|
A much younger me sat in a small classroom at church with my friends. I don't remember the lesson our teacher taught us but I do remember the question we were asked:
"If your house caught fire and you were only able to grab 5 things and save them from the fire, what would they be?" On the surface this question feels profound. It's supposed to reveal where your values truly lie. As a thought experiment where you visualize waking up to your house on fire with only minutes to grab a few things before reaching safety, it might uncover some truth about yourself. But in this “comfortable and safe” setting, the question often reinforces social values that are handed to us, not the ones that truly make up who we are. The "right" answers were predictable: family photos, religious texts, heirlooms, etc. Objects that reflected the values our community expected us to have, rather than what might genuinely matter most to us as individuals. The Challenge of Authentic Living Living authentically according to our core values seems much easier than it actually is. We're consistently influenced by everything around us. While traditional authorities may have weakened, we now contend with an unlimited stream of information constantly shaping our perspectives. The good news is that if we can dedicate time to identifying our true values, we have a better chance of finding like-minded people than ever before. The connected world that challenges our authenticity also offers unprecedented opportunities to find our tribe. We're naturally attracted to authenticity even when it differs from who we are. Discovering our values can also strengthen existing relationships, providing more purpose and meaning to our lives when we bring our full, honest selves to them. Moving Beyond the Blur Values are difficult to pin down, especially when many seemingly different value systems share common elements. The blurry lines make it incredibly hard to identify our place and our individuality. It's like staring at a page of Waldos. Sure, they're all slightly different, but when the spread is covered with them, they all essentially look the same. Without deliberately identifying who we are and what we value, we can easily get swept along with everyone else. There's nothing inherently wrong with this. Many people live perfectly happy, healthy lives without deep values exploration. The problem stems from that nagging feeling that there might be something more. It's the voice in the back of your head that points out the differences between you and others, highlighting those moments when you're with friends but feel slightly out of place. We long to sit comfortably in our own skin, confident in who we are regardless of circumstances. When we connect with our core values and allow them to guide our decisions, we're more likely to find this confidence, knowing our choices serve something bigger than momentary convenience or social approval. Beyond Shallow Authenticity While there's much discussion about "being our authentic selves," I want to echo Seth Godin's warnings about the "authenticity trap." Godin cautions against equating authenticity with unfiltered expression or chasing some mythical "purest" version of ourselves. True authenticity isn't about speaking every thought that crosses our mind or being "brutally honest" without consideration for context or consequences. Instead, identifying our core values provides a foundation for consistency in our actions and behaviors. Over time, this consistency creates an authenticity that's far more meaningful than impulsive self-expression. This process is about discovering what we truly value above all else, and then aligning our actions and words with these values to create a life of meaning and purpose. Rather than simply justifying whatever emotional state we happen to find ourselves in. As humans, we benefit from consistency and boundaries. It's better for us to create our own based on what we genuinely value. If we don't, someone else will inevitably make those decisions for us. Breaking From the Conveyor Belt One of the hardest parts of growing up is recognizing our ability to make our own choices. It's so easy to get on the conveyor belt of "good decisions" that it becomes difficult to step off and make the right choice for yourself. In college, I chose to study theater, which felt like a bold personal choice. Yet I soon found myself on an educational path with everyone else who had made this supposedly "unique" decision. One spring semester, I enrolled in a Directing II class with other upperclassmen who had been studying theater. Within the first week, I became disillusioned by both the curriculum and approach. In a moment of frustration after class, I walked to the library telling myself, "If I'm not going to learn what I need from the class or the professor, then I'm going to have to do it myself." I checked out every book on directing the library had and got to work. This pivotal moment transformed my educational journey. Here I was, paying tuition to professors teaching from limited perspectives. The education wasn't bad, it just wasn’t satisfying my curiosity. This was in the early days of the internet, making me dependent on whatever books I could access through the library. My paradigm shifted in those frustrating moments that led me to take independent action. I claimed ownership of my education, realizing that learning was ultimately my responsibility, not the authority I had given so much power to. This shift didn't just affect my education; it was the first domino in a series that led to shedding my dependence on others and taking ownership where I could. Just as I had accepted the educational system without question, I had also accepted my values because I trusted the adults who handed them to me. The Courage to Question One of the most transformative aspects of questioning is that once you start, it's hard to stop. Questions poke holes in the status quo and create opportunities to begin the work of creating personal meaning. Finding holes in inherited values is uncomfortable territory to navigate, which is why many people abandon the questioning process. But it's precisely in this wrestling that we gain insight into who we are and learn to live more authentically. The Amish tradition offers a fascinating example of structured value exploration. At age 16, Amish young adults participate in Rumspringa, a rite of passage where they temporarily leave their traditional life. This period gives them an opportunity to experience the outside world before deciding whether to be baptized into the Amish church or pursue a different path. This structured rite highlights what we all possess but often fail to recognize: the ability to choose. The high percentage of Amish youth who return to their community after Rumspringa is remarkable, though certainly influenced by many factors beyond simple value alignment. Our society would benefit from supporting individual choice more fully, acknowledging the complexity this creates. The beautiful thing about choice is that it never expires. No matter our age or circumstances, we can always reconsider and choose our values. I emphasize this point because recognizing our freedom to choose is perhaps the hardest part of uncovering our values. Our authentic values might differ significantly from what we thought they were, or from what others in our social circles hold dear. It's like discovering something unexpected about ourselves. Once we know, we can adjust and leverage this knowledge rather than letting it influence us unconsciously. Creating Space for Discovery The exploration of values can be surprisingly enjoyable when approached with curiosity. Having a private space where you can experiment with different perspectives without external judgment. Allow yourself to entertain ideas you've never voiced, thoughts you might hesitate to share with your partner, parents, or friends, and see what resonates at your core. This is your opportunity to explore questions that open worlds you've only imagined:
This process requires radical honesty, which is much harder than it seems. As my opening story illustrated, social influence runs deep, and it takes genuine effort to push through automatic responses when exploring values. For these exercises, we need to exit autopilot and enter a state of genuine introspection. Give yourself adequate time and space. There are no shortcuts or quick fixes. Let go of rushing to results and try to enjoy the process of discovery. When Discovery Brings Discomfort Value exploration should be enjoyable, but sometimes the results aren't what we expect. Introspection can be challenging when it reveals surprising or uncomfortable truths about ourselves. When such revelations emerge, accepting them becomes its own challenge. Early in my marriage, my wife and I read "The Five Love Languages" by Dr. Gary Chapman. The book examines how people experience love through five primary "languages":
I approached the book certain that my love language would be physical touch. What threw me completely was discovering that my primary love language was actually words of affirmation. Breaking my own expectations and learning something new about myself was surprisingly difficult. It shifted my self-perception in ways I hadn't anticipated. In a matter of moments, I needed to readjust how I saw myself in the world I had created. This might sound dramatic, but when we learn something unexpected about ourselves it can be genuinely unsettling. I spent weeks grappling with what this revelation meant about me and how I showed up in the world. If I'm being honest, I didn't feel great about needing words of affirmation to feel loved. I saw it as ego-driven, a way to seek validation through what seemed like shallow reassurance. How could something as intangible as words truly satisfy my need for love? I struggled deeply with this insight. Facing Your Reality When you uncover a truth about yourself that you're not proud of, the instinct might be to reject it or minimize its importance. Instead, give it more time and space. Sit with the discomfort and examine it without judgment. This discomfort is more common than we realize. Our society has constructed countless ways for us to avoid uncomfortable realities. Distraction is always available, making it easy to maintain a comforting distance from truth. We tell ourselves soothing stories: we manage our money just fine; the system is designed to keep people like us from getting ahead; our habits aren't "that bad"; if only we had more money, fewer responsibilities, or different opportunities. We might glimpse potential for improvement but can't see a path forward. Rather than facing reality, we pacify ourselves to avoid change. We maintain the status quo and remain in comfortable distraction. Acquainting ourselves with reality is difficult but necessary. It means seeing both the admirable and flawed aspects of who we are, and ultimately accepting both. This is easy to describe in an article but profoundly challenging in practice. Even when I logically understand the importance of self-acceptance, I still battle the narrative that I need to be someone different, that who I am isn't enough. Negative self-talk emerges in waves, and it becomes tempting to escape into my phone, searching for the productivity hack that will transform me into the person I "should" be. The Myth of Becoming Someone Else What makes this struggle especially difficult is that while we are adaptable and capable of growth, we all have inherent limitations. I will never:
This isn't because of some personal failing, but because these are all different people with their own unique combinations of talents, experiences, and perspectives. I've elevated them to mythic status in my mind, ignoring their human complexities and struggles. The benefit of understanding our own values isn't so we can emulate those we admire, but rather so we can be authentically ourselves in every situation. Getting comfortable with the reality of who we are (the good, the bad, and the complicated) is the first step in leveraging our strengths and living authentically. Values in Action: A Personal Example I've completed values identification exercises multiple times over the years, and one value consistently emerges for me: wisdom. This core value has been a major driver behind my career in education. Despite recognizing the education system's complexities and limitations firsthand, I've found great personal meaning in contributing to formal education. A few years ago, when my son entered high school, I asked him the question I was asked at his age, the same question that drives much of my current work: "What do you want to study in college?" Confidently, my son responded: "I'm not going to go to college." It took every ounce of parental restraint to avoid expressing judgment or criticism. His statement felt like a rejection of something fundamental to my identity: my belief in the transformative power of education, my career choice, my values. In that moment, I faced a profound test of what I had learned through my own values journey. Part of discovering what I personally value also means creating space for others to value something different. My son's divergent values weren't an attack on me or a rejection of my wisdom. They were simply a difference in perspective, the beginning of his own journey toward authenticity. The fire drill question from my childhood asked what objects I would save, but the more profound question is: what values will I choose to carry forward? And can I create space for others, even those closest to me, to make their own choices? This is the true gift of values discovery. Not just clarity about our own path, but the ability to recognize and respect the diverse paths of others, knowing that authentic living requires both personal conviction and generous understanding. Whether my son eventually chooses college or a different route entirely, my deepest hope is that his choices will reflect his authentic values rather than merely inherited ones. The journey of values discovery never truly ends. Each new relationship, challenge, or life stage invites us to reconsider what matters most. The questions keep coming, and if we stay curious and courageous enough to answer them honestly, the path to authentic living becomes clearer.
0 Comments
In our pursuit of productivity, we often seek to eliminate friction. However, the right kind of constraints, what I call "productive friction”, can actually enhance our focus and creativity. This essay explores how to intentionally apply analog wisdom to our digital tools for better results.
The Quest for Productivity Theatre production is notoriously chaotic. With countless elements happening simultaneously, success depends not on rigid systems but on a team moving together in a collaborative dance. As a young theatre teacher running an after-school program, I wore all the hats a typical production company distributes among specialists. Proper organization became essential to my survival. During this overwhelming period, a colleague introduced me to David Allen's Getting Things Done methodology. In an era when productivity information was scarce, this system seemed revolutionary. GTD promised to help me manage the countless moving pieces of theatrical production. I enthusiastically built an elaborate filing folder system to track everything I needed to reference. This resulted in process fatigue. Eventually, maintaining the system itself became the primary obstacle to actually using it. After a few months, I abandoned it entirely, recognizing I needed something simpler to maintain and use. The Digital Promise Thirteen years and a dozen productivity systems later, I encountered Tiago Forte's Building a Second Brain methodology. Though initially resistant after years of productivity system disappointments, I eventually watched a video outlining its concepts. The approach immediately struck me as different, addressing the fundamental issues that had plagued my previous attempts. I committed to building my own "second brain." The digital format eliminated much of the physical friction I'd experienced with Allen's paper-based GTD system. With Apple Notes as my tool of choice, I created files for projects, areas, resources, and archives (Forte’s PARA method). However, despite being more organized than ever, I wasn't actually more productive. This revealed a crucial insight: "Productivity" has evolved into a buzzword that often encourages busywork rather than meaningful progress. Digital tools, while removing certain barriers, introduce new problems, particularly through their lack of inherent constraints. The Paradox of Friction While digital tools eliminate the friction that makes difficult tasks challenging, it's precisely the friction inherent in analog processes that makes them valuable. Consider writing by hand versus typing. Handwriting forces deliberate thought due to its slower pace, while typing allows our thoughts to flow rapidly, sometimes too rapidly for proper consideration. Research from the University of Tokyo has shown that students who take notes by hand retain information better than those who type, precisely because the physical constraints of writing create productive cognitive engagement. This type of friction doesn't just slow us down, it improves quality. The challenge with many digital productivity tools is their frictionless nature. When faced with a blank document in a note-taking app, we have infinite possibilities. Which paradoxically can feel more paralyzing than liberating. As behavioral economist Dan Ariely has demonstrated, too many choices often lead to decision paralysis and lower satisfaction with our eventual selection. The allure of easier paths constantly pulls my focus toward new tools. I justify this distraction by telling myself that mastering this new system will eventually make me more productive. Yet repeatedly, I discover that the tool doesn't deliver on this promise. I still need to do the work, often after wasting precious time learning yet another system. One of the reasons I have stuck with Apple Notes is because of its lack of features. Because it’s not flashy I am forced to focus on the actual note taking. The Digital Tool Dilemma Digital productivity tools typically fall into one of two problematic categories:
Both approaches have theoretical merits. A uni-tasker can focus effort and streamline specific processes. A multi-tasker provides flexibility across different needs. Yet in practice, both create problems. Having too many specialized tools fragments your workflow, while overly generic tools lack the structure needed for specific tasks. The solution lies in thoughtfully customizing existing tools by creating constraints similar to those naturally present in analog tools. This requires deliberate effort because digital environments aren't naturally bounded the way physical ones are. The Power of Constraints During my high school years in England, I visited Scotland with my uncle, one of the most frugal people I've ever known. While there, he wrote a postcard to his son. Remarkably, he managed to fit the equivalent of three pages of text onto that single postcard, maximizing both space and money. What makes postcards effective is the clear boundary they provide. When writing one, physical limits force decisions about what's truly important to communicate. This constraint drives clarity and concision. Productivity operates on similar principles. To be truly productive, not just busy, we must make decisions about what deserves our attention. This often means saying "no" to distractions and low-value activities. When using boundless digital tools, we must manually create the limitations that would naturally exist in physical media. This includes establishing boundaries against both obvious time-wasters like social media and sneakier productivity-killers like constant email checking, unnecessary meetings, and excessive documentation. Avoiding Digital Chaos in Teams Setting appropriate boundaries becomes exponentially more complex with collaborative tools like Microsoft Teams or Google Workspace. While these platforms offer tremendous flexibility, shared workspaces can quickly descend into chaos without clear structure. In my office, after implementing Microsoft Teams, we discovered that different people were creating channels with inconsistent naming conventions and information architecture. The resulting confusion led to duplicated work and lost information. We had to establish clear naming patterns and channel creation rules to restore order. Although creating these foundational standards initially felt like it distracted from "real" work, it proved essential for long-term efficiency. A 2019 McKinsey study found that employees spend nearly 20% of their workweek searching for internal information or tracking down colleagues for help. A cost that proper digital organization can dramatically reduce. Smart Constraints for Smartphones Consider smartphones, devices that revolutionized global access to computing power. While they offer unprecedented capabilities for productivity, they simultaneously present unparalleled opportunities for distraction. These devices aren't merely multi-tools for lists, notes, tracking, analysis, media creation, communication, and automation. They're also endless sources of entertainment, information, and dopamine-triggering notifications. Although some advocate returning to flip phones, I've found valuable features on my iPhone that genuinely enhance important relationships. Rather than abandoning modern technology, I've implemented specific constraints that maintain core functionality while reducing distractions:
These boundaries transform my smartphone from a distraction machine into a genuinely productive tool without sacrificing its most valuable features. Translating Analog Wisdom to Digital Tools If analog tools have inherent boundaries that maintain focus and enhance productivity, we need to translate these principles into our digital environments by creating rules that prevent chaos. Physical tools like notebooks have two types of constraints:
Digital productivity tools typically lack both types unless we deliberately create them. For instance, in my digital note-taking system, I've established rules about what belongs where, how information should be formatted, and when items should be archived. With the idea of mimicking the natural limitations of physical systems. The Role of Productive Friction In their research-backed book The Friction Project, Stanford professors Robert Sutton and Huggy Rao explore how friction can function both negatively and positively in productivity. They argue that the right kind of friction helps us slow down and become more deliberate about our work and decisions, while misplaced friction creates unnecessary barriers. When establishing rules for digital tools, we should thoughtfully consider where friction proves helpful versus where it hinders progress. For example, requiring additional steps before sending all-company emails creates valuable friction that prevents communication overload, while complex approval processes for routine decisions often create harmful friction. Finding Your "Yellow Ochre" As a college student, I spent many hours in the art studio. A persistent obstacle for me was starting with a blank canvas. I was paralyzed by expectations and fear of inadequacy. My painting professor offered a technique that effectively removed this starting barrier: before beginning, she had us cover the entire canvas in yellow ochre paint. This preliminary step accomplished two crucial things:
The physical process of using analog tools provides similar momentum. With digital tools, we need to create our own equivalent of this "yellow ochre" technique. For writing projects, my digital "yellow ochre" involves recording a voice memo while walking, or wildly typing to capture rough thoughts before facing the blank document. I am also give myself permission to word-vomit on the page. Getting all the thoughts rolling around in my head out, without trying to create structure or connect them. These preliminary steps build momentum that carries into the main task. Building Digital Boundaries That Work Based on years of experimentation, here are the analog-inspired principles I use to structure digital tools effectively:
Evaluating Friction Points When assessing whether a particular constraint helps or hinders your work, ask these questions:
For example, the friction of having to manually transfer information between systems is typically harmful, while the friction of having to articulate clear acceptance criteria before starting a project is typically beneficial. Embracing Continuous Improvement Implementing these guidelines won't result in immediate perfection (there is no perfect). Identifying principles represents just the beginning. The endpoint emerges only after sustained trial and error as you discover what works for your specific needs. This continuous refinement process can be exhausting, particularly when encountering unexpected obstacles or exploring new capabilities. The more complex a tool, the more time you'll spend experimenting with optimal configurations. When Microsoft Teams became our primary collaboration platform, I found myself in a constant state of refinement. For instance, when organizing a cross-departmental event, I initially planned to simply add collaborators to our Team for access to shared materials. However, our recent implementation of Teams Phone created a complication: while I wanted other departments to access our files, they shouldn't receive incoming calls to our front desk. This required creating a dedicated shared channel for events with carefully calibrated permissions. As new features emerge or new needs arise, established practices inevitably require adjustment. This reality conflicts with our desire for set-it-and-forget-it solutions. Analog tools provide satisfying finality, when a notebook is full, we place it on a shelf and begin anew. Digital tools rarely offer such closure. Finding Peace with Digital Iteration Rather than resisting this continuous improvement cycle, we can choose to embrace it as a natural part of digital tool usage. Each adjustment brings us closer to systems that genuinely enhance our productivity rather than merely giving the illusion of organization. Digital tools create the false impression that everything should happen instantly. When improvements don't materialize immediately, we assume something must be wrong. However, truly effective systems require time and iteration before delivering their full potential. Consider Walt Whitman's approach to Leaves of Grass, which he published nine times during his lifetime. Each edition contained significant revisions as he continuously refined his work. Rather than viewing these iterations as failures, Whitman embraced them as essential to creating something truly significant. If we want our digital tools to serve us well, we must approach them with similar patience and perspective. The friction points in our workflows aren't always problems to be eliminated. Sometimes they're precisely what we need to slow down, make deliberate choices, and create something meaningful in our increasingly frictionless digital world. The next time you feel frustrated by digital chaos or distraction, remember: the right constraints don't limit creativity, they enable it. By thoughtfully applying analog wisdom to your digital tools, you can create environments that foster both productivity and deeper thinking. Two years ago, I left a locked box on our dining room table with a cryptic note about where to find the key. The note read: "Where morning light first touches your sanctuary of reflection." I meant the bathroom mirror, but my wife interpreted "sanctuary" as our bedroom and "reflection" as thinking rather than literal mirrors. The clue had three possible interpretations when it needed just one. Instead of enjoying a delightful morning surprise, I received a barrage of frustrated texts asking for hints while I was at the gym. What should have been a romantic gesture became a source of stress that taught me a crucial lesson: writing effective puzzle clues requires more precision than I had imagined. This Year's ChallengeFor my wife's birthday this year, I decided to try again. I wanted to create a scavenger hunt that would redeem my previous failure and prove I had learned from my mistakes. The experience taught me valuable lessons about puzzle design, though not all of them came easily. I discovered that successful puzzle creation involves two equally important elements:
My mistake was letting the physical puzzles lead the design process. I spent most of my time on construction details, building book safes and creating realistic library call numbers. While crafting these elements brought me joy, prioritizing the physical construction over the solving experience created unnecessary frustration for my wife. The Core PrincipleCreating effective puzzles follows the same principles as good storytelling. They unfold in carefully designed phases that guide the audience step by step. The solution should feel just out of reach, which makes solving it satisfying without becoming overwhelmingly frustrating. This sounds simple, but it requires understanding the solver's perspective completely. The challenge becomes exponentially more difficult when creating for multiple people, as each person brings different assumptions, knowledge, and problem-solving approaches. Research in cognitive psychology shows that puzzles work best when they operate in the solver's "zone of proximal development”. Create the puzzle so it’s challenging enough to require effort but not so difficult as to cause frustration. A well-designed puzzle should take 2-5 minutes to solve, provide one clear "aha!" moment, and leave the solver eager for the next challenge rather than stuck or annoyed. The Scavenger Hunt: What Worked and What Didn'tStep 1: The Starting Note (Success)I left this note outside our front door: Happy birthday Jocey! I've hidden something for you behind the bathroom island. — Wade This clue worked perfectly because it was specific and unambiguous. We have a photograph of an island in our bathroom, and behind it, I hid a UV flashlight with a piece of paper wrapped around it. The clue had only one logical interpretation and provided enough context to guide her to the right location without false leads. Step 2: The UV Clue (Major Failure)The note attached to the flashlight read: Bright shines the message that will lead to gift storage. This clue created a complete breakdown in the puzzle's momentum. I made three critical errors: Error 1: Misleading emphasis. The clue accidentally emphasized "storage" when the important word was "message." She focused on storage areas (closets, the shed, under the stairs) instead of looking for a hidden message. Error 2: Prioritizing wordplay over clarity. I chose "storage" because it rhymed with "message," a lazy decision that sacrificed clear communication for clever wordplay. The puzzle stalled completely. She postponed her search until I texted her and learned about the problem. Only then could I guide her toward the next step. Step 3: The Park Cache (Recovery)The UV message read: Geocache in Garfield Park This clue worked because it was specific and built on shared knowledge. We had discovered a geocache hidden in our local park during a previous walk, so she knew exactly where to look. The box contained a gift and the next series of clues. Step 4: The Library Challenge (Success)Inside the box was this note: Congratulations! You found the first of a few gifts. Before we move on, I need you to meet me here at 12:00: ///prices.trooper.pulling (what3words location).  The puzzle was an image of The Evergreen State College Library that I had glued to cardboard and cut into strips. These haiku clues worked perfectly because they were specific yet poetic. The first clearly pointed to our freezer ("Frozen time," "White guardian," "Dinner") while the second indicated our cat's food storage ("Kibble," "purrs," "Future feast"). Each location contained an envelope with library call numbers:
The Physical Centerpiece: Book SafesI had wanted to build book safes since middle school, and I loved the idea of disguising them as library books waiting to be discovered. This physical puzzle drove the entire scavenger hunt design. Creating convincing book safes required attention to several details:
I downloaded Bitstream Vera, matched the size and spacing of existing call numbers, and placed the book safes naturally among real library books. The result was two perfectly disguised book safes that blended seamlessly into the library's collection. It was fun to watch her search the library for the right books and realize they weren’t actual library books and that she needed to leave with them.
Essential Lessons for Puzzle CreatorsThe Primary Rule: Clarity Trumps ClevernessNever let wordplay override clear communication. My focus on making "message" and "storage" rhyme created confusion that stopped the puzzle's momentum entirely. Before finalizing any clue, ask yourself:
Quick-Win Tips for Better Puzzles
The Testing ProtocolThese lessons extend beyond romantic gestures. Escape rooms, video games, educational activities, and team-building exercises all follow similar design principles. The best puzzles aren't about showcasing clever construction. They're about creating moments of delight and discovery. Two years after my anniversary box failure, I've learned that successful puzzle design requires equal attention to both the physical elements and the solving experience. The book safes succeeded not because they were technically impressive, but because they delivered that satisfying "aha!" moment at exactly the right time in the hunt. My next puzzle will start with the solver's experience first, then build the physical elements to support that journey. After all, the most elegant construction means nothing if it leaves the solver frustrated instead of delighted. Troubleshooting Common ProblemsIf solvers get stuck for more than 10 minutes: Provide a graduated hint system rather than the complete solution.
If clues are too easy: Add a layer of encoding like simple ciphers or anagrams, but keep the core message clear. If logistics fail: Have a backup method to deliver the next clue. Technology and physical props can always malfunction. If multiple people solve together: Design clues that allow for collaboration rather than competition, and ensure everyone can participate meaningfully. The key is remembering that puzzles should enhance an experience, not overshadow it. When done well, they create shared moments of triumph that become better stories than the puzzle itself.
"Mr. Arave, I'm done with my list. What can I do next?" Alex asked me. I stood center stage with the strike list in my hand, my guide for coordinating 60 students and 12 parents in dismantling our set for White Christmas. Little did I know this experience would teach me vital delegation skills I'd later use in my career in higher education administration—skills that would save me countless hours and help me build stronger teams.
After closing night of a theatre performance, the cast and crew stay late and dismantle everything in a tradition called "strike." I had participated in these for a decade before needing to lead one. There were two things that made this particular strike unique:
The Challenge of Delegation This experience taught me a fundamental leadership skill that would later prove essential in my professional career: the art of delegation. In this article, I'll share how I learned to delegate effectively, the mistakes I made along the way, and a framework you can use to master this critical skill yourself. Running a smooth strike is almost as much organizational work as it takes to direct a show, especially with a group this big. The only way to really get it done is to delegate. After an exhausting 2-and-a-half-hour musical for the last three nights, everyone was eager to get out as soon as possible. There is an urgency and laziness that can be a challenge to lead. Without a plan, it can quickly turn into "too many cooks in the kitchen," and suddenly three-quarters of the cast is sitting down and chatting while the others are getting everything put away. Having experience in this area and knowing what needed to be done, it was easy to make the transition into a leadership role by delegating tasks so they were completed efficiently and effectively. Outside of this theatre context, delegation of tasks hasn't been so easy for me. According to a Harvard Business Review study, leaders who effectively delegate experience 33% less burnout and their teams report 28% higher engagement. Yet the same research found that 78% of leaders struggle to delegate effectively, citing concerns about quality control and time investment. Why Mastering Delegation Transforms Your Leadership When I finally began delegating effectively, three things happened:
Perhaps most surprisingly, relationships improved as trust deepened in both directions. Delegation is a skill that can be learned. Like any other higher-level skill, developing it takes some unlearning. In professional settings, we are asked to do “the work”. In higher education admissions, “the work” is a combination of:
This is a set of skills that is developed through training and experience. As we develop these skills and become confident with them, we have an opportunity to be promoted or take on a leadership role. These roles tend to be filled based on hight performance of “the work” like the skills mentioned above or whatever advanced skills are required for the entry level. While “the work” provides the context for the leadership role, leading and managing is a very different set of skills that need their own development. Delegation is one of them. Quick Delegation Self-Assessment Ask yourself these five questions to identify your delegation blind spots:
If you answered "yes" to three or more questions, you likely have significant opportunities to improve your delegation approach. The Leadership Learning Curve There are lots of hard lessons when getting into a leadership position, even if you have experience. Taking on a new role will have a learning curve, especially if you're new to the institution or company. Before you can lead, you'll need to embrace and understand:
Getting into my first director role, I understood that delegation was necessary. So, I got to work assigning people tasks. I was killing it in assigning tasks. There was one problem: assigning a task is like expecting that my alarm is going to get me out of bed in the morning. Just as the alarm is a reminder of what to do, so is an assigned task. Delegation doesn't work unless the tasks get done. No matter how I assigned the tasks, it was hit or miss whether or not they were accomplished. The process was inconsistent at best. Inconsistency can be detrimental to building a team. In a situation like this, it's very easy—and in some work environments, supported—to put the onus on the employee. Telling myself and superiors that I assigned the task and it's up to the employee to figure it out and get it done. This is easy because it removes the responsibility from me and puts it elsewhere. As a teacher, I saw this happen quite a bit. Teachers absolving themselves because the students failed to pick up and retain the information without consideration of the students' learning styles, knowledge base, or social supports. Calling this out doesn’t absolve the employee, or the student, from the responsibility of their employment or education. In an ideal world, this is a two-way street where the supervisor and the employee meet each other in the middle and develop a path to success together. This is ultimately what I want to accomplish, but like so many ideals, it felt like a distant abstract concept without any concrete steps to get there. As much as I like to hold on to an ideal, if I can't make some semblance of it work in real life, then I'm left living a fantasy. Remaining frustrated in my daily work, and wondering why what I was doing wasn't working consistently. I had to figure out how to reach that balance between meeting someone where they're at and keeping them accountable to the work required of them. Common Delegation Mistakes One of the frustrating parts of learning any new skill is the mistakes that inevitably come with the learning process. No matter how many mistakes I make, I am somehow still surprised when I make them, especially after I think I have a hold of what I'm doing. Despite having delegated in the past, because it is a process driven by people, it is slightly different every time I need to do it. Here is a list of mistakes that are common when learning how to delegate, or more specifically, mistakes that I made while learning how to delegate:
Working through all these mistakes multiple times, I learned that delegation is not a one-and-done sort of skill but something that is consistently adjusted with the dynamics of the team and the work. Alongside learning to delegate, I had to learn how to give myself the grace to be flexible in my approach. Despite the mistakes I made, there were some successes with delegation that gave my staff confidence in their own skills and our work together as a team. A Framework for Effective Delegation "If you want it done right, do it yourself." This old saying captures the burden many of us feel when asking for help or putting responsibility on someone else. I have a hard time asking someone else to do something when I am pretty capable or could do a better job. When a task is being done that I feel I could do better at, I have a tendency to nudge my way in. I struggle to sit still if I think I can do better. This makes it hard for me to let go, to provide someone else the opportunity to do the work and develop the skills. More so, this behavior tends to take on a burden that increases unnecessary stress and leads to burnout. Part of leading is developing a team and recognizing that a team is capable of more than the individuals who make up the team. The only way to get to that point is the delegation of tasks to work together. Lack of delegation will prevent you from developing necessary skills that will prepare you to move forward. Train for delegation. Train for your replacement. I had to learn to let go of my own ability and create a structured plan that can help me relieve tasks to others in a supportive and collaborative way:
Simple Delegation Template For each task you delegate, clarify these five elements:
I keep this as a simple checklist in my notes app and review it before delegating any significant task. The Power of Structure Of this process of learning how to delegate, I have found one section that has become incredibly valuable for me: Structure—for a long time, I pushed against structure, finding it too constraining. As a young professional, I enjoyed the "complete creative control" of making my own decisions once given the assignment. I have mistaken again and again in thinking everyone is wired that way. Structure doesn't have to mean lack of freedom but more direction. As a leader, that aspect of the job is often in the title "Director of Admissions"—somehow I was missing that piece. When I reflected on how I took on a project, I realized I was providing my own structure, much of which was taken from my days producing theatre. I saw that part of the delegation process is to provide enough structure that gives staff enough room to know where and how to make decisions so they aren't lost in the project itself. One of my favorite examples of delegation structure is Tom Sachs' studio manual "10 Bullets". It's a set of principles that guide how his art studio operates, covering everything from maintaining tools to communication protocols. The bullets include directives like "Always Be Knolling" (organizing tools and materials at right angles), "Keep a List" (document everything), and "Sacrifice to Leatherface" (admit mistakes immediately).
When going through these bullets for the first time, they felt harsh and like something I would never want placed upon me. But as Jocko Willink preaches, discipline is the foundation for freedom. Creatively, when we have boundaries to push against, they provide a leverage point for being able to be more creative.
It's similar to pushing water through a hose. The water holds potential energy, but the hose allows you to turn it into targeted energy. The real trick behind this is we can't just adopt Tom Sachs' Ten Bullets and call it good. The structures that work for me and my team are going to be different from what works for you and your team. To develop a structure for support, we each need to experiment and weed things out. The good news is there are lots of things to steal from to give us a starting point. This is where both Pablo Picasso and Austin Kleon's advice comes in handy. Steal the things that make sense, and play with them to see if they actually work. I loved the idea of Tom Sachs' 10 Bullets so much that I created my own. I even made a little book. Some of the bullets stuck and some of them didn't, but the exercise was solid. It reinforced the idea that there's no answer; it's all just trial and error until you come up with a solution that works for you. This alleviated the pressure I felt when solutions I had come across didn't work for me. Putting Theory into Practice Recently, in two very different circumstances, I helped two of my younger staff take the lead on an event our office hosts. For the first event, I provided minimal structure, leaving her to do much of the work on her own and figuring out how to do things. This ended with the staff needing to pick up where balls were dropped, not because she deliberately dropped them but because she didn't know which balls were in the air. Despite her involvement in past events, she didn't keep track of how the event was run. Never having led an event herself, she didn't know what it took to lead others up to and through an event. The event worked out fine; we repeat the events every year, so it's more or less taking what we did the year before, making some minor adjustments, and then executing. Learning from this experience, I went about creating the necessary structure that would make delegating the next event easier. One of the problems that we run into with collaborative events is that the collateral for the event (schedule, meeting notes, attendee list, campus partners, etc.) ends up in different people's digital filing systems. This made it hard to reference the next year due to turnover or forgetting what we did. I created a shared "events" channel in our office's Microsoft Teams. This allowed campus partners not in our Team to have edit access to the folder and anything we put inside. Having one collaborative location made managing the event easier, and now that everything is in one location, we'll be able to reference it next recruitment cycle and not have to reinvent the wheel. The other major structure change I made was asking the staff member to work alongside me on leading the event. This walked them through the process, seeing how I did things, and giving them the autonomy to complete tasks on their own. By working alongside my staff member (step 5: Provide support and resources), I was able to demonstrate clear expectations (step 4) while building trust in her abilities (step 2). The shared Teams channel created the structure needed to monitor progress (step 6) while allowing for reflection and adjustment (step 7). Due to this tag-team approach to managing the event, we ended up naturally completing the steps in the delegation process, resulting in a successful event and a team member who now feels confident taking the lead next time. When done right, delegation isn't just about getting tasks off your plate—it's about developing your team, building mutual trust, and creating systems that make everyone more effective. Start small, be patient with yourself and your team, and remember that becoming an effective delegator is itself a skill worth developing. Get more like this directly to your inbox
The Pattern of Avoidance
I sat across the desk from one of my direct reports as we looked over their numbers for the year. This was the third time we had done this. As a new supervisor, I was nervous. The numbers weren't good. They hadn't been all year, and I needed my employee to recognize this to make necessary changes. "What kinds of trends are you seeing in the numbers?" I asked. She stared at them blankly. The longer the silence continued, the more uncomfortable I felt. There was clearly something missing. As her supervisor, I felt a great deal of responsibility for that lack of understanding. I went over the year in my head:
"Take some time with them and come up with a plan for how we can improve them next cycle," I finally said. With that comment, I left her office, retreating to the comfort of my own. I had set out to have a tough conversation with my staff member and ended with the hope that she would pick up my subtext. I knew this wasn't the best approach, but I also didn't know any other way. Despite having considerable leadership experience, conflict was something I had managed to avoid throughout my career. I did mind it. It made me uncomfortable, never seemed to solve problems, and wrecked otherwise good relationships. Understanding the Cost of Avoidance Conflict is inevitable and easily one of the most misunderstood aspects of leadership. When embraced and approached with the right intention, it can provide the leverage needed to create great working environments, build strong relationships, and develop innovative solutions. The tricky part is overcoming the lack of experience and working through the overwhelming feelings, especially when past conflicts—whether with family, friends, or colleagues—have left emotional scars. Marcus Aurelius was onto something when he wrote, "The impediment to action advances action. What stands in the way becomes the way." It's unfortunate that human nature is so adapted to avoiding discomfort that we have to work hard to run toward what's good for us. My Conflict Avoidance Origins Growing up in the age of participation trophies, I didn't encounter meaningful conflict until high school and college. Even then, the conflicts I experienced were framed within academic settings and creative projects. In these environments, I remained on the sidelines. There was always someone with authority—a teacher, director, or professor—who took the reins and guided us through the conflict. When I finally reached a position where I should have picked up those reins and led a team through conflict, I struggled to find my authority. I would easily share my experience and opinions but relied on others to provide direction. I justified this by believing I was giving others a voice, but what I wasn't doing was providing the structure necessary to work through conflict and emerge stronger on the other side. The Turning Point Managing an office placed me in a position where the buck stopped with me. The results of our team were directly tied to my ability to lead safely through conflict and come out stronger. My passive approach wasn't working. Yes, it made conflicts easier to swallow—everyone felt heard, and we could sit in the same room together. But the results fell flat. There was no action plan, no accountability, no forward movement. We were sitting in conflict but not moving through it. This resulted in more conflict and a great deal of confusion as to why we weren't emerging in a better place. There are moments in life when you're presented with a clear crossroads. You can see the options before you, and a choice must be made. This was one of those times. As I observed these repeated conflict cycles at work, I noticed them outside the office too. Will Guidara's observation that "the way you do one thing is the way you do everything" resonated deeply. I didn't like this cycle of conflict avoidance. I didn't want this to be "my way" of doing things. I had a choice to make. Learning a New Approach One catalyst for change was a three-day certificate course I took at the University of Washington. The curriculum was designed to help leaders navigate change. What I didn't anticipate was how it would change my perspective on conflict. Due to change being the theme of the leadership certificate course, we talked extensively about conflict. These conversations expanded my definition of conflict beyond my simple expectation of "two people at odds trying to get the other to relent." I began to understand that conflict encompasses any situation where different needs, perspectives, or expectations create tension that requires resolution. The course curriculum seemed particularly relevant to the changes I was experiencing at work: staff turnover, searching for a new CRM, and restructuring admissions post-pandemic. Conflict emerged as a recurring theme. Throughout the three-day course, as we discussed leading through changes, the instructor outlined a process for incorporating conflict productively:
Despite having this framework for embracing conflict, I still felt considerable trepidation about putting it into practice. My brain kept searching for ways to navigate through change without conflict—either by avoiding it entirely or by creating an inclusive process where everyone could move together without friction. When I raised my hand to ask if this was possible, my professor looked me directly in the eyes and said, "No. There's only one path to change: through conflict." This was a profound learning moment for me that continues to resonate. It represented a seismic shift in my perception of the world: The one thing I can consistently count on is change, and the only way to navigate that change effectively is through conflict. From Theory to Practice Intellectual revelation is powerful, but implementation is where transformation occurs. A big reason I work in and love education is because of ideas and mental development. However, it's one thing to grasp a concept intellectually and quite another to put it into practice. That final step—practice—is crucial but challenging when it involves something you've avoided your entire life. When something is inherently uncomfortable, we tend to avoid it at all costs. Conflict affects me physically: my body fills with emotional dread, and some form of fight, flight, or freeze response kicks in. As a drama teacher, I once had a middle school student, Meredith, who loved my beginning drama class until she had to be in front of the whole class. Early in the year, I assigned a presentation to help students become comfortable performing. Each student could choose a process they enjoyed and then teach the class the steps. Meredith chose cupcakes. On presentation day, she brought in homemade treats. She was thrilled to share her love of baking—so excited that she could barely contain herself before class. When I asked for volunteers, Meredith's hand shot up first. As she made her way to the front, her classmates called out encouragement: "You got this, Meredith, just stay focused." "You can do it! Remember to breathe." "We got you, Meredith." I appreciated such a supportive class but was confused by their comments. Clearly, they knew something I didn't. Meredith set up behind a table, looking down at her cupcakes. Once at the front, she wouldn't look up, just staring at her hands. After what felt like forever, I said, "Whenever you're ready..." She took a deep breath, and as soon as she lifted her head, her body took over. Her eyes swelled with tears, her hands started shaking, and her voice trembled. Despite her excitement to share, her biological response took control. My experience with conflict isn't that extreme, but I recognize similar patterns. When approaching conflict, my sweat glands activate, and my mind goes blank. My physical body tries everything to escape what feels threatening, even when it isn't. Intellectually I know the modern workplace conflicts I face aren't actually life-threatening. Unfortunately, human evolution hasn't caught up yet—my bodies still respond as if they were. Finding My Way Through The two most valuable insights from the workshop that helped me develop a workable solution were:
Reframing has been part of my personal growth journey for years. It helps me contextualize experiences and behaviors within new perspectives, allowing me to move forward more effectively. Practice is essential for developing any skill, and fortunately, there's rarely a shortage of conflict, even small ones, at work or home. The challenge for me was addressing the biological component. My inherent discomfort with conflict made it difficult to begin practicing. This is where I drew on acting exercises from my college days. These visualization techniques are designed to help actors bridge mind and body, gaining control over emotional states so they can portray them authentically on demand. These visualization exercises, combined with journaling, deepened my reframing process and allowed me to engage in conflict practice while maintaining the capacity to make deliberate choices. The discomfort I feel during conflict isn't eliminated by these exercises, but it becomes tolerable. Ongoing Journey As long as I continue working with people, conflict will be inevitable. Rather than trying to create circumstances where I avoid conflict altogether—which is impossible—I'm better served by embracing it and learning from it. I can't claim to be an expert or to have fully integrated conflict into my leadership approach, but I am a more willing participant now. I still fall into old patterns when conflict arises unexpectedly, but thanks to practice, it's easier to recognize these tendencies and adjust my behavior in real time. I suspect this will be a lifelong pursuit. There's no way to become comfortable with all the different forms conflict can take. Seeing every conflict as an opportunity is far more productive than viewing it as a barrier. Real Results More recently, I needed to have a difficult conversation with a staff member about another performance issue. Rather than approaching it as a reprimand or corrective action, I reframed it as an opportunity for growth. This employee was consistently arriving late. This behavior was noticed by everyone in the office and was becoming a breeding ground for resentment. Intellectually, being late might not seem significant, but allowing this pattern to continue enables other standards to slip as well. As team members, we need to rely on each other, and if we can't count on someone to arrive on time consistently, we begin to question what else might be unreliable:
Due to human nature, our minds quickly construct negative narratives. Before addressing the employee, I took the time to prepare. With pen and paper, I wrote out the specific issues and various approaches to addressing them. Writing it out, especially on paper, serves both as reframing and practice. It provides notes to reference should my biological responses interfere with my intentions. Another valuable technique I applied came from Simon Sinek, who recommends stating your intention explicitly at the beginning of difficult conversations. Using our words to frame the interaction before addressing the issue creates psychological safety. This too was something I worked out on paper first. The conversation wasn't easy, but it went much better than it might have otherwise. We addressed the concern directly and created a plan that would lead everyone toward success. Lessons Learned After two years of consciously working to embrace conflict, here's what I've learned:
Whether you're leading a team, raising teenagers, or simply trying to live authentically, learning to work through conflict rather than around it opens possibilities that avoidance keeps locked away. The question isn't whether you'll face conflict—it's whether you'll use it as an opportunity for growth. Get these posts sent directly to your inbox.The Initial Resistance My journey with technology has been one of reluctant transformation. From actively avoiding coding in high school to eventually embracing technology as a tool for human connection and efficiency, I've discovered that my initial resistance was preventing me from accessing a world of possibility. Here's how that change happened. My senior year, I had a free period I needed to fill. Flipping through the course catalog, I stumbled upon a C++ coding class. My friend Alex had been coding video games in his basement for months and it seemed like magic—the kind I wanted to learn. With visions of creating the next King’s Quest, I signed up, unaware this would solidify a habit of dismissing technology that would take years to resolve. Arriving to class the first day, I knew I had made a mistake. There were a few things that should have tipped me off:
As soon as I sat down, next to a friend who was stoked about the class, I looked for another class. I don't remember what I ended up taking, just knew that coding wasn't for me. I placed technology at arm's length and moved on with my life. Technology at Arm's Length: Living with but Not Owning Technology From that moment forward, I saw technology as something outside of myself—something I've interacted with but never owned. It was the same approach I had with my body. I interact with the world through my body, but it's only recently that I've taken any kind of ownership with it, finally paying attention to how my body feels, moves, and changes with different circumstances. Similarly, I am attached to technology. It's a part of my everyday life. My lights automatically turn on in the morning and off in the evening. We only stream our visual entertainment. My phone is never far out of reach. When the internet is down, I can't do 90% of my work. Compared to my grandparents, I would appear to be the bionic man. The Turning Point: Building a CRM from Scratch This shift in my perspective of technology started 10 months ago when we began onboarding new software at work. The goal was to completely digitize our business processes. If you've ever been lucky enough to work at a small institution or company, you'll know what it's like to wear many hats. Ten months ago, I put on the hat of building the new CRM. I am not alone; there is a small team. But the dynamics put me into a leadership position. I got to work learning how to implement new software and build out the business workflows I was envisioning. This steep learning curve was like looking at the man behind the curtain. These back-end processes that I had skipped over out of disinterest I became interested in out of necessity. I could see how this new software could change the way the office functioned. I saw how it could make things easier for everyone. I saw it as a tool rather than another thing to wrestle with in order to get the work done. When technology works, creating a seamless experience that removes the drudgery of the work and opens up the path to enjoyment, it's a game changer. As I looked around at life after the pandemic, when such an event caused so many of us to embrace and integrate technology into our everyday lives, I could see a path I hadn't seen before. This path was remarkably similar to when I lost my teaching job—a time that very much felt like the boats were burning in the bay, and the only way through was to figure out how my theatre skills could be translated into other industries. In theatre, I had learned how to read audiences, craft compelling narratives, and adapt quickly when things didn't go as planned. These skills translated surprisingly well to designing digital experiences that engage students and streamlined communication flows. Just as I once crafted different experiences for different audience segments in theatre, I now design different engagement pathways for different users in our CRM. The Choice: Resist or Embrace The future of higher education recruitment—the future of just about everything—requires technology. Those who succeed are going to be able to create custom solutions to problems by leveraging technology. An industry that attracted me because of its social nature (recruitment and sales) has shifted to be based in technology. The way I saw it, I had two choices: I could either keep doing what I'm doing and hope that higher education would stay the course and I could ride the retirement wave, or I could take this opportunity to develop new skills and push myself to embrace the technology tools I had always skipped over. I chose the latter. I'm not one for waiting or holding out. If there's something that can be done, it probably should be done. Plus, I'm a big believer that: I am the master of my fate: The Learning Process: From Basics to Breakthrough
Part of the onboarding process for this new software was a 20-hour class that walked through the basics of how the system worked and how it could be built. I signed up and started learning. It was a very basic course, which was good for me but awful for everyone else. It didn't really tell us or show us how to do anything. Part of the mission of the company was to create a system that was accessible to anyone no matter their experience. My colleagues who wanted to get started building right away were frustrated about it not being helpful. For me, it was a crash course in database management—an introduction to concepts I couldn’t be bothered with. This basic training would prove to be just the beginning of a much deeper journey into understanding not just how the software worked, but how technology has reshaped my environment. In the process of learning how the system works, I realized how dependent the office is on software to do our work. It's central to everything we do. This dependency is a form of technological handcuffs—a situation where we become so embedded in systems that we lose perspective on alternatives. These handcuffs can be found outside the office into our personal lives. We live in a time where our lives are seamlessly integrated with some form of technology, often without conscious choice or design. This isn't forced dependence but something more subtle: unexamined reliance—which may be worse because we have the ability to do something else, yet our default is to remain on autopilot. The difference between being controlled by technology and controlling it often comes down to one factor: whether we've taken the time to understand how it works. This realization created a weight to the process I didn't anticipate. If my staff are going to be dependent on this software to do their work, then it better be good. We’ve all experienced software that doesn't support our work or makes the process more difficult than it should be. I was determined to not let that happen. The Technical Immersion: Learning by Doing The software utilizes several different aspects of computer science that I needed to learn. For months, I put my head down and dove head-first into learning as much as I could. I spent hours reading articles and watching YouTube videos on topics like:
But more importantly, I went in and built things—a lot of things. Most of the time, things didn't work, and then I’d have to rebuild them. There were so many problems that I came across that didn't have specific instructions because they could be done dozens of different ways. This required me to solve problems rather than seek solutions. After spending hours solving a problem, I would invite someone to look at what I had done. They would pull up the screen and see that, yes in fact, the student's application type was now showing up on their record. What they didn't see was the hours of work it took to make that happen correctly and consistently. Good computer science is like good magic. You're not supposed to see the work that goes into creating the effect. All the audience should see is the magic, or in the case of technology—the functioning. Key Realizations: The Power of Iteration This process of creating and recreating led to another realization: iteration is the way through. As much as I tried to research and work through the problem on paper, I would inevitably forget or not think of something. Rather than trying to create a perfect solution the first time, it was far more productive to figure out a basic solution, create it, and then see how it worked in day-to-day operations. My experience mirrors what researchers have found about technology adoption. Studies show that initial resistance often stems from what psychologists call the "ambiguity effect"—we prefer known situations (even if imperfect) over unfamiliar ones with uncertain outcomes. One study from MIT found that once people overcome this initial resistance and gain basic competency with a new technology, their satisfaction increases dramatically, creating a "conversion effect" where former skeptics become advocates. I tend to get stuck in the learning stage, concerned about creating something mediocre, halting all progress. After recognizing this behavior on this project I started seeing it everywhere:
An iterative process limits learning and gets your hands on a functional model and a potential solution. Which can be motivational fuel to keep the project going. Functional models and potential solutions are all well and good, until the models you’ve come up with result in frustration not potential solutions. Dropping you neck deep into the mire. The mire is part of any project, especially when learning something new. It is the tipping point of the learning process. The Wrestling Match: Persistence and Breakthroughs Due to my lack of software development and database management experience, I found myself in this challenging place quite a bit. It very much felt like I was wrestling with the software to try and get it to do what I wanted. It's in this space where perseverance became valuable, but not the kind of perseverance I expected. As much as it felt like wrestling, I rarely came to any real solution through these forceful interactions. The real breakthroughs for me came in the lull of the chaos. The solution would come after the wrestling, when I had exhausted mental energy and onto something completely different. I would step away from the project and work and go for a walk, or cook, stack wood, letting my mind wander. It was in this space that my mind would subconsciously connect dots that eventually led to a the solution. What shifted wasn't just my technical knowledge but my entire relationship with technology. Previously, I saw technological tools as impositions—that demanded I adapt. With this project I began to see it as extensions of my creativity, malleable to suit my needs. The workflows I was creating weren’t some abstract technical exercise; it was a form of communication—with both machines and the humans who would use them. This perspective shift transformed technology from something I tolerated into something I could shape. Embracing technology and being able to accept the challenges of learning something I was hesitant about opened a world I only half knew existed. Technology and Humanity: Finding Balance Technology is the great unknown. Zooming out far enough we are unsure how it will impact the world; all we know is that it will. There is a lot of hesitation to embrace it because of the fear around what it could do. I was worried about what it meant about me and why I couldn't understand it or even why I wanted to. Working in education, an industry that embraces change slowly, technology is directly impacting the way I do my work, the way I interact with my team, and the way I interact with students. Part of my fear was that technology would replace or remove many of the aspects of my humanity I value:
What I discovered is that when I keep these in mind, technology allows me to remove barriers that prevent me from more fully embracing these human aspects. Technology in Action: The Road Trip Example Recently, I went on a road trip with my in-laws down the Washington coast. There was a list of spots we wanted to visit. Not that long ago, road trips would unfold in real time, with decisions about where to go and how to get there being made spur of the moment. I appreciate the spontaneity of these moments. It’s one of the aspects of road trips I remember fondly. Alongside those memories are deep levels of frustration from a lack of decision-making with too many people. Especially with family, these can be potentially relationship-damaging. Thanks to technology and my willingness to embrace its tools, as a group we were able to:
Like a lot of preplanning, our eyes were bigger than our stomachs; we planned more stops than we actually had time for. The document gave us all the information we needed to make new decisions quickly. This gave us more time together, which was the whole point of the trip. What My Technology Journey Taught Me Looking back, several principles emerge that might help others navigating their own relationship with technology:
Looking Back to Move Forward Looking back to that high school coding class, I realize now what I was missing: context and purpose. Technology without meaningful application remains abstract and intimidating. But when connected to human needs, relationships, and real-world problems, it becomes not just accessible but transformative. My journey from technological avoidance to embrace hasn't removed my humanity—it's enhanced it. I've found that technology, properly understood and applied, doesn't distance us from what makes us human. Instead, it can clear the path for deeper connections, more creative expression, and greater agency in shaping our world. 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:
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. |
