You don’t need every customer.
You don’t have to go after every single opportunity.
You don’t need to be bound by traditional metrics of success.
You can choose to be big enough.

Bernadette Jiwa

On the autumn day in 1974 when my daughter set off for kindergarten, I set up a card table in my family room and started kindergarten, too. After becoming bored with three different jobs, I decided to take things into my own hands and start a business.

What I knew about running a business could have fit in a thimble. The existing information was not helpful at all since it assumed I had visions of a big operation with employees and pension plans. I just wanted to create something that would make let me experiment, try out ideas, figure it out as I went.

Quite simply, I wanted to continue making my business better, not bigger.

I set two goals for myself.

1 I decided I never wanted to have two years that were exactly the same.
2 I decided to treat my business as a laboratory where I was willing to experiment knowing that I’d have failures alongside successes.
(Note: this second goal really knocked out my fear of failure.)

For the first time, I’ve gathered my best
business building tools and am ready to share them in 
Small, Sassy & Successful.

Think of this as a mini-retreat for expanding your curiosity, creativity, clarity, community and confidence.

Many people assume that running a business is all about bookkeeping, marketing and taking inventory. While these tasks are part of most businesses, they may very well be the least of what it takes to create a successful enterprise.

You’ll learn specific strategies for creating:

  • the essential building blocks of an inspired business
  • techniques for using your imagination more and your pocketbook less
  • ways to make your business more fun and more profitable
  • easy ways to become a client magnet
  • the opportunity to connect with other inspired entrepreneurs

At its best, starting a business is about creating a vehicle to share your gifts with the world.

Whether it’s a one-person operation or a huge corporation, extraordinary businesses don’t just happen. They’re consciously created by people who understand that a satisfying business is one that honors ideas, information and inspiration. An inspired business enriches the lives of everyone who works in it and everyone who does business with it.

Although most businesses are born in a state of inspiration, the tricky part is to keep that enthusiasm and spirit going when business is booming—and when it’s not. Achieving such a business is what Small, Sassy & Successful is all about.


Starting with the premise that inspiration isn’t only for artists or mystics,
I’ll show you how inspired entrepreneurs create inspired businesses.

We’ll start off on Friday evening with an exploration of the superpower we all possess, but may have allowed to get rusty. This tool can turn an enterprise from gloomy to glorious. Best of all, the only investment it requires is a willingness to put it to work.

After a good night’s sleep, we’ll gather on Saturday morning and spend the day focused on the ways to keep making your business better. You’ll learn how to solve problems like Sherlock Holmes, how to uncover opportunities hiding in plain sight.

I’ll also show you a surefire way to diagnosis the problem if you get stuck so you can fix it quickly and be moving forward again.

You’ll also have opportunities to connect with your fellow explorers and share ideas. Feel free to come with questions and be prepared to leave with answers.

Thank you, Barbara, for a fantastic Joyfully Jobless Weekend in Houston, TX. The event was filled with encouragement and helpful, practical tips, insights and information about living a joy-filled life. The wattage above my head increased exponentially with each segment of the workshop. I came away bursting with energy, ideas, enthusiasm and hope that I can successfully create and live the life I choose and knowing some new friends who will enthusiastically support me in this endeavor!

Jean Morehouse

The best in business have
boundless curiosity and open minds.

- Robin S. Sharma

Since I’m big on smallness, enrollment is limited so everyone in attendance can have the fullest possible experience.

As of this writing, upcoming events are scheduled for Ajijic, Mexico, Houston, TX and Nashville, TN with other locations to be announced soon.

Is this for you?

Don’t think of yourself as sassy? That’s okay. What about unique? Determined? Confident?

  • You know there’s more to learn, but don’t have time to do extensive research right now.
  • You’ve got some profit centers up and running and it’s time to find another good idea.
  • You still catch yourself stuck in employee thinking.
  • You’re ready to regroup, restart, refocus.
  • You’re willing to invest a little time to learn a lot

You can’t Google this experience.

Put yourself in the room where it’s happening, where ideas are zooming around,
where you’ll meet some kindred spirits and get practical power tools for 
building a better business.

Small, Sassy & Successful  takes place on Friday evening 6:30-9:30
and all day Saturday 9:00-4:00 in the following places.

Ajijic, Mexico

Dates TBA

Houston, TX

June 1 & 2

Nashville, TN

September 14 & 15

Early bird tuition is $199 (regular tuition is $249).
Space is limited so enroll as soon as possible.

Bonus: All participants will receive a one-year subscription to Winning Ways
newsletter to keep the ideas, information and inspiration coming.

Barbara Winter here.

There are two places that are natural habitats for me. One is my business, of course. Whether I’m writing my column for Incomes Abroad, putting together Winning Ways newsletter, consulting with an entrepreneur on Skype, interrogating entrepreneurs that I encounter out in the world, doing research or auditioning a new profit center, I love the diverse creative adventure.

Meeting rooms filled with other creative explorers is my other favorite habitat. Even though I’ve had the pleasure of spending time learning in places like Sedona, Arizona and the Lake District in England, Glasgow, Scotland and cities around the US and Canada, the locale isn’t nearly as exciting as watching seeds get planted, new ideas unfold and problems get solved. That’s precisely what will be happening when we gather for Small, Sassy & Successful.

I spent yesterday organizing the stack of ideas generated by the workshop into things I can do NOW, things that will be "midrange" for time, and things that will be longterm (because they need more pital). Got my calendar for the next couple of weeks set up for the NOW stuff! Then spent an hour this morning out by myself working on my photography.

Shannon Hill

Wow! What a start to a year of Joyfully Jobless Weekends! Barbara Winter blessed us by visiting Dallas and gave us almost 10 hours of stories, tips, ideas, concepts, and of course charm. Barbara is organizing this project through the "Collaboratory," her system of partnering with a sponsor host in each city where the JJW is presented. Susan Hamm was the sponsor host in Dallas, and I have to tell all the others, she set a very high bar. She is warm, kind, generous, and extremely gracious. We were well tended with delicious treats! It was fantastic to meet other entrepreneurs, too, with creative business ideas and heart-based lives. People who "get it" when someone wants a "creative, juicy" life. My mind is still stretched out and full of new ideas. I had strange dreams all night long! Nothing that was helpful, but I'm sure a side effect of my mind trying to assimilate so much good and new. How do you do it, Barbara? I took it easy today after a couple of very busy days, and I'm already tired!

Steve Coxsey

Starting my own business is the greatest thing I’ve ever done for myself. I’ve learned more about myself and what I’m capable of in the last year than I have in the last ten combined. I feel at peace with myself for the first time since I was a kid. It’s amazing.

John Pompeo

Barbara Winter is a gold mine of encouragement and wisdom for the freelancer.

Jane Ingalls

I just really wanted to say that you have inspired me to get out of my comfort zone and go after my dreams and really become joyfully jobless as I’ve been so incredibly frustrated by my day job!

Nicla Williams

© 2018 Joyfully Jobless Weekends with Barbara Winter.