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Underneath The Title: When High Achievers Start Questioning the Success They Built

Underneath The Title: When High Achievers Start Questioning the Success They Built

Hosted by Kevin Simcock

Episodes

44

Latest episode

Jun 2026

Language

EN-US

About the show

You did everything right. Built the career. Earned the title. Hit the number. And somewhere along the way, you stopped recognizing the person doing it. Underneath The Title is a podcast for executives and senior leaders who have experienced a significant exit and are starting to ask the questions they've been too busy to ask: Who am I when the role goes away? What was I actually building toward? Is this it? Host Kevin Simcock spent 25 years leading creative work for some of the world's most recognized brands at global ad agencies like Y&R, Havas and Ogilvy. He was furloughed from a global VP role at 50, turned down the replacement offer, and chose to figure out what success actually meant to him. What he found changed everything. Each episode goes beneath the surface of professional identity to explore what drives the decisions we make, the success we chase, and the fulfilment we keep expecting to arrive. Kevin draws on his own experience, his work with senior leaders and business owners navigating major transitions, and his framework, The Dance, which holds that your professional and personal identity were never meant to be separate. If you're in the middle of a transition, questioning what comes next, or simply wondering why the success you've built feels quieter than you expected, this show was made for you. New episodes bi-weekly. Subscribe wherever you listen to podcasts. Kevin is also the author of Whose Ladder Is This? and an executive advisor working one-to-one with high-achievers navigating identity and transition. Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback and hardcover HERE Barnes & Noble here Indigo Books here Visit kevinsimcock.com for more information LinkedIn Profile https://www.linkedin.com/in/kevin-simcock/

Listen to episodes

44 recent
June 11, 2026Episode 714 min

How to Choose Your Next Chapter

Most people design their next chapter using the identity that built the last one. That's exactly why it doesn't fit.In this episode, Kevin unpacks why defaulting to your past self when planning what's next leads so many high-achievers back to the same feeling they were trying to escape: successful on paper, empty underneath.What you'll hear:Why "what do I want to do next?" is the wrong first question, and what to ask insteadThe pattern Kevin fell into after leaving his own global VP role, and what it revealed about identity versus achievementHow mapping who you actually are now, not who you were trained to be, changes every decision that followsWhat it means to build a next chapter that fits the current version of you, not the version that got you hereThis one is for anyone who's built real success and is now wondering why the next obvious move doesn't feel as obvious as it should.Underneath The Title is hosted by Kevin Simcock, author of Whose Ladder Is This? and advisor to people who have outgrown the identity they built their success on.New episodes every week. Visit kevinsimcock.com for more information.Purchase Kevin Simcock's Book: Whose Ladder Is This?Available on Amazon Kindle, paperback, and hardcoverBarnes & Noble | Indigo BooksCheck out more episodes of Underneath The Title on YouTube: https://youtube.com/@kevinsimcockHost: Kevin SimcockLinkedIn: https://www.linkedin.com/in/kevin-simcock/

June 1, 2026Episode 621 min

The Truth About Building Your Next Chapter

Most people think the hardest part of leaving an executive role is figuring out what comes next. It isn't. The hardest part is who you are without it.In this episode of Underneath The Title, Kevin Simcock unpacks the realities of transitioning out of an executive career or business ownership, and what it actually takes to build your next chapter. After more than two decades building his global advertising career, Kevin walked away from it to start over in a new industry. This is the honest version of what that journey looks like.What you'll hear in this episode:The grief no one warns you about. Why the empty calendar, the silent phone, and the loss of routine quietly destabilize your sense of self, and what to do when grief shows up in the middle of a professional shift.The role your inner critic plays. A grounded look at the Ego, the Super Ego, and the complex, and why understanding the difference helps you stop letting the wrong voice run your decisions.How to answer the question most accomplished leaders can't answer cleanly: tell me who you are without giving me a title, a role, or describing what you do. Kevin shares the values-based exercise he used to find his own answer, and the one his clients use to find theirs.This episode is for executives, founders, and senior leaders standing at the edge of a major shift, the ones who've built something significant and now find themselves asking what's underneath all of it.Mentioned in this episode: Kevin's book, Whose Ladder Is This? Available on Amazon (Kindle, paperback, hardcover), Barnes & Noble | Indigo BooksConnect with Kevin: Website: kevinsimcock.com LinkedIn: linkedin.com/in/kevin-simcock YouTube: youtube.com/@kevinsimcockIf this episode landed for you, share it with someone navigating their own next chapter.

May 18, 2026Episode 525 min

Who Is Your Inner Critic?

There's a voice in your head that shows up every time you're about to do something that matters.It arrives right on cue. You've thought the decision through. The logic holds. You can see the path. And then it starts. What if this goes wrong? What if you're not ready? What if people think you've lost your mind?You've probably spent years assuming that voice is just you. The honest, realistic part of you doing due diligence. The part that keeps you grounded.But what if it isn't you at all?In this episode, Kevin Simcock explores one of the most misunderstood forces shaping your decisions: the inner critic. Not as a concept to manage or push through, but as something with a specific origin, a real psychological explanation, and a much older source than most of us have ever considered.Drawing on the work of Sigmund Freud and Swiss psychiatrist Carl Jung, Kevin unpacks where the inner critic actually comes from, why it sounds so convincingly like your own voice, and what it's really been protecting you from. You'll learn the difference between the inner critic and the Ego, two things that are commonly confused, and why that distinction changes everything about how you respond to self-doubt.Kevin also shares something personal: the moment he traced his own inner critic back to a locker room at fourteen years old, and how recognising that a voice from the past had been quietly shaping decisions in the present was the beginning of something genuinely different.This episode covers:What Freud's model of the Id, Ego, and Superego actually means in plain language, and which part is responsible for the voice in your headWhy Carl Jung's concept of complexes explains how a single experience can create an autonomous inner voice that runs for decades without your awarenessThe difference between the inner critic and the Ego, and why confusing the two keeps people stuckA simple but powerful three-step practice for working with your inner critic when it shows up at a critical decision pointWhy the inner critic doesn't just affect individual choices. Left unchallenged, it can quietly build an entire life and identity around conclusions that were never fully yoursThis isn't a theoretical conversation. It's a practical one, built from Kevin's own experience navigating a significant professional transition after a 25-year global advertising career, and from the work he does with clients who are rebuilding their identity and direction after their own defining moments.If you've ever felt held back by a voice you couldn't quite explain, this episode is for you.Kevin Simcock is an executive advisor, author, and host of Underneath The Title. His advisory practice works with high-performers who have built success but feel misaligned with the identity and life they've created. His book, Whose Ladder Is This?, is available on Amazon, Barnes & Noble, and Indigo.Connect with Kevin: Website: https://kevinsimcock.com LinkedIn: https://www.linkedin.com/in/kevin-simcock/ YouTube: https://youtube.com/@kevinsimcockGet the book: Whose Ladder Is This? Amazon: https://www.amazon.ca/s?k=whose+ladder+is+this Barnes & Noble: https://www.barnesandnoble.com/w/whose-ladder-is-this-kevin-simcock/1148111984 Indigo: https://www.indigo.ca/en-ca/whose-ladder-is-this/9781069695413.html

April 16, 202611 min

The Days When Nothing Works

Some days after a big exit, nothing feels right. You're not inspired. You're not productive. You can't make yourself care. And underneath the flatness, there's a quiet question: is this even what I want to be doing?In this episode, Kevin Simcock breaks down what's actually happening on those days, and why most people misread them entirely.After leaving a significant role, there's usually a window of freedom. You travel, you explore, you take meetings about new ventures. But at some point, the exploration starts to feel like searching. And the searching starts to feel like something is missing.That's when the void shows up. Not as a dramatic breakdown, but as a slow realization that none of the new things have filled the space your old identity used to occupy.Kevin walks through the arc nobody prepares you for: from post-exit freedom, to quiet emptiness, to the flat days that follow real inner work. He explains why your nervous system needs time to catch up to the changes you've already made, why your old operating system keeps telling you that stillness means failure, and why these "reset days" are actually a sign of progress, not a sign that something is wrong.If you've been sitting in that flatness wondering whether you're on the wrong path, this episode will reframe what's actually going on.In this episode:The post-exit arc from freedom to searching to voidWhy flat, uninspired days are a nervous system reset, not a crisisHow your old identity keeps running in the background and misreading the signalThe difference between procrastination and integrationWhy stillness after an exit isn't failure, it's informationOne question to ask yourself on the days nothing worksPurchase Kevin's book Whose Ladder Is This? Available on: Amazon (Kindle, paperback, hardcover): https://www.amazon.ca/s?k=whose+ladder+is+this&i=stripbooks Barnes & Noble: https://www.barnesandnoble.com/w/whose-ladder-is-this-kevin-simcock/1148111984 Indigo Books: https://www.indigo.ca/en-ca/whose-ladder-is-this/9781069695413.htmlConnect with Kevin: Website: https://www.kevinsimcock.com LinkedIn: https://www.linkedin.com/in/kevin-simcock/ YouTube: https://youtube.com/@kevinsimcockHost: Kevin Simcock

April 2, 2026Episode 321 min

Success Doesn't Prepare You For This.

You built the career. You hit the numbers. And then one day, you woke up and didn't quite recognize yourself anymore.That feeling has a name. Most people never learn it.In this episode of Underneath The Title, Kevin Simcock unpacks identity loss, one of the most common and least talked-about experiences among high-achievers who've exited a career, sold a business, or hit a major life transition.This isn't about motivation or confidence or figuring out your next move. It's about something that runs deeper than any of those things: the story you've been telling yourself about who you are, and what happens when the role that anchored that story disappears.Kevin explores why identity loss so often gets misread as burnout, restlessness, or a midlife crisis, and why misreading it leads people to rebuild the same thing in a slightly different setting. He walks through the specific ways it shows up, from decision paralysis and comparison spirals to the quiet grief of losing clarity about where you fit.He also makes the case that identity loss isn't a crisis. It's information. And for the people willing to sit with that discomfort honestly, it's often the beginning of building something that actually fits.If you've been quietly asking yourself "is this all there is?" this episode was made for you.Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback and hardcover HEREBarnes & Noble here Indigo Books here If today’s episode resonated and you’re ready to start asking your own version of that question, you can find Kevin at kevinsimcock.com.Check out more episodes of Underneath The Title on Youtube https://youtube.com/@kevinsimcockHost: Kevin Simcock LinkedIn Profile https://www.linkedin.com/in/kevin-simcock/

March 22, 2026Episode 216 min

What the Most Cited Career Reinvention Book Gets Wrong

Herminia Ibarra's Working Identity is one of the most cited books in career reinvention. It's been assigned in business schools, recommended by coaches, and trusted by high-achievers navigating major transitions. And it gets something fundamentally wrong.Ibarra's central argument is this: don't wait for clarity. Act. Experiment with different versions of yourself, and let the feedback from those experiments guide you toward the right one. It sounds practical. It sounds liberating. But for the people I work with, people who have already built one version of success and don't know who they are after they have moved on from it, this approach doesn't produce a new self. It produces the same self in a new context.In this episode, I walk through exactly where Ibarra's model breaks down, why the "possible selves" she encourages you to explore are often unexamined personas built from fear, conditioning, and other people's expectations, and what needs to happen before action becomes meaningful.I draw on the work of Carl Jung to explain why acting from an unexamined identity isn't reinvention. It's repetition. And I use an example from Ibarra's own book to show that the introspection she dismisses is quietly present in every success story she tells.If you've read Working Identity, this episode will reframe it. If you haven't, it will save you from following advice that stops short of the answer you're actually looking for.Action validates direction. But only when the direction is actually yours.Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback and hardcover HEREBarnes & Noble here Indigo Books here If today’s episode resonated and you’re ready to start asking your own version of that question, you can find Kevin at kevinsimcock.com.Check out more episodes of Underneath The Title on Youtube https://youtube.com/@kevinsimcockHost: Kevin Simcock LinkedIn Profile https://www.linkedin.com/in/kevin-simcock/

March 5, 2026Episode 129 min

The Hidden Cost of Exit: What No One Tells You About Exiting A Business & Executive Leadership

Everyone talks about the exit. Nobody talks about what comes after it.If you've recently stepped away from a business you built, a company you led, or an executive role that defined you for decades and something feels off, you're not broken. You're navigating one of the most underestimated transitions a leader can face.In this episode of Underneath The Title, Kevin Simcock breaks down the three invisible costs of exit that executive leaders almost never see coming: identity shock, status withdrawal, and routine collapse. These aren't soft concepts. They are real, measurable forces that distort your decision-making, strain your relationships, and quietly erode the legacy you spent years building,  if you don't address them directly.Kevin draws on 25+ years of working with Fortune 500 leaders and founder-CEOs to explain why even the most accomplished executives are blindsided by exit, and what to actually do about it. IN THIS EPISODE YOU'LL LEARN:Why identity fuses with your role over decades and what happens when that role disappearsThe three danger responses to status withdrawal that lead smart leaders into bad decisionsHow to design a new operating rhythm when the institutional structure that organized your life is goneThe 90-day rule Kevin uses with every client post-exitThree conversations every leader needs to have before making any major next move WHO THIS EPISODE IS FOR:This episode is for founders and executives who have exited, or are preparing to exit, a business or senior leadership position and are navigating the identity, purpose, and direction questions that follow. If you've ever thought "Who am I, if I don't have my title anymore?" after a successful exit, this one is for you. CONNECT WITH KEVIN:Website: kevinsimcock.comPurchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback and hardcover HEREBarnes & Noble here Indigo Books here Interested in working with Kevin visit kevinsimcock.com for more information.Check out more episodes of Underneath The Title on YouTube https://youtube.com/@kevinsimcockHost: Kevin Simcock LinkedIn Profile https://linkedin.com/kevin-simcock

February 6, 2026Episode 233 min

Finding Your Direction After Exiting a Corporate Career or Business Ownership

Podcast Description: Finding Your Direction After the ExitAre you navigating the space between what was and what’s next? Whether you’ve recently sold a business, transitioned out of a long-term corporate executive role, or are simply hearing an inner voice suggesting you’re meant for something more, the path forward isn't always found by moving faster. It’s found by slowing down.  In this episode of Pivotal, host Kevin Simcock shares a foundational roadmap for professionals who are ready to decouple their identity from their titles and reclaim their self-authority. We dive into why the most productive thing you can do for your future career is to initially do nothing at all, and how to systematically "wipe the slate clean" to make room for a legacy with genuine meaning. Key Points of InterestThe 60-Day Decompression Rule: Why your body and mind require a minimum of two months to release the stress of "busy-ness" and break old corporate programming. The "Rearview" Evaluation: A step-by-step guide to documenting what you loved, what you tolerated, and what you refuse to carry into your next chapter. Identifying Your Non-Negotiables: How to filter your past experiences to find the five core values that will serve as your new compass. Designing the "Ideal Day" Blueprint: Moving beyond abstract goals to define the practical logistics of your life, from meeting times and travel to your revenue targets. Alignment Criteria: How to build a profile of your ideal clients and business partners based on character traits and shared conviction.  What You’ll Walk Away WithAfter listening to this episode, you will have a clear, actionable framework to stop reacting to outside offers and start authoring your next chapter with intention. You’ll learn how to listen to your "inner calling" and apply it to practical avenues like fractional work, advisory roles, or passion ventures. Most importantly, you will have the permission to sit in stillness, knowing that clarity comes only when you stop forcing the results.  Ready to build what's next? * Visit: kevinsimcock.com to learn about mentorship and "The Inner Agency."  Purchase Kevin Simcock’s Book: Whose ladder Is This? Available on: Amazon - Kindle, paperback and hardcover HERE Barnes & Noble – paperback and hardcover HERECheck out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-PivotalHost: Kevin Simcock LinkedIn Profile https://linkedin.com/kevin-simcock

January 27, 2026Episode 126 min

New Beginnings: Building What's Next After Pivotal Transitions in Life

In this episode of Pivotal with Kevin Simcock, we are talking about new beginnings, and why they rarely feel like a fresh start at first. More often, they feel like an ending that left you standing in a quiet room with an empty calendar and a loud question: Who am I without the role?If you are a former executive, exited founder, or senior leader in transition, you might know the “dog off the leash moment.” The structure is gone. The title is gone. The pace that used to define you is gone. What is left is you, and the opportunity to build what’s next from truth instead of pressure.In this conversation, I share personal stories and the inner shift that changed everything for me: identity decoupling, reclaiming self-authority, and choosing a legacy after exit that actually feels like yours. Not the version that looks good on paper, but the one you can live with.You will leave with a grounded reflection you can use today: Six months from now, what do you want to be true about you? What is one behaviour you will start today to build it, and one behaviour you will stop because it belongs to the old version of you?If this episode strikes a chord, share it with someone who might need it. And if you are navigating a career transition, executive exit, or founder reinvention and want support building what’s next, you can find me at kevinsimcock.com.-----Purchase Kevin Simcock’s Book: Whose ladder Is This? Available on Amazon Kindle, paperback and hardcover HERE Interested in working with Kevin visit kevinsimcock.com for more information. Check out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-PivotalHost: Kevin Simcock LinkedIn Profile https://linkedin.com/kevin-simcock

December 11, 2025Episode 1419 min

Scaling You: The Inner Work Founders Must Consider to Grow Their Business

Your business isn’t stalled because of your systems, team, market conditions, or even strategy. It’s stalled because of something far more uncomfortable. Something most leadership advice completely misses.You.In this episode of Pivotal, I break down the hidden force driving every decision, every bottleneck, every high-stakes moment in your business: your identity as a founder. Not the role. Not the title. The real you behind it. The version of you that shows up under pressure, risk and uncertainty.Most founders follow leadership advice built for corporations with layers of protection. But you don’t have that luxury. You are the business, which means your beliefs, fears, patterns and blind spots are either accelerating growth or quietly killing it.This episode digs into: • The biggest leadership mistake founders make without knowing it • Why your identity shapes revenue more than your strategy • How control, fear and avoidance sabotage growth from the inside • Real-world examples of leadership patterns that cost companies millions • What actually changes when a founder evolves into the leader their next stage demandsIf you’re staring at a growth plateau, wondering what’s really going on, this conversation will give you a clear answer. And it might not be the answer you expected.This is the work that separates founders who scale from those who stall.Tune in, get honest, and see what version of you your business has been waiting for.Purchase Kevin Simcock’s Book: Whose ladder Is This? Available on Amazon Kindle, paperback and hardcover HERE Sign up to work with Kevin to see how he can help you and your business - https://www.kevinsimcock.com/partnershiprequest  Check out more episodes of Pivotal: http://www.youtube.com/@KevinSimcock-PivotalHost: Kevin Simcock  LinkedIn Profile https://linkedin.com/kevin-simcock

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