The Unburdened Leader

The Unburdened Leader


EP 52: Charlie Gilkey: Leading With What Matters Most

May 06, 2022

When you are not clear on what truly matters most to you, how you decide to use your precious time can leave you feeling overwhelmed and lost. 


And even your sense of time and what you can get done gets skewed by the tyranny of the urgent. Or comparison to how others are doing life and work. 


Striving and grinding is still the norm in so many spaces. The message is still suck it up, chin up, get it done. And falling or failing is on you and you alone.


This mindset is deeply problematic as many are pushing back on these approaches to how we use our time and the expectations around how we do work recognizing how culture and many of the systems we work in contribute to burdening our sense of time. 


Boundaries around your time mean disappointing people. So if you are focused on over-delivering and making everyone happy, things can get messy, fast.  


If what matters most means meeting metrics that are set by others, burnout and disillusionment are inevitable.


These dangerous messages have us chasing something we think will give us relief when in fact, we only feel worse when we put this kind of pressure on ourselves 


My guest today has an approach and a philosophy to time and getting things done that has transformed my relationship with work, time, and my calendar.


Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing (2019) and The Small Business Lifecycle (2012), and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon.


Listen to the full episode to hear:


  • Why our problems are with expectations, not time management
  • How we need to shift our relationship to productivity to prioritize values, self-awareness, and compassion
  • How we end up with so much of what Charlie calls project debt, and how to dig ourselves out of it
  • Why we need to stop reinforcing the narrative of the busy party
  • Why leaders need to stop playing the hero or the martyr to their teams


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