There are hundreds of perfectly smart reasons to be Joyfully Jobless, not the least of which is that people who are doing work that they love tend to be, well, more loving and joyful.

One time after I’d visited my aunt Marge, she sent me a letter that said, “The Bible says a merry heart doeth good like a medicine. That’s how I feel when you come to see me.”

Besides that fact that it was one of the nicest letters I ever got, it’s remained a powerful reminder of why it’s important to stay merry. Here are some of my favorite ways to bring more fun and joy into a business.

° Specialize in Firsts. Challenge yourself to do things you’ve never done before. It can be as simple as trying a new food or taking a yoga class.

This is harder to do than you may think since we humans tend to build habits and then operate in familiar territory. Having Firsts requires conscious, creative effort.

° Exercise your entrepreneurial thinking to keep it in shape. You build entrepreneurial muscle by studying other enterprises, by acquiring new skills, by taking risks.

Just like physical exercise, it needs to be a daily activity if you want maximum results.

° Don’t be afraid to be whimsical. Small businesses should not look like miniature corporations.

Lighten up. Create a costume and wear it when you work or exhibit at a trade show. Have toys or a guitar in your office for play breaks.

And if whimsy’s not your style, from time to time purposely do something out of character. You’re bound to startle your friends and you might delight yourself.

° Celebrate all victories. Jim Rohn told a story about his early days in business and how he’d take his family out for dinner and say, “Tonight we’re ordering from the left side of the the menu. Pay no attention to prices.” He said it helped him stay on track.

Find your own way to celebrate milestones and progress. Send yourself flowers or invite a friend on an outing. Don’t let victories—large or small—go unnoticed.

° Plan Joyfully Jobless get togethers. Find 5 other self-bossers that like each other and let each one plan a monthly gathering, just to have fun.

You could find yourself salsa dancing one month and picnicking in a park the next. Hanging out with other entrepreneurs can be a lovely tonic, but don’t wait for somebody else to get things rolling.

° Turn ordinary chores into satisfying rituals. Got bills to pay? Instead of gritting your teeth, light a candle, put on some lovely music, pour a cup of tea and make it an event. Slow down and express gratitude for your current abundance.

Invent rituals to turn ordinary tasks into something special.

° Stay focused on rewards. On snowy days in Minnesota, my Joyfully Jobless friends and I would call each other to rejoice that we didn’t have to drive on bad roads.

Keep a running list of all the rewards that you enjoy because you’re self-employed. Post it in your workspace and remind yourself often of the benefits and pleasures of this lifestyle.

° Support that which supports you. This has been my personal and business policy for a long time and it hasn’t failed me yet.

For example, I give top priority to supporting the self-bossers who support me. My newsletter, Winning Ways, is designed to pass along ideas and resources that have helped me on my journey.

You get the idea.

° Expect the unexpected. Businesses often surprise us with new opportunities and directions. While this may be upsetting to control freaks, true entrepreneurs delight in it.

° Change the scenery. The creative spirit flourishes when exposed to new people and places.

Whether that means taking your laptop to the park for a morning writing session or attending a weekend seminar, give yourself the benefit of working in different ways. Rigid routine is the enemy of creativity.

° Be kind. When we commit an act of kindness our endorphin level goes up. Likewise, when we receive a kindness it raises our levels.

However, studies have also found that if we merely witness an act of kindness, it raises endorphin levels too.

Go ahead and spread some kindness around.

It happens every time I announce a new special event. Almost immediately, I begin getting messages that say, “Someday I’d love to attend your Storytelling seminar.” Or “When will you be doing your Inspired Livelihood event in Alaska?”

These questions come from folks who don’t understand effective goalsetting. They’ve got it backwards. Sadly, that is a recipe for frustration.

Several years ago when Valerie Young announced our upcoming Making Dreams Happen event, she was deluged with e-mails from people saying they’d like to attend but couldn’t afford the enrollment fee.

She called me to see if I had any ideas about how to handle this onslaught. I pointed out that since this event was about bringing dreams into reality, getting there was the first exercise. 

The ever-creative Valerie issued a challenge to her readers asking them to share what they were doing to fund the conference. We got wonderful stories about the creative ways that participants found to be involved. 

A year earlier, two friends and I decided we wanted to take a little vacation. My cash flow was good so I had the funds;  they had  both spent the previous months working on writing projects that had yet to pay off so their cash flow was squeaky. 

Once we set the goal for the trip, however, they  swung into action. They  had each built a nice little portfolio of cash flow options that included things like selling on eBay, doing market research, spending a Sunday as a flea market vendor. In less than two weeks, they both had the money  they  needed for the trip.

Last year, another entrepreneurial friend was experiencing a cash flow slowdown and decided to get creative. She wanted something that wouldn’t distract too much from other projects she was working on, so she put an ad on her local Craigslist offering her services as a pet sitter in her home. Not long after, I  was talking to her and she proudly announced, “I just passed the $1000 mark with pet sitting.” 

In his blog post Pennies and Dollars, Seth Godin writes, “In fact, too much worrying about cash is the work of the lizard brain, it’s a symptom of someone self-sabotaging the work. The thing to do is invest in scary innovations, large leaps, significant savings.”

So the order of making things happen is this: goal first, funding second. 

What successful goalsetters know is that the process goes something like this: focus on a goal, brainstorm obvious and crazy ways to make it happen, start taking action. 

Keep going until the goal is met. 

Set another goal and repeat.


Been thinking about joining Alice Barry, Terri Belford and me for Inspired Livelihood in Sedona? Don’t let your lizard brain keep you home. Commit to coming, register and create a funding project. And start your project by giving yourself a nice discount by signing up before March 15