreneurial approach to the individual careers.

Maynard Webb is a well-known figure in Silicon Valley circles. He has helped reinvigorate eBay’s technological backbone and push it into the stable and sophisticated online trading platform that it has become. In “Rebooting Work” he tries to distill decades of experience working in the high-tech sector, mentoring workers and colleagues, and helping launch a new online working platform in LiveOps. The book tries to instill the entrepreneurial mentality in all workers; regardless of what work environment you might find yourself in right now. The goal, in the words of this book, is to become a “CEO of your own career.” The book presents a simple four-square grid of four different types of career situations, and tries to help you to the successful entrepreneurial square.

One of the big points of the book is that the recent developments in technology, especially the wide penetration of fast internet, are finally making it possible for a vast majority of workers to work virtually from anywhere. I am afraid that this is still more of a desideratum than an actual reflection of the state of marketplace for work. However, just a few years ago I would have also thought that a book like this one is unrealistic in its expectations. Today I am much more cautiously optimistic. “Rebooting Work” presents the reader with the vision of work in the 21st century as it should be. I sincerely hope that it does become a fully functioning reality before too long.


**** What could have made this book even better. ****

I would have like more concrete examples of various careers options and steps in building them from scratch online. This would also include a proper assessment of various career tools and skills, and ways of acquiring them. In particular I would have liked a better advice of how marketable various skills are and will be in the upcoming years.

This book is a great resource, motivator, and a mindset builder for the kind of work world that will (hopefully) emerge in the upcoming years. It’s very to the point and largely devoid of hype and overselling of the case that it’s making. However, you should still be prepared to do most of the footwork on your own and be able to avail of various online and offline resources that are out there.
Profile Image for Julian Dunn.
384 reviews23 followers
July 28, 2015
Maynard Webb spoke recently at my company's all-hands meeting, so I was excited to read his book. It's a very quick read, perhaps 150 pages long, which should strike you as somewhat surprising for a topic as weighty as "rebooting work". Unfortunately, this is because Webb sings a one-note song: the somewhat reductionist proposal that everyone should become a freelancer in order to be "CEO of their own destiny" (paraphrasing his expression).

Reality, however, isn't so simple. And being CEO of one's own destiny has little to do with freelancing. It's also very easy for Webb, as a retired successful Silicon Valley executive, to propose this step. Webb has had a lengthy career in technology working for the likes of Quantum, Gateway and eBay, and is now wealthy enough to have his own investment fund, the Webb Investment Network. He certainly wouldn't have made it to this level of success in life solely by working for himself.

I wonder how much the co-authorship of this book with journalist Carlye Adler diluted Webb's intent. It's almost like Adler pushed him into adopting a more extreme position than he intended. There is some nuance in the book; it just doesn't come through as much as it should. Even if both Adler and Webb agreed on this central thesis, the book is poorly reported to support the argument. It contains only a handful of anecdotes about folks who have become successful freelancers, and trots them out again and again.

Altogether, the book feels like it was slapped together to meet a publishing deadline and doesn't contain the in-depth reporting and business case for working differently that I would have expected from an executive like Webb.
Profile Image for Ting Ting.
12 reviews9 followers
March 31, 2018
Interesting peeking into the mind of long-time tech executive who had started as a physical security guard at IBM.

In Maynard Webb’s Rebooting Work, he describes 4 types of people. People who believe in meritocracy in the paternalistic work era (Company Man or Woman), meritocracy in the entrepreneurial age (CEO of his or her Destiny), and people who feel entitlement in the paternalistic era (disenchanted employee) or feeling entitlement in the entrepreneurial age (aspiring entrepreneur).

How do you identify? How do you find work that isn't bound to geography? He argues that meritocracy and excellence is the answer. Technology is enabling the future of work to both be fulfilling and balanced.
Profile Image for Jeff Wilsbacher.
43 reviews2 followers
May 26, 2013
yawn. Maynard doesn't cover anything that hasn't been rehashed before and he doesn't do it more eloquently. If you're unfamiliar with the subject matter this could be an interesting book, but if you've already read a half dozen books, you won't find much value here. What I was hoping for was more of a "how to" for employees to start moving things in the (obvious) directions that Maynard and others have noted.
Profile Image for Teri Temme.
Author 1 book54 followers
July 2, 2013
Some great tips and things to think about concerning the future of work. I have had a lot of time to consider all of the aspects and it is a fascinating time we live in. I don't think outside of Silicon Valley (where I currently live) companies are as progressive, but they will get there. I enjoyed reading this book - it confirmed a lot of what I had "assumed" and it also gave me a few questions to answer about where I want my career to go. Here's to being the CEO of your own career destiny!
Profile Image for Elizabeth Smith.
6 reviews3 followers
June 24, 2013
Loved this book's central premise, which is that the entire corporate behemoth structure we exist in is not only outdated and bad for workers, but also bad for the environment. And that there are ways for us as workers to renounce it. Particularly enjoyed the portions on the gamification of performance evaluations.
2 reviews1 follower
March 18, 2017
The author is on the board of a company that supports freelance workers. This book mostly raves about how technology is enabling a massive freelance revolution while reminding you that most freelancers won't succeed people don't succeed. Also, a bit of life story/self-promotion sparkled throughout.
84 reviews5 followers
November 4, 2013
Someone sharing real experiences in the modern workplace. Recommended.
Displaying 1 - 15 of 15 reviews

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