What's Next After Success

Hosted by Kevin Simcock

Business Entrepreneurship Education

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Oct 2026

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About the show

Formerly Underneath The Title, What’s Next After Success explores the personal and strategic questions that emerge on the other side of achievement. You built the business, earned the title and reached the goal. Now you are asking a different question: What comes next after success? Underneath The Title: What Comes Next After Success is a podcast for founders, business owners, executives and accomplished professionals navigating life after selling a business, leaving a leadership role or reaching the point where the success they built no longer feels fulfilling. Hosted by Kevin Simcock, the show explores the personal and strategic questions that surface on the other side of achievement: Who am I without the role? Why can success feel unexpectedly empty? What gives me meaning now? And what do I want to do next? Through candid conversations and solo episodes, Kevin explores founder identity after a business exit, finding purpose and meaning after success, executive and career transitions, redefining success and building a meaningful next chapter. Rather than telling listeners to reinvent themselves, Underneath The Title offers another possibility: reconnecting with the parts of themselves they left behind while becoming the version success rewarded. Kevin brings more than two decades of global creative and corporate leadership experience, along with the perspective of navigating his own major career transition at 50. He is the creator of the RECLAIM methodology, author of Whose Ladder Is This?, and a private advisor to successful founders, business owners, executives and accomplished professionals world-wide. New episodes every two weeks. Follow Underneath The Title wherever you listen to podcasts, or subscribe to the video version on YouTube. Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback and hardcover HERE Barnes & Noble here Indigo Books here Subscribe to Kevin's Substack: https://kevinsimcock.substack.com Visit kevinsimcock.com for more information LinkedIn Profile https://www.linkedin.com/in/kevin-simcock/

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49 recent

October 8, 202638 min

If You Could Do Anything Next, What Would You Do?

You've sold the business. You've left the successful career. You finally have the freedom to choose what comes next. So why is it so difficult to figure out what you actually want? For many founders, executives and accomplished professionals, life after success brings an unexpected challenge. After decades of pursuing goals, building businesses and making important decisions, they're suddenly faced with a question that seems almost impossible to answer: What do I really want to do with the next chapter of my life? In this episode of What's Next After Success , Kevin Simcock explores why having unlimited possibilities doesn't necessarily create clarity, and why the pressure to find your next purpose can actually keep you stuck. In this episode, we explore: The paradox of freedom: Why having more choices after leaving a successful career or business can make deciding what comes next harder. The trap of past success: How we unconsciously evaluate new possibilities using the same expectations, ambitions and definitions of success that shaped our previous careers. Curiosity before purpose: Why finding something worth exploring may be more useful than trying to identify your life's next great mission. Building a possibility portfolio: A different way to explore potential directions without immediately committing to another business, career or identity. Experience creates clarity: How small, real-world experiences can help you discover what genuinely interests, energizes and fulfils you. Whether you're figuring out what to do after selling your business, finding purpose after leaving a successful career, or simply wondering what you really want from life now, this conversation offers a different way to approach the question. Maybe you don't need to know what you want to do with the rest of your life. Maybe you just need to discover what's worth pursuing next. Follow What's Next After Success for more conversations about life after success, finding meaning, exploring possibilities and building a next chapter that's genuinely your own. Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback, and hardcover Barnes & Noble | Indigo Books Contact Kevin at kevinsimcock.com Check out more episodes of What’s Next After Success on YouTube: https://youtube.com/@kevinsimcock Host: Kevin Simcock LinkedIn: https://www.linkedin.com/in/kevin-simcock/

September 24, 2026Episode 1121 min

Why Rushing Your Next Chapter Costs You More Time

You've spent years building, leading, and achieving. Now that you've stepped away, why does deciding what comes next feel so urgent? For successful executives and business owners, doing nothing can feel unbearable. The temptation is to jump straight into another venture, accept another leadership role, or fill your calendar with new commitments. But what if rushing forward simply recreates the life you wanted to leave behind? In this episode of What's Next After Success, Kevin Simcock explores why taking time to pause after a business exit or major career transition might be the most productive decision you make. Drawing on his own experience, Kevin challenges the instinct to keep moving and explores three important considerations for navigating your next chapter: The art of doing nothing: Why giving yourself permission to decompress creates space to see new possibilities. The power of better questions: How understanding your evolving values, motivations, and priorities can reveal what's genuinely worth pursuing. Rethinking your timeline: Why your next chapter isn't a destination to reach, but a direction that develops through exploration and experience. Whether you've recently sold your business, stepped away from an executive career, or are questioning what success should look like now, this episode invites you to reconsider what it really means to move forward. Before deciding what to do next, discover what makes it worth doing. Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback, and hardcover Barnes & Noble | Indigo Books Contact Kevin at kevinsimcock.com Check out more episodes of What’s Next After Success on YouTube: https://youtube.com/@kevinsimcock Host: Kevin Simcock LinkedIn: https://www.linkedin.com/in/kevin-simcock/

September 9, 2026Episode 1017 min

AI Can Help You Build Almost Anything. But What Should You Build?

AI is making it easier than ever to research an idea, test a business, and build something new. At the same time, it is changing how companies think about roles, headcount, and the future of work, raising a bigger question for accomplished professionals considering a career transition or next chapter. So what happens when AI gives you more possibilities, but no better answer about which one is actually worth pursuing? Kevin explores how AI can help you investigate and validate new directions, why the falling barriers to starting something create a new kind of decision problem, and why judgment, self-knowledge, and discernment become even more important as technology gets more capable. AI may help you build almost anything, but the harder question is: what should you build? Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback, and hardcover Barnes & Noble | Indigo Books Contact Kevin at kevinsimcock.com Check out more episodes of What’s Next After Success on YouTube: https://youtube.com/@kevinsimcock Host: Kevin Simcock LinkedIn: https://www.linkedin.com/in/kevin-simcock/ Research referenced in this episode • Challenger, Gray & Christmas - Challenger Report: March Cuts Rise 25% From February, AI Leads Reasons: https://www.challengergray.com/blog/challenger-report-march-cuts-rise-25-from-february-ai-leads-reasons/ • Gallup - U.S. Workers Continue to Report Downsizing: https://www.gallup.com/workplace/711287/workers-continue-report-downsizing.aspx • TechCrunch - Monday.com is the latest tech company to blame AI for layoffs - here are 20 others: https://techcrunch.com/2026/07/25/the-running-list-major-tech-layoffs-in-2026-where-employers-cited-ai/ • Government of Canada - Research summary: Artificial intelligence and automation in Canada’s labour market: https://www.canada.ca/en/employment-social-development/corporate/reports/research/summary-ai-labour-market.html • Gusto - 2026 New Business Formation Report: How AI Is Reshaping Who Starts a Business in America: https://gusto.com/resources/gusto-insights/new-business-formation-2026 • JPMorganChase Institute - Small Business in the Age of AI: https://www.jpmorganchase.com/institute/all-topics/business-growth-and-entrepreneurship/small-business-in-the-age-of-ai • International Labour Organization - Changing landscape of skills in the age of AI: https://www.ilo.org/publications/changing-landscape-skills-age-ai • Thomson Reuters - Future of Professionals Report 2026: https://www.thomsonreuters.com/en/institute/future-of-professionals-2026/report • Business Insider - Anthropic's AI fluency chief says the best AI users know when to do the work themselves: https://www.businessinsider.com/anthropic-ai-fluency-chief-discernment-tax-work-2026-9

August 5, 2026Episode 928 min

The Other Side of Success

Success was supposed to be the destination. So why doesn’t it feel like enough? After years of chasing promotions, growing businesses, building wealth, or reaching major career milestones, many accomplished professionals discover an uncomfortable truth: achievement doesn’t automatically create meaning. In this episode of What’s Next After Success , Kevin Simcock explores why success often leaves us asking a bigger question instead of providing the answer we expected. Drawing on his own experience as a former executive, along with conversations with founders, business owners, and senior leaders navigating life after success, Kevin explains why the feeling of emptiness isn’t a sign that you’ve failed. It’s often a sign that you’ve finally created enough space to hear what you’ve been ignoring. You’ll discover: • Why success cannot give us meaning, no matter how much we achieve. • What really happens after reaching the top of the corporate ladder or exiting a business. • Why high achievers often struggle with identity after success. • The difference between reinventing yourself and reconnecting with who you’ve always been. • Why meaningful experiences reveal more about your future than endless reflection. • Powerful questions to help you begin defining what your next chapter could become. If you’ve been asking yourself “Now what?” after achieving the success you worked so hard to build, this conversation will help you see that question differently. Your next chapter doesn’t begin with another achievement. It begins by reconnecting with what gives your life meaning. Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback, and hardcover Barnes & Noble | Indigo Books 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 What's Next After Success on YouTube: https://youtube.com/@kevinsimcock Host: Kevin Simcock LinkedIn: https://www.linkedin.com/in/kevin-simcock/

July 27, 2026Episode 827 min

Finding Your Purpose: Why Success Doesn’t Always Lead to Fulfillment

What if purpose isn’t something you find… but something you reconnect with? Many successful professionals spend years chasing achievement, believing that the next promotion, business milestone, or financial goal will finally bring fulfillment. Yet after reaching those goals, many are left asking a surprisingly difficult question: “What now?” In this episode of Underneath the Title , Kevin Simcock explores why purpose often becomes a question only after success, and why searching harder rarely leads to the answers we’re looking for. Drawing on his own journey, his work with business owners and senior leaders navigating major life transitions, and a powerful story about an unexpected creativity experiment, Kevin shares a different perspective: Purpose isn’t another destination to achieve. It’s a reconnection with the parts of yourself that may have been left behind while pursuing success. In this episode you’ll discover: • Why the search for purpose often begins after you’ve achieved success. • Why money, status, and freedom don’t automatically create meaning. • Why reflection alone isn’t enough to create clarity. • How meaningful experiences reveal who you really are. • Why your next chapter should be built on alignment, not someone else’s definition of success. If you’re navigating a career transition, life after selling a business, retirement from leadership, or simply questioning what’s next, this conversation offers a thoughtful perspective on finding purpose, creating meaning, and building a life that feels authentic. If this episode resonates with you, please follow the show, leave a review, and share it with someone who may be asking the same question. Purchase Kevin Simcock's Book: Whose Ladder Is This? Available on Amazon Kindle, paperback, and hardcover Barnes & Noble | Indigo Books 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/@kevinsimcock Host: Kevin Simcock LinkedIn: https://www.linkedin.com/in/kevin-simcock/

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 instead The pattern Kevin fell into after leaving his own global VP role, and what it revealed about identity versus achievement How mapping who you actually are now, not who you were trained to be, changes every decision that follows What it means to build a next chapter that fits the current version of you, not the version that got you here This 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 hardcover Barnes & Noble | Indigo Books Check out more episodes of Underneath The Title on YouTube: https://youtube.com/@kevinsimcock Host: Kevin Simcock LinkedIn: 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 Books Connect with Kevin: Website: kevinsimcock.com LinkedIn: linkedin.com/in/kevin-simcock YouTube: youtube.com/@kevinsimcock If 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 head Why Carl Jung's concept of complexes explains how a single experience can create an autonomous inner voice that runs for decades without your awareness The difference between the inner critic and the Ego, and why confusing the two keeps people stuck A simple but powerful three-step practice for working with your inner critic when it shows up at a critical decision point Why 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 yours This 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/@kevinsimcock Get 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.htm l

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 void Why flat, uninspired days are a nervous system reset, not a crisis How your old identity keeps running in the background and misreading the signal The difference between procrastination and integration Why stillness after an exit isn't failure, it's information One question to ask yourself on the days nothing works Purchase 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.html Connect with Kevin: Website: https://www.kevinsimcock.com LinkedIn: https://www.linkedin.com/in/kevin-simcock/ YouTube: https://youtube.com/@kevinsimcock Host: 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 HERE Barnes & 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/@kevinsimcock Host: Kevin Simcock LinkedIn Profile https://www.linkedin.com/in/kevin-simcock/

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