Please help crowdsource this section. Click here to submit suggested interviews or to let me know if you would like to be interviewed and share your story of reinvention.

Derek Sivers

~ Musician, programmer, writer, entrepreneur, and student ~

1. In your book Anything You Want, you talk about how people can create their own reality by doing what they love and by sharing what they create. How did you came up with that construct/concept?

Being a professional musician gives you this perspective as the norm. You make music because you want to – because you want to play and experiment with notes, sounds, or words – and then afterwards you see if perhaps you could also make money sharing what you’ve created.

It seems very normal to me. As I got out of my musician world and into the non-musician world, some people found this attitude surprising.

2. In general, how do you come up with ideas for your projects? You created CD Baby, sold that, donated the money to charity and are now creating another business. Where do your ideas come from?

So far, almost everything I’ve done has been by request. My musician friends asked if they could sell their CD through the little website I built to sell my own. People asked if I could host their website, since they didn’t like their web hosting company. Now my upcoming ideas are all coming from things that people are asking me to help them with, or seem very interested in.

3. What advice would you give someone who doesn’t think of him/herself as an entrepreneur or who doesn’t have any confidence in their ideas?

Don’t try to be an entrepreneur! Please see – “First Follower: Leadership Lessons from Dancing Guy.” There are lots of people who are trying to do everything themselves, without any help. You can be a lot more effective by finding a “lone nut” doing something great, and helping them. This has the benefits of being an entrepreneur – such as more hands-on control over your work – but without having to strike out and do everything yourself.

4. What advice would you give people who are financially challenged and who need to make money right now?

First, cut all expenses possible. This is something that musicians learn early. The only way to make a living as a musician is to ditch all the comforts that others consider normal, and live so cheaply that you don’t need to make much money to survive. Question every dollar spent, and cut every expense you can.

Then take any job possible, preferably one that isn’t a typical job at a big company, but perhaps helping a one-person startup get something done. You’ll learn much more this way than being one cog in a big machine.

5. You seem like someone who will always be able to “make it work for you.” What are you looking forward to next?

Learning as much as possible. Living in Asia now, it’s the opposite of a rut. Every week I’m experiencing new things, learning new things, meeting people with very different backgrounds and beliefs than I grew up with. It’s difficult, because it’s outside of my comfort zone, but that’s the whole point.

Bill Jacob

~ Transitioning into Addictions Counseling ~

1. How did you end up training to become an addictions counselor which is such a different line of work than your previous career?

Well… I basically asked myself, “What do you want to do now?” I took a look over my past work life… Where was I happy? Where was I not? I looked at my inner self… I was asking “What are you passionate about? – What would you like to do each and every day? – Where in this picture could I see myself whistling each day on my way to work?”

These were really pretty easy questions to answer… I knew where my true interests have always been – psychology, philosophy, neurology, sociology… Humanity! And the fact that so many of us struggle every day to find happiness. I knew (and have known for many years) that I would love for my ‘vocation’ to match my daily longing to help others with their struggles.

The beginning chapter of this new career ‘book’ is to counsel in the field of addictions. It is so ‘front burner’ and poignant… Alcohol and other substance addiction absolutely devastates personal lives, individuals, families and communities. To state one single statistic, currently, in Florida alone, there are 7-8 prescription opiate deaths per day!

2. Can you discuss the issue of shame in relation to being laid off?

Personally, it was a great sense of shame when I was laid off from my position. I had put a lot of my identity into my work and employment. I took it very personally… not able at first to view it from a business sense (the employer’s POV). Overall, I believe that my sense of shame is probably a common feeling among my generation (Boomers)… I think most of us were instilled with a large amount of loyalty to employers and a very strong work ethic. These may very well be generational aspects that are being left in the past…

3. Do men and women experience being laid off differently?

I can’t say. I’d rather leave this question to be answered by women that you interview. I will say that I believe that you will find that any experiential differences found will be more generational (see previous Q/A) than gender specific (I guess I’m predicting??).

4. How will the next chapter of your life differ from the previous one?

On this I clearly will not predict… I truly attempt to work my hardest at learning a new skill-set and put 100% of myself into this new direction and just see where it goes. In many ways, I do not want ‘this chapter’ to be very different from ‘the previous chapter’… I learned so very much from my previous employment/vocation… all of it melds into who I am today and what I bring into my new direction. I guess I’m saying… The book just wouldn’t be the book without this chapter…the previous chapter… and the next chapter. I am a book…

5. What advice would you have for someone considering going into a new field?

Look deeply inside – find what you truly want to do. Where and when and with whom are you most happy? Seek this when choosing a field or vocational endeavor. I think this is vocationally enduring… you will take your genuine self to work every day.

I have met way too many people (especially in my Boomer Generation – and I suspect it still happens a lot) that went into careers because “that is where the money is” – or because it was the direction “Mom & Dad picked for me.” What they did (or are still doing) seems like it is “someone else’s career.”

I liken it to this: You know when you purchase a new wallet & it has a picture of a stranger in the photo section? Well, being in a career/job/vocation that you “ended up in” because of the money or parental direction is like keeping that photo in your wallet and producing it each time you are asked for Photo ID (it must be me, it’s in my wallet every time I open it!)

Mary Greenwood

~ Attorney | Author: How to Negotiate Like a Pro and How to Mediate Like a Pro ~

1. Please explain how you decided to write your books.

When I was negotiating union contracts, I started writing down certain rules for the cases and situations that got resolved. I had my aha moment when I realized that that these “rules” not only applied to negotiating union contracts but to negotiating anything in our lives including negotiating with your boss, your spouse or your credit card company. That was when I knew I had a title for my book. After How to Negotiate Like a Pro: 41 Rules for Resolving Dispute was published, it was a natural progression to write How to Mediate Like a Pro: 42 Rules For Resolving Disputes since I had also worked for years as an online mediator. If someone cannot resolve a dispute directly with the other party (negotiating), then it may be advantageous to mediate the dispute with a third party (mediating). The third book in the series, How to Interview Like a Pro; 43 Rules For Getting Your Next Job, may not be as obvious, but it is based on the premise that the “dance” between the candidate and the potential employer is a type of negotiation topped off by negotiating salary. It is based on my legal background, my Human Resources background and my experience in over twenty-five jobs and countless interviews.

2. Describe the importance of being able to do more than one thing in today’s economy.

I have always had the philosophy of not putting all one’s eggs all in one basket and having different revenue streams or buckets. Even when I had a full-time job, I also taught, did some consulting and continued selling and marketing my books. I am a bit of gypsy at heart and get bored easily so I like having several projects going on. Previously I have worked as a secret shopper, tour guide, mediator, arbitrator and trainer. I like to try new things and if it does not work or gets tedious, I will move on to other projects.

3. On your 65th birthday, you were in “new employee orientation.” Please describe the new phenomenon of today’s worker having to constantly invent/reinvent him/herself.

If you had told me ten years ago that I would be starting a new job on my 65th birthday, I would have said you were crazy, but that is exactly what happened. I had a soft retirement in 2002 and had the luxury of writing my books and taking on several part-time gigs as well as being a volunteer docent and volunteer Art Deco tour guide. Because of the economic downturn in 2008, I got caught in the real estate bubble and felt I had to go back to work to avert disaster. I have had two great jobs since I turned 65 and have now 2.5 years later retired again. I know I will be a labor arbitrator and book marketer, but will also look into new opportunities and projects. I hope to go on a multi-city book tour and try new things.

4. What advice would you have for someone who is interested in starting a side business?

At one point, I was going to write a book on this topic; maybe I still will. At this stage in my life, I would only consider side businesses that I think I will enjoy. I would not take on something just to earn money. All the great quotes from Steve Jobs say it better than I can. Life is too short whatever our age or health to waste it on something we don’t like.

One has to be realistic about the side business and realistically a series of part-time gigs might not equal a full-time salary. For example, I spent a year or two doing mystery shopping. It was a lot of fun, but it was very labor intensive and often paid only $10.00 a job. It was a good way to eat at expensive restaurants since meal expenses are reimbursed, but it also made me gain weight. After giving it a try, I decided it was not worth the effort.

Whatever the side business is, do your research and give yourself a certain amount of time to see if it is successful. It is like a pilot program for yourself. If it does not work out, don’t be afraid to move on and try something else. Just because you move on, don’t think of it as a failure. It is just part of the learning experience.

5. Do you think entrepreneurs are made or born?

Of course, some entrepreneurs are born like Steve Jobs and Bill Gates, but others can learn to take risks as well. Some people cannot even think of life without a steady paycheck and benefits. I have always been a bit of a gypsy and not have held any position for more than 5.5 years. I have had careers as an attorney, Human Resources Director, Law School Professor, Negotiator, Mediator and Arbitrator. Usually I had another job when I left a job, but not always. Being an entrepreneur is often not a choice but a necessity after being laid off.

Other thoughts

I wanted to mention that my Mom and Dad were my role models. My father was a salesman and absolutely loved what he did. He was downright exuberant about the deals and the politics of his work. He dropped out of college at 19 and joined the British Merchant Marine and went around the world before coming home and finishing his degree. He was always a risk taker. At one point in his 50’s he quit his job and founded a new company with a patent from Sweden for a small compressor. The company became very successful and was later bought out.

My mother encouraged all three of her daughters to get an education and go out in the world and achieve in an era when women were not becoming professionals. I went to law school with three women in my class; my sister went to Harvard Med with few other women and my other sister became a success at Conde Nast Publishing.

My cancer diagnosis also has impacted my choices. When I was going through treatment, I decided that I would not waste my time with things that I did not like or were not meaningful for me. Even though I have a clean bill of health after five years, I still have that belief for my future.

James Smith

~ Kona School ~

1. Describe the partnership concept between the Kona Skateboard Park and the school. Include details about the curriculum and the focus on marketing, graphic design, video editing, and print media.

The whole idea for The Kona School came out of a conversation I had with Martin Ramos, Kona Skatepark’s owner. We were at an event in Tampa and were discussing our disappointment with the current educational options available. I was already in the process of looking into developing a charter school and when I mentioned this to Martin, he proposed the idea of starting a school on Kona Skatepark’s property.

The vision for the school evolved from there; we wanted to address all of the areas that are crucial to fostering a student’s ability to learn and function well. The Eight Elements that are at the core of The Kona School all sprang from our discussions and subsequent research into how kids learn best.

The Enterprise and Entrepreneurial aspects of our curriculum, which includes marketing, graphic design, video editing, and print media, were incorporated into our curriculum design from the beginning. We want our students to have as many options as possible when they graduate from The Kona School, and these skills will allow them to have an impressive portfolio to show prospective colleges or have the abilities to either get a job or pursue their own entrepreneurial opportunities.

2. Is Kona School modeled on any similar programs?

There are many schools moving toward blended learning models, and even two schools that target students involved in action sports. However, there are no schools that are incorporating all of the various educational elements that we are. It is our goal to become the model for progressive education.

3. When did this idea begin to germinate? How far along are you in the process of having Kona School up and running?

The original idea for The Kona School was hatched two years ago. Developing the idea has been slower than I’d like because I’ve been working full-time. The first step was incorporating the school, getting our 501©3 tax-exempt status, and then putting a board of directors together. Our efforts now are working with our architects on the campus design, continuing conversations with the University of North Florida about our partnership with them, creating the blended learning curriculum, and launching our marketing campaign to allow us to raise our first year’s budget.

4. Are you, by nature, entrepreneurial?

Up until recently, I would have answered No to that question. Once I began to get the vision of The Kona School and the impact it could have on students, however, I have never considered doing anything else.

5. Do you think entrepreneurs are born or made?

I would say I was made into an entrepreneur by the vision I had. I know others who have always been independent, so I suppose that it can vary.

6. From what you’ve learned with your Kona School experience, what advice would you give someone else who wants to start his/her own business?

I have had to embrace the knowledge that I’m not smart enough or in possession of all the skills I need to start a chain of schools that helps revolutionize the educational field. I am very aware of my limitations. This awareness enables me to seek others who do have the intelligence and abilities I lack in order to build a team that can do far more than one individual. One of my biggest jobs is to convey my vision to this team so we all stay motivated and focused on whatever the next task at hand may be. That vision and a good team are essential, in my view, to being able to start any successful enterprise.

Maynard James Keenan

~ Musician (Puscifer; Tool; A Perfect Circle) and Winemaker ~

These days the main “tool” on Maynard James Keenan’s mind is probably the one he’s using to painstakingly prune his Sangiovese vines. At the peak of his musical career, he is dedicated to learning the craft of winemaking and sees his future in developing a community around the up-and-coming northern Arizona wine country. So why would someone walk away from the spotlight to become a winemaker? The story is one of an intense individual whose life continues to evolve, and to use Keenan’s own lyrics, “spiral out.”

Keenan says, “I’ve been in a band since I was 27 years old.” Now at 43, he says, “I’m ready for a new challenge.” Disciplined and focused, Keenan seems to be one of those rare individuals who constantly challenges himself. He ran cross country in high school, turned down an appointment to West Point, went to art school, and performed in many bands. Now a farmer and winemaker, he has to overcome those powerful forces in his life that cling to his current image much like his vines cling to fragile wooden trellises. The fruit of his artistic success, however, allows him to cultivate a vital connection to nature and its surroundings that nurture his creative energy. The reluctant performer has an exit strategy to begin the next chapter in his outward spiral with the same focus he has applied to every other goal in life.

1. What is it about winemaking that intrigues you?

Every year is going to be a different process and every bottle of wine is going to reflect that if you’re successful in your process. Every wine will reflect a different set of moments. This bottle of wine is going to reflect this particular year and it’s going to reflect this particular site. You put them together in that way will never be the same ever again because the year will be different or the combination of elements will be different.

2. How did you get involved in winemaking?

It’s in my blood. My great-grandfather made wine and it’s a tradition I want to pass on to my son.

3. Are there similarities between winemaking and songwriting?

Yes. It’s all in the layers and complexities and the decision-making and, most importantly, the patience. It takes a lot of patience. You can’t rush anything. That’s one of the golden rules in winemaking — if you’re in the wine cellar working with the wine and you’re not sure what to do, don’t do anything. Just let it be. It’s similar with music. When you’re writing you just have to let it marinate, then come back to it. Don’t rush it, ever.