bjwun-job-fairIt’s National Boss’s Day, a day that I celebrate heartily since I have the perfect boss. It took her awhile to figure things out, of course, but lifelong learning is one of the gifts of self-employment.

When I started my first business, I didn’t know another self-employed person who was creating something unique. There was no internet and not many books that were written for someone wanting to start a one-person operation. It was all trial and error…lots of error.

Today there are abundant resources, but some of the most important things I learned still aren’t being acknowledged. Here are eight things I wish I had known sooner.

° The business you start out with is not the business you end up with. By its’ very nature, business is an evolutionary process. As you change and grow—and as the marketplace changes and grows—you’ll make adjustments.

The good news is that you can get started wherever and whenever you want without having to know every detail. Be willing for your business to deliver pleasant surprises and lessons.

° Refuse to take advice from uninformed sources. It’s easy when you’re filled with self-doubt to listen to dream bashers. Don’t do it. And don’t solicit advice from those who have failed.

It’s amazing to me how often I talk to people who have abandoned a great idea because someone who knew nothing about their business (and probably wasn’t even an entrepreneur themselves) talked them out of it.

As the Persian poet Rumi wisely advised, “When setting out on a journey, do not seek advice from someone who has never left home.”

° Know the difference between an expense and an investment. Many new self-bossers see any outlay of money as an expense. While your business will have costs associated with running it, spending money now to produce a greater good in the future is an investment.

Your money needs to go to both. Some of the biggest return on investment comes when you invest in yourself.

° What you don’t know can be learned. Learn how to research your ideas and connect with informed sources. If you operate on the assumption that you can acquire the information and skills you need at every stage of development, you’ll always have the pleasure of being a voluntary student.

Equally important is determining which parts of doing business make your heart sing and which make your heart sink. Once you know that, you can farm out the parts you’re not good at. Know what you want to know and know what you don’t care about knowing.

° Personal growth is a daily activity. Paul Hawken says, “Being in business is not about making money. It’s a way to become who you are.” I became an entrepreneur because I was curious about what I could become. Self-employment continues to be my best teacher.

In order for your enterprise to reach its’ fullest potential, you have to reach yours. An occasional seminar or personal growth book or CD isn’t going to have the impact that daily work does, even though those tools are also important.

° Don’t confuse a project with a dream. Your dreams are your ultimate destination. A project is a step along the way. Too many people use a project failure as an excuse to abandon their dreams.

Know the difference and don’t make that mistake.

° Patience is your best friend. There’s a fine line between being patient and being a procrastinator. It seems to me that what many people call failure is simply running out of patience, giving up before their idea had a chance to blossom.

Remind yourself that you can’t possibly know how long it will take to accomplish something you’ve never done before. Be willing to be impatiently patient.

° Know the difference between taking a risk and taking a calculated risk. Timid people who are not self-bossers think that you’re a wild person jeopardizing your family and your finances. Nothing could be farther from the truth.

Studies have shown that successful entrepreneurs take risks, but they’re cautious, calculated ones based on research and intuition. Do your homework. Take a step.

Of course, part of the appeal and adventure of being joyfully jobless is not always knowing exactly how things will turn out. Be willing to let things turn out better than you imagined.

Note: I drove to Ventura again today and got thinking about this story of the Pumpkin Farmer from two years ago. Decided it was worth a revisit.

Yesterday I drove to Ventura where my sister Margaret lives. I’d been assigned the task of finding a vacation rental apartment in Paris for our sibling outing next spring and didn’t know where to begin. Margaret agreed to coach me since she’d already tracked down our Amsterdam accommodations.

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.

Isn’t it amazing how much you can learn about running a business just by noticing how others are doing it?



One of the qualities that successful entrepreneurs share is the capacity for paradox management. Nowhere is this more apparent than in the need to be both patient and impatient at the same time. Impatience is necessary to keep things moving, but it carries a danger with it and can lead to quitting too soon. 

So why does it take so long to see progress? Before you declare failure, consider these reasons:

° Idea needs tweaking. You start a new project thinking your customers are retirees and nothing happens. Then you begin getting inquiries from golfers and shift your marketing to reach more of them. That’s a classic example of right idea, wrong market. Here’s where some Joyfully Jobless friends can be helpful, showing you options that you missed. 

° Need to grow into the bigger vision. When things aren’t working out, many people think there’s something they must do, but often it’s something they must be that solves the problem.

The best reason for dreaming bold and following through on that dream is what we become as a result. If we’re not willing to acquire the skills and mindset of our best self, and invest time in getting there, our ultimate goal will be stalled. Eventually, it will disappear.

° Missed a step. Here’s where impatience can get in the way. Trying to jump from Point A to Point L doesn’t work. When a project is in limbo, retrace your steps and see if you left something out, something that needs to be included to produce the final result.

° Miscalculated the time it would take. I can never decide if it’s naive or arrogant to think that we can predict the timeline of something we’ve never done before. An old proverb says, “Going slow does not prevent arriving.” That’s a good proverb to recall as you inch ahead.

° Ahead of the market. It’s not unusual for a new idea to take time to catch on. If you’re offering something that hasn’t been available before, the marketplace may need to learn more about the benefits they’ll receive or, even, rethink an old notion. Sharon Rowe is a perfect example of that. In 1989 she started importing reusable shopping bags. She was about 20 years ahead of time. Today, however, her Eco-Bags Products is a multimillion dollar operation.

° Divine intervention. Deb Leopold runs First Class in Washington, DC. The day after the tragic Metro train crash, she told her Facebook friends that she’d been detained at her business the previous evening because CNN was there to do a story about a class she was running. Had she gone home at her usual time, there was a possibility she’d have been involved in the accident.

All of us can look back at things that were disappointments that turned out to be blessings. The trick is to start looking for the gift in a frustrating situation to see if it’s pointing us in a better direction. Sometimes what feels like a detour is actually a call to eliminate ambivalent commitment.