As a first-year student at Yale School of Drama, my classmates and I received the “money talk” from Ben Mordecai, who was managing director of Yale Repertory Theatre and head of the administration program at the time. Attempting to manage our expectations about career prospects upon graduation, he clarified the salary levels one could expect in the nonprofit theatre.  He also reinforced the idea that the main reason for being in the program was to prepare to work in a nonprofit resident theatre. And he forbade us to start a new theatre company, because he believed there were already enough organizations and not enough funding. My first year out of the program, I was hired for a modest salary as assistant executive director at Minneapolis’s Guthrie Theatre. I was in my twenties, armed with an MFA and student loan debt that would take me about 10 years to pay off. Indeed, I wondered if I would be able to stay in the field if I didn’t ultimately find my way into higher-paying positions. Fortunately, I was given the rare opportunity to work side by side with two masters: artistic director Garland Wright and executive director Ed Martenson. It should be noted that I was also working in an institution that prioritized, in its strategic plan, compensating its company of actors at a level that allowed them to make a life in the theatre. Most owned homes and had families. While the Guthrie no longer has a full-time company, some of those actors are still beacons in the Twin Cities community. What I learned there, and the connections I made, enabled me to continue in this field. I gained skills and networks and moved into increasingly responsible positions in increasingly large institutions with increasing levels of pay. The rest is history, as they say. Two documents—Diep Tran’s article in this issue on student debt, and a recent, much-discussed blog interview with Philadelphia artist Charlotte Ford—are important reminders of the continuing economic struggle freelance theatremakers face, and a sign that it may be getting worse. In Tran’s article, the increasing pressure of student debt on artists who are educated, accomplished and consistently working is startling. When calculating the “return on investment” of a college or graduate degree, the fact is that some degrees pay for themselves and others don’t. The story of Freddy Arsenault’s successful acting career, dampened by $165,000 in debt, is proof. His conundrum inspired him and two other NYU acting graduates to form the Artists Financial Support Group in 2010 to assist others in managing their economic lives. Charlotte Ford explains why she went for a master’s degree in speech language pathology, which the training programs claim has a 100-percent hire rate. As a theatre artist, she’s never made more than $23,000 per year, and that was working 60 hours weeks. As she put it: “I’m sacrificing everything to be able to do my art, and I’m burned out. I want to be paid to work, not pay to work.” What stood out for me about Ford’s interview were her remarks about how people often extoll the virtues of the robust arts communities—in her case Philadelphia—but while there may be plenty of great art that residents enjoy and that makes the city more livable, many of its artists barely get by. Indeed, when we talk about whether the theatre field is doing well or not doing well, it’s usually the fiscal health of organizations that carries the most weight. But widening the lens to look at all aspects of our sector’s health brings other matters into the equation: What about the health and well-being of the artists, those who provide joy and insight to our communities, who help people imagine worlds they could never imagine on their own, and who do so without enjoying the same basic stability that others in the community enjoy? What is the impact on artistic ecosystems when foundations change their priorities and housing prices escalate, as in Philly? Ideally, theatre doesn’t replicate structural weaknesses in the larger society but rather models a new path. How to do this—how to reimagine an established system—is the key. On the individual level, there are strategic efforts to support artists. Some theatres, such as Rhode Island’s Trinity Repertory Company and Wisconsin’s American Players Theatre, have committed to resident acting companies. Others have focused on lessening the debt that students in the arts carry with them into the professional world—Yale School of Drama, under James Bundy’s committed leadership, is a great example. Beyond those efforts, what system-wide strategies are called for? Can more colleges and universities work to lower the debt burden for students graduating from professional training programs? Can more institutional and individual donors step up to the plate and make funds available to support individual artists? Can arts organizations, trustees, funders and other community leaders convene regularly to assess and address the state of the artist in their local ecologies? These are questions that continue to defy easy answers. What we can expect are more training programs, more students being invited into them, and less opportunity for artistic investment as economic stress impacts theatres. We’ve been talking about artists and money for a long time, and the conversation is still just beginning.