An entrepreneurial rite of passage: how I navigated pivoting my business, and how you can too

Jun 9, 2020


Though I wrote this article before the tragic events of the past few weeks, I see that many of us are now faced with pivoting our business in a new way, that recognizes the privilege and racism that may be embedded in our way of being and our way of doing business.  And so, if you are questioning how to change – how to become an entrepreneur or business with social justice as a central value, for example – I hope that you can read this article through that lens and that it is of value to you as such.



I am learning that entrepreneurship, by definition, requires constant change.  I feel as though, in the past five years of leading my business, I have pivoted approximately 935 times, in big ways and in small.


If I’m being honest, I’ve often thought: “oh my goodness, I’m changing again.  I am such a flake.  Why would people want to work with me when I can’t just seem to do one thing consistently?”

The wise part of me reminds me that this is actually called evolution and a commitment to learning and growth, not flakiness.

I’m guessing that if you’re reading this, that’s what you’re here for, too.

And I think that radical transformation in the tiny universes of our businesses is the norm – not just because of constantly changing markets and trends, but because of our collective desire to have our work reflect our authenticity, our complexity, and to be one big creative project.


A client of mine recently referred to the radical transformation she was experiencing in her business as “stepping into the work of her 40s.”


I had a full body FUCK YEAH.


As we talked, heads nodding and smiles broadening, we agreed that the work of your 40s is the culmination and weaving-together of a body of work and learning and growth.  It’s a reflection of our deepest desires, and the fact that we have fewer and fewer fucks to give about what “success” looks like (or at least the way we defined success in previous decades).

It’s more important to many of us that our work is meaningful and contribute to the world in some small way.

And so we dance with it.  We grow.  We pivot and change.

Over the last year, my work has gone through a radical transformation that felt bigger and gnarlier than any of the ones that have preceded it.  I wanted to share with you how I took (many many) doses of my own medicine and navigated this shift, in that hopes that it might help you process some of the change that you’ve made or want to make to your own work in the world.



The Catalyst.


Every major change begins with a catalyst, or series of catalyzing moments.  We can hope like hell that the catalyzing moments in our businesses come in the form of The Best Idea Ever while we’re in the shower one day, or meeting someone magical that we just have to collaborate with.  But, let’s be honest:  just as often as not, the catalyzing moments that end up being the harbingers of change are decidedly un-fun.

For me, it was a program that I was thrilled about launching, had spent months developing, that had royally flopped.  It was supposed to represent almost 50% of my revenue for the year.  During the process of the launch, I had a terrible health scare that I couldn’t help but feel was a sign, perhaps, that I was headed in the wrong direction.

The year leading up to that launch had been pretty categorically terrible for my business, in many ways, and I had headed in a downward spiral right along with it.  It was The Year of No Clients, and as we drained our savings and I became vitriolically jealous of anyone who I thought was “succeeding,” I knew things had to change.



Getting your feet on the ground.


I have become fond of saying that the first step in a process of radical change isn’t to set goals or *do things*:  I compare this time to being lost in the woods.  When you get lost in the woods, the first thing you’re supposed to do isn’t to barge through the underbrush looking for a way out; it’s to sit down, get your bearings, and attend to your needs.

And so it is with you.

And me.

As I found myself hurtling toward inevitable change in my work, I began to give myself lots of time to process and metabolize what had just happened and where I was.  For me, that meant plenty of long walks, and writing.  I called a halt to everything else I was working on at the moment – and rightfully so; all of a sudden, nothing felt like it fit anymore.

It was a wicked case of what I thought was writer’s block that finally tipped me in the direction I would eventually find myself moving toward.  For months and months, I had filled the squares of Instagram with bold and beautiful poetry and proclamation and provocation.  My writing was resonating deeply with the people in my orbit, and I would get messages every day about how my words had impacted them.  But I was also going through a time when my words were full of the rip and roar of rebellion:  there was a great deal of talk about smashing the patriarchy and waving my feminist flag, and while it got everyone’s knickers in a twist, it was nothing to build a business on.  I was offering no one tangible support or a clear indicator of how I could help them.  I began to notice that the writer’s block I was experiencing was actually the slow deflation of the riled up passion I had been expressing and that it was replaced by a completely different energy.  It was softer.  It came from my feet, or below them, and felt like solid ground:


But how can I help?  How can I be of service?


I was navigating scary territory in my health journey, and I was circling regularly with women whose lives were just. fucking. real:  there were no bra burnings and no one comparing themselves to this goddess or that (although there were always tarot cards; let’s be real) – there was just LIFE.  Heartbreak.  Healing.  Creativity.  Confusion.  All of it.

And so it is that getting quiet for a while, and paying close attention to what was moving me – what I was moving away from and what I was nudging toward – helped me to hear The Call into the next iteration of my work.

If you’re going through a shift in your business, or think one might be on the horizon, can you give yourself the gift of time to feel the uncertainty of that, and follow the breadcrumbs of what’s next instead of crashing through the woods trying to make things happen?  What are your favourite ways of processing what’s going on in your life?  Maybe you can walk in the woods, write in a journal, or talk it out with someone.  Focus on the parts of your work that are working well or can be automated in some way so that you can take the time you need to reorient yourself.



Let it go.  Seriously.  Let. It. Go.


The next part was where I levelled my business to the ground.  In my imagination anyways.  I started back where those entrepreneurship 101 books tell you to:  what do you love to do?  what are you good at?  what’s working well?  You know, that stuff.

In a way, this was a bit of a Tiny Experiment (I’ll get to those in a few paragraphs):  I indulged a curiosity, with coloured markers and blank paper, about what would happen if I completely started over.

It was a safe way to experiment:  I wasn’t rewriting my website or making any proclamations on social media, but even just imagining myself within the context of a new way of working was enough.  I imagined new directions my current work could take, and even dreamed up a whole new business idea.

What flooded through me during this time was a little bit of excitement, even more confusion, and a tremendous amount of grief.

Especially as entrepreneurs and especially in work that we are deeply passionate about, where everything we put out into the world was our creative baby at some point, we become deeply identified with the work we do.  It’s a part of us.  That’s what makes failure and pivoting in our businesses so hard, I think.

If there’s anything I might offer you here that is possibly a breath of fresh air as compared to the hyper-masculine start-up culture-drenched business advice you so often read, let it be this:  take time to process your grief around shift to your business.  Even if you’re excited for The Next Thing, acknowledge that you are leaving behind something you probably worked hard to create.   Hold that program, that idea, that product a little celebration of life ritual, if you feel called.

And go easy on yourself, too.  As a heart-based entrepreneur, somewhere deep inside you might be wondering: “Who am I, anymore, if I’m not….(taking 1:1 clients anymore, making that line of jewellery, or whatever it is).”  Pay attention to that feeling.  Give it some room to breathe.  The change you’re making is not just a shift in the identity of your business, but in your own identity, how you show up in the world, how you’re of service, and how you answer the call of the work you’re meant to do.



Give it time.


I know:  this is reading like the most anti-late-capitalist-patriarchy business advice ever.  It’s unusual.  Bear with me.

In every process of radical transformation, after we release what is no longer, there is a phase of liminality; of not-knowing.  During it, you’ll likely find yourself saying “everything is up in the air!” to everyone who will listen.

It is sooooooo uncomfortable.  Especially in said late capitalist patriarchy.

But in the world of heart-centred business, you need time to shift into this new manifestation of your work if it’s to be authentic and true.  Just filling the uncertainty with the next Thing You Think Will Sell Like Hotcakes might work for a while, but doesn’t allow you to mature into the new role you’re readying yourself to occupy.


You’re in the cocoon.


(also, let me be clear:  during my own process and when I’m supporting this process for my clients, it’s not like we’re all just tromping around through the woods pondering and not paying any bills.  This hearty reflective work is built into and around the parts of the business that are still ticking along)

My personal cocoon of liminality lasted months.  I wrote very, very little.  I went on a retreat that was well out of my usual context.  I jotted notes and ideas on those colourful papers as I imagined my way into different ways of working, and I sat with those ideas, allowing them to percolate.

But I did give myself a deadline.  I decided that if I hadn’t made a decision about the new direction of my work by Fall, I would seek external support.



Fire it up.


During that Summer of Confusion, I did begin to devise some Tiny Experiments to help me nudge at where I was headed next.

Tiny Experiments are rooted in complexity theory, or the idea that shifting and changing complex systems is, well, complex.  That you can’t necessarily know what the “right” thing to do is and then implement sweeping change On Monday.  In my work I have come to learn that women and the ecosystem of their lives are complex systems, and that shifting our lives, and indeed the businesses we create, is best approached with small shifts that nudge us in the desired direction, accompanied by a ton of real-time feedback along the way.  Tiny Experiments are by definition “safe to fail’ experiments, designed for gathering information and learning, not necessarily for “success.”

So, I created a couple of new offerings and tried them out with small groups of people.  I took the time to look deeply inward rather than solely toward my clients’ experience during these times, and noted what made me feel lit up and what didn’t.  I took notes about the work I had already been doing, too.  After every client session, retreat or women’s circle I would ask:  What about this do I love?  What is starting to feel stale, or what am I beginning to feel resentment about?  Does this offering belong in the new iteration of my business?

Some of my tiny experiments were “thought experiments.”  I would imagine myself in a new role, offering a new service, and see how that felt.  I read a lot of books that helped me explore new directions for my work, and noted what got me excited and what didn’t quite feel like me.

After a summer of Tiny Experiments, I knew a lot more about the direction I wanted to move in, but I also began to feel a lot of fear about shifting my business.  I noticed that I was beginning to enjoy Tiny Experiment Phase a little too much, devising more and more experiments that, ultimately, I realized, were beginning to act as a delay tactic rather than an information-gathering tactic.  It was time to shift.



Shift, shift baby.


My Tiny Experiments had gathered momentum in what would become the new direction of my work, and I was ready to make some bigger shifts – to “amplify what worked” about my experiments and begin to enact real change.

I realized first, though, that my fear of jumping with both feet into this new direction for my work was pointing me back toward some unfinished business.  I needed to complete the process of grieving and letting go of the work that I was leaving behind.

For me, at the heart of the shift I was making wasn’t so much changing my work as it was getting clearer on what it was and what it wasn’t, who it was for and who it was not for.  I had spent five years clinging to my identity as a multipotentialite entrepreneur, and so making a decision to narrow my focus and get clearer about my niche didn’t feel like “business-savvy behaviour change” so much as a dramatic reorientation of how I saw myself in the world.


(so, the next time you watch a webinar that asks you to just do this thing – like start a mailing list or show up more on social media or raise your prices – if it feels gnarly it might not be “resistance” or a “scarcity mindset” but in fact a request that you shift your identity.  You may be shifting from being a person who values accessibility of services and social justice to someone who needs to raise their prices to make a living, which also requires you to be a person who has a deep, steady sense of worthiness, for example.  Please don’t let anyone convince you this is simple, and then tell you you did it wrong because you didn’t follow the right steps.)

What happened next?  I hired a coach, and in doing so, I unearthed some deeply held fears and beliefs and ways of identifying myself that, once brought to the light, I could begin to transmute.  And then, finally, I made a decision. It didn’t feel totally right to me at first (see also:  not every right decision has to be a Hell Yes.  It’s okay to be unsure or afraid).  But I stuck with it and promised myself that, actually, very few decisions are permanent.  And so I spent the next few months redesigning my website, writing and creating and feeling my way into a new language for my work.  By the time that process was complete, so was I.  It took time to feel like I belonged in this new “skin” and, like any radical transformation, sometimes it just takes living it to fully embody it.



Honour it.


In times long ago and places far away, when we traversed radical change, the process was always accompanied by meaningful ritual to help honour, metabolize, release and celebrate the transformation.  And so, here we are.  As you’re reading this, I am engaging in a week-long series of rituals that are sort of like me, holding my own hand, and crossing the threshold into this new way of being.  Along with sending out this blog post, I am spending time with another friend who is also pivoting her business, doing things like burning old business cards and setting intentions for the future; I added some new decor – butterfly paintings, to be exact to my office to represent my transformation; I am taking some time for deep rest.

Ritual can help you stop time for just a moment and acknowledge the process of metamorphosis you’ve gone through.  It doesn’t have to be fancy or witchy; ritual is simply a way of putting a memorable (hopefully also multi-sensory, delightful and magical) pin in the map of your life and saying this was important.


I hope that if you’re pivoting your business right now that you’ve found some support in these words.  Be gentle on yourself.  It takes time.  Your confusion and your uncertainty is a willingness to grow and evolve authentically and in integrity, not a failure of your entrepreneurship.  And when you feel ready to step into your new way of working, you will have a body of work behind you that deepens the root structure of what you’re able to offer to the world, making it richer and more meaningful than ever before.



If you are also navigating a time of radical transformation in your business, I can help.


The process that I describe in this blog post is based on my 4 Elements Guide to Radical Transformation, which acts as the map and compass for my coaching with women navigating life transition and rites of passage.



Find out more about The Elements Sessions, the coaching and mentorship experience for women experiencing transition in any aspect of their lives, right here.

The Becoming Podcast has been on a short hiatus while I focus on writing my book, but oh what a comeback episode I have for you!

This month, I spoke to Toko-pa Turner, who many of you may know as the unofficial patron saint of many of my circles and gatherings because of the sheer number of times I’ve quoted from the wisdom of her book, Belonging.

Toko-pa is a Canadian author, teacher, and dreamworker. Blending the mystical teachings of Sufism in which she was raised with a Jungian approach to dreams, she founded The Dream School in 2001, from which thousands of students have graduated. She is the author of the award-winning book, Belonging: Remembering Ourselves Home, which explores the themes of exile and belonging through the lens of dreams, mythology, and nature. This book has resonated for readers worldwide, and has been translated into 10 different languages so far. Her work focuses on the relationship between psyche and nature, and how to follow our inner wisdom to meet with the social, psychological, and ecological challenges of our time.

Here’s some of what Toko-pa and I talk about in this episode:

> The dream that changed Toko-pa’s life, causing her to question her career and, ultimately, her identity

> How we can court our dreams to support us during times of radical transformation – and the reasons so many of us have a hard time remembering and working with what shows up in our dreamscape

> Toko-pa’s perspective on the message of Belonging after the divisiveness our society has experienced in the years since it was published

> What happened for both Toko-pa and I when we fell out of belonging from the ideologies of the “wellness world”

> How to build community when you’re under-resourced

> “The Big Lie” when it comes to belonging, and how we can reclaim a sense of belonging to the greater family of things, as Mary Oliver so famously wrote

Listen to the episode on iTunes


Show Notes

Toko-pa’s Website

Belonging:  Remembering Ourselves Home, Toko-pa’s book

The David Abram video about animism mentioned in the interview

Toko-pa’s self-guided program, Dream Drops

Companion, the program that accompanies Belonging


Also, while you’re at it, if you enjoy The Becoming Podcast, I would be so grateful if you would rate and review, and even subscribe to it on iTunes.  That goes a long way to helping more and more people find and benefit from hearing these interviews!  Thank you so much!