Leadership Conversations @ The Kitchen Table

Ep. 93: Paul Conway, Assistant Chief (Ret.) – A Life Full of Mistakes

Host: Berlin Maza
Date: February 23, 2026

Episode Overview

In this powerful kitchen table conversation, retired Milwaukee Assistant Chief Paul J. Conway discusses the lessons of a 40-year career in the fire service. Far from a highlight reel of triumphs, Conway centers the discussion on humility, faith, mistakes, and the importance of living a life anchored in family and purpose. Through heartfelt stories — some painfully raw — Conway and host Berlin Maza (with occasional contributions from Deputy Chief Bill Mack) explore leadership, work-life balance, the costs of work obsession, the necessity of humility, and actionable advice for both emerging and seasoned leaders.

Key Discussion Points & Insights

1. Conway’s Background & Philosophy

• Humble Beginnings and Brokenness
  From the outset, Conway rejects the hero narrative, speaking honestly about mistakes and regrets.

  "First off, I'm a broken man. I'd like to sit here and tell you that I've had all the answers my whole life...but the reality is that isn't the life I lived. I've made a lot of mistakes. I've learned from the most of them, I think." — Conway [03:41]

• Faith and Family as Anchors
  Both are cornerstones Conway returns to repeatedly, crediting his faith with helping him survive personal and professional lows.

  "My family and my faith are intertwined. As I said, I've made all kinds of mistakes…my heavenly father will always say, that's okay, sun's going to come up tomorrow and I forgive you. And through that, my family and everything has really come together.” — Conway [06:32]

• Open Admittance of Past Struggles
  Discusses his brother's suicide, his own unhealthy coping mechanisms, and divorce — all shaping his current philosophy of living in the present and valuing family above work.

2. The Allure and Danger of the "Job First" Mindset

• Work Obsession and Consequences
  Conway is candid about sacrificing family for work — a pattern modeled by preceding generations:

  "I always had this idea, well, you know, [family will] always be there. Well, the reality is that's not true for many of us...We lose our children or we lose...our wives just say, you know what? Peace. I'm out." — Conway [18:49]

• Being Present: "Be Where Your Feet Are"
  The tension of bringing one's whole self to work and also being present at home is a throughline.

  "My ex wife used to tell me all the time, can't you just be where your feet are for a minute?...Now I look at my son who runs my company, and when it's time for him to go home, he goes home and he spends his time with his son and his wife." — Conway [16:12]

3. On Leadership, Influence, and Missed Moments

• Climbing Mountains Without Enjoying the View
  Conway shares a memorable metaphor from a friend about constant goal chasing.

  "You climb mountains...every time you climb a mountain, you get to the top and you see another mountain, and before you even catch your breath, you run down that mountain and you start climbing the next. I've never seen you sit on the peak and enjoy the view." — Conway [27:38]

• Living With Gratitude and Intentionally Slowing Down

  "If we slow down for a minute, when we reach the peak, let's enjoy the view...that we get the opportunity to do it and to be there." — Conway [33:46]

• Balancing Fire Service Impact with Life Balance

  "The fire service is a mistress that will never love you back...you will give her everything...she will turn on you. And then you will spend your time bitter and angry..." — Conway [38:36]

4. The Reality of Legacy and Impact

• Letting Go of Ego & Role Identity

  “When you retire, kid, you will be 52083, no more, no less...Milwaukee Fire Department...has been going on for 150 years...I was only there for 30 of it. And it survived before me and it'll survive...after me.” — Conway [11:45]

• Perspective on Change

  "Time is the only restraint in the American fire service. Nothing happens overnight..." — Conway [41:04]

• Positivity Breeds Change

  “You will find that the changes you want to see...will come faster if your attitude is positive…get rid of the negativity. Because we will fail over and over and over again. But that's how we get better.” — Conway [43:49]

5. Humility, Introspection, and Learning From Mistakes

• Owning Mistakes and the Power of Apology Conway gives a painful account of a major regret: not relieving a paramedic after a tragic scene.

  "You left me in there for hours to stare at those children...if I could take that one back, I'd redo that in a New York second." — Conway [55:54]

• Creating an Environment for Honesty and Growth

  “To be a good leader, you need humility...have the ability to tell people when you're wrong...never stop with introspect and reflecting on you, on what you did, on how you can be better...” — Conway [60:54]

• Learning from Different Perspectives

  "We spend too much time swimming in our own ponds with our own school of fish. We don't look at everyone else." — Conway [65:57]

6. Faith, Mission, and Daily Practice

• Personal Mission Statement

  "I am passionate about positively impacting the world through my actions. I believe that this is achieved by following Christ's teachings and living each day with gratitude, humility, compassion, and love. And through my example, I hope to inspire others to do the same, creating a chain reaction of kindness and positivity that will spread far and wide." — Conway [69:33]

• Value of a Personal Mission Statement

  "I live by it because I'm weak and I have it so I can look at it every single day...I need these inspirations all the time." — Conway [70:38]

• Simplicity and Action Orientation

  "I take what I gave you and I literally turn it down to just, I will be positive today and I will impact the world in a good way." — Conway [73:49]

Notable Quotes & Memorable Moments

• “You have 936 weekends till they're 18 years old. 936. There ain't a lot of time, my friend. The job will always be there, but your kids will be gone.” — Conway [23:30]

• “Be the warrior. Be that guy that will do anything...But when you're home, you're the poet, you're the father...you're the loving dad to your kids. You're not on alert.” — Conway [35:38]

• “Negativity is so much more powerful than positivity ever will be...Don’t let it in your heart. Don’t let it dwell. Don’t give it a place to stay.” — Conway [46:12-47:00]

• “You have to have the courage to risk everything you have for the truth, for something greater than self...if those things, if you do those things, you stay humble...you might do okay, Might do okay, Might do better than okay...you might fall flat on your face like I did, but you might be okay.” — Conway [65:58-69:24]

• “Do good.” — Conway [70:07]

Actionable Takeaways

• Be where your feet are. Practice presence, both at work and at home.
• Balance your value system. Don’t sacrifice the people you love most for an institution that will replace you the next day.
• Express humility and apologize. Leadership comes from admitting mistakes and embracing vulnerability.
• Foster positivity and gratitude. Frame life as “I get to,” not “I have to.”
• Have and review a personal mission statement. Let it guide your actions and help reset your perspective.
• Reflect daily. Regular self-examination leads to better decisions and steadier leadership.
• Seek input from diverse perspectives. Avoid stagnating in your own experience and viewpoint.

Timestamps for Key Segments

• Intro & Conway’s Introduction: [01:08–03:41]
• Discussion on Faith & Family: [06:32–14:23]
• Work Obsession and Presence: [16:12–21:23]
• The Allure of the Job & “Be Where Your Feet Are”: [23:03–27:38]
• Climbing Mountains vs. Enjoying the View: [27:38–35:39]
• Work-Life Impact & “Mistress” Analogy: [38:07–41:04]
• Leadership Change, Time, and Positivity: [41:04–47:08]
• Example of Regret (The Paramedic Story): [55:54]
• Humility and Leadership Advice: [60:54–66:58]
• Father’s Three Rules, Leading Self, Mission Statement: [65:58–73:49]
• Closing Summary & Parting Advice: [78:21–80:17]

Final Thoughts

Paul Conway’s conversation is a masterclass in humility, regret, and wisdom forged in experience. Listeners are reminded that true leadership requires self-knowledge, presence, and connection to something larger than the job. Most importantly: do good — for yourself, your family, your colleagues, and your community.

Recommended Future Guest:
Battalion Chief Ryan McNulty, Milwaukee Fire Department — described by Conway as “one of the most dynamic and humble leaders in the fire service today.” [75:08]

End of Episode