Work 2.0: An Issue of Calling and Cause, Not of Career

By J.T. O’Donnell

I got an e-mail from a recent college grad who had the opportunity to work for a company as an Independent Contractor. It was a creative position as a freelancer. His parents were against the idea and wanted him to find a full-time job with benefits. He was not sure what to do.

At the same time, I had just been introduced to Matt May, author of The Elegant Solution. Matt’s been a freelancer his entire career. So, I asked him the following:

When do you think it makes sense to take a freelance gig to advance your career?

What are the ups and downs to doing this over the course of your career as opposed to playing it safe and only taking full-time jobs?

How has it shaped your career path, i.e. the writing of your books?

I think Matt’s response is one of, if not, the best explanations of why to train yourself to survive and thrive as a freelancer. Given our philosophy at, “Because EVERY Job is Temporary,” I also think it explains the future of work – Work 2.0. Here it is…

“Philosophically, I think the real question is about the work itself. That’s an issue of calling and cause, not of career. I think the young person you’re referring to is thinking about the work, not the job. And that’s exactly right. And really? The days of secure and salaried and benefited jobs are nearly behind us…that kind of security is an illusion…certainly for the multitudes of laid off workers of late. One of the things I like about freelancing is it forces you to build a resilience and reserve and resourcefulness full-timers don’t develop. That’s why everyone freaks out when they lose their job.

A freelancer learns how to focus on customers better, be ever on the edge in terms of value delivered, just to keep that customer. There’s no opportunity for complacency. You’re forced to develop a number of clients, because you know one of them could have a bad hair day and you’ll be out of work. You build a portfolio of work that you’re proud of. You can decide to accept or decline an project. You are actually more secure than a full-timer, if you think about it. You have a better safety net because you have multiple income streams. You’re far more in control of destiny.

Now practically speaking, if you’re mid career with family, house, plants, dogs and kids, and you’ve always been a salaried person, you take a huge risk in suddenly going solo, because you haven’t developed the skills and mindset described above. So start young, when things like benefits don’t matter so much anyway.

The downside is that it’s harder work. Longer hours…you have to not only perform the work, but market yourself. At least until you build a rep. And then it’s easier, but never easy. There are lulls in which you think you’ll have to take a job if something doesn’t pop, but then you get aggressive and make it happen, and that’s a great feeling.

Some people, many people, simply don’t have the appetite for free agenting. That’s understandable. But I watched my neighbor search for nearly 18 months for a new sr exec sales job after a reorg…I would have been able to develop short term projects that entire time and have income, rather than spend my savings and waiting!

And if you really want to grow a business, and you want to manage others, you build your practice beyond yourself, into a company. Your company. And you can then have a salary and benefits…on your terms.

I have no regrets. I would never have had the opportunity to write books as an employee. I wrote a book about my experiences in advising Toyota and what I learned about everyday creativity and innovation from them…employees can’t do that because it’s against policy. My new book wouldn’t have been possible either, because I had to travel all over the world researching and interviewing. So free agenting has led me in exciting directions in which I’m always amazing myself with what I learn.”

Now, I ask all of you readers….what additional advice can you offer on the subject?

And, if you’d like to learn more about Matt, here’s his BIO:

MATTHEW E. MAY ( is the author of critically acclaimed The Elegant Solution, which won the Shingo Research Prize for Excellence. A popular speaker, he lectures to corporations, governments, and universities around the world, and is currently Senior Lecturer on Creativity and Innovation at Pepperdine University Graduate School of Business. He spent nearly a decade as a close adviser to Toyota, and his articles have appeared in national publications such as USAToday, Strategy & Business, and Quality Progress. He has appeared in The Wall Street Journal, and on National Public Radio. A graduate of The Wharton School of Business, he lives in southern California.