The first half of 2025 has been marked by turmoil and uncertainty in higher education. On top of declining public perceptions of the value of higher education and worries over a looming "enrollment cliff," federal and state cuts to institutional funding have grabbed national headlines. Meanwhile, institutions continue to face staffing challenges and budget constraints that diminish their operational capabilities, and emerging AI technologies are becoming more sophisticated, seemingly by the day, threatening to upend the enterprise of education entirely. Caught in the midst of it all, technology leaders are faced with tough decisions about resource allocations, new technology procurements, staff development and team management, project planning, and alignment with shifting institutional cultures, priorities, and values. These are challenging times, and many technology leaders simply are not okay. Against this backdrop we undertake this exploration into the current attitudes and experiences of technology leaders tasked with boldly guiding digital strategies and building the technology infrastructures of their institutions.