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A few years ago at my annual review, my division chief inquired about the funding for each of my activities. I am of that not uncommon clinician–educator ilk with lots of satisfying work and never enough funding. Somehow each year at the 11th hour, I come up with my salary, usually by adding a few more activities to my already-overfull professional plate.“No funding for these?” my chief asked, pointing at my Public Medical Writing class for medical students and Writing for Change program for residents.No, I had to admit. No funding. And no administrative support either.He crossed them off my list and moved on. He told me that what I wanted was a portfolio of activities that paid for more time than they required, not vice versa. I balked internally but said nothing because he was right. Over the years, I had learned that he was always right about such things, particularly in situations where my initial reaction to his advice was outrage or defensiveness.Except this time was different. This time, I knew I wouldn’t listen. This time, despite his skill at academic strategizing, my chief had addressed only one of the two questions required to adequately assess my situation. He had asked about funding, which is undeniably essential, but not about passion, which serves a different but equally critical role. For me to thrive—for me to work to my capacity and make my best and most unique contributions to our division and university—he also should have asked about what made me most happy, most inspired, most excited, and most satisfied.Over the next couple of years, I not only continued to teach both classes but also expanded my work in public medical writing until it became one of my defining activities and until, finally, it was funded.Since then, the question my chief asked that day and, equally important, the one he didn’t ask have come to define how I advise fellows and junior faculty. I don’t pretend they don’t need funding or that, especially for clinician–educators, securing enough funding will be anything but an ongoing challenge. But I also ask what work they would do for free, or even if nobody else believed in it, or first thing on a sunny Sunday morning. I ask them what they love best in their work, then I help them strategize how they might both get paid and be happy, even when the activities that fill each of those requirements overlap little or not at all on the Venn diagram of their careers. Finally, I tell them that I came to this career-planning approach by blatantly ignoring the advice of a valued mentor, and they should feel free to do the same.Louise Aronson, MD, MFADr. Aronson is associate professor, Department of Medicine, Division of Geriatrics, University of California, San Francisco, San Francisco, California; e-mail: firstname.lastname@example.org.