How to Leverage "Both/And Thinking" in the Fluid Soups of Solopreneurship
The Solopreneur Series Free Issue No. 8
Ethical decision-making. Navigating ethical dilemmas. Part of life - AND - part of business. Part of business life and life business.
Last night, I took a course on ethical decision-making in sport. I’ve been a coach in various sports for nearly three decades. This past year, I’ve stepped back into coaching volleyball, as our youngest son is keen on the game.
Stepping back in, meant I also had to update some learning and certification — including the course last night on ethical decision-making in sport.
I’ve been reflecting on that today- and it was front of mind as I prepared this latest issue of The Solopreneur Series (Free Issue No. 8). As I was writing some notes in my Learning Journal this morning, it was clear this was a good topic for this issue.
Welcome to new subscribers!
There has been an encouraging influx of new subscribers over this past month. Thank you for being here. And, loving the increase in comments and shares of recent posts.
Balancing Action with Thinking (especially “Thinking about Thinking”)
Over the past week to two, I’ve written several articles and posts about our human hardwired “Action Bias” — the survival mechanisms hardwired into our brains over hundreds of thousands of years.
Often, “Acting” is a simple pathway in our brains and bodies.
For example, big hairy animal jumping out of the bush?
👉 RUN! SCREAM! FIGHT!
However, ‘thinking’ and rationalizing and weighing options places a heavier toll on our brains and bodies. It’s often messy, slow, and gets clouded and murkied by all sorts of things (past, present, and future)
Though evolution has wired us for action – quick, decisive, often binary – the realities of human life have shifted in many ways. Technology has made life far more ‘comfortable’ than it was a hundred years, a thousand years ago, or more.
We also now pursue things and live in communities and societies that instigate more decision-making… more thinking. And, yet there are so many influencers and impacts on our abilities to do that — to do it half-ass well — and to do it in ways which fit with the complex and fluid world we live in.
I was reminded of this a lot this past week to two, and it came to roost in my reflections on the course from last night.
It’s also deeply intermeshed with the world of business, being a Solopreneur, and thinking about a Solopreneur mindset.
Back Briefly to the Coaching Clinic…
I played volleyball quite competitively for many years — in my younger days — and coached (and played) quite a bit as an adult. I stepped away from coaching that particular sport when our kids were younger.
A lot has changed in coaching over the years. For me to even be an assistant coach with a local volleyball club, I had to do a bunch of upgrading to my certifications (including some valuable courses on things like concussions, injuries and more.)
This one I completed last night, on ethical decision-making was quite curious.
There were about 20 people in the evening class and a range in ages — from early 20s, to 30s, to a few of us in our late 40s and early 50s.
We did some theory and definitions (e.g. liability, negligence, etc.). And, some case studies. The 3-hour course is built around a continuum based on 3 types of ‘decision-making’ that a coach may face:
. Moral … Ethical … Legal
Much of the last half of the course was case studies. These included exploring, in groups, certain situations that could arise in a coach’s typical activities. Things like kids that may be injured, but being pressured to play by parents.
What to do?
Kids that may be struggling in their home lives and a coach becoming aware of this.
What to do?
Coaching older athletes and the potential for relationships between coaches and athletes.
What to do?
Some of the group work included some checklist activities for considering decisions and comparing them against a Code of Ethics, as well as identifying where on the decision-making continuum the particular situation existed (e.g. moral, ethical, or legal)
(Things have certainly changed a lot in coaching since I started in my late teens and early 20s. Moral and ethical decision-making was not part of required certifications when I started coaching)
Things Change…
Change is a steady constant in life, the world, and so on. And, things have definitely changed in the realm of amateur sports.
On one hand, it’s great to see more time, resources and efforts being directed toward making sports safer and better for athletes (and coaches).
On the other hand, I was struck by how many participants in the course wanted the “right answers” — for the case studies and discussion. However, the thing with many ethical dilemmas — and dilemmas in general — is that there are generally no ‘right’ answers.
A dilemma is not a “true” or “false” question.
The ancient roots of the word go back thousands of years to the Proto-Indo-European word “*(s)lagw” meaning "to seize, take". Over time this evolved into the Greek word lemma “something received or taken; an argument; something taken for granted."
“Di-” means two. So a dilemma, in ancient Greek meant a "double proposition". In the late 1500s, it came to mean “a choice between two undesirable alternatives.” Originally, it generally referred to a situation with two choices, each leading to an undesirable outcome.
It seems though, that this use (and meaning of dilemma) has softened over time — and is bandied about now as simply a difficult situation or problem.
In some ways, this is unfortunate, as difficult decision-making is not necessarily a “dilemma”. And, it may often include a wide suite of options — not just two difficult ones, with potentially undesirable outcomes.
And, the challenge with this is that a ‘dilemma’ by its etymology and words within — is, in fact, an Either/Or decision. It is either this one shitty decision here Or that crappy decision there.
It’s Binary.
However, difficult decision-making — across a range of options — is not Either/Or and sometimes can be supported and navigated with Both/And (a very powerful tool and way of thinking).
Either/Or Versus Both/And Thinking
The original concept of a dilemma involved a choice between two alternatives.
This binary structure is reflective of Either/Or thinking—where options are viewed as mutually exclusive and decisions force a choice between two opposing outcomes. (More often than not, shitty ones)
In contrast, Both/And thinking accepts that things often called ‘dilemmas’ are, in fact, often more complex than simply two choices. It recognizes that multiple truths can coexist and that solutions can involve a synthesis of different perspectives or options.
This approach challenges binary structures by finding value and possibility in integrating and synthesizing seemingly contradictory options. And, potentially mishing-and-mashing previously not thought of options.
However, schooling and education systems are built upon teaching and instilling systems of Either/Or thinking.
It is: ✅ or ❌
It is: “True” or “False”
And, last night I saw this in plain form. In discussions about the case studies, it was suggested by the content and facilitator that we were navigating “ethical dilemmas” — but we were not.
These were simply situations where coaches would have to make potentially challenging decisions.
And, the thing with making potentially challenging decisions and navigating situations where we don’t have all the information, are forced to make some assumptions and navigate situations with so many factors of uncertainty and fluidity… is that there is often no one RIGHT or WRONG answer.
Schooling and Embedded “Either/Or” Thinking
Traditional schooling often reinforces Either/Or thinking. For example, look to standardized testing, grading systems (right or wrong, pass or fail), and the structure of debate and argumentation taught in schools.
(Note: the word debate originally meant "to fight,." It comes from de- "down, completely" plus batre "to beat" — and so a debate means to beat down another position… Either/Or)
These systems largely teach, educate and embed in learners — binary ways of seeing the world. The result is limitations in perceiving nuance and complexity in real-world, real-life, fluid and changing situations.
It’s also often a race to the ‘right answer’…
Impacts on Decision-Making
This educational background frequently makes it challenging for individuals to adopt Both/And thinking later in life.
People trained to see the world in black and white may struggle to recognize or accept gray areas and muddy interfaces — leading to difficulties in handling complex, multifaceted situations, or a life that doesn’t fit neatly into binary frameworks.
The challenge in learning and adopting Both/And thinking lies in retraining the mind to see beyond binary oppositions ingrained by traditional education.
It involves developing a mindset that sees, appreciates, and values complexity, tolerates ambiguity, and seeks integrative solutions moving beyond simple dichotomies.
A central challenge of moving towards Both/And thinking often involves unlearning some of the binary ways of seeing the world that are reinforced by traditional schooling. This includes leaning into more nuanced, integrative approaches to complex and fluid problems and challenges.
I watched this in plain display last night. Younger participants, in their 20s, were very concerned about getting the “right answer”. About doing the exercise “right”. About making sure each ‘option’ and each ‘check-box’ was filled out correctly.
And, yet, it’s not entirely their fault.
They’re fresh out of (and some still in) schooling and education systems that have immersed and steeped them in that tea for decades.
But what if we challenge this binary?
What if we hold that Either/Or thinking that so many of us have deeply etched in us — place in a storage shed in our brain — and then open up to the possibilities of Both/And thinking?
Of approaching difficult decisions (maybe even actual dilemmas) — with a Both/And mindset?
This sort of mindset isn't just about making choices or decisions—it's about better navigating
in complexity,
in paradoxes (with increased comfort), and
with fluidity and flexibility in decisions.
Leaning into and building this can then assist in navigating the biggest bottleneck in every Solopreneur enterprise…
Or, anyone taking a Solopreneur mindset to various things in their life.
The Biggest Bottleneck for Every Solopreneur
The biggest bottleneck for every Solopreneur?
Them-Self!
As explored and outlined in the last issue of The Solopreneur Series (No. 7), the difference between an Entrepreneur and a Solopreneur — is that the Solopreneur is generally purposely: Solo.
That means most actions, choices, and decisions are made Solo — and all the work is done Solo (from cleaning toilets to writing articles and filing taxes).
And generally the pressure of “NOW” is ever-present.
In this regard, there are similarities shared with coaching amateur sport. Often a coach may be in a situation where they are faced with making challenging decisions right then and there.
In solopreneurship, there is frequently some demanding urgency requiring immediate attention and action. The next project, invoicing, bookkeeping, responding to emails, and so on, and so on…
The challenge is often more than just the volume of decisions but their nature and weight. It’s always just You.
No team. No admin support. No “Finance” or “HR” to call. Just you.
Thus, Solopreneurs often grapple with choices that are complex, murky and multifaceted. This is where binary Either/Or thinking doesn’t only fall short, it can be disastrous.
Often, these situations require a Both/And approach that is considering a spectrum of factors and potential outcomes — many of which can be paradoxical, heavy conundrums.
For instance, deciding whether to invest in a new project isn't just a matter of financial viability (Either/Or), but also considering personal values, short and long-term goals, market trends, and emotional well-being (Both/And).
This kind of decision-making demands a holistic view and the ability to hold multiple truths and possibilities in a fluid, flexible soup of options — without becoming overwhelmed by ambiguity and a thousand options.
Learning and leaning into Both/And thinking and mindsets — becomes more than just a skill but a necessity for Solopreneurs and Solopreneur mindsets.
Building these muscles, often requires continuous self-reflection, learning, unlearning, and the willingness to step beyond the comfort zone of binary choices (or at least perception of).
By doing this, Solopreneurs can work through (and with) their biggest bottleneck — them Self.
Tips for Building “Both/And Thinking”
For Solopreneurs (current and aspiring) building a Both/And mindset — and reducing the grip of Either/Or thinking — is incredibly beneficial for navigating the complexities of business and life.
I often use the dual realities of light as a fitting example. Light is Both waves And particles. However, you cannot see both at the same time. You can only see one or the other.
Here are some tips and prompts to help build this mindset:
Tips for Cultivating “Both/And Thinking”
Lean into Complexity: Acknowledge and appreciate that most real-world situations are complex and cannot be neatly categorized. When making decisions, consider multiple facets, angles and dimensions in play — for example through reflection (looking back), introspection (looking in) and prospection (looking forward).
Learn from Nature: Observe how nature works in systems where elements coexist and support each other in complex ways. Consider for example, where some situations are simply “good enough for now”. Reflect on how this interconnectedness and fluidity can be applied to your decision-making processes.
Integrate Opposites: Just like the duality of light, look for ways to combine opposing ideas or strategies in your business. Ask yourself how you might apply strengths of each 'opposite' to create a more robust, or simply different approach.
Expand Your Perspective: Regularly engage with content and ideas that challenge your usual way of thinking. Whether it's a book, podcast, or discussion, expose yourself to different worldviews and problem-solving approaches. Far too many folks start to exist in their own echo chambers.
Adopt a Fluid & Flexible Mindset: Lean into challenges and setbacks as opportunities for change. These sorts of things take on the meanings and definitions that we apply to them. They are not inherently ‘bad’ or ‘good’. Consider how each experience provides a chance to learn (unlearn) and how you can integrate these lessons into your personal and professional life.
Prompts for Building a Both/And Mindset:
Reflect on Contradictions: Think of a time when two opposing strategies or ideas led to a successful outcome in your life or business. What can this teach you about the value of synthesizing diverse perspectives?
Visualize Integration: Using the concept of light as both a particle and a wave, create a visual map of how different aspects of your business or personal goals can be integrated into a cohesive whole. For example, map one as waves and another as particles.
Contemplate Balance: Consider a situation where you felt torn between two options. How could a Both/And approach have brought balance and perhaps a more satisfactory resolution? Too often binary thinking locks us into Either/Or thinking.
Explore Interdependence: Identify areas of your life or business that seem to be at odds. How might these elements be interdependent or mutually exclusive areas? How could recognizing this curious relationship improve your approach and labelling of these things?
Question Boundaries: What are the 'either/or' boundaries you have accepted in your life or business? What ‘boxes’ might you need to cut out of? How might questioning these boundaries open up new possibilities?
Exploring these tips and prompts, you can explore a shift in mindsets that is flexible, resilient, and more open to different interpretations and ways of being.
Some Articles to Consider (with friend links)
This week, I had a story Boosted on Medium — meaning it’s getting much wider distribution. It’s made about $100 in the last 2 days.
It’s also related to exploring and thinking about things differently — or at least from different angles. Each image has a ‘friend link’ embedded— meaning anyone can read the story (you don’t have to be a Medium member).
And one from November, that has been doing very well on Medium:
The other nice thing here is that by you stopping by for a read, it generates a little bit of income on my Medium account.
And here’s one from our new writing account on Medium: The Learning Journal Initiative:
That’s it for this week for The Solopreneur Series.
Do you have any questions about Both/And Thinking and Mindset? (If so please leave a comment).
Do you already engage this type of approach— what’s been your experience?
Thank you to those who have become paid subscribers. It’s a key piece of continuing to support our writing, research, and sharing — as well as building and sharing Freemium products.
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The next Free issue of Box Cutter Co. will be out shortly.
Good issue. It is an interesting way to catalog thinking with "both/and" and "either/or". "Both/and" thinking allows you to pivot more easily between ideas