When Plans Meet Reality: The Case for Emergent Strategy - EP 053

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What if your plans are holding you back from bigger possibilities?

In this episode, I’m diving into the idea of emergent strategy—an approach to business that embraces flexibility, creativity, and responsiveness. The pandemic in 2020 revealed just how quickly plans can shift, and it invited many of us to rethink what it means to grow and thrive as entrepreneurs. Instead of clinging to rigid, step-by-step plans, emergent strategy invites us to pay attention to the patterns unfolding around us, adapt with intention, and stay rooted in our values and vision. 

I’ll share how holding plans lightly can open space for evolution and new opportunities, and why uncertainty can actually be a powerful source of creativity. Join me as we explore a more fluid, sustainable way to approach business and success.

Episode Takeaways:

• Emergent strategy contrasts with traditional planning methods.
• Adaptability and creativity are essential in business.
• Uncertainty can be a source of creativity.
• Planning should be flexible and responsive.
• Pay attention to emerging patterns in business.
• Hold plans lightly to allow for evolution.
• Intentional planning focuses on values and vision.
• Business success is not just about revenue growth.
  
  

Key Insights:

“There is so much power in holding plans very lightly.”

“Emergent strategy is not about abandoning planning or goals. It's about approaching them differently. It's about being deeply rooted in your values and your vision while remaining flexible about how they manifest.”

Resources I Mention:

• Emergent Strategy by adrienne maree brown
• Notes on Complexity by Neil Theise
• Interview with Neil Theise on Armchair Expert
• Spring Equinox: Rebirthing Your Business through Seasonal Wisdom - EP 041
  
  

Question for Your Reflection:

How can you create more space for adaptability and creativity in your work? What emerging patterns in your business might be pointing you toward new opportunities?

Connect With Me:

• Email: [email protected]
• Instagram: @RachelAnzalone
• Facebook: Rachel.Anzalone
• LinkedIn: RachelAnzalone

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Episode Transcript

It is early 2020, and I had my big, beautiful wall calendar laid out for the whole entire year. And then we all know what happened next.

Pretty quickly, I realized that this big, beautiful wall calendar that I had laid out to perfection was irrelevant. I remember the day that I took it off the wall, I crumpled it up, and I stuffed it in the garbage because there just was no scenario in which I could see, being able to plan or predict for the foreseeable future.

We could either cling to the plan and try to force it all to work regardless, or we could just let go and see what wanted to emerge instead.

Hello and welcome to Pleasure and Profits. I'm your host, Rachel Anzalone, and I wanna start today with a story that may feel familiar to you. Imagine that it is early 2020, and like so many of us, including all of my clients, I had my year mapped out. I had my big, beautiful wall calendar, fully laid out, dry erase markers in coordinated colors for different types of activities and events laid out for the whole entire year. And that planning included my wedding, which was scheduled for October of 2020. 

And then we all know what happened next. The world completely shifted overnight. And in a matter of days, weeks, everything had to change. When this happened, it was like every cell in my body was screaming, yes, it is time to slow down. Like we have just been on too fast of a sprint. 

Me, my clients, the whole world, it just felt like it was moving way too fast. And every part of me was just feeling almost a sense of relief of like, yes, let's just slow down for a moment and take a breath.

But for a lot of my clients, the response was actually the opposite. They had a visceral sort of, I don't know if it was fear or an intensity of just like, now we need to double down, we need to go harder, we need to make sure that we don't lose momentum during this time. And it was such a clash with my own sort of feeling of like what I needed and what I felt like we needed as a collective. And frankly, what I felt like some of my clients needed, but they weren't really willing or able to accept. 

And like I had contracts, I had clients, I had projects, we had all these things in the mix. And in an effort to keep up for a few months, I stuck to my calendar and I stuck to my plan. And then I just reached the point where that just did not seem feasible anymore. It seemed, it felt in every fiber of my being, like I just had to put on the brakes.

And when I did that, I realized that I either needed to cancel or postpone or just reschedule so many things in my life, including my wedding. 

And pretty quickly, I realized that this big, beautiful wall calendar that I had laid out to perfection was suddenly completely irrelevant. And I remember the day that I took it off the wall, and I crumpled it up, and I stuffed it in the garbage because there just was no scenario in which I could see being able to plan or predict for the next few months for the foreseeable future.

And what was happening during that time on a grand scale that so many of us were experiencing was, our own personal lives were changing, our work lives were changing, the market was changing. Everything that we knew and everything we were accustomed to was in the process of either becoming completely obsolete or evolving into something completely different, barely reflecting the life or the experience that we had been having previously.

And so it was apparent to many of us that we had two choices to make. We could either cling to the plan and try to force it all to work regardless, or we could just let go and see what wanted to emerge instead, see what the next evolution or the next iteration would be without trying to control the outcome.

And that difference between planning in detail, planning to perfection, and allowing for the emergence to happen is what we're diving into today.

The question underlying all of this is, what happens when your carefully laid plans meet reality? And reality isn't what you expected it to be. What if instead of seeing disruption, which is inevitable, as failure, we could see it as information? And what if there was a way to build businesses that are both intentional and adaptive, both strategic and responsive to what's actually happening around us, in our lives, in the market, in the world at large.

So today we're exploring emergent strategy in business. It's a different way of thinking about planning and growth that embraces change rather than resisting it. And in the next episode, we'll dive even deeper with leadership strategist Gina Gomez, who's been using these principles to transform businesses for over two decades.

But before I share that episode with you, I want to lay the groundwork, starting with what exactly is emergent strategy?

Emergent strategy is a term from strategic management. It originates with management scholar Henry Mintzberg, who contrasted deliberate strategy, what leaders intend, with emergent strategy, the consistent pattern of actions that form over time as an organization responds to real conditions.

Decades after Henry Mintzberg coined the term, writer and facilitator adrienne maree brown brought the concept into the worlds of social justice and movement building, expanding it with insights from complexity, biomimicry, and relational practice. I was fortunate to be introduced to adrienne maree brown's book around this time. It was in 2020 or 2021.

When I read this book, first, it was like my entire being was just screaming, yes, yes, yes, as I was reading. You can see if you're watching this, if you see the video of this on YouTube, I have 10,000 page flags and highlights through the entire book because it was so profound as I was reading it. felt as if, you know the difference between when you read something that's like new information and your brain is trying to process it and understand it and decide if it makes sense or not and you're being really analytical about it? 

This book, reading this book was not that experience for me. Reading this book was like reading my own history. It was like reading my own essence, my own understanding of the world and having somebody take these ideas that I have been leaning into and these experiences that I knew to be true on so many levels and just articulating them in the most beautiful way possible. And the entire time I was reading it, I just kept thinking that all of this applies to every aspect of life. 

It was written for the social justice and movement building worlds, and yet it applies to every single interaction that we have as human beings and it applies to business in the way that I want to do business, which is in alignment with nature and in flow and it just beautifully encompasses all of that. It just weaves so beautifully into everything that I am leaning into, that I'm wanting to connect more with, that I am evolving in my own business and supporting my clients and evolving in their business, and where I feel we really need to be moving as a collective of entrepreneurs who want to do business in a way that's really just more in alignment with our humanity, with nature, with the way the world works instead of forcing against it.

And another piece of this that I think is really compelling is that the framing in this book is deeply influenced by complexity theory. And again, this was one of those moments where I listened to an interview with Neil Theise, and I'll share the link to these books and this interview in the show notes. 

I listened to the interview with Neil Theise on the Armchair Expert podcast, and I just loved what he was saying so much. I loved what he was presenting and how he was presenting it. And then when I read his book, Notes on Complexity, again, it was just like, yes, this feels like the truth to me in such a powerful way. 

And so these two pieces of literature, these two philosophies, these two theories of existence, weave so beautifully together. And I think as we talk through this, you'll recognize the parallels. And one of those key parallels is that order doesn't always come from top-down control. It emerges through interactions and adaptations and through relationships.

At its core, emergent strategy is about recognizing that effective strategy doesn't just come from top down or from some predetermined plan. Instead, it emerges from small intentional actions that respond to what's actually happening in real time. 

So think of it like gardening, which we've talked about in the spring equinox episode, in the summer solstice episode with my friend Krissy Shields, we talked about the parallels between gardening and business building and all of our interactions in life. And one of the things we talked about in detail is this idea of planting with intention, but then not being in control of all of the variables, like the weather and the soil and just the flow of the seasons have their say in what actually is produced. So your role as a gardener isn't to control every single leaf, but to tend to the conditions to the best of your ability so that growth can flourish in its own way.

One of the ways that this comes alive in business is through a framework that my guest Gina Gomez will share with you on the next episode of Pleasure and Profits. And this framework is called ACES. It stands for Adaptability, Creativity, Evolution, and Strategy. So I will let Gina unpack this in detail on the next episode. You'll hear that conversation. 

But for today, I'll just say that these four qualities capture exactly how emergent strategy looks in practice. And I love these ACES also mirror what complexity science is teaching us. So adaptability reflects self-organization. Creativity is emergence itself, new patterns arising out of interactions. Evolution is not linear. Small changes can lead to really big shifts. And strategy is about coherence, finding a steady through line without needing total control.

One of the beautiful things about emergent strategy is that it honors both your vision and reality. You can have a clear sense of direction, a strong sense of values, a deep knowing of what you want to create in the world, and you can hold all of that lightly enough to let it evolve as you learn and grow.

Now, before we go further, I just want to be clear that I'm not anti-planning, not at all. Planning is so important. Having goals is important. Having step-by-step actions to take is important for us to move forward. And otherwise we would just be, you know, floating in ambivalence forever, right? But I think we've been taught to plan in ways that set us up for frustration and failure that doesn't have to be the way things are done. 

So traditional business planning often operates from the illusion of control. It's based on this idea that if you just do A and B and C, then you'll get the result. You'll get D. And it's neat and tidy and predictable. And it makes for great marketing copy. And this is one of the challenges that I see, especially in the digital marketing space, is that this idea of a formula where if you just follow these specific steps, you'll get this perfect result.

That sounds so appealing and it's so easy to sell that, but in reality, that's rarely the case. Occasionally it works out that way. If all of the conditions are aligned perfectly for that, but there are so many variables all the time in every circumstance, that there is absolutely no way that you can promise that result for any, even percentage of people in reality. 

So as Neil Theise reminds us in Notes on Complexity, uncertainty isn't a flaw in the system. If you follow the plan and you don't get the result, it's not because you failed or because the system failed. It's because our perception of the system was incorrect. Uncertainty is not a flaw in the system. It is the engine of creativity. Complex systems thrive because they're unpredictable, not in spite of it. And the same is true for business. So when we cling to rigid certainty, we choke off the very conditions that allow new opportunities to emerge.

Here's what I've learned after all of these years in business. That linear approach works for some people, some of the time. But for the majority of us, especially those building values-driven creative businesses, that rigid approach can become like a prison. And then what happens when we feel like we're being overly constrained is we rebel and we resist. And so it becomes counterproductive.

So we don't get the result by following the rigid approach and we don't get the result we're looking for by completely resisting the rigid approach either. It's about finding the sweet spot where we have the structure but we hold it loosely and allow for things to evolve. 

I cannot tell you how many conversations I've had with clients who are beating themselves up because they're behind on their plan, because they set a goal to hit a certain revenue mark by the end of the year and you know, maybe it's August or September, October, and they’re nowhere close to that goal. And so they decide that they're failing or they go into a panic that they have to like double down and work twice as hard. And they force themselves to follow through with their plan, even though it's not producing the desired results.

And some of the time this is because that plan, that initial plan was so overly ambitious that there was no way somebody could have executed it the way that it was laid out. And then they end up falling behind on a plan that they never could have kept up with. And things just keep snowballing to the point where it just feels like they're failing all the time.

The cost of this kind of inflexibility is enormous. We miss opportunities because they don't fit our predetermined idea of what success will look like. We continue strategies that aren't working because they're part of the plan or because somebody else told us that this is the way to do it. And we burn ourselves out trying to force outcomes rather than responding to what's actually happening around us.

What I see that works in a more effective way and what I encourage my clients to do is to lay out that vision for the year and plan in varying levels of detail from one to three to six months out and then adapt and flow based on what actually occurs. And holding that vision for the year and a loosely held plan for the year, but focusing on just what are the next steps to take right now and in the next couple of weeks and whatever shorter time period feels aligned, that that allows for more focus, more productivity, because we're not being pulled in so many directions. And then it allows for things to evolve in a way that feels really natural and allows for opportunities to spring up that we couldn't predict for.

There is so much power in holding plans very lightly.

So what exactly does emergent strategy look like in practice? Let me paint you a picture of this. Imagine that it's March, and you're reviewing your numbers for the year. You realize that you're running about 20% under your revenue projections. In a traditional planning mindset, you might panic, you might push harder, or you might just accept that you're not going to hit your numbers for this year. But with emergent strategy, you ask some different questions.

What is this information telling me? What wants to shift here? What new opportunities might be trying to emerge in the circumstances? So maybe a particular service that you want to sell isn't going the way that you thought it would, the way you expected, but you're getting a lot of requests or a lot of indications that something else you hadn't planned for might actually be a better offer or a better experience to deliver at this particular time.

Maybe your audience, your customers are responding enthusiastically to something that you thought was just a little side project or a little side offering, but maybe they're telling you that that's what they actually want. And maybe the market is shifting in a way that creates a completely new opportunity for you.

The key here is being willing to adjust your strategy based on what you're actually learning and not just powering through with the original plan. This requires intentional planning versus goal-based planning. When you're planning with intentions, you focus on your values, your vision, the impact that you want to make. You're asking, how do I want to feel in my business? What kind of leader do I want to be? What kind of impact do I want to have?

When you're overly focused on the goal, focusing solely on a specific outcome, the exact revenue number, the exact launch date, the exact way things should unfold.

But here's the thing, intentions are steady, they're consistent. They can guide you through all kinds of changes and pivots. But goals, goals can become outdated the moment you set them. They can become outdated in a matter of hours or days or months when circumstances around us change and evolve.

This is the reason why I always ask my clients, what is the end game? I want to know what are you really trying to create? Not the surface level goals, like I want to sell X amount of this product or I want to hit this revenue goal. But what's the deeper vision? What's the impact that you want to have? What's the experience that you're looking to create, not just for your customers, but also for your team and for yourself? Because when you're clear on the end game, your real reason why, you have so much more flexibility in how you get there.

This is often the circumstance I find when clients come to me thinking that what they really want is to increase their revenue. And then when we dig deeper into the reasons why and the layers behind that, very often it's because they actually want to be more profitable. They want to be paying themselves more. They want to be able to pay their team more. They want to be able to invest in certain things in their business.

And being more profitable doesn't always require more revenue. It doesn't always require increased growth. Sometimes it requires optimization of systems. Sometimes it requires focused attention to the financials of your business, where money can be found in ways that you've never even considered if all you're focused on is hitting a top line revenue goal.

So here are some examples of what this really looks like. We've talked about this many times, seasonal rhythms. Instead of maintaining the same pace year round, you might notice that your energy and your audience's needs naturally ebb and flow around the calendar. Maybe summers are perfect for community building while winters are ideal for deep work or creation, or maybe everybody, including you, is looking for a little bit of downtime in the summer or around the holidays in the winter.

And planning for that and allowing for those ebbs and flows gives you so much more grace. And it's often in those time periods where creativity comes to the surface.

Product evolution is another way. So maybe you launch something expecting it to serve one need, but you discover that it's actually solving a completely different problem. Instead of forcing it back into your originial vision, you let it evolve into what it wants to become.

Revenue strategies. Maybe you planned to grow through one-on-one client work, but you discovered that you're naturally attracting opportunities for speaking or for partnerships. And instead of dismissing those because they weren't part of your plan, you explore where they might lead. 

Team building. Rather than hiring based on a predetermined organizational chart, you notice what kinds of support your business is actually calling for and you build your team responsively. And you take into account the variables between team members. You might think that you need to hire someone for a specific role. And in the process of interviewing people, you find someone who really fits into like two or three different categories or has something that they're really passionate or excited about. And they're a perfect fit for your team, even though they're not the exact fit for the role that you were looking for.

The common thread running through all of these is attention. In complexity science, we'd call this noticing patterns. In business, it's the same, paying attention to what's emerging rather than just pushing through with what was planned.

Emergent strategy requires that we pay attention to our numbers, to our energy, to our audience, to the broader environment that we're operating in. It requires that we get comfortable with not knowing exactly how things will unfold while staying deeply connected to why we're doing this work in the first place.

So how do you actually implement emergent strategy in your business? Here are some essential practices. Regular reflection and assessment. This is not just looking at your revenue numbers once in a quarter. This is checking monthly or even weekly with both the quantitative and the qualitative data. How are you feeling? What's working? What's not? What patterns are you noticing? What wants to shift here? 

Creating space for experimentation. Building buffer time into your plans, leaving room for the unexpected, for opportunities, for the creative tangent you might go on, for the pivot that might emerge. This might mean not packing your calendar completely full or keeping a portion of your budget available for new opportunities.

Building feedback loops, staying closely connected to your audience, to your clients, to your team. What are they telling you, both directly and indirectly? What patterns are you seeing in their responses, in their questions, in their needs?

And this one that's so important, developing comfort with uncertainty. This I think is maybe the biggest shift that so many of us have to make. Most of us have been conditioned to believe that not knowing exactly what's coming next is a problem that needs to be solved. But emergent strategy requires that we get comfortable with uncertainty, that we use that uncertainty as information and not a measurement of success or failure.

And again, this is where science meets strategy. Complexity theory shows us that uncertainty is where creativity lives. Systems, whether they're cells or ecosystems or businesses, evolve by allowing uncertainty to generate new possibilities.

When you approach business this way, you're not fighting against chaos. You're aligning with the way that life itself operates. So how do you know if you're being too rigid in your approach? Here's some warning signs for you. 

You might find yourself continuing strategies month after month that consistently underperform just because they're part of the plan. You might refuse to explore opportunities because they don't fit into your predetermined timeline or structure. You might find yourself working incredibly hard, feeling burned out, and yet feeling really stuck despite all of that effort. You may find that you're so focused on your original goals that you're missing what's actually trying to emerge right in front of you. 

The antidote to all of this is conscious flexibility. It's being willing to hold your plans as hypothesis rather than commandments. It's letting it be a little bit of a game, asking what if, instead of stating how it must be. It's staying deeply rooted in your values and vision while remaining open to unexpected ways that might manifest.

Now, so far, I've been describing emergent strategy in broad strokes, in very conceptual ways, because I want you to have an understanding of what this all means and start to marinate on what this might all mean for you. And in the next episode, we're going to get way more practical with it. I'm talking in the episode with Gina Gomez, who has been applying these strategies and these principles in the real world for over two decades.

So Gina's background is really fascinating and it gives her such a unique perspective on adaptive strategy. As she shares in the episode, she’s worked in a lot of environments that really required some very quick adaptability in order to survive and in order to support the businesses to thrive. And later on, she moved into DEI work and realized that she's been practicing this emergent strategy all along and didn't realize that it had a name very similar to my own experience.

Gina has a really beautiful way of weaving together strategic business insights with what her clients describe as metaphysical transformation. She honors both the practical realities of running a business that drives visionary leaders. 

In our conversation, we'll explore her ACES framework in much more detail. We'll talk about how to know when it's time to pivot versus when to stay the course. She'll share stories from her decades of helping leaders navigate complex challenges, and she'll give you concrete tools for building what she calls adaptive leadership into your business. 

So my invitation is for you to take what you've heard today, and start to consider what areas of your business feel like maybe they're a little too rigid. Where are you forcing outcomes rather than responding to what wants to emerge? What would it look like to lead with both intention and flexibility? 

So here's what I want to leave you with today. Emergent strategy is not about abandoning planning or goals. It's about approaching them differently. It's about being deeply rooted in your values and your vision while remaining flexible about how they manifest.

This week, I invite you to notice where you might be gripping too tightly. Where are you trying to force outcomes? Where might you be missing opportunities because they don't fit your predetermined path? And I invite you to experiment with holding just one area of your business a little bit more lightly, not carelessly, but with a kind of attentive flexibility that allows for new possibilities to emerge.

Remember, the goal is never perfection. The goal is responsiveness. The goal is building a business that can dance with change rather than be broken by it. 

And as both adrienne marie brown and Neil Theise remind us, that's not just a nice metaphor, it's literally how life works.

Thank you so much for being here. Thank you for listening. If this episode resonated with you, I invite you to share it with someone who you could discuss it with, have a conversation, and explore what these possibilities mean for you and your business.

And be sure to subscribe so that you don't miss the next episode's conversation with Gina Gomez about adaptive leadership and emergent strategy. 

Until then, stay curious, stay flexible, and keep building businesses that serve both your bottom line and your soul's calling. 

And remember, your pleasure is your power. Take care.