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Making Money: The Right and Wrong Questions to Ask

jura_machine_135.jpgReaders Steve and Sean dropped by the house the other day for coffee and a chat. We talked about Portland, hiking, music, Steve’s new magazine article, Ken Kesey, Eugene, New York, writing, and, of course, jobs.

Sean, an accomplished poet and an emerging travel writer, is a former teacher who’d been struck hard by Theresa Collins’s essay, The Truth about Quitting. After we’d polished off our Portland-sized iced coffees, Sean asked the big question:

How can I make more money?

As Soul Shelter’s Director of Fortune, I consider it my solemn duty to help readers become more prosperous.

So I offered Sean some hard truths about book publishing and some alternative ideas for making money with writing. And I described how some writers (not copywriters) regularly pull down $10,000 per month.

Sean jotted down a few furious notes, Steve chimed in, and the conversation moved on.piggy_bank.jpg

But afterwards I realized Sean had asked the wrong question. Worse, I had offered the wrong “answer.” My response should have been a counter-question:

“Sean, how do you want to spend your days?”

Because if Sean can truthfully say he wants to spend his days writing, then finding ways to achieve the goal of making more money is simple (not easy, but simple). One can’t examine methods until goals are defined. “Making more money” is merely a by-product of work. It isn’t an acceptable goal because it isn’t predicated on how you want to spend your days. If you want to experience fortune or fulfillment, you must spend your days—first and foremost—in a manner satisfactory to you.

Last month, Three Questions Seekers Must Ask Themselves described the process of setting a goal, identifying a strategy to achieve it, then appraising both the strategy and one’s own ability to execute it. Taken together, the Three Questions form a powerful goal-achievement methodology. The core question is, What is your Goal?

If Sean’s goal is clear, surely there are many ways he can go about achieving it.

Let’s consider Reality A—today, with our goal unachieved—and Reality B, the future, with goal achieved. Our mission is simple: To journey from Reality A to Reality B. Reality A is defined by a set of behaviors that keep us grounded—or tethered—to current circumstance. Moving toward Reality B, therefore, requires adopting new behaviors. But “behavior” is shorthand for “habits.”

So to move from Reality A to Reality B, we must break our Reality A habits. Long-standing habits limit us to long-standing behaviors. As reader Brigid puts it, “if you keep doin’ what you’re doin’, you’re gonna keep gettin’ what you got.”

Reaching Reality B demands acquiring new, uncomfortable, habits. In fact, achieving any significant goal is sure to require uncomfortable action. It’s amazing how frequently we relearn that one can’t create Reality B by repeating Reality A behaviors.

Here are The Three Questions revisited:

1. What is my goal?


2. What new behaviors does Reality B require?


3. Which Reality A behaviors should I replace?

Look at the steps defined in The Three Questions: They provide the clues to new actions needed.


Part of the challenge is that even positive behaviors can hold us back when we become too dogmatic about them. For instance, I’m pretty anal about my Monday through Friday morning stretching/exercise routine. But a pulled muscle recently forced to me to cancel my heretofore inviolable regimen for a week, so I started walking instead. What a difference that made! Now I’m hooked on taking a couple of long walks each week, while continuing the morning exercises—minus the drillmaster attitude. So one cornerstone of achieving greater prosperity is breaking habits.

The other is asking the right question: How do you want to spend your days?

You may also enjoy:

Entrepreneurship: A Primer

The Soul of an Entrepreneur, the DNA of a Business

The Heroic Journey

5 Comments to Making Money: The Right and Wrong Questions to Ask

On Jul 25, 2008, MM commented:

The part I find difficult about answering “How do want to spend your days?” is that I don’t want there to be one answer. This makes the specific goal setting difficult since the scope is greater than “I want to spend my days on the beach” but saying “I want to be free to do what I want when I want” as too vague for a specific action plan.

I suppose setting and achieving small specific goals may help to refine the grander How do you want to spend your days question.

On Jul 25, 2008, Tim commented:

I hear you. It might be more accurate to say “on what activity, or closely related group of activities, do you want to spend between four and six hours every day, four to five days a week?”

Though I’m a big fan of the Four Hour Workweek and the ideas and tools described therein, most of us do better being centered on something that involves both mastery and service. That requires devoting a significant chunk of time to our vocations (though less than most corporate jobs, where much time is unproductive).

On Jul 25, 2008, Anne commented:

My problem is that I know how I want to spend my days; I know what kind of “job” I want to be doing; I know that I must rely on someone else to do their “job” which will get business so I can do mine; but I can’t figure out how to get there from here.

How is it that I determine which things need to be replaced and how to make this happen?

On Jul 25, 2008, Hank Byington commented:

I like the fact that you’re facilitating such a discussion. It gives me the picture of a frank exchange taking place in one of the salons of late 19th century Europe.

There should be more opportunities for entrepreneurs and creative types to discuss, in non-threatening fashion, what are very challenging issues. The “What do I want to do?” question is not identical, but quite intertwined with the “Who am I” question. As such, it needs to be conducted with both candor and compassion. It is is the antithesis of the hubris manifested in your average business networking event.

On Jul 30, 2008, by Tim commented:

Anne, take a look at the previous post on this topic and see if it helps. Also, Derek Sivers has a great way of putting it in his free e-book. He calls it “Ask for Directions.”

Hank, the salon is yours! Thanks for the kind words, and apologies for the radio silence. Had to get off the grid for a few days …

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