Think Outside the Lines

Shawn Feeney

The old scripts for how to live, work, and belong are breaking down. Think Outside the Lines is a podcast for anyone ready to stop checking boxes, step off autopilot, and start living with intention. Host Shawn Feeney spent over a decade leading teams at Apple, Microsoft, and high-pressure tech startups before dedicating his work to helping others live more intentionally. The show explores what happens when we choose to build the life we want rather than accepting the one we were handed.

  1. 3d ago

    Nathan Conradie: What If Staying Costs You More Than Leaving?

    Nathan Conradie was at a friend’s wedding in a beautiful castle in England when he noticed something he couldn’t ignore. He was surrounded by a moment worth celebrating, but he felt empty. A career that looked right from the outside had started affecting his ability to enjoy the rest of his life. A paramedic and university educator, Nathan had never imagined becoming an entrepreneur. He loved teaching and had followed a path that offered stability and respect. But an idea from a research project gave him something new to pursue, and over time, he began putting the pieces in place to build a business of his own. In this conversation, Nathan shares what that transition actually required: investing his savings, building alongside his university role, learning unfamiliar skills, and facing a level of stress he hadn’t anticipated. We talk about the financial and emotional realities of relying on a partner, why support needs an ongoing conversation, and the uncertainty that remains even when you’ve planned carefully. We also explore how losing close friends changed his relationship with time, and how becoming a father has brought a new question into focus: is he living a life he would want his son to see? This is an honest conversation about purpose, partnership, and weighing the discomfort of change against the cost of staying where you are. In this episode, we explore: The quiet moment at a wedding that helped Nathan recognize something needed to change How dissatisfaction with work can spill into the parts of life you care about most Becoming an entrepreneur because of an idea, without having always dreamed of owning a business What his gradual transition from academia to a tech startup looked like The difference between understanding a risk and experiencing it Financial pressure, disrupted sleep, and the strain uncertainty can place on a relationship Why conversations about a partner’s support need to evolve as circumstances change How grief influenced his priorities and his decision to pursue triathlon What new fatherhood is teaching him about the life he wants to model Asking for help, learning from experienced people, and making room for life beyond work Resources & Links: Explore Nathan’s business, Proficien → proficien.com Listen to his podcast, Bedsides & Boardrooms, exploring the intersection of medicine and business → bedsidesandboardrooms.com Ready to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearly Explore 1:1 coaching and other resources at thinkoutsidethelines.com Follow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don’t miss what’s coming next.

  2. Oct 30

    What To Do When Old Patterns Resurface

    You were choosing differently. Trusting yourself more. Feeling the change. Then the people-pleasing, the overthinking, or the need for someone else’s approval showed up again, and suddenly it felt like all that work had disappeared. When old patterns return, it’s easy to turn a difficult day into a verdict on your progress. To assume you’re back at the beginning, or that the change wasn’t real in the first place. In this short solo episode, I explore what it means to recognize a familiar pattern without letting it define you. We look at the pull of old habits when life gets demanding, the self-judgment that can follow, and why noticing yourself slipping is a meaningful part of learning to choose differently. This is an invitation to meet yourself with a little more patience. To name what’s happening, remember what you’ve learned, and make one small choice from where you are today. In this episode, I explore: Why a return to familiar habits can feel like losing all the progress you’ve made How stress, fatigue, and overwhelm can make intentional choices harder The difference between experiencing an old pattern and letting it define who you are Why noticing people-pleasing, overthinking, or approval-seeking matters, even when it takes time Meeting a setback with curiosity instead of turning it into a reason to judge yourself What it looks like to notice, name, and choose again in everyday life Resources & Links: Ready to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearly Explore 1:1 coaching and other resources at thinkoutsidethelines.com Follow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don’t miss what’s coming next.

  3. Oct 23

    Tanna Brodbar: When Is It Finally Enough?

    My guest today asked herself a question a lot of us are afraid to ask: was she building a life that was truly hers, or one designed to prove she had overcome her past? She grew up below the poverty line, in a home without running water and shaped by instability, and she put herself through school as a single parent. On top of that, she built a career of more than twenty-five years in the financial industry, leading strategy for multinational corporations, global risk management teams, and large-scale technology programs. She holds an MBA in Leadership and a Master of Arts in Humanities, holds numerous coaching accreditations, teaches leadership and risk management at two universities, and is completing her training as a Student Therapist in supervision through the Ontario Psychotherapy and Counselling College. Today she is the founder of Percepta Leadership, which provides psychotherapy for leaders and executives, and the Center for Applied Psychodynamics, which provides specialized coach training. She left the corner office to help other high achievers understand what is really driving them. Join me as we think outside the lines with Tanna Brodbar. In this episode, we explore: Achievement as a survival strategy, and the shame that can quietly power a whole career The difference between "it's not enough" and "I'm not enough," and why success can't fix the second one Growing up below the poverty line and building an executive life on top of it The moment she realized she was genuinely good, that she had enough Why most people don't lack ambition, they lack support and self-permission The one mentor who treated her like a human being, and the difference it made Leadership versus management: people as human beings, not human capital How the pandemic cracked open bigger ques tions about the human cost of success Severance as an uncomfortably familiar picture of leaving your whole self at the office door Building an internalized sense of security that no title, salary, or status can take away Retraining as a psychotherapist mid-career, and letting two worlds collide Resources & Links: Connect with Tanna and learn more about her work → perceptaleadership.com and centerforappliedpsychodynamics.com Ready to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearly Explore 1:1 coaching and other resources at thinkoutsidethelines.com Follow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don't miss what's coming next.

  4. Oct 16

    What If the Messy Middle Is Exactly Where You're Supposed to Be?

    You’ve left something that no longer fit, but what comes next hasn’t taken shape. The clarity you hoped for hasn’t arrived. There’s no clear plan. And some mornings, you wonder whether making a change was a massive mistake. We hear plenty of stories about the before and the after. The life that felt wrong, followed by the freedom of finding something better. But the space between those chapters can feel lonely, confusing, and difficult to explain while you’re living it. In this short solo episode, I explore the messy middle of change: the uncertainty of outgrowing an old identity before a new one feels familiar, the pressure to figure everything out, and what it means to lead yourself through a transition you can’t neatly plan. This is an invitation to give yourself room to be in between. To notice what’s emerging without demanding an immediate answer. And to consider whether the part you’re trying to rush through might have something important to teach you. In this episode, I explore: Why the middle of a transition can feel more like free fall than growth The discomfort of no longer being who you were, while still discovering who you’re becoming How the pressure to have a plan can make uncertainty feel like personal failure The difference between managing yourself toward an answer and leading yourself through the unknown Making space to listen for what comes next instead of rushing to fill the gap Giving yourself permission to move at a pace that allows something meaningful to take shape Resources & Links: Ready to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearly Explore 1:1 coaching and other resources at thinkoutsidethelines.com Follow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don’t miss what’s coming next.

  5. Oct 9

    David Nassief: What Happens When the Script Stops Working?

    After eighteen years with the same company, David Nassief walked to his car carrying a cardboard box. Inside was a crayon drawing from his son with the words, “My dad, an important man.” At sixty-three, newly fired and worried about how he would support his family, David felt anything but important. What followed forced him to rethink more than his career. He had to confront how much of his identity belonged to a job title, how fear had kept him in a role he had outgrown, and why decades of earning good money had left him without the security he thought he was building. In this conversation, David shares the ordinary grocery-store moment that became a turning point, the lessons he carried forward from two failed businesses, and the experience of starting again when the world seemed to expect him to wind down. We also explore the difference between earning money and building wealth, the relationship between simplicity and peace, and the thinking behind his book, The One-Page Wealth Compass. At the heart of it all is a different definition of an important life: showing up for your family, contributing to others, and knowing who you are even when the title disappears. For anyone facing an unexpected ending or wondering whether it is too late to choose a different direction, this conversation offers an honest look at fear, identity, and finding a next chapter you want to live. In this episode, we explore: The parking-lot moment after eighteen years with one company, and the fear of starting over at sixty-threeHow a job title can become an identity, and what remains when it is taken awayThe grocery-store experience that pushed David to rethink who he was and what came nextWhy he stayed in a role he had outgrown, even when he knew it was time for a changeWhat two failed businesses taught him about building his next oneThe difference between earning a good income and building lasting financial securityThe thinking behind The One-Page Wealth Compass, and his search for a simpler approach to moneyHow financial independence changed his relationship with work, choice, and stressWhy he sees this stage of life as an opportunity for a new adventureRedefining importance through family, contribution, and helping other peopleWhy clear direction can matter more than moving faster Resources & Links: Connect with David, learn about his book, and sign up for the free One-Page Wealth Compass PDF → onepagewealthcompass.comReady to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearlyExplore 1:1 coaching and other resources at thinkoutsidethelines.comFollow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don't miss what's coming next.

  6. Oct 2

    What If Doing Less Isn't Lazy—But Intentional?

    Let me guess. You feel like you're not doing enough. Even right now, there's a background loop in your head saying you should be doing more, be further along, be more productive. And it doesn't matter how much you actually get done, the feeling stays. Because it was never really about the work. It's about a belief: that your worth is tied to your output. This short solo episode takes that belief apart. Hustle culture didn't just tell you to work hard, it told you that working hard is who you are, until slowing down started to feel like falling behind. But doing more of the wrong things doesn't make you successful, it just makes you tired. There is a real difference between being busy and being aligned, and busyness is often the socially acceptable way to avoid asking whether any of this is what you actually want to be doing. In this episode, we explore: The belief that your worth is tied to your output, where it came from, and why the feeling never quiets no matter how much you doThe difference between being busy and being aligned, and how much of a full week is really just motionBusyness as a shield, and the hardest question it keeps you from having to sit withIntentional rest versus numbing, and why choosing to stop on purpose takes real courageWhat opens up when you do less of the wrong things, and why you are not your output Resources & Links: Ready to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearlyExplore 1:1 coaching and other resources at thinkoutsidethelines.comFollow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don't miss what's coming next.

  7. Sep 25

    Amanda Udis-Kessler (Pt 2): What If You Traded Control for Presence?

    When Amanda Udis-Kessler came back for a second conversation, the ground had shifted again. In Part 1, she told the story of rebuilding her entire life at sixty. This time she goes inward, to the harder, quieter work of showing up as her whole self once the external obstacles are gone. What she keeps hearing, in her job, her friendships, and her own healing, is a single instruction: trade control for presence. After sixty years of managing life's challenges by trying to control everything, she is learning to simply be there, to listen more than she speaks, and to trust that presence alone can meet the needs of a moment. She calls the old habit the conscientious cartographer. The new practice is being a steady witness. Amanda is a queer pastor leading a progressive Christian congregation in Colorado Springs, which she calls the Evangelical Vatican of the United States. From that vantage point, the conversation opens out into attention and overwhelm in a culture built to keep us reactive, what it means to witness someone rather than fix them, and the internalized homophobia many of us absorbed without ever choosing it. This is a conversation about presence over control, listening over solving, and finding creativity and hope in a loud, fast, divided moment. In this episode, we explore: What it means to trade control for presence, and why that is so hard after a lifetime of managing everythingThe difference between being a witness and being a fixer, and why people often just need to be heardHow the urge to give advice can come from insecurity rather than confidenceWhy our feeds, our culture, and even our institutions are built to keep us overwhelmed and reactivePractical ways to notice the default toward negativity and gently choose something elseWhat it is like to be a queer pastor in one of the most conservative cities in the countryInternalized homophobia, how it shows up, and why we don't talk about it enoughReclaiming language and faith that were once used to cause harmWhere Amanda finds hope, and why her creativity feels like evidence of something bigger than herself Resources & Links: Connect with Amanda, her books, music, and work → amandaudiskessler.comHer free progressive worship music → queersacredmusic.comReady to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearlyExplore 1:1 coaching and other resources at thinkoutsidethelines.comFollow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don't miss what's coming next.

  8. Sep 18

    Amanda Udis-Kessler (Pt 1): What If the Wake-Up Call Isn't One Big Moment?

    At sixty, in the span of a single year, Amanda Udis-Kessler ended a thirty-year relationship, left the home she shared, walked away from a two-decade career in higher education, and became the pastor of a small church. From the outside it can look like one dramatic reinvention. Up close, it was anything but. There was no single lightning-bolt moment. There was a cancer diagnosis that reminded her she would not live forever. There was a health crisis that interrupted a lifelong eating disorder and, for the first time, left her unable to numb what she was feeling. There was a quiet, years-long knowing that something was off, and a marriage she could not bring herself to leave until her partner found the courage to ask the question first. Amanda is a writer, a musician, and now a pastor in Colorado Springs, a city she calls the Evangelical Vatican of the United States. In this first of two conversations, she traces how all of these threads came together, and what it took to finally say yes to a life that fit. This is a conversation about the slow, stumbling nature of real change, the difference between numbing a feeling and facing it, codependency and the boundaries that finally set her free, and why creating the life you want is rarely one big leap and more often a series of small, brave gates you walk through one at a time. In this episode, we explore: Why a wake-up call is rarely one dramatic moment, and more often a slow stumble through many smaller onesHow ending a long relationship, leaving home, and changing careers all unfolded in a single yearWhat it means to finally say yes to a change you have avoided for yearsHow a lifelong eating disorder kept hard emotions at bay, and what surfaced when she could no longer numb themCodependency in both a marriage and a career, and the boundaries that made a healthier life possibleThe boundary described as "the distance at which I can love both you and myself"Why you cannot change another person, only model change through the work you do on yourselfChoosing progressive Christianity as a form of resistance, and stepping into ministry in a deeply conservative cityHow to sit with a discomfort you can't yet name, and gently ask it what it is about Resources & Links: Connect with Amanda, her books, music, and work → amandaudiskessler.comHer free progressive worship music → queersacredmusic.comReady to step off autopilot? Visit thinkoutsidethelines.com to access free worksheets designed to help you cut through the noise, ask the right questions, and finally hear yourself clearlyExplore 1:1 coaching and other resources at thinkoutsidethelines.comFollow along on all platforms → @thinkoutsidethelines Enjoyed the episode? Please share it with someone who might need to hear it, and subscribe so you don't miss what's coming next.

5
out of 5
29 Ratings

About

The old scripts for how to live, work, and belong are breaking down. Think Outside the Lines is a podcast for anyone ready to stop checking boxes, step off autopilot, and start living with intention. Host Shawn Feeney spent over a decade leading teams at Apple, Microsoft, and high-pressure tech startups before dedicating his work to helping others live more intentionally. The show explores what happens when we choose to build the life we want rather than accepting the one we were handed.

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