Fans of Prairie Home Companion know that they’ll be catching up with the wandering Dusty and Lefty on the weekly skit called Lives of the Cowboys. Since Dusty is a rough-and-tumble cowboy and Lefty is his sensitive sidekick, the somewhat unlikely pals are often at odds about how to handle tricky situations they encounter out on the trail.

Dusty and Lefty aren’t the only ones who need pals, of course. Even the most independent self-bossers discover that an entrepreneurial friend or two can be a valuable asset—in more ways than one.

When I started my first business, I made some attempts at connecting with other businessowners. I attended a workshop sponsored by SCORE, checked out my local Chamber of Commerce. Neither felt like a fit for me and I gave up my search for entrepreneurial buddies.

What a mistake that was. In my determination to be independent, I made things far more difficult for myself than necessary.

I can pinpoint the moment when my business went from frustrating to flourishing. That moment occurred when Chris Utterback and I became friends.

Chris and I  became sounding boards, idea-generators and co-conspirators as our friendship grew. Even though we both left Colorado shortly after we me, we were diligent about connecting frequently.

Quite simply, we need to have entrepreneurial friends if we’re putting ourselves in the Innovative Minority. Finding kindred spirits is an on-g0ing part of the Joyfully Jobless Journey.

When the homebased business movement began to grow, numerous attempts to create both local and national organizations began to pop up, but most of them disappeared rather quickly.

It appeared that folks who’d left corporate life were not interested in hooking up with another large organization. This new breed of entrepreneur was not about to conduct business as usual.

However, the need to connect with other self-employed people didn’t disappear, it did, however, seem to take a different form as entrepreneurs built friendships that were fewer, but richer.

Author Jess Lair once wrote, “All of us need four or five people who’s faces light up when we walk in the room.” That sounds like a description of the new Joyfully Jobless mini-tribes.

New entrepreneurs are often stumped about how to connect with other creative self-bossers since years spent in the job force has kept them away from those who are self-employed. Then there’s the uncertainty, the fear that a successful entrepreneur won’t want to be bothered hanging out with a newcomer.

When I hear such concerns, I point out that our entrepreneurial circle needs to include people at all stages of growth.

What matters most is that our relationships, include what Stewart Emery calls “a balance of contribution.” That’s a slightly more elegant description of what is commonly referred to as a win-win.

Building those relationships, reaching out, connecting, takes time, of course, but most importantly, it takes a willingness. Remind yourself that your life will be richer for these new friends.

Or remind yourself of this observation from C.S. Lewis: “Good things as well as bad are caught by a kind of infection. If you want to get warm you must stand by the fire; if you want to get wet you must get into the water.

“If you want joy, peace, eternal life, you must get close to, or even into, the thing that has them. They are a great fountain of energy and beauty. If you are close to it, the spray will wet you; if you are not, you will remain dry.”

If you need some suggestions for hunting down the self-employed, check out my article, A Field Guide to Genus Entrepreneurus. It’s a helpful list of the natural habitats of these elusive creatures.



Steve Merritt grew up in Iowa dreaming of a life of social activism. When he told his high school counselor that he wanted to find a solution to world hunger, the counselor scoffed and said he needed a more practical career plan.

Following that advice, he ended up in the cable television industry earning lots of money and little personal satisfaction.

Eventually Merritt turned his growing discontent into a life-changing event and today he happily heads up a community garden project in California.

Merritt’s story is a great reminder of the dangers of well-meaning advice.

Here are some things to consider when receiving advice so you can sort the wheat from the chaff.

Rule #1: Consider the Source

The most important thing about receiving advice is that you know your source and trust them. I was once reading a newsletter written by a woman I have watched build a lovely business.

One of the articles really struck me as special and I e-mailed her suggesting that she send it to some other publications. (Okay, I confess that violates my own policy of giving unsolicited advice.)

She wrote back saying that she had thought about submitting some of her newsletter material to other markets, but someone had told her that she couldn’t do that since it was already published.

I was flabbergasted. Who would have given her that erroneous advice?

If it was a professional writer giving the advice, they would have known about resubmitting material. If it wasn’t a professional writer who told her this, why would she have listened?

This isn’t an isolated incident. We’ve all probably allowed inaccurate advice to influence us.

Sometimes it happens because the advice-giver sounds authoritative and so we look no further. At other times, maybe out of laziness, we accept negative or discouraging words as an excuse for not giving something a try.

And sometimes we just don’t know if the advice is accurate. (This is a particularly new and thorny problem caused by the Internet where advice is posted but not edited or verified.)

Rule #2 : Get a Second Opinion

While too many opinions or too much advice can serve to confuse us, if you’re exploring unknown territory, some serious research is in order before setting out.

Get advice from people who know what they’re talking about—and then get a back-up opinion or two.

I once got e-mail from a woman who said that all of her life she’d wanted to be a professional caricaturist, but everyone told her she couldn’t make her living doing that.

I asked her if she was getting advice from other caricaturists.

Having numerous opinions from uninformed sources doesn’t make the information accurate. Having several opinions from experienced sources is another matter altogether.

Rule #3: Make the Most of It

When you ask the advice of another person, your initial role is to be a quiet listener or to ask clarifying questions. Whether or not you act upon the advice is a matter for a later time.

When you’re trying to make a decision or need information so you can proceed with a decision you’ve already made, seeking outside input is just part of the information-gathering process. Sifting comes after you’ve got all the information collected.

When you are the recipient of advice, whether you use it or not, don’t forget to say thank you. I mention that only because I’m stunned by the number of people who don’t bother with this courtesy.

The world is full of teachers, experts and amateur advisors—with varying qualifications. Jess Lair once said, “When I’m working on my life, I want the very best teachers I can find.”

Finding the right ones to help you learn what you need to know so you can move forward in your own life is not to be taken lightly. The experience of others can save us time, add deeper insights, prevent us from making costly mistakes.

Ask those who can help, not hinder, your success.





After an especially hectic year that included two moves, one cross-country and one across town, plus the birth of her third child, my daughter Jennie has been gearing up Sweet Beginnings, her birthing doula business.

She’s been connecting with the local doula community and recently attended a day long seminar on marketing for doulas. She was invited to assist another doula who has three clients with the same due date. Jennie’s got her doula bag ready to go since babies have a way of choosing their own arrival time.

Last night she sent me an e-mail that said, “Do you have a couple of tip sheets that I could look at? I want to write one on making the perfect birth plan to give out to clients when I interview with them. I think it would be a nice touch.”

I agreed and promptly directed her to the Tip Sheet section of my Website.  I also promised to get a copy of my Tip Sheet On Tip Sheets to her.

Of course, it’s a pleasure to watch my daughter put her creative energy into building a business that thrills her, but she’s also reminded me of a basic success principle that I learned many years ago.

What’s the first lesson of  Success 101?

It’s simply this: If you want to be successful, you’ve got to do what successful people do.

Although it seems so obvious to me, I’m always surprised that everyone doesn’t know and use it.

That one little sentence launched my lifelong learning project. I became obsessed with hearing what the people I admired had to say, what they thought, how they made decisions, what actions they took.

I wanted to know what they read, what influenced them. I discovered that many of my early role models were enthusiastic seminar attendees, so I began showing up at seminars.

I asked questions, interrogated them whenever possible. I wrote letters, invited them to lunch, put myself in their presence and watched. I listened and I learned. I began to think of myself as an apprentice.

Then I experimented in the laboratory of my own life. I found my own voice.

Eventually, I created my own definition of success that included much more than financial achievement.  Personal qualities, such as caring for others, generosity, sense of humor and attitude got high marks from me. I discovered that teachers and role models were everywhere—but I had to take the initiative and seek them out.

Barbara Sher reminds us that, “Isolation is the dreamkiller.” So is hanging out with people who do not have dreams.

Author Jess Lair once commented, “When it comes to my own life, I want the best teachers I can find.” Whatever it is that matters most to you, deserves the support of the best teachers you can find, too.

Yes, it can take courage to put yourself in the presence of those who are farther along, who have achieved what you’ve only imagined. Take a deep breath and do it anyway.

Whatever you long to do next, start your apprenticeship now. Your teachers are waiting for you to show up.