Andy Crissinger: The Art of Asking Better Questions

Since the very first episode, Good Work has been about exploring why our work matters and how it helps us become the people and leaders we’re meant to be. Normally, I interview world-class guests, diving deep into their unique stories and insights. But today, I’m sharing my own experiences, lessons, and reflections. I’ve gathered questions from you, my listeners, as well as past guests, covering a wide range of topics: business advice, lessons learned from podcasting, life philosophy, and how I approach my own work. This episode is a chance to connect on a different level as I reflect on the year and answer your questions. I hope it brings value and inspiration as we wrap up the year together. Let’s get to it! In this episode: (00:00) - Intro (02:44) - What's the number one process business owners need to have to stay happy and engaged?  (05:14) - What are the biggest tactical challenges that $1m+ creator/founders struggle with? (14:05) - What are the common threads in the life ambitions or mentality of the people you've had on the podcast? (27:25) - How have you changed, matured, or grown as a result of something you've learned from a guest on Good Work? (31:22) - What have you learned about podcasting that you didn't know or didn't expect when you started? (39:14) - Has podcasting changed anything about your views on the impact and importance of various forms of media in society at large? (44:16) - Of all the people you talked to, for whom did your respect increase the most after all the research and conversation, and why? (47:44) - What's up with the podcast artwork? And is there any meaning behind the studio design? (56:50) - What is your definition of "enough"? (01:04:04) - What are some challenges you're proud of solving, and how did you solve them?  (01:13:21) - Over the last 10 years, what's become more important to you, and what's become less important? Does his weekly calendar match the answer? (01:16:14) - What are you avoiding just because it will take longer than you'd like? (01:17:09) - What was most surprising about 2024, and how are you feeling about 2025? (01:19:07) - is there anything you've learned in your life that you wish you didn't know? (01:22:23) - What six-month period of your life was the most energizing and fun, and what can you learn from the answer? (01:32:26) - How do you manage your day and your week? (01:38:27) - What would young Barrett think of the work you're doing today? (01:44:43) - If you were the teacher for your kids and a few other local kids, what's one class or curriculum you'd love to teach them and why? (01:48:08) - Why are garbage trucks stinky? And what makes buses awesome? (01:49:56) - Final thoughts Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Ruthie Ackerman—a talented author, journalist, and writing teacher who has turned her own journey into a blueprint for helping others find their voice. Ruthie’s work has appeared in The New York Times, Modern Love, and many other renowned outlets, but her true passion lies in empowering others to discover and write their own stories. Through her workshops, one-on-one coaching, and book incubators, Ruthie helps writers connect with their experiences, heal from the past, and find deeper meaning in their lives. We explore Ruthie’s journey—from traveling the world in her 20s, to pivoting into journalism, to teaching creative nonfiction and memoir to students around the globe. We also dive into the deeply personal moments that shaped her path, including her journey to motherhood. Ruthie’s insights on storytelling, healing, and personal growth are inspiring, and I hope our conversation encourages you to reflect on your own story and its potential to create meaning and connection. Let’s get to it! In this episode: (00:00) - Intro (02:48) - How Ruthie ended up in Malawi (10:31) - The path to journalism (13:19) - Brooklyn dreams (18:38) - Reporting from Liberia and Lebanon (28:18) - The Forbes experience (32:05) - Starting Write Your Life (36:12) - How Ruthie teaches writing (47:51) - The importance of memoir (53:25) - Balancing personal and professional life (01:03:55) - The journey to motherhood (01:09:28) - Dealing with changing desires  (01:16:14) - Understanding self-silencing and emotional repression (01:24:02) - The reality of fertility treatments (01:28:24) - Dating after divorce (01:33:17) - Finding love and facing heartbreak (01:44:19) - Meeting Rob (01:48:37) - Reflections on the journey and personal growth (01:52:06) - Ruthie's most beautiful future (01:55:09) - Who Ruthie is becoming Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Andy Crissinger, a world-class coach and master facilitator who has guided leaders at some of the world’s most renowned startups and companies. Andy’s journey to coaching is remarkable, weaving through ministry, startup leadership, and eventually finding his calling as a coach. In the first half of our conversation, we explore his personal story, which is deeply relatable and filled with lessons about growth and resilience. In the second half, we dive into a coaching curriculum built around five transformative books, offering practical insights for personal and professional development. These resources can help you grow into the leader, partner, and parent you aspire to be. I loved this conversation with Andy about finding purpose, building trust, and achieving meaningful growth, and I think you will too. Let’s get to it! In this episode: (00:00) - Intro (00:05) - Who is Leonard? (03:25) - What music represents for Andy (07:28) - Family, integrity, and sense-making (14:15) - Andy's transition to ministry (17:09) - What Andy learned about community through ministry (23:13) - Coaching vs teaching (30:20) - The journey through infertility (39:16) - How impact and joy of fatherhood (43:15) - Transitioning to coaching (48:00) - Founding Worksong (01:00:23) - Humble Inquiry by Edgar Schein (01:13:11) - Inherited Family Trauma (01:19:42) - Andy's beautiful future (01:22:18) - Who And is becoming (01:24:19) - Trees by Howard Nemerov Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Patrick McKenzie, better known online as “patio11.” Patrick has built an impressive career by sharing his insights publicly, with more than three million words published to date. From his years at Stripe to his current sabbatical, Patrick’s journey proves that the “traditional path” is not always the best one. We explore how his love for systems thinking and complex problem-solving has shaped his career. He shares candidly about his 20 years in Japan, navigating work-life balance, his evolving thoughts on autonomy, and how writing has opened doors to unexpected opportunities. Known for his deep dives into topics you didn’t realize you cared about, Patrick brings fresh perspectives on tech, culture, and finding meaning in work. Let’s get to it! In this episode: (00:00) - Intro (03:10) - Why gaming is underrated for learning real-world skills (06:21) - Why do thieves steal soap? (08:54) - Following intellectual curiosity (13:18) - Call centers and organizational systems (22:39) - Lessons from 20 years in Japan (28:30) - The salaryman (37:08) - Patrick's transition to entrepreneurial ventures (39:09) - How to know what to keep and what to change (42:14) - Dealing with career uncertainty (52:08) - Professionals vs amateurs (57:14) - Lessons from Stockfighter (01:01:07) - Stripe and stepping into the void (01:21:50) - The impact of writing and sharing knowledge (01:26:30) - The relationship between community and impact Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Tim Grahl, CEO of Story Grid and author of The Shithead, a novel that’s both thrilling and deeply personal. Tim made a name for himself as a book marketer who landed multiple titles on the New York Times  Bestseller list at the same time. Tim’s work with Story Grid, alongside his partner Shawn Coyne, has guided hundreds of aspiring authors in mastering the essential elements of storytelling, helping them transform “I hope I can write a book someday” into a published reality. We cover a range of topics, from Tim’s journey as a book marketer to his insights on the power of structure in storytelling. We also dive into his personal experiences, including the impact of therapy on his growth as both a person and a professional. Tim’s work ethic and passion for meaningful storytelling are infectious, and I think you’ll find our conversation both inspiring and thought-provoking. Let’s get to it! In this episode: (00:00) - Intro (05:06) - Tim's perfect vacation (11:54) - Doing work that people don't understand (15:19) - The "secret" to Tim's success (20:34) - The moment Tim knew his business was broken (31:06) - What is an object of desire? (34:10) - The problem with online courses (and how to fix it) (01:03:47) - Behind the scenes of writing a meaningful book (01:13:37) - Success and the half warm beer theory (01:18:03) - Reflecting on regret (01:24:28) - How therapy changed everything (01:32:58) - Chasing insight vs integration (01:38:19) - Tim's beautiful future (01:42:47) - Who Tim is becoming Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with my friend Mo Bunnell, founder of GrowBIG and the Bunnell Idea Group, which offers one of the most in-depth, relationship-driven trainings on sales and business development. Mo is the author of Give to Grow, a book I recommend to anyone interested in learning business development with a values-centered approach. We start by diving into Mo’s personal life, his deep commitment to family, and the strength of his marriage. In the second half, Mo shares his unique business development framework, applying it to my business in ways that make it practical and actionable. Mo’s insights reveal how success, when rooted in genuine connection, transforms careers and lives. I hope you enjoy this conversation with one of the kindest, most relationship-driven people I know. Let’s get to it! In this episode: (00:00) - Intro (03:32) - How Mo ended up tied to a donkey in the Colorado mountains (09:22) - Reflecting on 32 years of marriage (12:41) - The power of writing down goals (16:13) - Case study: Pursuing a dream home (24:45) - Parenting and the importance of family rituals (34:59) - Celebrating achievements and friendships (37:21) - The role of community and friendship (39:26) - Building a sense of belonging (40:00) - The Breckenridge and Mashup experience (41:01) - Creating and hosting events (49:28) - Writing, publishing, and becoming an author (01:03:35) - Applying the Give to Grow framework (01:11:52) - The five lies we tell ourselves (01:14:31) - Overcoming the lies and setting goals (01:19:35) - Designing a buy-in process (01:22:14) - Identifying and engaging with clients (01:24:49) - The power of specialization (01:30:37) - Creating scalable systems (01:38:37) - Mo's beautiful future (01:40:23) - Who Mo is becoming Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Dr. Erika Siegel, a naturopathic doctor with nearly 20 years of experience. I discovered her work through a recommendation from my doctor and was immediately drawn to her two-volume book set, The Nourish Me Kitchen, which combines essential health wisdom with practical recipes. As a coach, I see many entrepreneurs burning out due to the immense physical and mental demands of their work. In our conversation, Erika shares her journey and insights on how to maintain wellness as an entrepreneur. We explore how to sustain your health, just like a professional athlete, to keep performing at your best. If you’re looking for practical tips on managing stress, taking care of your body, and making an impact without sacrificing your well-being, this episode is for you. Let’s get to it! In this episode: (00:00) - Intro (04:45) - Erika's 40-mile hike  (08:46) - Why mental preparation is key (11:02) - The Importance of Honest Communication (15:56) - Erika's Journey into Medicine (22:02) - Choosing a Path in Naturopathic Medicine (27:05) - The Evolution of Functional Medicine (33:40) - Life in Portland and Embracing Nature (44:02) - Nature's Healing Power (52:03) - Parenting with Intention  (01:03:47) - Healthy expressions of emotion (01:15:19) - Holistic Health Strategies (01:24:35) - How psychology impacts biology  (01:29:41) - Starting points for managing stress (01:35:52) - How to kick bad habits (01:40:55) - Detoxifying in a Modern World  (01:55:58) - Erika's beautiful future (01:56:52) - Who Erika is becoming Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with my friend Kevin Lavelle, founder of Mizzen+Main, a company that revolutionized the dress shirt industry. We talk about how Kevin built Mizzen+Main into a successful brand, and why he ultimately decided to step back and bring in a CEO. We dive into Kevin’s early career in management consulting and the journey to his prior role at Stand Together, a nonprofit backed by Charles Koch, including how he navigated the challenges and opportunities that came with that. We also explore Kevin’s new venture, Harbor, and the lessons he’s learned as a second-time founder. Kevin has a lot of insight into what it takes to be a successful entrepreneur and how to become the kind of leader capable of building deeply meaningful companies where people love going to work. Let’s get to it! In this episode: (00:00) - Intro (04:20) - A Valentine’s Day story (07:10) - Kevin’s early career and experiences in the Middle East (22:01) - Global Shapers and Stand Together (32:13) - Complexities of societal issues and solutions (36:00) - The importance of nuanced conversations (39:10) - Building bridges across political divides (45:52) - The power of personal engagement in business (50:30) - What Kevin is doing differently as a second-time founder (01:01:45) - The art of storytelling in business (01:09:23) - Marketing and educational content at Harbor (01:12:34) - Innovating baby monitors (01:22:58) - Competitive positioning and market strategy (01:31:34) - Kevin’s beautiful future Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Brie Wolfson, someone whose reputation precedes her. She’s the kind of person people rave about getting to work with. Brie was instrumental in bringing Stripe Press to life, partnering with John Collison and the Stripe team to build something truly special. After her time at Stripe, she moved to Figma before eventually facing burnout and needing a break. Brie has been open about her journey through depression, which we dive into during our conversation. Brie recently joined Colossus (founded by Patrick O’Shaughnessy) as Chief Marketing Officer. She also runs a consultancy called The Kool-Aid Factory (a truly brilliant name, I think), helping startups shape their company culture. Brie is empathetic, thoughtful, and relatable—traits that shine throughout this conversation. Let's get to it! In this episode: (00:00) - Intro (03:52) - Writing to one person: techniques and inspirations (06:57) - The role of writing in personal identity (09:59) - Navigating the AI landscape (12:21) - Turning down the noise: digital detox (17:03) - Paul Graham’s ‘Founder Mode’ essay (26:48) - The importance of taste and curation (35:06) - Brie’s creative explosion in 2022 (37:12) - The writing process & self-editing (40:19) - Is the nature of writing online changing? (44:34) - Career docs and personal achievements (54:26) - Brie’s essay on depression (56:51) - Navigating depression and loneliness (01:01:19) - The power of self-soothing (01:07:59) - The importance of setting boundaries (01:09:13) - On trusting others (01:12:03) - The impact of athletics (01:18:51) - Identity loss after sports (01:22:17) - On leaving Stripe (01:24:33) - Optimizing for good vibes (01:26:55) - Communicating your value (01:30:46) - What’s next for Brie? (01:34:51) - Brie’s beautiful future (01:39:38) - Who Brie is becoming Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I sit down with Nat West, founder and former CEO of Reverend Nat’s Hard Cider, a pioneering craft cider company in Portland, Oregon. Over 12 years, Nat helped shape the city’s thriving cider scene before making the bold decision to close his business, despite its post-pandemic stability. Seeking a change, Nat spent six months driving a public city bus—a dream he’d always had—and rediscovered his love for Portland, a city (my city) often misunderstood in national media. Inspired by this experience, a friend encouraged him to run for city council during a pivotal moment of governmental restructuring in Portland. Though we don’t always agree on the solutions, I admire Nat’s passion for public service and his unique entrepreneurial perspective. In this conversation, we explore what motivates someone to shift from business to public service and what it’s like to be on the cusp of a new political journey. Let’s get to it.  In this episode: (00:00) - Intro (06:02) - The art and science of cider-making (11:51) - Growing the business vs enjoying the craft (14:20) - On the importance of marketing (20:34) - Challenges and changes during the pandemic (32:25) - The moment Nat realized it was time to move on (36:40) - Nat’s approach to building culture in his team (49:17) - Moving on from a business (54:47) - Seeing the city as a bus driver (01:08:02) - Running for city council (01:15:21) - Defining the role of a city councilor (01:19:02) - Nat’s collaborative approach to politics (01:22:49) - Challenges and opportunities for small businesses (01:25:36) - A vision for Portland’s future (01:39:56) - Nat’s beautiful future (01:43:14) - Who Nat is becoming Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.