The podcast episodes cover a range of challenges faced by music artists in the modern industry, including financial and logistical obstacles as well as creative and societal pressures.

Many episodes discuss issues such as the impact of streaming platforms and social media algorithms on artist visibility and revenue ('Introducing 'Lately': The Globe and Mail's business and tech podcast'), the difficulties of selling concert tickets due to low demand and high prices 'Why big concerts are getting canceled, a quest for the perfect mango, and more', and the internal conflicts and external pressures that have challenged prominent labels like Motown and Stax '19 | Knock on Wood | Motown Vs. Stax'.

Artists have also discussed the challenges of maintaining creative integrity and authenticity while navigating the industry's demands 'Sunday Pick: Design Matters with Carrie Brownstein', 'Episode 231: Adelaide', as well as the specific hurdles faced by marginalized and independent artists 'Episode 231: Adelaide'.