Re-imagining our ambition: a year-long exploration

Join me and others as we unpack and rethink what ambition means to us at this season of our lives. And as we put in strategies, systems and supports to keep it all sustainable.

A year ago, I wrote my first post here on Substack.

I moved my newsletter to Substack — a platform designed for writers — because after 15 years of business-building online, I was tired and a wee bit bored.

I loved my client work (and still do!) but all the stuff that came with it — the relentless attendance to social media, the constant nudges to create sales funnels and webinar strategies etc — it all felt hard and not at all like me.

Add in everything else: a global pandemic, inflation, peri, devastating wars, mis-and dis-information, my father’s death, and raising teenagers in a complex, always-on world and I just didn’t have the hustle and grind in me anymore.

I wanted to get back to the work that mattered most to me: coaching amazing leaders (at every level) and sharing my ideas through writing (with some podcasting sprinkled in).

As my enthusiasm for the way I was working waned, my ambitions started to shift and change, encouraging me to explore a different way forward.

For those of you who aren’t Substack enthusiasts (and who simply enjoy reading my posts in your inbox), the details of the Substack move don’t much matter — but for me, the move marked a line in the sand and a declaration that I was following a new old ambition to invest in my writing, alongside my work as a leadership coach.

I was saying to myself: it’s time to give this ambition the place and space to flourish.

The weight of our unrealized potential

Early this week, I was speaking with a client and helping her map out her plan for the rest of the year. I’ve worked with her for years, and she’s a kind, smart and thoughtful small business owner with incredible value to bring to the world. Her work matters.

And…she’s had a string of unexpected health challenges this year that have put her in a perpetual state of one step forward, two steps back.

We’ve had to re-calibrate multiple times over the past eight months to keep momentum up with her plans, while also giving her the space and grace to recover and rest.

The way I’m writing this sounds straightforward and simple, however it’s been anything but. It’s never easy to be able to envision what you want for your life and work, all while feeling too exhausted or stretched to pursue it.

As we talked through things, I suggested that we build, plan and strategize to match where she is now rather than around where she wants to be soon. My hope was that we could create a business model that matched the season of her life and offered her room should another health challenge present itself, while still being able to sustain herself financially and keep her interests and motivation high.

The nuts and bolts of this plan meant she wouldn’t be doing as many things as she often hopes and plans to do. Instead, she’d simplify and get very focused on creating success around one core idea and offer.

The plan was sound and straightforward, but she hesitated as we finalized it.

And I knew why.

It was the same hesitation I had a year ago when I made the move to Substack to focus on coaching and writing, and letting go of ‘entrepreneurial empire’ building that everyone online told me I should be pursuing.

She worried this decision was downgrading her dreams. She feared that all the effort she’d put in this far might have been for naught. She was worried she’d be playing small.

I encouraged her to re-frame it as an opportunity to re-align her ambitions with her life now, rather than hold on to ambitions past. I reminded her that her ambitions weren’t being reduced, they were being redirected toward a way of working and living that would sustain her, rather than exhaust her.

She took a deep breath and said, “I’m in.”

Ambition, Re-Imagined

Starting in October, I’ll be releasing Ambition, Re-Imagined — a year-long exploration of how we can re-think, re-engage and re-imagine the role ambition plays in our lives.

We’ll take a fresh, more human-first approach to ambition, helping you reconnect with what truly matters, without burning out or losing sight of your core values. All while recognizing the cultural context under which the idea of ambition has lead to an unhealthy, hustle-oriented culture of pursuits at all costs.

My hope is that we can have a more expansive conversation about the place ambition fits in our lives and how we can re-imagine it so that no longer feels like a relentless quest to do more and achieve more, and instead a travelling companion of desire and drive toward our dreams.

Ambition, Re-Imagined will help us redefine our ambitions in a way that aligns with who we really are. It’s about:

• Living in seasons: Recognizing that different seasons of life require different kinds of ambition.

• Prioritizing what matters most: Ambition doesn’t have to be relentless—it can be intentional and grounded in values.

• Sustainability: How do we pursue meaningful goals without burning out or staying in overwhelm?

• Growth and progress on our terms: Pursuing ambitions aligned with our definition of success, not everyone else’s.

We’ll explore these ideas through monthly essays, community threads, and practical resources like worksheets, prompts, and templates—designed to help you integrate ambition into your life without sacrificing your well-being.

What’s next?

For now, I invite you to think about your own relationship to ambition.

Is it serving you? Is it still aligned with your vision for your life? Is it connected to the season you’re in or a relic of ambitions past? Over the coming months, we’ll dig deep into these questions.

If you’re not yet a paid subscriber, now is a great time to upgrade. By upgrading, you’ll get access to the full Ambition, Re-Imagined experience, including exclusive content, deeper conversations, and a growing community of like-minded leaders.

*Note: existing paid members! Watch your email next week for a special perk just for you.

How it will play out:

• Two in-depth essays per month on key themes like sustainable ambition, living in seasons, and redefining success (plus one extra essay in 5-week months!).

• Monthly community threads to dive into discussions together.

• Resource roundups with worksheets, prompts, book suggestions, and more.

• Plus extra pop-up workshops, small group offerings and more

If this sounds like the conversation you’ve been waiting for, I invite you to join us.

While much of the Ambition, Re-Imagined series will remain free, you’ll get many extra perks including the ability to connect with other leaders who are re-imagining their ambitions — by becoming a paid subscriber.

And you’ll be supporting me with my ambition to build my writing. :)

Here’s to re-imagining what’s possible, together.

Steph