How to Enjoy Your Job and Never Work a Day in Your Life

Despite the fact that work can be one of life’s greatest sources of satisfaction, too many of us believe the opposite: that work is an inevitable joyless slog.

It’s not our fault. It’s what we were conditioned to believe.

As children, many of us remember adults returning from work, grumpy and irritable. The Sunday sermons about work I heard as a child were full of words and phrases like “toil,” “sacrifice,” and “the sweat of our brow.”

It hardly sounded like something I should be looking forward to doing.

So I toiled and I sweated—and feared I was serving a lifetime sentence. Happily, that all changed when I decided to adopt Richard Branson’s motto: “Fun is fundamental.” It’s a mantra that I use to keep myself on track.

Nevertheless, for decades I’ve encountered people with deeply held beliefs that make it difficult to imagine getting paid to enjoy themselves. Then along came the 4-Hour Workweek, Tim Ferriss’s best-selling book on maximizing your productivity that took the world by storm. Now everyone would be having more fun, right? Not exactly. Ferriss’s solution (in case you haven’t read the book) is to create a money machine that cranks out a passive income in order to free up your time to do fun things. It’s really just a variation of working for the weekend—with a minimum of work.

That’s not what I’m talking about here. Doesn’t it make more sense to build a portfolio of profit centers which are fun to operate? Adopt the radical notion that anything worth having is worth having fun getting it.

When you’re inundated with messages that earning money should be dull drudgery, accepting payment for having a good time may be surprisingly difficult. Challenge that mindset by creating regular projects that ease you into the world of money for fun.

Here are some other ways entrepreneurial folks have added an extra dose of fun to their undertakings.

Tax Deductions: Yes, I’m serious. Bear with me here. Newly self-employed people are often giddy when they discover that what once was an ordinary expense when they were employees becomes a tax deduction when they work for themselves.

A writer friend of mine was just telling me about the time he got a call from his accountant challenging his listing Cirque du Soleil tickets as a business expense. “After I explained that it was part of a bigger research project, the expense was allowed,” he laughs.

The Perpetual Treasure Hunt: For collectors of things—whether it’s Pez dispensers or post-modern crockery—the hunt is always on for the next treasure. The money fun comes in when treasures are resold for a profit.

David Robinson and his wife enjoy selling new and used books that they buy at yard sales, library sales, and sometimes at bookstores on the bargain tables. “I bought a book about the Beatles for $7.95,” he recalls. “And sold it via Amazon for $149.95. I went back to the bookstore, bought the remaining eleven copies of the book, received a 10% discount for buying them all, and then sold them for $149.95 each.”

Be a Temporary Resident: Lynn Mottaz was dreaming of becoming an innkeeper. Unable to finance the purchase of her own bed and breakfast, she started an inn-sitting business, keeping things running smoothly so innkeepers could have their own getaways.

Property caretaking, both short and long term, has become increasingly popular. One of the more innovative examples of this was a yacht-sitting business started by a young man.

The year that I took my first sabbatical, I received several invitations to house/pet sit. Since I had given up my apartment, these offers were especially appealing, including a flat sit in London. What I hadn’t anticipated was how much I’d enjoy living in someone else’s home for a limited time. It’s an idea I’ve kept in my Possibility Portfolio.

Beyond a Hobby: Many successful enterprises began as a hobby and evolved into something more. Rich Wagner is a photographer who also teaches workshops on selling photographs. “Over the years, I’ve had different hobbies including metal sculpture, leatherwork, painting, and cabinet making,” says Rich.

“It may sound strange, but after traveling all over the globe and hitting six of the seven continents, I can say it was my camera that made it the most fun. If I couldn’t take a camera, I’d rather stay home and take pictures.”

So don’t overlook the fun factor when planning new enterprises. As the author, Phil Laut liked to remind his readers, “Start a business that’s so much fun you don’t care if you go broke with it. With that attitude, you’re bound to succeed.”

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