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

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

Underneath The Title: When High Achievers Start Questioning the Success They Built is a business podcast hosted by Kevin Simcock, with 47 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Kevin Simcock hosts Underneath The Title: When High Achievers Start Questioning the Success They Built, a business show with 47 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Episode #10

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

  Sep 9, 202618 minS4

  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

  ListenShow Notes
• 

  Episode #9

  The Other Side of Success

  Aug 5, 202629 minS4

  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/

  ListenShow Notes
• 

  Episode #8

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

  Jul 27, 202628 minS4

  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/

  ListenShow Notes
• 

  Episode #7

  How to Choose Your Next Chapter

  Jun 11, 202615 minS4

  <p>Most people design their next chapter using the identity that built the last one. That's exactly why it doesn't fit.</p><p>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.</p><p><b>What you'll hear:</b></p>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...

  ListenShow Notes
• 

  Episode #6

  The Truth About Building Your Next Chapter

  Jun 1, 202622 minS4

  <p>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.</p><p>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.</p><p>What you'll...

  ListenShow Notes

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.