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Want to Change Careers? Think Life First, Work Second

The public radio show, Marketplace, recently had a segment on entrepreneurs who choose their business to fit their desired life. The first of a five part series was based on a new book called Not Just a Living: The Complete Guide to Creating a Business That Gives You a Life by Mark Henricks.

I haven’t yet read the book (definitely plan to) but was intrigued to hear Henricks introduced by the show’s host as a “Lifestyle Entrepreneur Expert.” Imagine my surprise to learn that there is actually a title to go along with my rather unconventional “figure out what you want your life to look like first, then come up with ways to make a living that will allow you to have that life” approach to career counseling. Who knew? Time for new business cards!

While some listeners may have been surprised to learn that 90% of small business owners are seeking a life and not just a living, I wasn’t surprised in the least. The 55 women who recently joined PBS “star” Barbara Sher, Barbara Winter (author of Making A Living Without a Job), and myself at the Making Dreams Happen workshop would not be surprised either. The main reason workshop participants ventured out to Boulder was because they want more than a job change, more than a career change. What they want is a life!

But even this group of avowed dreamers discovered that it’s not always easy to think life first, work second. Things started out well enough. In the very first hour of the very first day I asked the group the same question I ask each of my individual career consulting clients, namely, “What do you want your life to look like?”

This question always seems to evoke some common themes. By and large people are looking for their lives to be more in balance. They want an end to office politics. They want to work at something they really love. They want to call their own shots. But from here they diverge. Some want to work at home. Others want to head out to a sun-filled studio or to the garden or to their little shop or to the recording studio or a dozen different places where their dreams happen.

Some want to work alone, others need that connection with others. Some want to more fully enjoy their present surroundings and if they never see an airport or hotel again it will not be too soon. Others, like the client of mine from Australia, wanted to spend part of the year in the mountains, part of the year at the shore, and at least two months a year in Italy.

As the workshop progressed and participants began to talk excitedly about their dream businesses I couldn’t help but wonder if in their enthusiasm to escape the j-o-b world, some may have already lost site of the life part.

Take Tina. Tina was so excited about her idea of starting a centralized clearinghouse that school districts could call for qualified substitute teachers that she’d made a 22 hour bus trip from Minneapolis to be there. Over a break I got a chance to chat with Tina. When I asked her how she felt about getting up at the crack of dawn to match subs with schools, trouble shooting no-show teachers and other likely blips, and to otherwise sit in front of a computer all day, Tina looked utterly panic-stricken.

That wasn’t what she wanted her life to look like at all.

Tina’s real dream is to travel the country in an RV taking photos while her husband Mike pursues his love of bikes. A very different life than that of a program administrator.

At one time I’d thought I might like to try my hand at being a comedy show writer. Maybe that’s why I felt an instant connection when another workshop participant named Lynn told me of her comedy writing aspirations. In my case anyway, comedy writing never passed my life first test because it would mean having to work in New York or LA. Both great places to visit, but not my style on a full-time basis.

Even though Lynn already lives in Southern California, I wasn’t surprised to learn that her ideal life had nothing to do with spending hours every day sitting in commuter traffic on the Los Angeles freeway trying to get to and from her studio job. Once Lynn realized that she a) wanted to work from home and b) pretty much wanted to work alone, her entrepreneurial options changed accordingly.

So Lynn and I went back to the career change blackboard. This time though, we used the life first model to come up with some options that would allow for a more harmonious life-then-work fit. When we landed on the idea of being a work from home writer of a humorous slice of life column (think Erma Bombeck for baby-boomers) Lynn practically levitated out of her chair.

Lynn just sent me her first column yesterday. It was not only hilarious but dead-on. If anybody can launch a career as a nationally-syndicated columnist, this very funny and determined dreamer can. (If you’ve always wanted to write a column check out Charlotte Digregorio’s You Can Be A Columnist: Writing and Selling Your Way to Prestige.)

The reason I’m so fixated on the life first, work second approach is because it worked for me. You see, one of the biggest reasons I stayed stuck in an unfulfilling job for so very long was because I didn’t know what I wanted to be “when I grew up.” Now if I’d waited until I knew the answer to that question then, well, I might still be there today.

But there was a very important piece of information I happened to know A LOT about – namely, I knew what I wanted my LIFE to look like… I wanted to go to bed and get up according to my own internal clock. I wanted to take time off when I needed to and not when the employee manual said I could. I wanted to work from home and live close to nature. I never wanted a boss again and I didn’t want to work in an organization of any kind. And, as importantly, I wanted whatever work I did to feel meaningful to me.

When it finally dawned on me that I could start working on the part I did know about it became infinitely easier to come up with ideas for making money that would let me live my life in my own way. So what exactly did I do? First, some history…

At that time I was spending two hours a day commuting to my corporate marketing job. Step one of my new “life first, work second” approach was a no brainer. I had to get a job with a shorter commute. Doing so would allow me to dedicate my commuting time to the task of figuring out what I wanted to do on the work front.

I read every one of Barbara Sher’s books, re-read Barbara Winter’s Making a Living Without a Job, dove into Marsha Sinetar’s Do What You Love the Money Will Follow, Laurence Boldt’s Zen and the Art of Making a Living, and about a dozen other career-change oriented books including a wonderful little book called How to Get Off the Fast Track and Live a Life Money Can’t Buy by Melanie M. Kirsch. (Kirsch’s book is unfortunately out of print but you can get a used copy for as little as 36 cents at

To my delight, what I gradually came to realize was that what I really loved was reading and talking about the whole topic of finding your life mission and living it! But how to make money at it?

Using my ideal life as my compass I settled on the idea of starting a newsletter. And that’s when the original, pre-Internet Changing Course Newsletter was born. I spent the next six months learning everything I could about how to create a successful newsletter. I even published the first six issues while still gainfully employed. Then about a year into the new job I pitched the idea of doing my job from home and my boss at that time went for it. (To learn how to put together your own effective work from home proposal check out the Telework Job Seekers Handbook at

My dream life was starting to come together. It was only a matter of time before the no-boss, no-organization part would be realized as well.

What about you? If you identified with the 90% of small business owners who said they were seeking a life and not just a living then you need to start by getting crystal clear on what having a life means to you. If I could offer all of you aspiring self-bossers out there only one piece of advice it would be to take the time to really answer the question, “What do I want my life to look like?”. Then use your answers as the touchstone to evaluate any and all possible business ideas.

Only when you know what you want your life to look like can you come up with ideas for satisfying work that will allow you to have the life you really want. As B.C. Forbes once said, “Don’t forget until it is too late that the business of life is not business but living.”


A New Direction

I decided to take the Work @ What You Love Workshop and also work one-on-one with Valerie. The workshop explored so many unusual and unexpected solutions to my specific questions. I made so many new connections to what clearly works for me in crea...

Julia Raymond
Curvology Studio

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