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Embrace Entrepreneurial Thinking


In this tech-enabled world where job opportunities and loss can happen more swiftly and in more ways, many of us are interested in how to grow our work options and security. That’s why, when heard about the theme of Dorie Clark’s new book, Entrepreneurial You, I thought she might have relevant help so I reached out to interview her.

Kare Anderson: Dorie what’s your definition of what it means to be an entrepreneurial thinker?

Dorie Clark: One of the great case studies that I share in the book is John Lee Dumas, who has become one of the most successful business podcasters. Back in 2012, when he was getting started, everyone “knew” that you couldn’t make money from podcasting. It was a nice hobby, but that was about it. John completely revolutionized the industry, however, by noticing a flawed assumption underpinning that belief. Advertisers were only interested in sponsoring shows if they had a lot of downloads, of course – but most shows only released episodes weekly. John realized that he could juice downloads by more than 7x, instantaneously, if he ran a daily show instead of a weekly show. Of course, it’s far more work, but he quickly grew his audience, attracted sponsor interest, and perfectly exemplified the best of entrepreneurial thinking: don’t take others’ assumptions as fact. Always question them.

Anderson: You believe that everyone, even if they have a day job, should develop multiple income streams. Why?

Clark: I started my career as a print journalist – and I’m no longer one because I unexpectedly got laid off only a year into the job. You never know when disruption is coming, especially these days. If you want to create real security for yourself, of course it’s great to have a savings account, but that’s not enough: that money gets spent and goes away. On the other hand, if you’ve developed a side income stream, that opens up new ways to make money, helps you develop new skills, and creates a safety net for yourself that can keep earning money regardless of what else happens in your career. That was the case for Pat Flynn, now the creator of the successful Smart Passive Income blog and podcast. He worked at an architecture firm and got laid off in 2008, and would have been in real trouble – except that the previous month, he’d created an e-book and started offering that for sale online. It was so successful that, after his layoff, he decided to double down on online business, instead of looking for another architecture job.

Anderson: You’ve written about how creating an entrepreneurial side venture can be helpful for your career, even if you have a day job. How so?

Clark: In Entrepreneurial You, I profile Lenny Achan, who started his career as a nurse and eventually became the head of communications for a prestigious hospital system. He was able to make this unusual career leap because, on his own time and because of his own interest, he decided to develop a couple of iPhone apps. When his boss found out, instead of being mad (as Lenny had initially feared), he was impressed. It shows a tremendous amount of initiative to teach yourself a new skill and start an entrepreneurial side venture, and those skills are eminently transferable to a day job. On the strength of his entrepreneurial foray, Lenny’s boss asked him to head up social media for the hospital, and he did such a great job, he eventually was asked to run all communications. Starting a side venture can actually be transformative for your existing career.

Anderson:  After interviewing more than 50 highly successful entrepreneurs, what’s the top lesson that you applied to your own business?

Clark: The most direct lesson I applied was in how to create a compelling online course. As a business school professor – I teach part-time for the Fuqua School of Business at Duke – I know that online education is reshaping how we think about adult learning, and I was eager to explore that more deeply.


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