The Self-Leadership Podcast

Anna Tsyupko and Josh Winterson
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  • SELF-IMPROVEMENT
  • UPDATED BIWEEKLY

Lead yourself first, the rest follows. Most people spend their lives reacting to whatever comes next. But what if you could live with intention instead? Join hosts Anna and Josh Winterson as they explore practical self-leadership strategies with fascinating guests who've mastered the art of leading themselves first. Each episode unpacks actionable habits, mindset shifts, and frameworks you can implement immediately to design a life that feels authentic, grounded, and purposeful. New episodes bi-weekly. Produced by JamieEverett.io

Episodes

  1. Why I DELIBERATELY Skip My Morning Routine - Jessy Conflon

    6D AGO

    Why I DELIBERATELY Skip My Morning Routine - Jessy Conflon

    What happens when a startup founder learns that ruthless prioritisation isn't about doing more? Jessy Conflon, co-founder of an AI content quality platform, shares the mindset shift that transformed her from box-ticking employee to intentional leader. Jessy shares her framework for managing competing priorities across business, family, and personal wellbeing. She reveals how calendar blocking became her non-negotiable tool for protecting time with her daughter, why she reflects weekly instead of daily to adjust priorities on the fly, and the surprising freedom she found in making rituals flexible rather than rigid rules. Whether you're drowning in tasks that don't move the needle, struggling to protect personal time from business demands, or simply trying to lead yourself more intentionally, this conversation offers practical advice that you can implement today. Jessy Conflon:https://www.linkedin.com/in/jessy-conflon/ Connect with your hosts:Anna: https://www.linkedin.com/in/atsyupko/Josh: https://www.linkedin.com/in/joshwinterson/ Timestamps:00:00 - Introduction: Self-Leadership Podcast with Jessy Conflon01:55 - Defining Self-Leadership: Intentional Time, Energy and Focus05:21 - The Growth Hacking Analogy: Test, Learn, Adjust, Repeat15:45 - Self-Care Rituals Without the Rigidity Trap24:10 - Making Peace with Imperfect Consistency43:16 - Boundary Management: Blocking Calendar Time Like It's Sacred48:59 - Closing Thoughts: Balance Through Intentional Blocking Keywords:founder time management, self-leadership practices, intentional priority setting, startup work-life balance, calendar blocking strategies, boundary management techniques, employee to founder transition

    50 min
  2. What Burnout Taught Me About Intentional Living - Anna Tsyupko

    JAN 28

    What Burnout Taught Me About Intentional Living - Anna Tsyupko

    Most people live on autopilot, chasing external markers of success without asking if they actually want what they're chasing. Anna Tsyupko's wake-up call came as a severe panic attack that her body used to force what her mind refused to accept. As a fintech startup founder and COO, Anna ignored her coach's burnout warning for eight months. Then the panic attack hit. Even after that, she pushed through for three more years before finally questioning: Am I living my life or someone else's expectations? Now as founder of Expansion Zone Coaching, Anna reveals the five self-leadership tools that transformed her autopilot existence into intentional living. You'll discover why conventional success often leads the most capable people astray, how to recognise burnout signals before your body shuts you down, and practical methods for developing genuine intuition without forcing it. Connect with your hosts:Anna: https://www.linkedin.com/in/atsyupko/Josh: https://www.linkedin.com/in/joshwinterson/ Resources:Positive Intelligence: https://www.amazon.co.uk/dp/B007R0IQ70 Timestamps:00:00 - Introduction & Meet Anna Tsyupko03:28 - Intentional Living Defined: What, Why, and How06:33 - Anna's Wake-Up Call: The 2019 Panic Attack Story10:07 - Analyzing Life Choices: Breaking Down Autopilot16:57 - Tool #1: Saboteurs Framework Deep Dive23:38 - Tool #2: Values as Your North Star40:52 - Tool #3: Wheel of Life Assessment56:58 - Tool #4: Developing Intuition Without Forcing1:08:57 - Tool #5: There's No Coincidence Philosophy1:12:35 - Reframing Failure: The Startup Sale Story1:17:01 - Integration: How All Five Tools Work Together Keywords: self-leadership, intentional living, burnout recovery, life coaching, saboteurs, values clarification, Wheel of Life, intuition development, authentic living, personal growth

    1h 19m
  3. I Quit Annual Goals for 8-Week Sprints - Josh Winterson

    JAN 13

    I Quit Annual Goals for 8-Week Sprints - Josh Winterson

    Most people treat life like a series of reactions to whatever happens next. In this debut episode of the Self-Leadership Podcast, co-host Josh Winterson reveals the five transformative practices that helped him shift from reactive living to intentional life design. As a startup founder, father, and personal development enthusiast, Josh breaks down practical self-leadership habits anyone can implement, from the "you can have anything but not everything" razor to the surprising power of daily walks for mental clarity. You'll discover why periodising your life with 8-week planning cycles beats annual goal setting, how to separate yourself from your thoughts through simple practices, and why reading fiction might be the best professional development you can do. Whether you're an entrepreneur struggling with overwhelm, a professional seeking more intentional living, or someone ready to stop reacting and start leading your own life, these five self-leadership practices offer a proven framework for transformation. Josh candidly shares his journey from materialistic hustle culture to meaningful personal growth, complete with actionable steps you can start implementing today. Timestamps: 0:00 Introduction: What Is Self-Leadership? 1:55 Meet Josh Winterson: Founder, Father & Personal Development Nerd 3:36 Josh's One-Sentence Philosophy: "Living Life by Design" 15:05 Practice #1: You Can Have Anything, But Not Everything 17:14 The Razor Framework: Making Powerful Trade-Off Decisions 23:58 Practice #2: 8-Week Planning Cycles (Life Periodisation) 26:53 Why Annual Goals Fail & How 8-Week Seasons Work 37:05 Practice #3: You Are NOT Your Thoughts 38:41 Separating Identity from Mental Chatter 43:59 Cold Showers & Uncomfortable Practices for Mental Strength 48:30 Practice #4: Reading: Fiction as Personal Development 50:24 The Alchemist, Harry Potter & Why Stories Transform Us 56:07 Practice #5: Walking for Mental Clarity & Meditation 59:09 Bringing Meditation Into Daily Walks (No Mountains Required) 1:03:11 David Allen's Brain Dump: 90+ Thoughts in 30 Minutes 1:04:24 Recap: 5 Self-Leadership Practices Summarised 1:05:52 Final Thoughts: This Is a Practice, Not Perfection Keywords: self-leadership, intentional living, personal development practices, life by design, goal setting strategies, mindfulness habits, productivity tips, leadership development, daily routines for success

    1h 6m
  • 3 Episodes

About

Lead yourself first, the rest follows. Most people spend their lives reacting to whatever comes next. But what if you could live with intention instead? Join hosts Anna and Josh Winterson as they explore practical self-leadership strategies with fascinating guests who've mastered the art of leading themselves first. Each episode unpacks actionable habits, mindset shifts, and frameworks you can implement immediately to design a life that feels authentic, grounded, and purposeful. New episodes bi-weekly. Produced by JamieEverett.io

Information

  • Creator
    Anna Tsyupko and Josh Winterson
  • Years Active
    2K
  • Episodes
    3
  • Rating
    Clean
  • Copyright
    © Anna Tsyupko and Josh Winterson
  • Show Website
    The Self-Leadership Podcast