Work with Me
Hi! I’m Stephanie Pollock — a leadership coach who’s spent 18+ years working with ambitious women navigating the questions that don’t have tidy answers. Questions like: what do I actually want now? Is the success I built still the one I want to keep building? How do I lead — and live — in a way that feels like mine?
This is the home for the different ways we can work together, from free to deep. Wherever you are, there’s a place to start.
Start Here (Free)
If you’re new, begin with the writing. My weekly essays explore ambition, human-first leadership and the interior life of accomplished women — the questions underneath the questions.
A good place to start is Root to Branch, a seven-week series on rethinking how you carry your ambition, built around my Ambition Tree framework.
No cost, no commitment. Just a way to see if how I think resonates with how you’re thinking.
Become a Paid Subscriber
The deeper layer of Leaders in Progress — for the women who want to do the work, not just read about it.
A paid subscription is where the real practice lives. It includes:
The Ambition Edit — my guided diagnostic for getting honest about where your ambition actually stands (available June 3)
Seasonal arcs — each season, we explore one dimension of ambitious living together, with a guiding theme, focused reflections and a sense of moving through it as a group rather than alone
Monthly Leadership Letters — a more personal monthly note on what I’m thinking about, noticing and reading, delivered in writing and audio
It’s the most accessible way to go beyond the free essays and actually do the work — at your own pace, in your own time, with the structure to keep you moving.
**Save 20% with special Ambition Edit pre-launch until June 3, 2026.
The Ambition Intensive
A focused 90 minutes with me — plus the full Ambition Edit.
Sometimes the work you most need can’t happen in an essay. It needs a real conversation.
The Ambition Intensive is for the woman who can feel that something about her ambition has shifted — and she’s ready to figure out what it means for her now, in this season of life.
Here’s how it works: you complete the Ambition Edit beforehand (my guided diagnostic for getting honest about where your ambition actually stands). Then we spend a focused 90 minutes together, making sense of what surfaced — what’s grounding your ambition, what’s depleting it and what it’s asking of you now. You leave with clarity on what matters most and what to do next.
It’s focused, honest and built for women who are done waiting for the right time to pay attention to this.
$495 $395 including the full Ambition Edit.
Only a handful of spots available at a time. Special pricing if session booked before June 25, 2026.
The Ambition Reset
Six sessions. The deeper work, over time.
For the woman who wants more than a single conversation — who’s ready to do sustained work on what her ambition is becoming and how she wants to lead and live going forward.
The Reset is a six-session 1:1 engagement. We use the Ambition Edit as our starting place, then work together over time to develop real clarity and a path forward that’s genuinely yours — not borrowed, not inherited, not running on autopilot.
This is depth work. It’s for the woman who’s ready to stop circling and start moving. If you’ve already purchased the Ambition Intensive, you’ll have that investment credited toward the Ambition Reset.
$2500 CAD, including the Ambition Edit.
Book a free call to see if it’s a good fit.
Leadership Coaching
For when the work is bigger than ambition alone.
Alongside my ambition work, I coach women leaders on what it actually means to lead right now — in a world that keeps shifting under us, with all the change, uncertainty, and complexity that comes with it.
This is leadership coaching of the human kind. Less about frameworks and competencies, more about how you show up, stay grounded, and lead in a way that’s true to who you are — especially when there’s no clear playbook.
If you’re navigating a transition, a stretch role, a hard season of leadership, or simply the question of how to lead more like yourself, this is the work we’d do together.
Not Sure Where to Start?
A paid subscription is the most accessible way in — the Edit, the seasonal arcs, the Leadership Letters, all at your own pace.
The Intensive is for focused clarity — the Edit plus a single deep session with me.
The Reset is for sustained 1:1 work over six sessions.
Leadership coaching is for the broader work of leading well through change.
And if you just want to read and think alongside me for a while first, the essays are always here, always free.
Have a question, or not sure which is right for you? Reach out — I’m happy to help you find the right fit!