Joyfully Jobless Jamboree

The (hopefully First Annual) Joyfully Jobless Jamboree took place at Dolce’s Lakeway Resort on Lake Travis near Austin, Texas, October 15th and 16th.

The Jamboree coincided with National Boss’s Day to focus attention on the fact that self-employed people, or the “joyfully jobless,” as Barbara Winter calls us, are our own bosses. We celebrated having the most innovative, creative, and supportive bosses we have ever had.

Okay, not all of us find it easy to embrace the idea that we are innovative and creative. Some of us spent time at the Jamboree getting comfortable with the fact that in our choice to be self-employed we have embraced our own creativity and innovative problem-solving ability. We learned ways to treat ourselves better, to lighten up and extend ourselves a little grace when we make mistakes, because we learn mainly by trying new things and making mistakes. No mistakes means very little learning.

One of the first things I did after arriving Thursday afternoon was to shoot this video of the view from my 3rd floor balcony overlooking the lake. It’s gorgeous, isn’t it?

My experience of the Jamboree started shortly afterwards when I met fellow posse members Sandy Dempsey and Jami Yanowski. I went to Sandy’s room to pick up my posse t-shirt. The shirts were designed especially for the Jamboree and say, “I’m the boss of me.” (available to order?) I was standing on the balcony of Sandy’s room talking with her and Jami when the door to the adjoining room opened and – suddenly, magically – Barbara Winter appeared.

Just like that.

I’m a fan. Kind of a groupie. Okay, very much a groupie. I was expecting to have time to prepare myself mentally – as in “Don’t be stupid. Breathe. Close your mouth.” – before meeting her. But there she was, in real life. She was warm and witty and very easygoing, just like she has been on the group phone calls where I’ve talked with her before. I got to speak with these women for just a little while before I had to leave.

There was a get-together that evening of the organizers, the posse, and all the Jamboree’ers who had arrived. I missed it because I had volunteered to pick up John Williams from the airport. John was flying in from London. He is the author of Screw Work, Let’s Play and was a keynote speaker at the Jamboree.

What do you do when you’re in the car for over half an hour with an author of a new powerhouse book in your field of work? I’ll tell you what I did. I tried not to sound stupid. John played along flawlessly. He told me about his scanners’ night monthly events in London and his idea for an upcoming online program for self-employed people to grow their businesses. John is a fan of Barbara Sher, a superstar in the world of guiding people to discover what they love and develop a plan to do it. He really gets the importance of passion and enjoyment in work, and how they are keys to doing great work.

One of John’s colleagues, Marianne Cantwell of Free Range Humans, was also presenting at the Jamboree but came in on a later flight from the west coast. I volunteered to pick her up as well, because I thought it would be nicer for her to have a personal welcome instead of chasing down a shuttle. Marianne was enthusiastic and joyful as she talked with me on the ride back to the resort about her work helping self-employed people get very clear about the people they serve and how to connect with them through the design and marketing of their businesses.

Friday morning the posse had breakfast with Barbara. We had joked about making sure we didn’t overwhelm her with questions because she wouldn’t have a chance to eat. We behaved ourselves and took our turns talking and eating, too. We learned Barbara was getting hoarse and developing a cough.

That did not deter her as she opened the Jamboree with an engaging talk about “bringing your soul to work.” For me the defining idea behind Barbara’s work is her statement that self-employment is the best personal development program ever devised. She brings that mindfulness and that respect for humanity and the importance of individuality into everything she does.

Next up we heard from Alison Marks, an up-and-coming star in the work-from-home consultant world. Alison guides people through workspace design and is a trained coach, organizer, and classical feng shui consultant. Her ideas were so specific and clearly useful that for a time I actually thought about applying them to the hodgepodge mess that is my home office.

At lunch I got to talk more with Alison and learn about an upcoming telesummit she has planned to share the home office design and time management secrets of successful women entrepreneurs who work from home offices. Follow her on Twitter to get updates about the telesummit as plans are confirmed.

After lunch we had a lively presentation from financial planner Mickey Mikeworth. The most memorable thing about Mickey’s presentation for most people will probably be when she had Alison help her with a demonstration about the flow of money and wound up splashing water all over Alison and then pouring some onto the carpet. Alison was a good sport! The visual was great, and it was memorable. But the point was even better. When we freak out about money as it flows to us we get nervous about what’s going to happen. We think, “Okay, that’s enough for now,” when our cup is getting full, and accidentally invite the flow to stop. Until we’re comfortable with it flowing to us in abundance we’ll get anxious and ask it to hold up every time.

During the break after Mickey’s presentation I shot a video off the balcony next to the conference center. I was looking at the lake and then peeking in the room where I was about to attend a breakout workshop, trying to figure out what was going to happen.

I had no idea how cool it was going to be! Connie Hozvicka of Dirty Footprints Studio told us a little bit about her calling to be an artist and her journey to self-employment. She described a process she calls “fearless painting” and had us try it out.

During the activity I asked a question: Where will I take my business next year? Then I painted “freely” for fun. Here’s the result:

I saw the result and thought it was a chaotic mess. But Connie told us that over time we think about the process and what we were thinking and feeling as we painted, and we study the picture, and we get inspired. I decided to study the painting and the experience and see if there were clues as to my direction. It didn’t start making sense until the next day. I was laughing at myself on the way to the next breakout.

Marianne Cantwell of Free Range Humans led the next workshop. She gave us loads of ideas, but I’ll share a couple. One is that you don’t have to stand out from the competition, because when you become clear about exactly how you serve your specific target audience, there is no one who does exactly what you do. Pretty cool, huh?

The other idea was when she asked us to imagine getting up in the morning excited about doing the work we love doing, and then asked us to describe it in one word. We walked around introducing ourselves using that word. I met “remarkable” and “easiness” and “launch.” I introduced myself as “liberator.” That’s the clearest I have ever been about the core theme of my work – I help people free themselves from boxes, from ruts, from limiting beliefs, and from other people’s expectations so they can discover their true nature, develop it, and share it with the world. Liberator. I’m liking that one.

We had a short presentation by Barbara that afternoon, but her voice was failing so she didn’t get to talk much. Turns out she was supposed to talk about ways to have more time in our lives, but joked that she didn’t know anything about it so she had little to say. Ironically, that meant the afternoon session ended a few minutes early and gave us all – more time!

After the day’s workshops and presentations I recorded an audio on the balcony of my room using my new Snowball microphone. As you listen, close your eyes and imagine your sitting on a hillside overlooking a lake on a warm autumn day.


That night we had a “Taste of Texas” dinner on the patio near the pools. This photo from Jamboree’er Cheri Harvey of Yoga for Real shows the view from the pools towards the conference center and the lake. Our tables were set up just to the right of the area were Cheri was standing when she took the photo.

Before dinner we did a group dance led by fellow posse member Lynn Girardi of Whole Life Boogie. The food was a taste of Texas (barbecue), Lynn’s dance was a taste of Texas (with simple country dance steps including the Texas two-step!), and the view of the lake was a taste of Texas. Enough? Not even close! As a native Texan, I added my own taste of Texas with my outfit, especially my Texas flag shirt.

Thank you to Carol Robert for taking the picture. Carol is married to Ken Robert who writes the blog Mildly Creative. People were talking animatedly after meeting Ken because he is sort of a rock star among inspired entrepreneurs because of the elegance and authenticity of his writing. Okay, I’m part of the fan club, too, and was really excited to get to meet him in person. He has some things planned for the coming months that I can’t wait to see unfold.

After dinner we gathered around the fire pit and all us posse members took turns telling our stories about our journeys to self-employment. Take the time and visit their sites and follow them on Twitter to have the chance to get to know them. They are remarkable and enjoyable women.

Liz de Nesnera kicked things off and let us know that she went from employed to self-employed five years ago. Her business as a voiceover talent is growing and she is poised to step up to an elite level in the coming year. @LizDen

Jami Yanowski is a true Renaissance woman, with many interests and projects underway. @JamiSki

Lynn Girardi is integrating ballroom dancing with inspirational events and loosening people up through movement. @WholeLifeBoogie

Terri Belford told us her very daring tale of traveling the country in a Volkswagen Eurovan so she could live and work in different places. Terri is a small business growth accelerator who, based on what I heard from Jamboree’ers who got to have lightning consultations with her, specializes in adding profit centers to businesses. @TerriBelford

Sherri Garrity has the kind of story that puts a big smile on my face. After becoming self-employed, she was repeatedly approached by people asking how she did it, so she became a self-employment consultant. @SherriGarrity

As we headed back to our rooms, I passed the golfcart limousine I saw the first night outside the front door of the resort.

Only in Texas!

Saturday morning breakfast started quietly since the dining room was nearly empty. But after a few minutes fellow Jamboree’ers came in. I was so caught up in the interesting conversations I lost track of time and had to rush to get back to my room and prepare for our opening ceremony for the day. You see, Saturday was National Boss’s Day. Barbara, Alice, and Sandy had come up with an idea of having us ceremonially cut pantyhose and ties to declare our freedom from corporate dress codes as self-bossers. It was a very somber ceremony. (Please, God, let there be no photos!)

Our opening keynote address was from John Williams, author of Screw Work, Let’s Play. The theme as I experienced it was honing in on excellence by getting very clear about what we as small business owners do best for our target market. The most memorable part for me – aside from the audience blowing noisemakers as John enumerated the three points of his presentation and I got to try out my vuvuzela app – was when John explained it is obvious to all that it’s a good thing to give up mediocre work to make room for good work, but it’s hard to wrap our minds around the fact that we have to give up good work sometimes to make room for great work.

During the mid-morning break I used my iPhone to record a little of the energy and enthusiasm. Barbara Winter showed up near the end, but she was pretty hoarse. Her voice was spotty the rest of the conference.


That quote we were wondering about? We think it’s the one about giving up good to make room for great.

Next up was Karyn Ruth White, self-described motivational comic. “Self-described” is a very cool phrase when you think about people who are self-employed in inspired businesses.

Karyn Ruth told us a little of her story about being a stand-up comic for several years, and then realizing it was time to use her talent to bring something positive to people’s lives in addition to laughter. She uses outrageously funny stories to help people gain perspective and re-center our priorities.

Friday afternoon I recorded a second audio on my phone while we were waiting for everyone to gather for lunch. We were sitting on the large balcony outside the restaurant overlooking the pools, which overlook the lake. Gorgeous! Financial planner and money-flow maven Mickey Mikeworth was explaining the mystery of “143” in texting code right before I started recording.

You can hear Sandy Dempsey, one of the organizers and the “get-‘er-done” woman of the Jamboree, briefly on the recording. I had told her I would like to sit down and talk with her about planning the Jamboree and about her business, so she would disappear when I was recording audio or video.


After lunch I realized I hadn’t solved the logic problem of the breakout sessions so I wound up taking one twice. I didn’t mind at all, because it was Connie Hozvicka’s
Fearless Painting!

First up for me was Charles McCool’s presentation about innovative ways to travel and save money doing it. Barbara Winter refers often to the “wanderlust” that many self-employed people have. It’s a main reason that some want to be self-employed, to have the freedom to travel and to be paid to travel or be able to work while traveling. He and Jamboree’er Sharon Williams, The Lady Nomad, know very cool tricks for saving money and in some cases earning more travel credit than you initially pay.

For the second breakout session I attended posse member Jami Yanowski’s workshop on creating a vision board. My background is in therapy so I’ve learned different ways for people to use collages of images and words to express their aspirations and even to express their identity. Through coaching I’ve heard people talk about putting visual representations of tangible goals on a vision board. I thought I knew what we would be doing. Jami surprised me.

She asked us to think about goals of quality, like the themes of the Jamboree, “More time,” or “more money,” or “more fun.” Renegade that I am, I decided to choose another quality, a positive psychology quality known as flow. Flow is when what you are doing seems aligned with your strengths, your natural gifts, and your values. Flow is when you get lost in the moment and lose track of time. Focusing on the idea of flow, I created my vision board. We had less than half an hour since it was just to get a taste, but I was really happy with how it turned out.

In the third breakout session of the day I created another fearless painting and explored more ideas about the coming year for my business. What does it say? Since I help people break out of boxes and ruts it won’t be an orderly business. Life is messy. Authentic living does not fit in a nice line. It’s complex. At least that’s what I think it says. What do you think?

Since I hadn’t planned both days of workshops from the beginning, I wound up missing posse member Sherri Garrity’s breakout session. I got to speak with her at different points during the Jamboree so I know her specialty is converting the self-employment dream into reality. There are a few quotes you may have heard that are variations on this theme: the difference between a dream and a goal is a plan, or goals are dreams with deadlines. Sherri understands dreams, but since she has experience developing a plan to leave the corporate world to start her own business she helps people create and implement their “escape plans.”

At the end of two days of presentations Barbara told us a hilarious story about her granddaughter Zoe. If you don’t already, you should follow her on Twitter and sign up for her e-mail newsletter. If you do no more than study her storytelling approach to connecting and marketing you will gain much.

In the middle of the day I had realized the Jamboree needed what I call a “coaching close,” an invitation to take the information and self-realizations and apply them. Many books, seminars, and training products can give us ideas and even help us generate our own ideas, but all these are pointless if we leave them in the world of imagination. They transform our lives when we translate them into the world of existence. I challenged each attendee to choose one simple next step he or she could take based on an idea from the Jamboree. I also challenged everyone to find an accountability partner and commit to reporting to that person after taking the step.

I know some people were making plans to follow up with each other later on so I imagine good things will happen to many of my fellow Jamboree’ers. My strongest take-away was my interest in developing and presenting seminars and workshops. I have sketched out ideas and gathered resources in the past but not fleshed out most of them. I will be laying out plans for the ones where colleagues also have an interest. I will also bring the enthusiasm of live presentations to my project with fellow coach Francie Cooper. We are starting a podcast called Tapa Palapa. A test episode is on the site if you care to preview it.

After the sessions were done we had some activities available to continue the Jamboree into the “endless evening.” Some of the posse gathered on the Back Porch (the coffee and wine bar with a beautiful lake view) to brainstorm with other Jamboree’ers and offer lightning consultations (quick and focused). I offered ideas throughout the Jamboree to attendees based on the Profiting From Your Passions coaching model to help people design their businesses around what they want their lives to look like. Here’s a photo of me next to the PFYP display on the balcony of the Back Porch.

While some of us talked on the Back Porch, other Jamboree’ers went on a walk around the resort’s trails, and a group went to Austin to watch the bats take flight at dusk. That evening I had the pleasure of dinner with three fellow Jamboree’ers at a local Mexican restaurant, Los Piños. Delicious pork braised in tomatillo sauce, freshly made tortillas, and very authentic beans.

Sunday turned out to be a pretty long day, although the Jamboree was formally over. I woke up before the alarm clock (I know – amazing), had breakfast with one of the Jamboree’ers, and then went to interview Sandy Dempsey.

Sandy publishes The Dreaming Café and was one of the three organizers of the Jamboree. She would disappear suddenly because she was instrumental in making sure equipment and supplies were set up in the rooms for the presentations and workshops.

But she also disappeared when the spotlight was headed her way. On the Saturday lunch recording she joked about me harassing her because I was recording our conversation.

She agreed to find time to sit down and chat after the event was over and finally tell her story. I’m very grateful that she did. Her story is special, and it was rewarding to get to know Sandy better.

We were sitting on the balcony of the Back Porch, very close to where I was standing in that picture with the PFYP banner. The chair just behind me in the picture is at the table where Sandy and I sat Sunday morning when I recorded our conversation.

The audio quality is good because we used the Snowball mic, but it’s a little soft because I moved it away from us so we could talk without staring at it and being distracted. You might have to turn your speakers up more than usual.


Sandy had to pack and get ready to go to the airport before noon, so I spent some time talking with a couple more Jamboree’ers before I packed my things and loaded the car. My goal was to talk with each person at the event to know something about his or her existing business or plan for a business. Fortunately, I succeeded.

After I checked out I got to spend a couple of hours hanging out poolside with some fellow posse members and a Jamboree’er. We talked about how important it is to get together with people who “get it” and support each other’s dreams and goals.

If you haven’t had a chance to gather with your tribe of encouragers and butt-kickers lately I suggest you put it on your calendar.

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