Sherry Waddingham MBA, PCC

About Sherry Waddingham

Why Smart, Capable Leaders Get Stuck

(And How I Help Them Move Forward)

Accomplished leaders often come to me stuck in transition — even though they know what they should do.

They’re intelligent, strategic, and self-aware. They’ve made difficult decisions before. They understand their options.

And yet they still can’t move forward.

This isn’t a lack of discipline or clarity.
It’s what happens when unconscious patterns formed decades ago override conscious plans made today.

Most transition advice focuses on strategy: make a plan, take action, push through resistance.
But strategy isn’t why people stay stuck.

I help leaders work with both layers:

  • the conscious decisions they need to make

  • and the unconscious patterns blocking their progress

The result?
Changes that actually stick — because we’ve addressed root causes, not symptoms.

My Story

 

I Understand This Work From the Inside

For years, I ran a successful corporate career at full speed — MBA, senior leadership roles, the kind of drive people admire.

On the outside, everything looked right.
On the inside, I was running on autopilot, driven by unconscious beliefs about achievement and worth.

It wasn’t burnout.
It was a quiet identity shift I didn’t yet have language for.

I was successful by every external measure but increasingly disconnected from myself. The strategies that got me “there” weren’t aligned with where I wanted to go. But I couldn’t see the patterns beneath my choices.

What changed everything wasn’t better time management or a new career plan.

It was learning to work at the level where the real blocks lived:

  • childhood beliefs about worthiness

  • protective mechanisms that once helped but now hindered

  • identity attachments that made change feel unsafe

That experience taught me something fundamental:

You can’t think your way through an identity shift.
You have to work at the level where the patterns live.

Who I Am Today

 

Self-Leadership & Transition Guide

Today, I help leaders navigate transitions by working directly with what’s actually blocking them: the unconscious patterns beneath the surface.

I bring a unique combination of:

Former Corporate Executive

I understand the pressures, responsibilities, and complex dynamics leaders face because I’ve lived them — from the inside.

17+ Years Developing Deep Expertise in Leadership, Psychology & Human Behaviour

My work blends lived executive experience with advanced training in coaching, depth psychology, unconscious pattern work, and human development.

Professional Coaching & Facilitation Expertise

I’ve supported hundreds of leaders navigating uncertainty, change, and identity shifts.

A Distinctive Ability to See What Others Miss

I read patterns, emotional architecture, protective dynamics, and hidden drivers with clarity — helping clients understand what’s actually shaping their experience.

A Clear, Grounded, Insightful Communication Style

I integrate psychological depth with practical strategy. Leaders don’t have to choose between insight and action — they need both.

My Approach

How I Work

This isn’t surface-level coaching or generic mindset work.

This is depth work — the kind that helps leaders understand why they stay stuck even when they “know what to do.”

We work with two interconnected layers:

1. The Conscious Layer

Your strategies, decisions, goals, and practical next steps.

2. The Unconscious Layer

The deeper patterns, beliefs, protective mechanisms, and identity attachments quietly shaping your behaviour.

When these two layers conflict, the unconscious wins every time.

Real, lasting change requires working with both.
Once you understand what’s happening beneath the surface, clarity returns.
You stop fighting yourself — and start leading yourself.

Credentials

Background & Training

  • Professional Certified Coach (PCC), International Coaching Federation

  • MBA, Queen’s University

  • Psychology Certificate, Toronto Metropolitan University

  • Advanced Training in Depth Psychology & Coaching (in progress)

  • The Judy Project for Executive Women, University of Toronto

Additional training includes trauma-informed approaches, conflict facilitation, and personality frameworks that deepen my understanding of human behaviour and change.

Who This Work Is For

I work with leaders who:

  • Are navigating a career or life transition

  • Know what they should do but can’t move forward

  • Are successful on paper but misaligned inside

  • Keep repeating similar patterns in new situations

  • Want to understand the real source of their resistance

  • Are ready for depth, not just encouragement

  • Want transformation that feels lasting and integrated

Beyond the Work

Outside of coaching, you’ll find me walking my dog, working in the garden, experimenting in the kitchen, or reading about psychology, leadership, and how people change.

I am endlessly fascinated by what drives human behaviour — and what makes real transformation possible.

Next Steps

If you’re navigating a transition and tired of fighting yourself, let’s talk.

I work with leaders one-on-one and facilitate workshops and leadership development programs for organizations.

Real change begins here —
not in forcing decisions, but in understanding what’s beneath them.

Schedule a conversation to  explore how self-leadership coaching can support your next chapter.