top of page
KevinSimcock_personalcoach_whatsnextaftersuccess

Clarity & Direction For 
What's Worth Pursuing Next

For people who've built real success but whose old self is standing in the way of deciding what's worth pursuing next and how to make it a reality.

Explore Private Advisory

Who This Is For

For accomplished people who have exited a career or sold a business and exploring what's next

You built something real: a career, a business, a reputation, or a body of work. The role and the version of you that built it has shifted. You want something more, something meaningful. You have opportunities but you are stuck, uncertain which opportunity is right for you now. You are in between who you were and who you are becoming and want help finding a path forward.

Life After Career

You have left, or are preparing to leave, a senior role. Retirement does not feel like the full answer.

Life After Business

You built and possibly exited a business. You want what comes next to offer more balance, meaning, and personal connection.

Life In Transition

An unexpected change has altered how you see yourself, your work, or the future you were building toward.

Successful But Uncertain

You still have ambition and options, but no longer know which possibilities genuinely feel right.

Kevin Simcock Personal Advisory Next Chapter

How Do You Find a clear, confident way to decide what is worth doing next?

  • What opportunities actually fit me now?

  • Who am I without my old title or role?

  • What kind of life do I want to build next?

  • How do I define success now and why?

  • What gives me a sense of meaning and purpose?

  • What assumptions am I making because of my previous identity?

  • What business or career model fits the life I want?

  • How do I trust that I'm making the right decision?

  • How can I test it without committing years to finding out if its right?

  • What's the smartest sequence for bringing it into the world?

  • How does AI impact my decision?

  • How do I use AI to help me in a way I can trust?

Who You Were
No Longer Fits

You built real success. A rewarding career. A successful business. Your old life provided deadlines, priorities, colleagues, feedback, status, and a steady stream of problems to solve. Your old identity has fallen away. You are becoming someone new, wanting something new and wondering what that could possibly be. 

 

You are at a threshold of transition. How you used to define yourself no longer fits. That can bring uncertainty, grief, loss and even fear.

You are stuck between knowing what you don't want but uncertain about what is meaningful and worth pursuing next. 

 

Before you spend years chasing a direction, you need to figure out what’s actually worth building. I built RECLAIM to help navigate the blind spots that often come with building a next chapter:

  • Identify Who You Are Now: what you offer beyond your former title and corporate brand.

  • Define success for the next phase: income, impact, autonomy, learning, lifestyle, relationships, or legacy.

  • Prioritize options: distinguishing genuinely attractive paths from options that merely preserve status.

  • Test possibilities safely: through advisory expeditions, board roles, mentoring, teaching, or short-term consulting before making a major commitment.

  • Build a new personal operating system: including structure, relationships, routines, and accountability.

 

Starting with a stronger sense of self-awareness provides the foundation for answering; what is worth building next.

RECLAIM helps separate the person from the roles and expectations accumulated through success. It combines self-authority work with practical exploration so future decisions can be based on evidence, alignment, and real-world viability.

Kevin Simcock Personal Advisor Career Transition
KevinSimcock_personaladvisor_nextchaptermeaning_purpose

One-on-One Guidance

The Clarity You Need To Make Confident Decisions

You have no shortage of possibilities, but that also makes it harder to judge which ones are worth pursuing. My guidance and 25+ years of experience guide you through the uncertainty that emerges after a major career, business, or life transition.

I’ll help you find stability in who you are becoming now, clarity in what opportunities are right for you, and certainty in how to chart a path forward towards a next chapter that brings you greater fulfillment.

Turn Uncertain Options
Into A Clear Path

How does an accomplished person determine what should come next when the identity, ambitions and definitions of success that defined them no longer does?

 

In order to clearly understand which of the many possibilities are worth exploring, you first must have a clear understanding of who you are now, your values, and how you define success.

My approach is anchored in a fundamental belief: Reconnect the person first, before constructing the next chapter.

Having greater self-awareness becomes the lens by which all decisions for what to do next are measured. When you know what aligns to your values, the right direction and the right decisions become clear. The action you take in that direction feels exciting, aligned and meaningful.

RECLAIM is built around three phases:

Identity Decoupling
Separate who you are from the roles, achievements, and expectations that have defined you.

Realignment
Determine what matters now and evaluate which possibilities fit your values, strengths, energy, and circumstances.

Next Chapter Construction
Translate the strongest direction into a viable real-world path.

Each phase can be explored through a dedicated three-month Expedition combining private advisory, structured reflection, creative experiences, and real-world experiments.

kevinsimcock_personaladvisor_nextchapterpurpose

Three questions. Three Shifts. One methodology.

Kevinsimcock_personalAdvisory_fieldsession_identitywork

Shift 1 - Connect
"Why Can't I Decide?"

A personalized three-month program for people who have built real success to shift out of circling the same decision and finally land on an answer.

Kevin Simcock Personal Advisory Client

Shift 2 - Realign
"What Is Worth Building?"

A personalized three-month program for people who understand who they are now and are ready to shift toward knowing what's actually worth building.

kevinsimcock_personalcoach_nextchatpermeaning

Shift 3 - Construct
"How Do I Make It Real?"

A personalized three-month program for people with a direction who are ready to shift from having a plan to living it.

This Isn't For Those Looking For A Quick Fix, Magic Bullet, or Someone To Do The Work For Them

KevinSimcock_personaladvisor_FindingPurpose
kevinsimcock_personal_advisor_identity_rebuild
kevinsimcock_personaladvisor_lifeaftercareer

Advisory Shaped By Experience

After nearly three decades in global creative leadership, I reached a transition where much of what had defined me no longer did.

What followed was a period of identity loss, psychological study, creative exploration, and entrepreneurial experimentation. I learned that understanding yourself intellectually is rarely enough. You also need experiences that reveal who you are when the old role is no longer directing your choices.

That insight became the foundation of RECLAIM.

My role is that of a personal advisor. I bring an outside perspective, challenge assumptions, recognize patterns, and help you evaluate what is worth carrying forward, releasing, or building next.

This work requires time, honesty, and a willingness to test possibilities beyond reflection alone. I provide the structure and perspective needed to keep moving when the answers are not immediately obvious.

kevinsimcock_personaladvisor_nextchapteraftersuccess
kevinsimcock_personal_advisor_whatsnext

Results That Give You
A Clear Path Forward

My approach combines private strategic advisory with creative experiences designed to help accomplished people reconnect with themselves, explore what is possible and make better decisions about what comes next. My role is not to provide you with all the answers, but to create the conditions in which you can recognize them on your own.

One-on-One: While most life coaches or executive coaching programs may offer cohorts and group sessions for finding your purpose, I offer personalized one-on-one advisory. This provides greater focus and dedication to your specific needs that can't be experienced in a cohort setting.

Structured Guidance: Using my proprietary methodology Reclaim™, your progress is focused on three core phases: Identity Decoupling, Realignment, and Next Chapter Construction. Through constant and constructive support, Kevin is alongside you every step of the way.

Accountability That Works: It's easy to start but it's more difficult to keep going when things get uncomfortable or uncertain. It's easy to fall back into old patterns and do what you've always done. I am here to support you and prevent that from happening.

Apply Today!

A Guide For Navigating Who You Were to Who You Are

In Whose Ladder Is This?, former global executive and creative director 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 rediscovery. 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.

whoseladderisthis_kindle
whoseladderisthis_amazon

Get Your Copy Today

whoseladderisthis_barnes&noble
whoseladderisthis_indigo_bookstore
kevinsimcock_WhoseLadderIsThis_author

Listen

What's Next After Success Podcast

Hosted by: Kevin Simcock

Honest Conversations For Rebuilding Who you Are & What's next

What's Next After Success Is for accomplished professionals who have built success but want to move beyond the version of them that created it. Each episode explores the realities of reconnecting with your purpose, sense of self and what's next.

  • What's Next After Success Spotify
  • What's Next After Success Apple Podcast
  • Youtube

Questions People Ask

kevinsimcock_personalAdvisor_nextchapter

180 John St, Toronto, ON M5T 1X5

©KevinSimcock 2026. All Rights Reserved

bottom of page