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I’ve come face-to-face with these two questions countless times as a writer, an entrepreneur, a painter, a musician, and even a lawyer. On a more immediate level, the questions relate to the project you’re working on. If you’re a painter creating a collection of work, you may start to feel the questions arise as you explore whether a canvas or the collection is taking shape as you have envisioned it. On a more expansive level, the question emerges in the context of whether you should even be a painter or a writer, a coder, an entrepreneur, a CEO. I’ve seen actors struggle to build careers for decades, never coming close to earning enough to cover their bills. Yet they keep on keeping on, because their big break could be one audition away. And this is what they feel called to do. These are some of the most difficult and defining moments every creator faces. I’ve been told by legendary entrepreneurs, “If you have to ask, assume it’s resistance and soldier on.” They claim that you just know whether or not a project is meant to be. But I’ve witnessed countless people commit to perpetually unsuccessful projects or careers or, on the other side of the spectrum, come a breath away from what would’ve been breakthrough success had they just held on a bit longer. So I began to explore a more systematic process, a set of benchmarks, tests, and questions that might better guide these moments and help people decide whether to keep leaning into the journey, alter their course, or walk away and do something entirely different. We start by asking, “What was your inciting motivation?” What made you undertake this endeavor to begin with. Was it, in some form, the expression of a calling? Was it something to keep you busy? Was it about serving a group of people, solving a problem, or serving up a delight? Was it about money or doing anything you could to get your parents off your back and avoid grad school? Begin by going back to the time surrounding your decision to create whatever it is you’re creating and answer this question. Then move on to the next question. In light of the information and experiences you’ve had along the journey to date, does that original motive still hold true? Are you still equally or even more determined to make it happen? And given what you now know, do you believe you can make it happen?
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