The Truth No One Talks About
Old Identity
You spent decades building a business or a career. Every inch of you, your blood, sweat, tears and time went into it. It wasn't just a business or a title, it was your identity. When you sell it or when it ends, a part of you ends with it. This is extremely hard to deal with. Did you make the right decision? Will your employees be ok? What will your legacy be, now this chapter is over? Who are you now, without the title?
Sense of Loss
The silence. The loss of importance. The absence of problems to solve. Everything that defined who you were, is gone. You chase endless potential and countless "maybe this" ideas. Only to be left feeling empty and uncertain. This stage of transition is far more impactful than most people realize. Until they are in it. I know this first-hand because like you, I went through it, too.
Time
Building your next chapter doesn't happen over night. Not in a week. Not in a month. Some people take years. Most entrepreneurs underestimate the dislocation and disorientation triggered by exiting a business or career. Most are blindsided by the feelings of loss, sadness and difficulty that comes with an exit. It takes time to rebuild from the inside out. Everyone's timeline is unique to them.
Clarity & Guidance Built From Experience
I’ve spent nearly three decades leading, building, and advising inside global businesses where the decisions carried real consequences. Growth, change, reputational risk, and the pressure to get it right were part of the job, not abstractions.
I’ve also lived the moment when the role you’re in no longer fits the decisions you need to make next. When the old playbook stops working and familiarity becomes a constraint instead of an asset.
That combination matters.
It means I don’t approach this work from the outside, and I don’t offer generic advice from a distance. I work with leaders the way I would want someone to work with me: grounded in context, honest about trade-offs, and focused on helping you find clarity when the answers aren’t obvious.
This isn’t coaching. It isn’t a packaged framework. And it isn’t about telling you what to do.
It’s a structured, one-to-one advisory partnership designed to help you regain clarity, pressure-test your thinking, and make decisions you can stand behind when the stakes are real.
The Manual for when success stops feeling like success
In Whose Ladder Is This?, former global executive and creative strategist Kevin Simcock shares a raw, honest account of what happens when achievement no longer aligns with identity.
Part memoir, part guidebook, this is not a story of burnout or breakdown. It’s a story of awakening. Through vulnerable storytelling, insight-rich reflection, and hard-won clarity, Kevin walks you through the messy but necessary process of letting go of who you thought you had to be, so you can step into the version of yourself that was waiting all along.
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Honest conversations on self-authority, Decision Strategy, and Building what's next
The Knee Deep in Uncertainty Podcast discusses navigating pivotal transitions and how to evolve into the identity your next chapter requires.
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