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

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, ...

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? I...

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 t...

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 wi...

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. Wh...

When your business looks successful but feels off, something deeper is happening. In this episode, Kevin breaks down one of the most expensive leadership mistakes: leading from misalignment. He shares how even high-performing founders lose clarity, why it stalls growth, and the simple steps that help you get unstuck and rebuild momentum. If you have felt off but cannot explain why, this episode will hit home. Purchase Kevin Simcock’s New Book: Whose Ladder Is This? Available on A...

Spoiler: it’s not a French villa, a gold watch, or a bigger business. If you’ve built success that looks great on the outside but secretly feels exhausting, disconnected, or empty this final episode of The Clarity Series is for you. Whether you’re leading a fast-scaling business or navigating the weight of past success, you’ll learn: · The illusion of “more” that leads to burnout · What true fulfillment feels like (and how to recognize the signs) ·&nbsp...

What if your exhaustion isn’t from doing too much—but from doing the wrong things? In this episode of Pivotal, I challenge one of the most toxic beliefs in business: that success requires constant hustle. If you're a founder or leader running at full speed but still feeling off… this is the reset you didn’t know you needed. We’ll break down: Why hustle masks deeper misalignmentThe real cost of chasing success without clarityHow internal alignment unlocks sustainable momentumPractical steps to...

You’ve hit your goals. The revenue is strong. The team is growing. But deep down… you feel disconnected, restless—even empty. Why? In this episode of The Clarity Series, I unpack one of the hardest truths founders face at the height of success: growth doesn’t guarantee fulfillment. If you’ve scaled your business but lost sight of your purpose—or the spark that once drove you—this episode is for you. We’ll explore: – Why traditional success often leads to internal dissonance – How your busin...

In this episode Kevin shares his experience and knowledge on the one key element most business founders struggle with to maintain their growth - staffing. There is an art to finding the right people and knowing exactly who and how many people you need to sustain your growth trajectory. Kevin shares the key steps you need to take to build the best team possible. Check out more episodes of Nifty Thinking: https://podcasts.apple.com/ca/podcast/nifty-thinking/id1680610153 Subscribe to my ...

Want to turn your business challenges into more money, more clients and more time, without increasing your marketing budget? In this episode, I'll show you proven strategies to set growth goals for your business, how to avoid common pitfalls most companies experience how to improve your marketing and sales and the critical AI tools you need to have in your business to grow in 2025. Over 42% of all global businesses are using AI to grow their business, and I'll teach you what tools and p...

In this episode Kevin talks about the current state of AI in small and medium-sized business and what the current major advancements are in AI as well as what to expect and prepare for in 2025. We go in-depth on the impact AI is having on business operations, workflows and content creation. We get into the nitty gritty details of what AI tools you need to be using now and what new tools will be impacting your business in 2025 and how you can be preparing for them now. Kevin also launches t...

In this episode Kevin walks through the importance of brand authenticity and the role it plays in differentiating your brand from your competitors. If you are a creative service business you understand the intense competition for projects and landing your ideal clients. When every business is claiming to be creative, is a storyteller and uses the latest technology, the key to standing out is to find your authenticity and focus on your client needs. You will learn the strategies and approach ...