When I drive the 40 miles or so to Ventura, much of the trip takes me through an agricultural area. There are vineyards and fields bursting with a variety of fruits and vegetables.

The road is also lined with produce stands run by farm families. It’s a lovely contrast to the big city environment of Los Angels.

One October trip was especially memorable. In the springtime, this drive reminds me of Ireland because the craggy hills are so lush and green. Right now they’re festooned in shades of beige and brown, but it’s still a pleasant drive.

The road goes through an agricultural area with two small towns on the way. There are orange and lemon groves alongside a little red schoolhouse, a honey tasting place and small stands selling produce.

Something had been added since I made the drive a couple of weeks ago. The produce places now had big displays of pumpkins for sale. I passed a field where big fat pumpkins laid waiting for buyers to come and pick them.

That got me thinking about the folks who grow these autumn favorites. If you’ve taken my Making a Living Without a Job seminar, you may even recall my talking about pumpkin growing as an example of a seasonal business.

If you’re a pumpkin grower, I point out, you don’t have much cash flow for most of the year. Then around the first of October, millions of us are suddenly eager to go out and buy a pumpkin or two.

A cash flow avalanche for the pumpkin farmers ensues.

Then it stops until the next pumpkin season rolls around.

Of course, it’s not just pumpkin farmers who deal with long income gaps. Anyone who grows crops learns valuable lessons in patience while dealing with uncertainty of every sort.

When I passed another pumpkin patch on my drive, I began thinking that all of us who are self-employed could learn important lessons that we could apply to our own undertakings. There’s no picking if we aren’t planting, I thought.

As I was musing on such things, I glanced in my rear view mirror and saw a large black pickup truck advancing rapidly in my direction. Since I have a policy to avoid tailgaters, I slipped back into the right lane and he soared past.

Even though he was speeding and driving aggressively, I couldn’t help but notice that his rear window was painted with a large ad for his plumbing services. “Hey, Dude,” I wanted to yell, “you’re driving a billboard.”

I made a mental note never to use his services.

The Impatient Plumber. The Patient Pumpkin Grower.

During the days when I taught high school English, I would never have assigned a book that I hadn’t read myself.  That carried over into my self-employment journey where I vowed to only recommend things I’d found worthwhile

That showed up in other ways as well. I decided to treat my business as a laboratory where I would experiment, test ideas, pay close attention to what worked—and what didn’t. I vowed to never teach what I hadn’t learned myself.

What I didn’t know back at the beginning was that the learning would never end. My curiosity never went on vacation.

There have been some wonderful surprises, of course. Along the way, I filled up two passports with stamps as I discovered my business could support my wanderlust. On top of that my travels became legitimate tax deductions.

While we all know that we’re living in a big, noisy Information Age, I’ve been thinking a lately about how incredibly valuable genuine learning is. The real thing goes way beyond a quick Google search.

I’m not the only one who has found being in a room with curious explorers is amazingly valuable.

My mentor, Bob Conklin, once added up all his investments including real estate, stocks, and money spent on attending seminars. He concluded that the biggest returns came from the time and money spent learning.

Earlier this year, I began to gather my best business practices. At the beginning, I was just reviewing my lab results and checking to see if I was forgetting anything.

I even surprised myself at how much great information I had gathered. I’m pretty sure I  said, “Wow” dozens of times.

As the list began growing, so did my desire to share these best practices with others. Could I do so in a weekend event?

It seemed daunting, but with a bit of editing I knew that I could share the brightest and best ideas that have kept me joyfully jobless for over three decades.

And I’d love to pass them along to you. If you join me in Nashville on September 14 & 15 for the upcoming Small, Sassy and Successful, I promise you’ll leave with a toolbox filled with ideas and information that will make running your own business even more fun and profitable.

Trendspotters agree that the market for unique and customized items is having a resurgence as more and more of us are learning to cherish the work of human hands.

Not all artisans are taking advantage of the opportunities, however.

Several years ago, I met a man who was a masterful carpenter who loved restoring old houses, flawlessly repairing woodwork and cabinetry.  At that time, he had abandoned his craft believing that no market existed for his services.

He had bought the myth of the starving artist and was living proof.

Happily, that myth is becoming outmoded as artisans are carving out their own merchandising niche proving that old-fashioned craftsmanship can be profitable.

If you want to put your arts or crafts skills to work for you, don’t make the mistake of thinking you’re in the business of marketing to everyone. Specialized products will attract a specialized clientele who appreciate and value such craftsmanship.

Once you are convinced that you do, indeed, have something to offer, you’re on your way to creating a profit center that’s as unique as you are.

In The Ice Palace That Melted Away, Bill Stumpf writes about exploring the Isle of Skye  where he and his wife came across a sign that read, “Woolen Socks for Sale.” They knocked on the door of the house and were welcomed by a friendly couple who fed them tea and scones and told them about their business.

The husband was a retired Army officer and the wife a part time artist. They decided they didn’t want to fade into oblivion upon retirement. They chose knitting as a business although they were untrained in the craft.

“They sold socks in local towns but worked no more than three days a week. In addition, they raised raspberries and Australian shepherds,” Stumpf recalls.

There’s plenty of evidence that as mass production continues to fill malls and online catalogs, those who create and market one-of- a-kind or limited edition products lovingly made will find an appreciative clientele.

 It isn’t only handmade clothing and decorative household items that will find a welcome market.

Skillful woodworkers and plasterers and preservationists are finding their special talents in demand by those who long to salvage buildings from the past.

There’s a renaissance going on that is bringing a new appreciation and prosperity to those who use old-fashioned skills and patience to create wonderful things. If you have such a talent, your next profit center may be as close as your fingertips.

Every business has times that are less busy than others. You can use this time to fret and worry that your entrepreneurial life has come to an end—or you can view it as a gift of time to do some of those things you’ve been telling yourself you’ll do when you have time.

It just makes sense, it seems to me, to spend this time wisely and well.

Here are a few possibilities.

° Review and revise your support system. Is it time to hire a virtual assistant? Find a new tax accountant? Get expert advice?

Unless you’re will to settle for the first person that comes along (and we all have had times when we’ve done that and regretted it later), this is a perfect opportunity to clarify what you need from various service providers and make sure you’re getting it.

If you’re ready to add to your support team, start interviewing potential candidates.

° Simplify, simplify. Been meaning to clean out your closets and pass things along to a charity shop? Get your office in shipshape? These are time-consuming tasks that aren’t very glamorous, but the psychic rewards are huge.

Get out some trash bags, put on some upbeat music and have at it. Get rid of the junk in the junk drawer. Weed your library. Update your filing system. Clean out your mailbox. It’s as liberating as losing twenty pounds.

° Up your wellness. Use this extra time to walk or workout. Get a massage or facial. Read up on nutrition. Experiment with new healthier foods that take time to prepare. Start meditating again. Plan a stress reduction program.

Work these things into your schedule now and you’re more apt to keep up with them when your busier times return.

° Volunteer. Pass your gift of time along to someone else by helping out. Why not volunteer at your kids’ school or at a local food bank or shelter? You could even instigate a project of your own and get friends involved.

If you live in a major metro area in the US and are needing ideas, go to www.volunteermatch.com which lists a wide variety of projects in search of help.

° Learn something new. Build some brain cells with a class or seminar. Add to your computer skills, start learning a new language, take up salsa dancing.

Use this time to saturate yourself in a new subject that catches your fancy.

° Finish things. Okay, not everyone has unfinished projects gathering dust, but chances are there’s an article you started writing or a home improvement project that got bogged down and abandoned because it didn’t seem urgent.

Imagine if all those loose ends were tied up before you plunge back into your business. It would feel great, wouldn’t it?

° Take a mini-sabbatical. Got a stack of books you’ve been wanting to read? Been meaning to visit a historic site that involves a road trip? Need to refresh your creative spirit? Plan some purposeful time away.

Borrow a friend’s cottage. Rent a motor home. Don’t check your messages. A change of scenery may be just what you need to recharge your batteries and come up with some fresh insights.

° Invest sweat equity in a long-term project. Been putting something off because it will require lots of hours to get to completion? This could be the time to start putting in those hours to get it launched.

Since most of us flourish when working on new projects, getting started has the added bonus of re-energizing other more familiar things.

° Host an Idea Night potluck. Invite four or five other positive self-bowsers to share food and ideas with each other. Make sure that everyone gets equal time and that all ideas get a hearing.

Idea Parties are more successful if you lay down the ground rule that arguing or discounting ideas is strictly forbidden. Guests go home with an inventory of potential ideas which they can evaluate later.

° Expand your visibility. Write a press release. Have a new photo taken. Start a blog. Get yourself interviewed on a local radio show. Revamp your website. All this seed planting takes time and is easy to overlook when you’re busy.

Why not do it now and see what doors might open?


Blessed are the curious for they
shall have adventures.
Lovell Drachman

Small, Sassy & Successful
Time Out to Build a Better, not Just Bigger, Business

Got an idea but you don’t know where to take it?
Think your business is ready to move to the next step?
Are you sitting on the next big thing?
Have an idea that’s suffering from neglect?

If you said “yes” to any of those questions, it’s time to roundup your good idea, take them to a roomful of creative thinkers, and see where they want to go next.
Barbara Winter here. I’ve been fretting lately about a frustration I’ve seen in folks on their Joyfully Jobless Journey who are no seeing results, not making progress, not finding the time or resources or ideas they need to create the life of their dreams.
I can’t begin to count the number of wonderful ideas I’ve heard over the years that are orphaned, abandoned by neglect.
Then there are the excuses:
When I have more time…
When I have more money…
When I know exactly what to do…
When I’m sure this is the best idea in the history of the world…
You know that none of that works. In the words of Colin Powell, “A good idea will not become a reality until it has a champion.”
Join me at Small, Sassy & Successful and become the champion of your own good ideas. In this 9-hour idea fest, you’ll gather a toolbox full of techniques for improving every corner of your enterprise.
We’ll be rolling up our sleeves and getting to work. You’ll get:
Time away from distractions
Time to focus on the things you most want to make happen
An inspirational environment
Support and expert guidance
If you’re ready to stop looking for formulas and ready to grow the ideas you have or acquire
some new approaches, make plans now to attend. Quite simply, you won’t be leaving with a plan about what you should do. You’ll be leaving with tools that make it possible (and fun) to do what you want to do.
Is Small, Sassy & Successful for you? It is if you:
See business as a creative outlet for your passions
Want to have a business that’s as unique as you are
Are feeling a little stuck
Believe that fun is fundamental
Love connecting with other small business creators

Want to come?
This is a small group, interactive experience and enrollment is limited. If this sounds like a great way to spend an evening and a day, don’t miss out. You can join me at Small, Sassy & Successful at Spectrum Center, Houston, TX, June 1 & 2  by registering at www.joyfullyjoblessweekend.com.

Coco Chanel, who said a lot of smart things, once observed, “There are people who have money and people who are rich.” It’s not hard to figure out which is which.

The people whom I think of as rich are those who have a practical prosperity consciousness. My sister Margaret is such a person. I have long admired her ability to use whatever resources she has to the max.

When we were in a pottery shop in Sienna, Italy, Margaret was captivated by a beautiful plate. We left the shop to contemplate making such a hefty purchase and as she considered the pros and cons she said, “I have noticed that when I’m anxious about money and start skimping, I never have any money. When I’m relaxed about it, I always have enough.”

I believe that’s true for everyone, whether we know it as well as Margaret does or not. This Wealth-as-a-State-of-Mind attitude is not an easy thing to master in a world that often speaks loudly about scarcity and impoverishment. In fact, most people are unaware that their thinking influences their sense of wealth or lack — far more than their bank balance does.

Years ago when I was living in Santa Barbara, I went out one day to begin my Christmas shopping. Although I seldom carried much cash, that day I had more of it with me than usual.

From the moment I got downtown, I began to experience anxiety. Everyone looked like a potential mugger. The distress was so intense that I went home without buying anything.

Shortly thereafter, I realized that I had a deep belief about money that went, “If I have money, people will harm me.” I decided that I needed to change my belief and, also, discover what other thoughts had kept me from enjoying financial ease.

I began reading Catherine Ponder’s Dynamic Laws of Prosperity every day. I was also greatly helped by the writings of Sondra Ray. One of her suggestions was to start carrying a large bill, eventually working up to $100.

The purpose, she explained, was that every time you spent money and saw the large bill in your wallet you’d be sending a powerful message to your subconscious which was, “I have plenty. I have a surplus of money.”

Within months, I went from seeing the world as full of muggers to carrying large amounts of money with ease. It felt like a huge victory over an old adversary.

Since money is a source of so much upheaval, each of us needs to thoughtfully examine our own attitudes and beliefs and create the healthiest approach we can muster. Going along with unchallenged ideas about money, old scripts from our parents, will not do the trick.

Getting smarter about money is a starting point, but taking a creative approach can also be a big help. You might begin by creating miscellaneous income sources. Creating odd income sources can be as good for your imagination as it is for your pocketbook.

A friend of mine who lives on a busy street holds regular yard sales whenever he wants to generate additional cash flow. He stores boxes of things, all priced and ready to go, in his basement. He keeps adding to his inventory and when the weather is nice, sets up tables and spends the day selling his bargains to motorists who stop to investigate.

Look for new ways of doing things using the resources you have. The more fun you can create with what you have, the more you’ll get.

Most importantly, be willing to invest time and money in yourself. When you invest in yourself, you’re making the most valuable expenditure of your life. The ups and downs of the economy will have no effect on an investment in yourself. You’ll trust that you know how to insure that there’s always enough.

During my brief stint as an employment counselor, I spent all day every day talking to people about jobs. It wasn’t usually a cheerful conversation.

Not only did most of these folks arrive at the Employment Service in a state of frustration, they seldom had any idea about what kind of job they wanted. “I’ll take anything,” is the career plan of the desperate.

Like so many of us, these folks considered work a necessary evil. In this perspective, a job was the price you paid to get the money you needed to buy the stuff you wanted. And it lasted a lifetime.

This sad notion about work is still wildly prevalent. A new book, Dying for a Paycheck, explores the hazards caused by the peril facing job holders today.

What a contrast that is to this observation from Frances Mayes about her life after leaving her college teaching job and becoming a writer who shares her passion for living in Italy. In Every Day in Tuscany she writes, “I rifle through my four project boxes, dreaming of several books I will write…Work like this feels like play.

“From living in Italy and seeing how people live and love, I saw that play is something you don’t always know you’ve lost in daily life. So much energy poured into my job.

“Leftover time seemed full of a lesser reward: enjoyment. But not play, the exuberant rush of fun that comes naturally to Italians. At home, many of the activities I planned for fun seemed like summer reruns.

“Learning from another culture is one of those mysterious movements of the psyche. I think you learn what you need to unlearn.”

I think unlearning is a huge part of the joyfully jobless journey. We don’t even realize how much of our employee mindset we’re still carrying around. Unlearning was certainly on my agenda.

As Frances Mayes discovered, “Writing is play. You choose a subject and set out to learn and think as much s you can about it. Then you get to let your imagination loose in the arena.”

Sounds to me like the perfect way to build a business, too. That’s precisely what we’ll be doing in my upcoming Small, Sassy & Successful seminars

If you’d like to collaborate and bring this fun learning adventure to your part of the world, I still have time available later this year. Feel free to let me know you’re interested and we’ll explore the possibilities. Email me at barbara@joyfullyjobless.com.

When I was digging around in my office this morning, I came across an old scrapbook that I hadn’t viewed in years. It was filled with memories of places I’d been and people I’d spent time with about twenty years ago.

One of my favorite discoveries was a letter I’d written to the editor of Minnesota Monthly magazine. I’ll let it speak for itself. I wrote:

As a one-person business and self-employment advocate, I was delighted to see the cover story on “Making It Small” in your July issue. Like the people spotlighted in your article, I am ferociously devoted to keeping my business human-scaled and giving passion a higher priority than profit.

When I began some twenty years ago, I found it impossible to find any information that didn’t assume all entrepreneurs wanted to create a gigantic enterprise.

Did I really want a building with my name in six-foot high gold letters? A board of directors? Stockholders? Employees? Pension plans?

None of that appealed to me and for a brief moment, I thought I’d gotten on the wrong train.

But I had a hunch that it was possible to create a livelihood that was both satisfying and profitable. And I have. Thank you for showing your readers that small is still beautiful.


If I were writing that letter today, it would say the same thing. My passion for small scale enterprise has never waned. That’s why I’m so eager to share what I’ve learned in my upcoming event, Small, Sassy & Successful.

And if you share my passion for creating a business that uses your imagination more and your pocketbook less, please join me. I’ll be sharing my very best discoveries for building a business that fits you perfectly.




In Living Out Loud,  Keri Smith’s a fun book of creative exercises, she writes, “In recent years lifestyle stores have become the rage selling products related to all aspects of living, eating, decorating, bathing, sleeping and dressing.

“If you were to open your own lifestyle store, what would you sell?”

Here’s how I answered that question.

The first thing you notice when you walk up the stone path to the sprawling English cottage that houses Cottage Industry is that the front yard is a luscious garden where flowers and vegetables grow side by side.

Pass under the rose-covered archway and you’ll enter a large room that resembles a comfy old library. You’ll be greeted by the faint smell of nag champs incense and soft music.

There are shelves of books and inviting chairs for browsing. Each corner has a different subject:
there are personal growth books in the Taking Care of the Boss corner, and eclectic mix of favorite authors in the Kindred Spirits corner.

In another are helpful books for Making a Living Without a Job and in the fourth corner  you’ll find books to Feed Your Wanderlust.

Vintage travel posters hang on the walls and favorite quotes are painted over the doorways.

Shelves in the center of the shop hold a collection of tools for creative entrepreneurs. You’ll find arty file folders, kaleidoscopes and framed quotations to add to the decor in your own World Headquarters.

But Cottage Industry isn’t just about stuff. It’s also about stuff happening. Walk toward the back and you’ll enter a glass conservatory known as The Idea Room overlooking another garden. Tea and coffee and treats are served in this room that invites gathering to brainstorm ideas.

Another large room to the left, known as the Follow Through Center, serves as a perfect setting for classes and coaching. 

I like to think of Cottage Industry as a spa for your imagination.

Do you have any idea how much fun that was for me to write? Try it for yourself. As Smith urges, “”Make a list of what it would contain. Draw pictures of what it would look like. What items best represent you? Come up with a name for your store.”

Feel free to rave about your store in the comment section below.

As I was reclining at the end of my recent blood donation, a young nurse came to tidy things up. We began chatting and she asked me a few questions about myself.

I told her that I was self-employed, did seminars and (almost as an after thought) said, “Oh, and I wrote a book called Making a Living Without a Job.”

The moment I said that, she got tears in her eyes. “You were sent to me,” she said softly. She regained her composure and told me how she dreamed of quitting her job and traveling.

I grabbed one of my cards and promptly wrote the book title on the back. “I think this will help,” I told her.

I left the blood bank marveling, once again, how often the opportunity to be of service comes in ways and places we’ve never anticipated.

A few days later, I posted this on Facebook:

As I’ve been crocheting scarves for the homeless, I keep thinking about how I’ll never know who the recipients are.

Today I realized that writing is very much the same. We send it out and have no idea who it will impact. That’s a good enough reason to keep creating and sending it out.

That elicited a reply from Dyan deNapoli, also known as The Penguin Lady. She wrote:

“It’s so true, Barbara! Just last week, I received a lovely note from a college student who had read my book about the penguin rescue when it came out 7 years ago, and was so moved by the story that she decided to become a marine biologist!

“She’ll graduate college in 2019, and wanted to thank me for inspiring her to follow this path. Did I get a little weepy when I read her letter? You bet I did!!

“It’s a big part of why I do what I do. And when someone takes the time to let you know how you’ve influenced them, it truly means so much.”

So this is just a little reminder to keep creating because you never know where you’ll be sent to solve a problem or inspire someone else’s dream.

As writer Annie Dillard points out, “The impulse to keep to yourself what you have learned is not only shameful, it’s destructive. Anything you do not give freely and abundantly becomes lost to you.”

Keep sharing and trust that someone somewhere is looking for exactly what you have to offer.