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.

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.

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-three
• How a job title can become an identity, and what remains when it is taken away
• The grocery-store experience that pushed David to rethink who he was and what came next
• Why he stayed in a role he had outgrown, even when he knew it was time for a change
• What two failed businesses taught him about building his next one
• The difference between earning a good income and building lasting financial security
• The thinking behind The One-Page Wealth Compass, and his search for a simpler approach to money
• How financial independence changed his relationship with work, choice, and stress
• Why he sees this stage of life as an opportunity for a new adventure
• Redefining importance through family, contribution, and helping other people
• Why 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.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.

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 do
• The difference between being busy and being aligned, and how much of a full week is really just motion
• Busyness as a shield, and the hardest question it keeps you from having to sit with
• Intentional rest versus numbing, and why choosing to stop on purpose takes real courage
• What 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 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.

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 everything
• The difference between being a witness and being a fixer, and why people often just need to be heard
• How the urge to give advice can come from insecurity rather than confidence
• Why our feeds, our culture, and even our institutions are built to keep us overwhelmed and reactive
• Practical ways to notice the default toward negativity and gently choose something else
• What it is like to be a queer pastor in one of the most conservative cities in the country
• Internalized homophobia, how it shows up, and why we don't talk about it enough
• Reclaiming language and faith that were once used to cause harm
• Where 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.com
• Her free progressive worship music → queersacredmusic.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.

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 ones
• How ending a long relationship, leaving home, and changing careers all unfolded in a single year
• What it means to finally say yes to a change you have avoided for years
• How a lifelong eating disorder kept hard emotions at bay, and what surfaced when she could no longer numb them
• Codependency in both a marriage and a career, and the boundaries that made a healthier life possible
• The 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 yourself
• Choosing progressive Christianity as a form of resistance, and stepping into ministry in a deeply conservative city
• How 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.com
• Her free progressive worship music → queersacredmusic.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.

There's something you want to do. You've thought about it for months, maybe years. You've imagined it, researched it, talked around it with friends who told you to go for it. And still, you haven't started. If someone asked you why, you'd have a list of good, practical reasons. But underneath all of them is a simpler one you probably haven't said out loud: you're waiting for permission.

This short solo episode sits with that quiet truth. Nobody hands out permission slips for career changes, creative projects, or hard conversations, and the signal you keep waiting for is never going to come, because that is not how permission works. The people who love you can tell you they're proud, that they support you, that you're ready, and it helps, but you still go home and don't start. The permission gap was never between you and them. It's between you and yourself.

In this episode, I explore:

• Why "the timing isn't right" and "I need to learn more first" are often permission-seeking in disguise
• Where the habit of looking up for approval begins, and why it outlives the childhood that taught it
• The difference between managing, waiting for the green light, and leading, giving it to yourself
• Why no one in any hierarchy is going to authorize the choices that matter most to you
• What it looks like to grant yourself permission, quietly and without apology, and start now

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.

At fifty-something, Gila Melamed gave away ninety-eight percent of what she owned, converted first a small car and then a minivan into a home, and drove off to live nomadically in the wild she had always felt she belonged to. She does not call it an escape. She calls it an experiment in alignment.

The road was the last step in a much longer story. Years earlier, at her lowest point, Gila survived a moment that nearly ended her life. A single sentence from her therapist, that a decision made seventeen years ago could be remade, gave her back her breath. She asked for a divorce that same day, and slowly began the years-long work of coming back to herself.

Underneath it all was a childhood shaped by an abusive father, a loneliness she carried for decades, and the belief that her sensitivity was something wrong with her. Through her own healing, she came to understand it as her greatest strength. On a hot morning in Yosemite, off the trail and drawn toward the view like a magnet, she had the realization that anchors her life now: she had been on the right path all along.

Gila is a former home and color designer turned nomad, writer, and self-published author of three books who documents her journey on Substack. She lives simply, works seasonally to fund her travels, and treats fear not as something to eliminate but as a dance partner she walks with every single day.

This is a conversation about surrender, learning to trust yourself after a lifetime of other people's voices, the difference between fear and intuition, breaking generational patterns, and what becomes possible when you stop waiting and finally give yourself the life your heart has been asking for.

In this episode, we explore:

• Leaving a conventional life to live on the road, not as an escape but as an experiment in alignment
• The turning point that gave her back her life, and the single sentence that changed everything
• Coming home to yourself after decades of living by other people's voices
• Why she came to see her sensitivity as a strength rather than a flaw
• Breaking generational trauma, and choosing to parent differently than she was raised
• The realization in Yosemite that she had been on the right path all along
• Fear as a dance partner, and how to tell the difference between fear and intuition
• Surrender, uncertainty, and finding aliveness in not having a plan
• How solitude in nature became a mirror and a teacher
• The quiet ceremony of a slow morning, and presence as a daily practice
• Writing as a way to process, and letting a loud inner voice lead her to finally share her story

If you or someone you know is struggling, the 988 Suicide and Crisis Lifeline is available 24/7 in the US. Call or text 988.

Resources & Links:

• Connect with Gila, find her three books, and follow her blog → gilacolorguru.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.