The Human Side of Tax: Navigating Pressure, Priorities & Practice with John Oakey

In this episode, I sit down with tax educator and industry leader John Oakey for a refreshingly non-technical conversation about life inside the tax profession.

While John is well known for his deep technical expertise, this episode goes in a different direction.  We explore the real-world challenges tax practitioners face every day: competing demands, client expectations, time pressure, and the constant balancing act between doing great work and staying sane.  

This episode covers: 
  • Why even the most seasoned tax professionals struggle with the non-technical side of the job... and how imposter syndrome lives within us
  • Navigating uncertainty in tax while clients expect clear, confident answers, and the invisible weight of responsibility that comes with advising clients on high-stakes decisions
  • How experience changes your perspective on workload, boundaries, and what really matters.
  • There are so many different avenues and ways to practice tax.  John gives some advice for listeners on how to find out what will bring you the most joy!
Looking to get more involved in the tax community? John and I also share our favourite ways to give back to the community as tax practitioners. 

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