Elance Blog

10 Questions With Maynard Webb, Author of Rebooting Work.

Elance was fortunate to catch-up with tech veteran Maynard Webb this week, author of Rebooting Work: Transform How You Work in the Age of Entrepreneurship. His new book is the definitive guide to understanding how and why today’s workplace is changing, and how you can Work Differently to achieve your career and life goals.

Maynard WebbRebooting Work

Maynard should know a thing or two about adapting. He began his career as a traditional “company man” at IBM, gradually evolving to the Silicon Valley “way” while working at eBay (COO) and LiveOps (CEO). Today he has a clear view of our transforming world of work, sitting on the boards of Yahoo!, Salesforce and LiveOps – all while juggling other enterprises and writing a best-selling book (with the help of Carlye Adler). Here’s some of our conversation:

1. In Rebooting Work you note that 47% of American workers today are unhappy. Why do you think this is?

Maynard Webb: People today are accustomed to choices. The TV has 200 channels plus on-demand movies, the smartphone has 50 applications, the car radio is programmed to their musical tastes. But at work, there is very little choice. At the office you’re told what to do, and there’s little or no satisfaction in that. People want control and many businesses won’t yet let go of that control.

2. You also mentioned that traditional “paternalistic” companies actually hinder employee growth and productivity. Can you elaborate?

Maynard Webb: When management dictates exactly what to do, and how to do it, it takes the soul out of the job. There is no incentive to excel or go beyond the minimum expected. Companies also try to protect their workers from being poached by other companies, hence they don’t want individuals to shine too bright or know what their real worth is. But now with LinkedIn, this information is out there regardless.

3. You foresee a huge shortage of qualified workers coming – “a war for talent” as you say – what’s behind this insight?

Maynard Webb: Among skilled positions, there continues to be many job openings that can’t be filled. This means the most-demanded workers now have more opportunities and more options, and they are increasingly choosing to work online rather at an office. As a business, if you want to attract the best talent, you have to be at places like Elance where top workers are offering their skills.

4. In a nutshell, what is Rebooting Work?

Maynard Webb: Rebooting Work is a change in mindset among workers and businesses. It is people realizing that what worked yesterday doesn’t work today. Rather than being afraid, people need to embrace change and take control. The faster you realize this the better position you will be in as work evolves to a point where you’re completely in charge of your own destiny.

5. You speak of “meritocracy.” What is this, and why is it critical to Rebooting Work?

Maynard Webb: Football is the perfect analogy of a meritocracy. Every season, every game actually, you have to earn your way onto the team. Nothing is handed to you. This is where business is quickly moving. Jobs will be awarded to the best performers regardless of who they know or how long they’ve been doing a job. The playing field is leveled.

6.  You mention that to remain competitive, businesses need to “appeal to a modern workforce” and have an “elastic” team. What all does this entail?

Maynard Webb: Companies have traditionally thought of people as a disposable resource. They have valued their buildings much more than employees. If times were tough they would lay-off workers but continue paying an enormous rent. This doesn’t make sense in a world where the best people can choose to work wherever they want. Businesses have to realize that some jobs can be done from anywhere, anytime, and save the brick and mortar buildings for the few jobs that demand a physical presence.

7. You note that self-employed people are twice as likely to be passionate about their work? Is there a consistent underlying reason for this?

Maynard Webb: There is a liberating feeling when people realize that there is no longer a safety net, and that they are in control of their own fate and work. There is no company that will hire you for 40 years and give you a pension and gold watch. Once you embrace this, you gravitate towards work that you really enjoy and that you are passionate about.

8. In your work philosophies chart, you stress evolving to Frame 2: CEO of Your Own Destiny. What is this, and how does this quadrant differ from the other 3 Frames?

Maynard Webb: I’ve found that nearly all workers fall into one of four categories, although throughout your career you often move from category to category as situations change. Frame 2, CEO of Your Own Destiny, combines the principles of meritocracy and the Age of Entrepreneurship. When you are firmly entrenched here, you tend to be successful, fulfilled and self-aware. In the book I give suggestions on how to always be moving in this direction.

9. In the worksheet of exercises for Rebooting Work, you mention “the spirit of And.” Why is this so important?

Maynard Webb: To be the CEO of Your Own Destiny is to be in control. You’re not in control if you’re compromising on what really matters to you. The word “and” is critical. “And” is what gives you permission to have a rewarding career “and” spend time with the family. “And” is what allows you to make lots of money “and” contribute time and money to worthy causes. In short, “and” is what frees you to be fulfilled.

10. What are the major roadblocks and timeframes for Rebooting Work?

Maynard Webb: The technology is there, and will only continue to make it easier for people to work away from the office. Legislation and healthcare options will eventually catch up to the thinking too. But what needs to change is people’s belief that this can actually happen. Through my experiences I’ve seen so many people work so hard and yet feel so empty. When people let go of the old way and start Rebooting Work, tentativeness will fall like dominoes.


Thanks Maynard. As Elancers Work Differently, we’ll take your advice to heart.

Again, we appreciate Maynard Webb taking time out from his business schedule to chat with Elance. It’s great to hear that we’re already well on the path to the future of work (and fulfillment). Learn more about Maynard Webb and Rebooting Work.


Just watched the other day another interview with Maynard on fool.com and was impressed by his insight. Definitely will buy the book, thanks Mr. Webb.