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Three years ago I got a new boss. A year, he asked me about my approach to leadership. He told me that if my intention was continue in leadership roles in my career then it would be a good idea to develop a philosophy. Something I can rely on when I’m struggling inside the leadership. I thought this was pretty good advice. Not just because I have currently hold a leadership role, or because I plan on “moving up” in leadership. More because there are always opportunities to lead. I like the idea of having a reason why I do something. After that conversation two years ago I got to work. I took a lot of notes and wrote down a lot of things. Tried on many different hats to figure out what fit best. At the end of the day I came up with this: This is what I wanted to share. If you had asked me when I started what my leadership philosophy was going to look like I would have said told you some kind of academic paper. Every time I went down that road it didn’t feel right. Rather than edit I would start over. During this time I stumbled across this book series but the Stanford D School. One of the books is about creating a manifesto. From what I remember it tries to breakdown all preconceived ideas of what a manifesto is freeing the way expression. While I love that idea I found it very hard to execute. I kept Googling: how to write a manifesto. I finally had to force myself to let go of trying to make anything and let myself make a thing. Pulling from some different inspiration:
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There's a common misconception that the most creative solutions require absolute freedom— that unlimited resources provide boundless possibilities. Yet reality tells a different story. Some of the most innovative solutions emerge not from abundance, but from scarcity. When faced with limitations, our minds often perform their most remarkable feats of ingenuity. I have recently started writing haikus. While the strict structure of seventeen syllables seem suffocatingly restrictive, it's these constraints that force me to distill my thoughts to their most basic. Each syllable must earn its place, and this economy of language eliminates unnecessary fluff. The best poems I’ve written create moments of clarity. But limitations don't just drive artistic problem solving—they're equally powerful in our roles as leaders and supervisors. Working within a tight budget often forces us to come up with our-of-the-box solutions. When faced with a strict deadlines, we cut through procrastination to find focus. When the sky is the limit, it’s easy freeze in decision paralysis, but when our choices are constrained, we become more decisive and resourceful. My own behavior and psychology in these situations is interesting. Constraints provide a framework that actually enhances my creative thinking. Without limitations, my mind tends to aimlessly wander. But when I have boundaries to push against, my brain engages more deeply with the problem, searching for novel solutions within the set parameters. The traditional creative process supports these anecdotes. This isn't to say that all limitations are beneficial. Some constraints can be too stifling rather than stimulating. The key is in finding a sweet spot—enough structure to guide our thinking, but not so much that it stops progression. So perhaps instead of viewing limitations as obstacles, we should welcome them. Whether they're self-imposed, like a writing a haiku, or externally enforced, like a budget, limitations can push us to explore possibilities we might never have considered in their absence. Next time you face a constraint in your work or creative endeavors, try embracing it rather than fighting against it. Ask yourself: How might this limitation actually help me? What opportunities does it present? You might find that it’s from the limitation that innovations emerge. Creativity isn't about having everything at your disposal—it's about creating something new with what you have. Frustrating contraints
Are obstacles in the way Leverage to break free I don’t play Dungeons & Dragons. But I like the idea of it. I love the concepts around games in general, even though I don’t consider myself a “gamer”. Rules, goals, mechanics, characters, worlds, and story all fascinate me. There is something about being a Dungeon Master that has snagged me. It’s a topic I’ve researched for parallels I could find useful. Most recently I stubbled across this series of videos on learning the craft, and then this video on planning your first campaign: While I’ve never run a D&D campaign, I have organized other activities that would have benefited from this particular advice. I’ve broken down the ideas form this video I found useful into two categories:
Practical AdviceDigital Notes. This has been a big one for me recently. I have moved most of my writing and note taking into an Apple Notes; using the Second Brain framework. Making them digital makes them searchable, moveable, and at my finger tips at all times. This has been a complete game changer as far as staying organized. When everything goes into the same place I know exactly where to look. I won’t go into the details a second brain here but rather lean on Coleville’s concept of putting everything you need for the campaign into the same digital note or folder. This will make a huge difference if the campaign (or project) takes several weeks or months of planning and organizing. Then you have a place for everything including ideation, maps, notes, characters, monsters, etc all in one place. From a players perspective this makes the DM look like a true Master. It will build trust and structure so the players can let go and just play the game. (There’s so much leadership crossover here). ConceptualEmbrace Ambiguity. You’re not going to know the answers to everything and you don’t have to. It’s better to make friends with ambiguity and the discomfort it brings then to pretend it does’t exist or trying to over-prepare it out of existence (which is impossible).
You’re Going Screw Up. This is s tough one to swallow as this fear is often enough to prevent us from trying in the first place. Like ambiguity we need to get used to the idea that we’re going to mess up and create a practice of getting back on the horse afterwards. This includes owning the mistake. I love his quote, “I was DMing for 10 years before I could be counted on to draw a map with stairs to the second level.” 10 years! - We’re going to screw up for a long time. We Always Over Prepare. I know I just said not to worry about this, but the way he describes over-preparing is not what you’re thinking. It’s not necessary to have every detail planned down to the minute. Most of the time this is will actually hurt you because things are going to change. Knowing the direction and having a plan is most important. The video walks you through prepping for three encounters and over and over again he says, “And what does this mean? I don’t know. I don’t need to know until later. Right now I like the idea so I’m going to go with it.” Not needing to plan every details gives you some leeway to let your mind wonder and get creative. This is a valuable skillset. Plus a lack of structure provides wiggle room for last minute adjustments. Flexibility is key when leading anything and it will help prevent burnout. Even without an intention of ever becoming a Dungeon Master I will continue to learn how. There’s lots of skills here. It’s a great framework for understanding abstract ideas. Transitions are difficult. Switching from one mode to another, especially if not by choice, is a challenge. It’s why the first day of school was so hard, or why bath time with kids is a fight, and big reason why morning coffee is so important (not because of the caffeine).
The wildcard in any transition is our emotions. They’re hard to control and can come out of nowhere and tip the scales. Irrational emotions are easy to spot and a major reason I and many others choose to avoid them all together. Their wildcard nature hides their value and it’s much easier to suppress an emotion than it is to manage it. But like middle schoolers the more we suppress our emotions the deeper, darker, and more erratic they become. Transitions are full of potential triggers for erratic emotional outbreaks. Keeping this mind and being cognizant is the first step in creating smooth and manageable transitions. Noticed I didn’t say emotionless. That’s never going to happen unless you suppress them. But this short term solution will only revert us back to the 7th grade. Whenever anything has the potential to be volatile we will benefit from routine and practice. The right muscle memory will get us through any unknown situation. This is why parenting books emphasize consistency and routine. They give kids (and parents) something to rely on when everything else goes to shit. I love the concept of tools: a device or implement, used to carry out a particular function. Over the course of my life I have increasingly romanticized tools. Placing them at the center of production, as if the process to the result relies on a specific tool. Causing me to wait until the “right” tool is acquired. I have used this approach with both physical and digital tools.
It’s fun to look at the latest gadgets, apps, and processes. Researching until it’s too late to get started. This is where I feel minimalists have a leg up. Often the simplest solution proves to be the most effective. Emphasizing tools overlooks the simplicity of getting started and leans into creating complexity. My ego feeds on complexity. It makes me feel advanced, unique, and smart. Waiting to start prevents me failing. Getting stuck in this middle ground feels oddly amazing. I get to enjoy the fantasy of what all my work is going to produce without having to do anything…yet. Feeling the mental high of success without the feeling the risk of failure. While tools can make the process easier they will never prevent the necessity of work. Hard conversations are uncomfortable and love is comforting. The way these two emotions feel puts them at odds. I have spent the my life keeping them separated.
True to human nature. They are paradoxically connected. But the connection depends on the definition of love. M. Scott Peck differentiates these two kinds of love:
The feeling of wanting the best for someone else is genuine love. When hard conversations are based in this, not anger, then the hard conversation has a chance at being successful. Every hard conversation is painful which is why we avoid them. Genuine love can motivate us to risk our own comfort for the benefit of the other person. Seeing that willingness to be uncomfortable is the kind of love I want in all my relationships. But damn, it’s hard. Since the pandemic and the discovery of the Libby App I have developed a book listening practice. This concept was first introduced to me by Seth Godin who talks about it on Tim Ferriss’ podcast. Godin primarily practices listening to Pema Chodron but he mentions Zig Zigler if you want to learn sales, or motivation. I like this osmosis approach; allowing the information to wash over me and absorb it over time.
When I read a nonfiction book I tend to read it incrementally taking in one concept at a time. I am depended on the processing power of my brain. While once concept at a time feels like a good approach and has value there is something lost from not gaining a broader perspective of the entire book as a whole. Individual trees are great but understanding hot he trees, together, make up the forrest holds a lot of value. I find that I get the best of both worlds when I practice with audio books. But it can’t be done once. An audio book practice is just that, a practice. Consistency is key. Listening to the same book repeatedly brings familiarity and depth in understanding. The process is similar to an actor memorizing the script. Eventually a threshold is crossed where it’s hard to tell the difference between the actor and the character. There is some information and knowledge valuable enough that we would benefit from having it part of us. I supposed this probably a form of indoctrination, just led and chosen by person being indoctrinated. Here are list of books that I have indoctrinated myself with:
The reason these books is because I own them on Audible so they are always available. That is not the case with Libby, and having to check books out. For the last two weeks I have been listening to Underestimated - The Wisdom and Power of Teenage Girls, by Chelsey Goodan. I heard about the book through Neil Strauss. Goodan wrote the book as part of Strauss’ annual writing workshop. In his promotion of the book he talks about Oprah’s praise, which had me skeptical. With an eleven year old girl myself, and having just finished Untangled, the topic was of interest.
As a disclaimer I do have a tendency to internalize the information I consume. Figuring out how it might fit in, relate to, or solve problems I am currently wading through. This book was no exception and opened up channels I didn’t expect. If you haven’t read Untangled and a girl or woman plays a significant role in your life then I recommend checking it out. It takes a research approach to understanding and helping teenage girls that will support the relationships you have with them. This academic approach is very different from Goodan’s Underestimated, which does site research but rather than the unbiased and somewhat sterile presentation that research can offer, Underestimated is anecdotal and quote-heavy. This makes the content feel real and vulnerable. Many of the quotes I could hear my own daughter say, or reflected conversations we’ve already had. Which was helpful and terrifying. The goal of the book is to provide practical tactics to support teenage girls to be themselves. Goodan’s performance on the audio book is casual which matches the tone of the quotes. There were times when her vocal patterns reminded me of the SNL sketches about high school theatre. In any other book this would have bothered me but for a book that quotes a lot of teenaged girls it felt like an appropriate artistic choice. One of the surprising aspects of the book for me was Goodan’s ease in talking about contemporary issues. Working in academia these issues are at the forefront of my daily tasks. I can tend to get lose interest in the anger and the research and miss the reality of the actual issues. Goodan addresses eating disorders, sex, social media, identity, and shame with the voices of teenage girls who are going through it now. This highlights the subtleties and the impact of the issues in a way that grounds them. From the examples I was able to see how they show up or could show up in my own life and ways that I have added to the social narrative, and how I can do better. As someone who has never been a woman they were eyeopening and sparked a lot of empathy. Despite the book being about teenage girls the advice is universal. I can easily see myself using the tactics to create space, empathy, and connection with my teenage son, wife, colleagues, and staff. Like a good allegory, the choice to focus on teenage girls made it more powerful. After the few chapters I recommended to my wife. It’s the kind of book that needs to be discussed and reviewed to put it into practice and get the most out of it. Here are some of my major takeaways:
This is really just a short list of things that floated to the top as I was writing this. The book is written in a way that it could be revisited and discussed. Although because of its poignancy I’m not sure about its longevity. Another interesting aspect of the book that came up quite a bit was when Goodan would mention her inner teenage self. Reflecting back on her own experience and how working with teenage girls helped her reconcile and understand some of her own angsty experiences. There is a lot of carry over from childhood into our adult lives and addressing these things can help us untie the knots we previously tied (to use an image from the book). It multiple places in the book I found my own connections to my teenage self. Looking back with empathy and forgiveness rather than the harsh criticism. This kind of self compassion is challenging to maintain. Especially with societal pressure to hold oneself to a higher standard. I was glad to have the guidance to do that. It’s not something I’m apt to do on my own. Another knot I’m trying to untie. There is a Buddhist perspective I like that walks through looking at our past and seeing the influence of where we come from. This opens up a viewpoint of what got us to where we are and how nothing we’ve done has been independent of others.
The visualization is look at a flower and think about everything that it took for that flower to bloom. We go down the list:
From this simple list we can start get a little deeper:
It quickly turns into a mirror in a mirror situation. To the point where it can start to get overwhelming. It’s much easier to stick with those initial answers and be done with it. Given the chance to sit in that complexity provides a beauty to the plant that doesn’t exist without it. The time and energy it took to create this one-of-kind flower. And this is just a plant. Looking at a human existence the complexity is exponential. It makes any life appear inconceivable. A miracle that happens daily. Frequent enough that it feels common place and dismissible. Supporting the decision to simplify, categorize and ignore. I fell off the daily writing train last week, breaking my chain since the beginning of the year. I got off track on Monday due to the holiday and couldn’t seem find my stride to picking it back up. I did however spend quite a bit of time trying to finish Mastery, by Robert Greene (funny how we prioritize).
Throughout the book he talks about the importance of understanding reality and the complexities of the modern world live in. Despite having some familiarity with the book this concept stood out. While grappling with trying to understand the nuances of a complex reality my son interrupted me. He asked me why we had decided not get him a phone this summer in preparation for a school trip he’s taking.He asked me what he had done wrong and we we changed our ming on his ability to handle the responsibility of a potentially life changing object. During this interaction I realized I was staring at complex reality. My son and I had a 40 minute conversation around the addictive nature of phones, the time, energy, and financial commitment to having one. Plus the influence this will have on his younger sister and our decisions around her getting a phone. It’s clear that this seemingly simple decision: whether or not to get phone, is much more complicated than the decision itself. As I saw this complexity I could start seeing them everywhere. Every aspect of my life brings with it layer upon layer of complexity. It’s overwhelming. My brain isn’t suited to handle this level of complexity all the time all at once. Decision fatigue is real. Rather than recognizing the complexity of everything it’s easier to simplify and then process. Reducing a situation into tropes or archetypes and then making broad decision based on my broad categorization. In one vein this is how I have to function, any other way is inefficient and ineffective. But if I allow myself to sit with my process of categorization I can see I was ignoring complexity. Passing them over because it was too hard. Simplification should streamline the process in order to make way and celebrate complexity, not overshadow it. Theoretically this streamlining will lessen the overwhelm of such complexity and increase capacity for the daily onslaught. Reality is complex. Anything I do to reduce or ignore the complexity is only giving me a false sense of what’s real. |