The Law of Financial Viability

When I explained what I was after, Derek got it right away.

“You mean, the type of mental algorithm that prevents the lawyer, who has had this successful career for twenty years, from suddenly saying, ‘You know, I love massages, I’m going to become a masseuse’?” he asked.

“That’s it,” I replied.

Derek thought for a moment.

“I have this principle about money that overrides my other life rules,” he said. “Do what people are willing to pay for.”

Derek made it clear that this is different from pursuing money for the sake of having money. Remember, this is someone who gave away $22 million and sold his possessions after his company was acquired. Instead, as he explained: “Money is a neutral indicator of value. By aiming to make money, you’re aiming to be valuable.”

He also emphasized that hobbies are clearly exempt from this rule. “If I want to learn to scuba dive, for example, because I think it’s fun, and people won’t pay me to do that, I don’t care, I’m going to do it anyway,” he said. But when it comes to decisions affecting your core career, money remains an effective judge of value. “If you’re struggling to raise money for an idea, or are thinking that you will support your idea with unrelated work, then you need to rethink the idea.”

At first encounter, Derek’s career, which orbits around creative pursuits, might seem divorced from matters as prosaic and crass as money. But when he renarrated his path from the perspective of this mental algorithm, it suddenly made more sense.

His first big move, for example, was to become a professional musician in 1992. As Derek explained to me, he started by pursuing music at night and on the weekend. “I didn’t quit my day job until I was making more money with my music.”

His second big move was to start CD Baby. Again, he didn’t turn his attention full-time to this pursuit until after he had built up a profitable client base. “People ask me how I funded my business,” he said. “I tell them first I sold one CD, which gave me enough money to sell two.” It grew from there.

In hindsight, Derek’s bids for control remain big and non-conformist, but given his mental algorithm on only doing what people are paying for, they now also seem much less risky. This idea is powerful enough that I should give it its own official-sounding title:

The Law of Financial Viability

When deciding whether to follow an appealing pursuit that will introduce more control into your work life, seek evidence of whether people are willing to pay for it. If you find this evidence, continue. If not, move on.

When I began reflecting on this law, I saw that it applied again and again to examples of people successfully acquiring more control in their careers. To understand this, notice that the definition of “willing to pay” varies. In some cases, it literally means customers paying you money for a product or a service. But it can also mean getting approved for a loan, receiving an outside investment, or, more commonly, convincing an employer to either hire you or keep writing you paychecks. Once you adopt this flexible definition of “pay for it,” this law starts popping up all over.

Consider, for example, Ryan Voiland from Red Fire Farm. Many well-educated city dwellers, fed up with urban chaos, buy some farmland and try to make a living working with their hands. Most fail. What makes Ryan different is that he made sure people were willing to pay him to farm before he tried it. In more detail, because he wasn’t a rich ex-banker, buying his first property required a loan from the Massachusetts Farm Services Agency—and the FSA does not give away its money easily. You have to submit a detailed business plan that convinces them that you’ll actually make money with your farm. With ten years of experience on his side, Ryan was able to make this argument.

Lulu provides another good example of this law in action. Here, the definition of “willing to pay” concerned her paycheck. She judged her moves toward more autonomy by whether or not someone would hire her or keep paying her while she made them. Her first big move, for example, was to drop to a thirty-hour-per-week schedule. She knew she had enough capital to support this change because her employer said yes. In later jobs, when she negotiated a three-month leave or insisted on working freelance with an open schedule, these were also bids for more control that were validated by the fact that her employers accepted them. If she had had less career capital they would have had no problem telling her good-bye.

On the flip side, when you look at stories of people who were unsuccessful in adding more control to their careers, you often find that this law has been ignored. Remember Jane from earlier in Rule #3: She dropped out of college with the vague idea that some sort of online business would support a lifestyle of adventure. If she had met Derek Sivers, she would have delayed this move until she had real evidence that she could make money online. In this case, the law would have served its purpose well, as a simple experiment would have likely revealed that passive-income websites are more myth than reality, and thus prevented her rash abandonment of her education. This doesn’t mean that Jane would have had to resign herself to a life of boring work. On the contrary, the law could have provided her structure to keep exploring variations on her adventurous life vision until she could find one to pursue that would actually yield results.