 Last Sunday I drove my work car up to Everett, Washington. Before leaving, I ran through the mental travel checklist I created years ago when travel was a much bigger part of my work schedule. It still holds up:
When everything was checked off, I got into the car for the first two-hour drive of a week of much longer drives. The drive was smooth. Relying on habits, reassured by having done this a million times before. Until I got out of the car and grabbed my bags to check into the hotel. I had forgotten to pack tabling materials. My travel schedule is not what it used to be. The rituals and habits I had come to rely on were out practice. Making this transition into a week of travel more challenging than it needed to be. Everything ended up just fine, but I spent the next week thinking about all the transitions I experience and how little things can make or break them. Why Transitions Matter Transitions are hard for everyone. We experience far more of them than we'd like. During transitions, things can spiral out of control. Without proper support systems, transitions become difficult to navigate, much less overcome. In this post, we'll explore how transitions work, why they can be so challenging, and what we can do to ease them, make the most of them, and perhaps even enjoy them. Before becoming a parent, I had no idea what role transitions played in our lives. Growing up in a military family, I recognize now that my life was in constant transition. I just didn't have language for it. It felt normal. When I became a parent, the benefits of managing our kids' transitions became clear. Routine and consistency became a new religion. We suffered immediate consequences when we broke away from them. What I didn't understand, partly because of how I was raised, partly because of my ego, was how transitions continue to affect me on a daily basis. The Pandemic Awakening When the pandemic hit and everyone was forced into a new reality, I became hyperaware of my daily transitions. Mostly because I didn't have the typical processes that supported those transitions. When we first went into lockdown, I set up a temporary desk in my bedroom. Having work so close to my personal space quickly became too much. Two weeks at the bedroom desk, I caught myself checking work email as I was settling into bed to go to sleep. I was trying to maintain work boundaries in a space that had no boundaries. The physical proximity had erasied the mental separation I needed. I needed a transition from home life to work. This transition is a natural boundary that helped me manage my daily activities and relationships. After seeing that lack of transition and how it affected me, I started seeing them everywhere. Just about everything we experience involves a transition. If we don't have the things in place to help move from one step to another, there's an opportunity to be derailed. This also became obvious at work. I watched my staff struggle to balance their own lives with their work schedules. We spent many staff meetings talking about what this larger transition felt like in our day-to-day lives and trying to figure out how to balance it all. A Framework for Understanding Transitions In my search for a solution, I came across William Bridges's Transitions: Making Sense of Life's Changes. In it, he outlines a process that every transition has and where we get stuck. Each transition has three phases:
Not surprisingly, it's in step two, the Unknown, where we tend to get stuck. For many of life's transitions, there are no plans or preparations that can get us through. This is what the majority of Bridges's book addresses: catastrophic transitions like the sudden loss of a loved one, cancer diagnosis, or unemployment. But for every catastrophic transition, there are a million small ones where we have a great deal of control. How we handle these smaller transitions directly impacts the quality of our lives. The better we navigate these transitions, the better our lives become. Investing energy into understanding transition patterns, both universal and personal, will improve our experience with transitions and, therefore, improve the quality of life. What Religions Knew About Transitions Over millennia, religions designed rituals and rites of passage to help with small and large transitions. Things like baptisms, wakes, meditation and prayer, sacraments, Sabbath observances. While tied to specific belief systems, these practices offer practical wisdom for managing daily transitions, even in secular contexts. It's easy to look on these practices as quaint and dismiss them as misguided relics of a different time. Because they tie so closely to the dogma they're a part of, we can throw out the baby with the bathwater without fully knowing what we're discarding. Most religions preach peace of mind and a sense of relief in a very noisy world. As the world becomes more educated, faster, and more connected, more of us seek that sense of peace but without the religious baggage. I think one solution to continued progress lies in lessons from rituals created over thousands of years. Transitions Hit Hardest with Stress and Decision Fatigue Two factors directly affect how we manage transitions: stress levels and decision-making capability. These are moving targets that depend greatly on how the day goes, the type of work we do, and how well we manage both components together. Both stress levels and how we make decisions have their own patterns and cycles and are, in a sense, transitions themselves. Understanding these patterns reveals when and how to implement rituals into our daily lives. The Stress Cycle In their book Burnout: The Secret to Unlocking the Stress Cycle, Emily and Amelia Nagoski outline the stress cycle as:  The goal is to create ways that get you back to recovery faster, shortening the activation and resistance stages.  If you're unaware of how you manifest stress, you can see how this cycle mirrors the transitions cycle, where activation and resistance become the Unknown. When navigating activation and resistance, the Nagoski sisters offer these recommendations to shorten the cycle:
Making these regular practices could be considered rituals. Which stress-relief practice works depends on the transition type:
After observing my own transition for three months, patterns emerged. Decision Fatigue When we make many decisions throughout the day, it leads to mental exhaustion that results in decreased willpower, increased impulsivity, and a decline in decision quality. This is why it feels like our worst decisions are made late at night or after a stressful day at work. Understanding stress cycles and decision fatigue reveals when rituals are most crucial. In Bridges's "Unknown" phase, our stress peaks and decision-making weakens, precisely when pre-established rituals can carry us through. If we know our decision capability will decrease throughout the day, we can determine where rituals may best serve us. We can implement rituals throughout the day so we rely on the system to make decisions for us. Or we can implement them at day's end, when our decision-making ability has weakened. The ritual can bolster us as we let go and give in to the process. A good example is meal planning and prep. Our Sunday meal prep ritual eliminates 14 dinner decisions per week:
The ritual isn't the cooking, it's the decision-making session on Sunday that removes daily friction. If you're getting hung up on the word "ritual," you can use system, routine, practice, or habit. Anything that denotes building a process structured enough so you don't have to think about it. This allows you to give in to the process and let go of other things. Lessons from Religious Rituals Sabbath: The Rhythm of Rest Different religions approach the Sabbath differently, but the concept stems from verses in the Old Testament: "Six days thou shalt work, but on the seventh day thou shalt rest: in plowing time and in harvest thou shalt rest." - Exodus 34:21 While many of us assume this is a commandment rather than a ritual, the perception stems from the duration and how different religions define "rest." I want to clarify that the ritual portion is this: one day a week should be set aside for rest. In America, we love work. I'd even go so far as to say work is the new American religion. We pride ourselves on putting in long hours, hustling, working hard, and resting very little. It's a badge of honor, awarded socially as much as monetarily. There's plenty of research now about the benefits of rest. Sleep, in particular, now joins exercise and diet as a pillar of health regimens. If you were to talk to anyone who exercises seriously, they'll tell you about the importance of rest days. Recovery becomes part of the process. After all, muscles grow during recovery, not during the workout itself. When it comes to non-physical activity, rest plays a major role as well. One of the key steps of the creative process is incubation, the place where you allow the material you've been consuming to take a back seat, letting your subconscious do the heavy lifting. Stop forcing a solution and see what comes. This can be hard to schedule because it feels intangible, and we're a culture that loves being in control. But if you've experienced it, you know the power your subconscious can wield after you've exhausted yourself with trying. I think the ratio is also important: 1:7. Six days is still substantial work, and taking that seventh day will boost your productivity and make your work more sustainable. Your weekly rest day doesn't need religious framing. Some questions to design yours:
My version: Sunday is no obligations. Sleeping in. Prolonged morning coffee. Late brunch with my family. Jack Johnson’s Banana Pancakes is my anthem. Just pleasure, play, and presence. Wake: Structure for Grief Judaism holds a wake, not just a funeral, but a series of rituals over a period of time. It's the structure I find most interesting. After the funeral, Jewish tradition continues with "shiva," a structured seven-day mourning period held in the mourner's home. Friends and family visit, comfort the bereaved, and participate in rituals such as lighting a memorial candle, sitting on low stools, covering mirrors, and refraining from entertainment or grooming. Shiva focuses on comforting the living rather than on the deceased's body or the funeral service itself. Death is another topic where we struggle to create space. Having the space predetermined before death occurs, and having practiced similar rituals during smaller losses, makes it easier to enter that space when needed. Connecting Small Rituals to Big Transitions What does this have to do with daily transitions rather than big transitions? It's easy to see how these kinds of rituals and structure help with major life transitions. But it's less intuitive when we're working with our daily transitions. Here's why daily transition rituals matter for major life changes: When restrictions around the pandemic loosened we were balancing going back to work and school, I couldn't make any new decisions. My morning coffee ritual continued automatically. Weighing beans, grinding, brewing. These mindless actions created 15 minutes of stability each morning. I didn't have to decide to do them; muscle memory took over. If I hadn't already established this ritual during normal times, I'd have had nothing to fall back on during times of stress. You can't build new habits in the moment, you can only rely on existing ones. When our daily transitions become strong and structured habits, we're more likely to maintain them during major transitions. These habitual smaller transitions keep us afloat during larger life-altering transitions. Habits and daily rituals can be done without much thinking. We can allow the habit to carry us through while our emotions and minds wrestle the larger transition. In this case, the ritual is like a conveyor belt we can step onto while navigating the unknown. We can remove our thinking and decisions from the mix and continue forward movement. The unknown can compound itself and make navigation more challenging. Having some stability that handles the daily transitions has the ability to bolster and sustain. Part of the reason the pandemic caused such disruption was that it upset so many routines simultaneously. Making it hard to know what to do, how to make decisions, or what the best way forward looked like. Overnight, the things we counted on became unreliable. Those dominos led to other dominos, and we faced a mess. Building Your Own Rituals Identify Your Transitions Before you can deliberately build your own rituals, you need to identify where you need and want them. This requires observation and note-taking. Track your transitions for one week:
My tracking revealed my worst transition was 5pm (work to home). I'd arrive home mentally still at work, unable to be present with my kids. That insight led to my "commute” ritual. For me, the morning is the most important transition. It either sets up my day for success or leaves me feeling like I'm running downhill, chased by a boulder. To manage this, I have a few different rituals for different morning transitions. My Morning Rituals First Thing: Getting to the Gym When I can get to the gym, my day tends to move more smoothly. I have more energy throughout the day and sleep better at night. My morning gym routine addresses all three phases of Bridges's framework:
To help with this transition and combat the morning fog and infinite possibilities that await each new day, I:
These smooth out the process of getting from my bed to the gym. Getting up before everyone in my house cuts down distractions even more. After the Gym: The Coffee Ritual This one is probably my favorite and the one with which I am most consistent: Coffee. I came late to coffee and fell in love with the process as much as the taste. For this example, it's more about the process than about drinking it. It helps with the transition from gym to home, which then leads into the transition to work/school. This process shifts my mood and mentality, getting me into the right frame of mind for taking on the next steps:
My methods have varied, but it's the process that matters. I do it without thinking, so I can then settle into the next phase. Starting Work: The Physical Transition My next morning transition is entering the office to start work. This is where I've felt a huge difference from making a physical move. Working from home, while I enjoyed it, meant I was consistently fighting justifiable distractions: laundry, dishes, another cup of coffee. They're all decent things to do, but if I can't fully transition, I'll constantly fight distractions and struggle to achieve focus for deep work. Going back into the office made this transition key to starting my day well. It all starts with leaving the house on time. I catch the bus into work, and if I miss it, I'm 20 minutes behind schedule. I have a 10-minute ride to campus. Not having to worry about driving provides mental space to ease into the day ahead. I'm often listening to a book, but if I'm not holding my second cup of coffee, I have both hands free to write on my phone. I try to avoid scrolling. When I get into the office, I set up the space. This means:
What Didn't Work Failed experiments teach us what pitfalls to avoid. Here's what I tried that didn't work:
The lesson: Rituals must match your energy level at that transition point. Morning gym works because exercise energizes me. Evening journaling failed because it required mental energy I didn't have. Rituals Have Costs Setting up these rituals and habits is all well and good, but what happens when they don't work? When you fall off the train? Rituals have costs: time, mental energy to maintain them, rigidity that can frustrate others. My morning routine requires waking at 4:45am. Which means I need to go to bed early. This has been hard to balance as my kids are getting older and don’t want to go to bed at 8:00pm anymore. Before building a ritual, ask: Is the transition problem bigger than the ritual's cost? For my morning, yes, absolutely. My pre-ritual mornings were chaotic enough to affect the whole family. But not every rough transition deserves an elaborate ritual. Sometimes "good enough" is fine. When Rituals Break Down At the end of the day, we're all human. Holding to a strict code of work, while ideal and required by hustle culture, simply won't happen consistently. I never thought of myself as a perfectionist until I examined my approach to habits. A common thought that ran through my head was, "I'll do it tomorrow." I saw this as giving myself grace, but underneath this grace narrative was a fear of failure. I feared my inability to keep up, to do it properly, to be consistent. Rather than get started and try, I held off until a “better time”. The problem is tomorrow never comes. "The road to hell is paved with good intentions." Even after identifying where we'll benefit from rituals, building them, and having moderate success, there will come a day when it all stops. We're too busy, we get sick, we're traveling. Something will eventually interfere with habits we desperately want and need. It's at this point where we have a decision. We can either let this derail us or dismiss it and keep going. The Triage System When everything falls apart (sick kids, work crisis, travel), identify your keystone ritual, the one that, if maintained, keeps you minimally functional. For me: the coffee process. Even when I skip gym, work from bed, eat cereal for dinner, I still make coffee properly. Those 10 minutes preserve my sense of self. During my worst work crisis, I did nothing else consistently for two weeks. But daily coffee ritual signaled: "You're still you. This chaos is temporary." When the crisis passed, I rebuilt other rituals one at a time, starting from that anchor. The Self-Criticism Trap I have been a practitioner of this my entire life. Turning inward toward my inability to meet my personal commitments brings out my harshest critic: myself. It's at this point where the negative self-talk comes out in droves. Like a fresh wound discovered by my tongue, I can't leave it alone. I am convinced that if I can get to the bottom of the missing ritual, then I can prevent the mistakes from happening. Believing that self-criticism is the path to perfection. And so I press on with incessant callouts to what I've clearly done wrong and why I'll never actually reach my goal. Instead of being a way out, this is a vicious cycle that prevents me from moving forward. This process pushes me back to square one rather than letting me pick up where I left off. At this point, when feeling like a failure for not keeping up with what I've promised and set out to do, I am reminded of something that Gandhi said: "Each night, when I go to sleep, I die. And the next morning, when I wake up, I am reborn." Failure is something I learned at an early age to avoid. Despite knowing this wasn't what I wanted to do, I did it anyway.
This framework is based on how I compare myself to others. According to Robert Greene, we see others not as they are but as they appear to us. This perception misleads us, creating myths around simple humans. It's in this comparison where I get stuck. The solution, akin to what Gandhi said, is to see people, including myself, as they really are: fallible human beings. Dying and Being Reborn Gandhi's "die and be reborn" isn't metaphor. It's a method. Here's how I practice it: Each night laying in bed: I go through the day and close it out. This mental ends my day, giving me a chance to let it go. Each morning: I mentally start fresh. Setting aside everything from the day before. The mental act of closing and opening the day creates the boundary. Without this ritual, I'd mentally rehearse failures while trying to sleep, then wake up already defeated. When I can accept this truth, I am better able to let go and allow myself to die, so I can be reborn, not starting over, but continuing from where I left off. The Purpose of Rituals Ultimately, the rituals and habits we create are designed to help us navigate transitions that can throw us for a loop and disrupt our forward momentum and sense of self. These rituals can guide us through the Unknown when our expectations get interrupted. Rather than leveraging the habit or ritual primarily for productivity, we can use them as stability anchors. When framed in this way, it can eliminate the judgment that comes with any kind of outcome or lack of consistency. I have found establishing these rituals helpful for maintaining a level of equilibrium when I face the unknown. Start Small Start small. Choose one daily transition that consistently derails you, morning wake-up, work start, evening wind-down. Design one simple ritual for it this week. When you inevitably miss a day, remember: the ritual exists to serve your transition, not to judge your consistency. Each morning offers a chance to begin again.
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 Every weekday at 4:00 PM, my computer interrupts me with a simple Apple Note that has transformed how I end my workday. It's not glamorous, but this AI-powered solution solved a problem I couldn’t beat on my own. The Pattern I Couldn't Break I struggle to maintain new routines, even when I know they'll make me more productive. In 2024 alone, I've started four different review systems: Monday morning calendar blocks, Todo list collection apps, a weekly planner notebook, and a custom Notion template (which has only been opened once). The longest I maintained any system was twelve days. This start-strong, fade-fast pattern is frustratingly common. Without fail, I'll commit to a new productivity routine, do it once or twice with genuine enthusiasm, then completely forget about it and return to what I call my "magpie management style”. I am constantly distracted by whatever shiny problem demands immediate attention. The routine I most wanted to build was Cal Newport's shutdown sequence: a deliberate end-of-workday ritual that clears your mind and prepares you for tomorrow. This made sense to me for couple of reasons:
The Shutdown Sequence Newport's approach includes five key steps:
This type of review forces you to slow down and ensure you're headed in the right direction. Without it, I get pulled away from my real priorities by whatever fire needs putting out. I Needed an Interruption Because this was a new habit, I needed something invasive, something I couldn't ignore. Since I spend most of my workday on a computer, I thought: what if AI could interrupt me with a note at the of the day, forcing me to stop what I was currently work on and transition into planning mode? I turned to Claude with what I now realize was a charmingly naive question about creating an automated shutdown ritual using Apple Notes.  The AI-Powered Solution Process Here's where my beginner's mind became an asset rather than a liability. I had no idea what was possible with AppleScript and Apple Notes, so I asked Claude everything:     One of AI's biggest benefits is that it takes your beginner's mind and guides you efficiently toward your goal, without the social pressure that normally prevents us from asking "stupid" questions. After several iterations with Claude, here's what we built: Every weekday at 4:00 PM, my Mac runs an AppleScript that creates and displays a new Apple Note with:
The note pops up automatically, looking like this:  Why This Actually Works
Apple Notes can’t have a custom formatted template, so I have to manually organize my thoughts and fill in my priorities. But this manual work is exactly what makes it effective. Taking time to format and complete the note slows me down enough that it becomes a genuine review. Unlike habit-tracking apps that require daily input (which I forget) or calendar blocking that I could ignore, this system interrupts me whether I want it or not. And because it requires active participation to be readable, I can't just dismiss it. The Unexpected Results After three weeks of using it I end my workdays with significantly less mental clutter. More importantly, I have a plan each morning instead of letting my email dictate my direction. The system isn't perfect. Sometimes I'm in meetings at 4 PM. But it works consistently enough. The Bigger Picture: AI as a Personal Problem Solver This project embodies how I think AI is reshaping how we work. Rather than slapping AI onto everything, what AI has actually done is democratize computer science and database management. Two disciplines that traditionally required significant expertise for mediocre results. As someone who works in higher education admissions, I've watched coders manipulate complex software to solve seemingly impossible problems. It's like magic when you see true expertise in action. Thanks to AI, these problem-solving skills are becoming more accessible. I'm not suggesting that coders are becoming obsolete. Instead, AI now helps me solve my weird little problems that only I have, making me more efficient at whatever my work happens to be. I wasn’t willing to pay for a custom app to get me to focus. This represents a fundamental shift: instead of waiting for IT departments or hiring developers, knowledge workers can now solve their own workflow problems in real-time. We can build exactly what we need, when we need it, without requiring formal technical training. My shutdown sequence is a small example, but it demonstrates something larger. When AI helps you move from "I wish I could..." to "Here's how I did it," it gives you greater problem solving capabilities. It's not perfect, but it works. And I would never have been able to build it without AI.  A few weeks ago my 16-year-old son taught me how to use a micrometer, measuring engine bores to thousandths of an inch, when I realized our relationship was transforming. 18 months ago, our conversations rarely went beyond logistics and homework. Now we are collaborating as equals on rebuilding a 1969 Mini Cooper, and in the process, we’ve rebuilt our connection. The Challenge of Parenting Older Kids With my kids getting older and more independent, it has been more challenging to maintain a relationship with them. Being a parent sits in a strange place. I recognize what I needed as a kid and what my parents couldn't provide, so I try to provide that. There's a strong pull toward the approach of parent as friend. I know from experience that this approach makes discipline and behavior correction significantly more challenging. Because I value independence, I had erred on a more hands-off approach. This might be a father's stereotype. I likely would have continued down this road had it not been for a project that pulled me in a completely different direction. I call it project-based bonding, and it has allowed my son and me to connect and build a deeper relationship than I expected. Learning to Fail and Repair I hate giving parenting advice because the variables are too vast for me to have any authority, and I'm not interested in conducting research to find the statistically best approach. I'm living as a parent every day with a very short time frame in which to work and build something meaningful with my kids. I need to make the most of it now, which means being agile and willing to experiment. And a willingness to fail. The fear of failure, especially with kids, is stronger than I care to admit and has prevented me from having necessary conversations or taking action. I freeze and hope it will just go away. It never does, and then I get stuck with a compounded problem. A few years ago, my wife and I came across a concept called "repair work." It's saved not only our relationship but our relationships with our kids. The idea is that after a blowup that hurts the relationship, you spend time repairing it. You come back together after things have cooled down to listen and talk. This creates space to process the heat of the moment and the emotions, then rebuild connection. This practice emphasizes the relationship rather than the conflict. Here's how it worked with our Mini project: When we accidentally stripped a bolt head and I snapped at him for not being careful enough, we used repair work. Later that evening, I apologized for my reaction and we talked through the frustration we both felt. Instead of creating distance, working through it actually brought us closer. The Mini Cooper Story In high school, my dad was stationed in England, and I spent my last year there overseas. This was both an amazing experience and ridiculously hard. While we were there, my dad and I got into Minis, the tiny British car that became an institution and saw a resurgence in the early 2000s when BMW bought the brand and relaunched it. When it comes to Minis, I'm a purist. Minis became something we worked on together. My dad ended up buying three, and when it came time to leave, he brought one back with him: a 1969 Mini Cooper S.  While we did drive it in England, it hasn't been driven since. It became a project both my dad and I had the best intentions for. Like many old car projects, it continually took the back seat. Life became busy and it continued to sit untouched, in pieces.
The Decision to Rebuild Two years ago, my wife and I started having conversations about the Mini because our son had developed an interest in cars, especially European cars. We went back and forth about what it would be like to bring the car home and what it would take to get it back up and running. It's the kind of project that if I was going to take on, I knew I was taking it on completely. After coming to terms with that and being willing to lead the effort to put the old bird back together, I committed. My dad was thrilled to get the space back in his garage, and my mom was happy it stayed in the family. Right after making the commitment and starting the process of bringing the car to the Pacific Northwest, I reconnected with Kerry, my youth leader from high school in England. He ran into my parents, which brought up that we had just picked up the Mini and were beginning to work on it. In a catch-up email, he commented about the Mini, saying, "What a great bonding experience for you and your son." This surprised me because it wasn't my intention for it to be a bonding experience. My approach was that I thought he would enjoy taking part in putting it back together. I think this is where my hands-off approach was kicking in. Kerry's comment shifted my perspective and made me more open to having the project be something more than just deepening my son’s interest cars. Everything I Assumed Was Wrong The way this project has unfolded is so different from what I anticipated. This reflects both the circumstances of our time and who my son is. I approached the Mini the way I had approached it in high school. I knew nothing, my dad knew slightly more, and we were dependent on someone else to make up the difference. In getting the Mini, I took on the role of ‘dad’, assuming authority and that I’d be teaching my son how to get this project done. My assumptions were wrong. It turns out my son's interest in cars far exceed my knowledge. He has a working knowledge of combustion engines, and Minis have about as basic an engine as it gets. Thanks to the internet, we have access to expertise that wasn't available when I was in high school. I assumed that my authority put enormous pressure on me to learn everything before passing it off to him. A big reason why this project has been so successful is that all those assumptions were blown out of the water. From the start, it was clear he knew more than me. I had to quickly change my perspective and listen to him. I had to allow myself to be open to the idea that a 16-year-old could teach me something. Part of his knowledge stemmed from his interest in cars and having a group of friends who were also interested in cars. They would talk engines and performance. The other part came from the internet, the biggest difference from when my dad and I worked on Minis. For us to access any knowledge about Minis circa 2001, we had to know someone or have the right books. Even then, sometimes books aren't the best resource. Now I'm not just figuring out how to put a Mini back together. I'm learning how small engines work, understanding why mechanical engineers made specific design decisions, and discovering how slight adjustments can make a significant difference. The Real Learning Began What I think has made this project pave the way for bonding at this point in my son's and my relationship is that it accurately reflects the transition our relationship is going through. The older he gets, the more independent he becomes, and the more different my role as his dad becomes. It's been surprisingly fun for me to approach this project with him as a peer, not as a parent. When we talk about the Mini, our conversation is collaborative. He has valid thoughts about how to approach things or what to focus on. Just as the school year was getting out, we pulled the pistons out and needed to measure the bores so we knew which size piston rings to order. We ended up borrowing a set of snap gauges and micrometers, neither of which I had ever used. When you measure parts of an engine, everything is measured in thousandths. This ensures a high degree of accuracy and precision. Listening to a machinist talk is like dropping into any jargon-filled industry conversation. I had a vague idea of what was going on but couldn't share that information or take action with it. He showed me how the tools worked, and I assisted him in measuring the bores. It was humbling to have him show me the ropes. My contributions to the project are very different from what I expected. Instead of teaching him about the car, I'm providing perspective on project management, budgeting, and tool and shop management. Things that took me a lot of trial and error to learn and make a project like this more bearable. For example, I help him think through which parts to order first based on lead times, how to organize our workspace so we don't lose small parts, and how to budget for unexpected expenses (everything is an unexpected expense). The Deeper Connection Having a long-term project for us to work on also means we have a reason to check in and talk. It's almost every day that we're discussing when new parts are arriving, what the next task is, sharing a new video, or talking about upcoming Mini events. While these daily check-ins are great for keeping the conversation going, what they've allowed is for us to open up about more complicated life topics. The conversation about Minis is the small talk that makes it feel safe to dive a little deeper. Our time together has opened up avenues to discuss college, social life, self-esteem, goals and habits, relationships, disappointment, frustration, internet safety, money, investment, retirement, language, and many other things. We went from two or three meaningful conversations per month to daily check-ins. He started asking my advice on non-car topics. I learned to say "I don't know, what do you think?" instead of pretending to have all the answers. I still have to stand my ground on a few things and be the parent, but it has been incredibly rewarding to see and take part in his growth and maturity. Letting go and allowing him to become himself is an exercise in patience and love, helping me have greater respect for my own parents. What Makes Project-Based Bonding Work Not every attempt at connection worked. My earlier efforts to bond over hiking backfired when I turned them into lectures about perseverance. The difference with the Mini was that I couldn't lecture, I genuinely needed his help. Here's what I've learned makes project-based bonding effective:
The Reality Check Taking on an old car project isn't for everyone. It's way more expensive than I thought. I justify the money as an investment in the relationship, not just in the car. It takes up significant space, which is only possible because a Mini fits just about perfectly in the leftover garage space we had. A project like this requires more project management skills and emotional investment than I realized. This approach also requires acknowledging that you might not be the expert, which can be uncomfortable. And it assumes you have disposable income, space, and time that many families don't have. If car restoration isn't your thing, the same principles apply to other collaborative projects: coding a website together, learning a musical instrument, cooking through a challenging cookbook, building furniture, starting a garden, or even planning family trips where the teenager takes the lead on research. The key is finding something where:
What This Has Taught Me At the end of the day, having this project has been the perfect way to transition my relationship with my son. If you can find something like this for you and your kids, I can't recommend it enough. The most surprising lesson has been that some of the best bonding happens during problem-solving, not during success. When we're both scratching our heads over how to put things back together, we're truly collaborating. When we finally figure it out together, the victory belongs to both of us. This experience has fundamentally changed how I think about parenting teenagers. Instead of trying to remain the authority on everything, I'm learning to become a collaborative partner in their learning and growth. It's messier and more unpredictable than the traditional parent-child dynamic, but it's also more honest and, ultimately, more rewarding. The Mini still isn't running, we're probably 18 months away from that. But the relationship we've built while working on it is running better.  We live in an age of constant connection, yet loneliness persists. As philosopher Alain de Botton observes, "If you are not lonely about 40% of the time, you are actually doing quite well by human standards." This paradox reveals a crucial opportunity: how might technology bridge the gap between connection and genuine understanding? I’m convinced the answer lies not just in what our technology does, but in how it makes us feel. As talent futurist Allyn Bailey notes, "Great tech isn't just about what it does. It's about how it makes people feel: empowered, understood, capable." The Disconnection Paradox We all long to be accepted and appreciated for who we are, not just for our strengths, but for our flaws and complexities. The complete makeup of experiences that define us as unique individuals. If we're lucky, we experience this acceptance with family and friends. For many, this remains elusive. Some believe true understanding is impossible, that our fundamental separateness means we can never truly be seen by others. There's too much difference between us all. The best we can hope for are brief moments where our experiences overlap, like intersecting circles in a Venn diagram. For most of human history, this sense of isolation was normal, woven into everyone's daily experience. But now we carry escape machines in our pockets. When disconnection strikes, we face a choice: feel through the discomfort or escape at the first sign of it. This constant option to avoid discomfort may actually be making genuine connection harder to achieve. Where Technology Succeeds This doesn't make me technology-averse, quite the opposite. When technology helps us bridge gaps that were previously unbridgeable, it's transformative. One of our biggest social wins has been the ease with which people can now find community. A teenager in rural Montana can connect with others who share their interests, struggles, or identity in ways that were impossible a generation ago. Greater connection has illuminated injustice and accelerated social change. This visibility has helped people feel more comfortable being themselves, whatever form that takes. While we have far to go, we continue moving in a positive direction. Recognizing the Barriers The ease with which we feel disconnected often signals where technology can help most. These moments also reveal unnecessary barriers that prevent us from moving forward. When we encounter friction, especially in processes we expect to be simple, we often jump to feelings of disconnection and create meaning that isn't there. Consider the last time you tried to cancel a subscription online. Those deliberately confusing cancel buttons and hidden contact forms aren't just bad design, they're barriers that can make you feel manipulated and undervalued. Similarly, when a prospective student struggles with our application for admission, I witness firsthand how poor interface design can make someone feel they don't belong in higher education. As someone who works with mission-centered institutions, this is a constant battle. I continuously seek ways to provide greater access to students, removing barriers and creating space for them to feel welcomed and ready for success. As a parent, I try to teach my children resilience so they can navigate these situations and recognize when their meaning-making minds are working overtime. I watch my daughter get frustrated when asking Alexa question because the voice interface has delays and feels clunky. A reminder that even advanced technology can create emotional barriers. As a consumer and human, I try to remember that I'm remarkably good at creating meaning where none likely exists, and that I have a choice to hold onto that meaning or let it go. This practice proves much harder than I'd like. As someone who builds technology tools, I see tremendous opportunity. The Experience Economy and Emotional Design  - signull vs noise (Substack) This insight perfectly captures our design challenge. When we build experiences, we must pay attention to how they make people feel, not just how they function or what data they process. We shouldn't ship anything until we understand its emotional impact.
This focus on feeling was once a luxury reserved for those who could afford it. Premium hotels like Ritz-Carlton built their brands on emotional experience, the feeling of being anticipated and cared for. Technology and decreased production costs have made "feeling" a major marketplace factor, one that's becoming increasingly important. We're witnessing a continued shift toward an experience economy, moving from Commodities → Goods → Services → Experiences. A technology experience can be tested and refined repeatedly, then maintained once optimized. Making it an incredibly valuable asset with potentially exponential returns on investment. Apple has mastered this game and built an empire on it. When Steve Jobs returned to Apple in 1997, he didn't just focus on faster processors or more features. He obsessed over the moment someone first opened an iPhone box. Paying attention to details such as the satisfying resistance of the lid and the careful layering of components. Jobs understood that the relationship between human and technology begins before you even turn on the device. I remember heated debates with hardcore PC users who wouldn't touch a Mac under any circumstances. They despised Apple's limitations, the closed, end-to-end environment where customization was restricted and, until recently, inaccessible without coding knowledge. Yet Apple's approach worked. For the last 20 years, tech companies have invested billions in customer experience. Using their apps feels enjoyable, even addictive. This emotional engagement drives sustained usage and loyalty. The Path Forward: Designing for Empathy The question is this: Does your digital experience make people feel more capable and understood, or does it add to their sense of isolation? The answer determines not just your success, but whether technology fulfills its promise to enhance human connection. Here's a practical framework for empathy-driven design: The Connection Checklist:
When we deliberately design technology to build community and limit friction, we create space for people to feel welcome and understood. This isn't just good business, it's how we honor technology's potential to bring out the best in our shared humanity. The tools are in our hands. Are we using it to bridge the empathy gap or widen it? 
When I was an associate director, I received a request from a school district that wanted a presentation for their junior and senior classes about the college search process. They were looking for advice on how to approach it, what questions to ask, what to consider, and how to make decisions.
Taking on this assignment excited me because I had created a similar presentation a few years earlier. Updating existing content would be simple. There was one problem. When I went back to find my presentation and notes, everything was gone. I had to start from scratch with nothing but vague memories of what I'd presented before. Unfortunately this was familiar territory. My disorganization created a clear path back to the beginning with just about every project I took on. Starting over eventually turned into my default mode despite its obvious inefficiencies. That experience taught me something crucial: sustainable creativity isn't about inspiration—it's about building systems that prevent you from losing your work and having to restart every time. In this article, I'll walk you through the specific changes I made that allowed me to spend less time at square one and develop daily creative habits that help me solve problems efficiently. These systems have saved me hundreds of hours and transformed how I approach creative work. The Problem with Creative Mythology Growing up, I heard "an ounce of prevention is worth a pound of cure" constantly. Because my dad worked in medicine, I always framed this concept around physical health. When I wanted to be creative, I dismissed sustainable practices because I had bought into the mythology of the struggling artist. Art and creativity required suffering and hard work. I had experience spending hours wrestling with creative endeavors before they resembled anything close to my vision. The longer I work and the more problems I solve, the more I believe in this principle: "Think like an artist, work like an accountant." The more efficiencies we create around our work, the more creative we get to be. My Failed System: Notebooks Without Reference In high school, I learned to write ideas in notebooks. Over the years, I filled hundreds of them. What I never mastered was referencing the information in those notebooks and turning it into usable creative output. My notebooks became like academic learning without practical application, especially when information was collected over longer periods. I had learned to be creative in a linear, time-constrained way. Producing theater, for example, provides a clear timeframe with defined beginning and end points, when rehearsal starts and when the show opens. This creative process fit neatly onto a calendar. But most meaningful creative work develops over longer periods. Cal Newport discusses this in Slow Productivity, citing many great works as being built over years or decades, busting the myth of quick inspiration-induced creative bursts that produce masterpieces. While I excelled at collecting information, I struggled to recall it or maintain momentum unless I could focus completely on the project. The Game-Changer: Building a Second Brain This began to change when I developed a second brain, a digital system that became my central, searchable repository for everything. This single change opened up possibilities that allowed me to tap into creative processes when needed, picking up projects where I left off without being tied to physical spaces or objects. Building a system is key for inviting spontaneous creativity. The foundation makes easy reference possible and allows you to return to where you left off. While your system will never be perfect and will need consistent updating, it can handle much of the organizational labor. Without a digital system, having learned creative processes through physical means, I struggled to organize myself in ways that made consistent creative progress possible. A notebook follows linear structure, but project completion requires non-linear actions. I needed to manage various creative project aspects non-linearly, allowing me to pick up where I left off regardless of time elapsed. Writing things down only works if you can find what you wrote. When I couldn't remember where I'd written something, the note became useless. The second brain framework allowed me to create a digital filing system where anything and everything can be added, categorized, and searched, enabling me to move forward and stay organized when it's time to utilize information and act on original ideas. I discovered this concept in What is Scenography? by Pamela Howard. She tells a story about traveling to Israel and encountering Hebrew characters. She liked their shape so much that she spent time filling sketchbook pages with them. Years later, she used them in her stage design work. This story illustrated the power of systematic collection and reference, capturing ideas when they appear and having systems to rediscover them when they become relevant. The Four Elements of Sustainable Creative Problem-Solving After studying various creative processes and testing approaches over three years of implementation across 50+ projects, I identified four critical elements that must have dedicated space in any sustainable creative practice: 1. Research This was never my problem, I can research endlessly. The challenge was integrating research with the other three elements and turning research into action. My System: I built my digital system using Apple Notes with three folders: 'Capture' for quick ideas, 'Projects' for active work, and 'Archive' for completed items. Each note starts with a date and project tag like [PRESENTATION-2024] for easy searching. Key Insight: Research means identifying what you know and don't know, not collecting information indefinitely. 2. Saturation This is action-oriented and feels passive, but it's anything but. Saturation means I spend 2-3 focused hours wrestling with the problem using specific techniques: mind mapping all possible solutions, sketching rough concepts, and writing stream-of-consciousness about obstacles until I literally can't think of another approach. When you can't find another way to examine the problem, when you become so intimate with it that you begin dreaming about it. That's when most people give up. But this is exactly when the breakthrough becomes possible, leading to the next step. 3. Incubation This is where you stop actively trying to solve the problem because you've exhausted everything you could generate consciously. Letting go, you engage in something else. Ideally something that feels mindless like walking, working out, showering, data entry, or drawing. I keep my body engaged while giving my mind space to work subconsciously. This space allows my mind to solve the problem for me, creating conditions for breakthrough insights. 4. Brainstorming Perhaps the most fun, but most people confuse brainstorming with saturation. Real brainstorming only happens after incubation, when you've exhausted everything without finding a solution. This brainstorming often occurs in conjunction with incubation, where you're mulling over solutions and pulling from not just current project research but from your entire archive of collections and experiences. You're laying out all pieces to find something that works, this is where the magic happens. Implementation: From Theory to Daily Practice Start with Action, Not Research The most pivotal insight I learned came from Dan Koe's approach to projects. Rather than starting with research, he starts with what he knows and begins building immediately. Only when he encounters something he can't complete does he turn to research. This approach grounds you in reality and provides clear direction for both the project and your learning. You don't get stuck in one phase and can't figure out how to escape. Six months after implementing this system, I faced another presentation request. This time, I found my research notes from the original project in under 2 minutes, had a rough outline within 15 minutes, and completed the presentation in half the time. Choosing Your Deep Work Philosophy Cal Newport describes four philosophies for deep work that provide frameworks for implementation: Monastic Philosophy: Eliminate or radically reduce shallow obligations to focus entirely on deep work on a single, high-value goal. Bimodal Philosophy: Divide time into clearly defined periods, some dedicated entirely to deep work, others open for everything else. Rhythmic Philosophy: Schedule deep work sessions as regular habits, typically daily, for set periods. Journalistic Philosophy: Fit deep work into your schedule wherever possible, often in short bursts as opportunities arise. I initially hoped to be bimodal, but my schedule as director of admissions proved too erratic. Between software issues, staff concerns, student walk-ins, and family needs, I developed a combination of rhythmic and journalistic approaches. I schedule dedicated time when possible while remaining ready to dive into projects when opportunities present themselves. The key difference now is having better systems that make these sessions more effective. Practical Implementation Strategies Create Your Ideal Calendar I created an ideal calendar outlining what I'd love my day to look like. More than anything, this gives me something to strive for—a place to return to that reminds me of my priorities and helps me lead myself rather than get pulled into others' influences. This sets up the schedule for creative problem-solving practices and establishes frameworks for each element. Design Your Focus Space Knowing what you need to focus and creating necessary space to support it will transform your creativity, fueling your ability for research, saturation, and brainstorming. The pandemic made working with closed doors culturally acceptable, dramatically improving my attention and focus. Everything pulls my attention, I needed to acknowledge this and create boundaries. Actionable Step: Identify your biggest attention drains and create physical or digital barriers. This might mean closing your door, using website blockers, or establishing "creation hours" when you're unavailable for meetings. Master the Art of "Putting It in a Box" My wife and I use a relationship technique where, during intense conversations that need to pause, we ask if we can "put it in a box" and revisit it later. This becomes necessary when we're at an impasse or when time constraints require us to move on. The same works for creative projects. When you hit a spot where you start spinning or face time commitments, setting current creative work aside leads into incubation and provides space for subconscious processing. Critical Warning: Don't use this before getting started. Initial resistance feels like you need to put it in a box, but this is self-doubt convincing you not to begin. Put work in a box only after you've wrestled with material, medium, or process and genuinely need incubation time. Leverage Incubation Activities After saturation and hitting a wall, incubation allows your subconscious to do heavy lifting. Classic examples include shower thoughts, walks without music or podcasts, long drives, and gym sessions, activities that keep your body busy while letting your brain work subconsciously. I first experienced this deliberately as a young performer trying to memorize scripts quickly. Pacing helped my brain focus on remembering words. Separating mind and body allowed me to concentrate. Warning: I used to fall into processing mode before bed. While it felt productive, it ate into sleep, eventually catching up to my overall productivity. The System in Action: A Complete Example Here's exactly how this system worked when I had to recreate that presentation:
This approach saved me 4 hours compared to my usual method and created a reusable resource for future similar requests. Common Mistakes to Avoid Research Rabbit Holes: If you find yourself stuck in research mode for more than 2 hours, you're avoiding the harder work of creation. Set a timer and force yourself to start building with incomplete information. Premature Incubation: Don't confuse initial resistance with genuine need for incubation. Push through the discomfort of starting before allowing incubation space. System Complexity: Your system should reduce friction, not create it. If your organizational method takes longer than the creative work, simplify it. Perfectionist Collection: Don't let the pursuit of the perfect system prevent you from using an imperfect one. Start simple and evolve. Moving Forward: Your Next Steps The transformation from scattered creativity to sustainable systems doesn't happen overnight, but it can begin today. This Week:
This Month:
This Quarter:
Remember: sustainable creativity isn't about inspiration striking, it's about building systems that capture, develop, and execute ideas efficiently. When the next presentation request comes, you'll be ready to build on your past work instead of starting from square one. The choice is yours: continue losing your creative work and starting over, or invest in systems that compound your efforts over time. I know which path has transformed my creative practice, and I'm confident it can transform yours too. Every week brings new headlines about AI revolutionizing industries, replacing jobs, and fundamentally changing how we work. Yet for most professionals, the daily reality feels far different. Every day I wrestle with overhyped tools that promise everything and deliver frustration. The gap between AI's potential and its practical application reveals a critical truth: we're approaching this technology all wrong.
Rather than waiting for AI to revolutionize everything overnight, professionals should adopt a practical "Levi Strauss approach”. Focusing on incremental integration that builds real competency over time. While others swing for the fences chasing the next AI unicorn, the smart money is on outfitting the fence-swingers. The Problem with Current AI Narratives The prevailing assumption about AI is that it will majorly disrupt everything, the way we think, work, and feel. Society will finally transform into the anticipated push-button age of the 1950s. We've seen glimpses of this potential, but human nature and our complex global society make overnight transformation unrealistic. Three false assumptions drive the current narrative: Assumption #1: AI adoption is binary: embrace it or get replaced. This oversimplifies a complex integration process. According to McKinsey, AI could automate 30% of current work activities by 2030, but only 5% of occupations can be fully automated. The reality lies in augmentation, not replacement. Assumption #2: AI provides ready-made solutions. AI functions as a powerful tool, not a solution. When we frame it as a solution, we expect immediate results without investment in learning or customization. This sets unrealistic expectations and guarantees disappointment. Assumption #3: Early adoption means diving in completely. The current "all-in" mentality creates unnecessary pressure. True early adoption means thoughtful experimentation, not wholesale transformation. The Levi Strauss Approach During the California Gold Rush, while miners swung for the fences hoping to strike it rich, Levi Strauss made consistent profits by outfitting the prospectors. This approach of focusing on infrastructure rather than speculation offers a superior model for AI integration. The Levi Strauss approach means building the foundation that supports AI adoption rather than chasing flashy applications: Instead of: Building an AI chatbot to replace customer service Do this: Use AI to analyze customer conversation patterns and improve human agent training Instead of: Automating entire workflows immediately Do this: Use AI to identify bottlenecks and optimize one step at a time Instead of: Seeking AI solutions for every problem Do this: Map current processes and identify where AI adds genuine efficiency This approach recognizes that sustainable AI integration requires the same skills as effective leadership: delegation, clear communication, and patience with the learning curve. A Practical AI Journey My own AI adoption illustrates these principles in action. Like many, I initially approached AI through content creation when ChatGPT launched. The results felt uninspired and clunky. They were nowhere near the quality I could produce after a decade of writing experience. Frustrated, I dismissed AI as overhyped technology. Eighteen months later, my brother introduced me to Perplexity. This changed everything. Rather than starting with creation (high stakes), I began with search (low stakes). Perplexity quickly replaced Google for me because it allowed follow-up questions and conversational clarification. Creating a more enjoyable and effective search process. Lesson 1: Start with search, not creation. Search builds trust in AI capabilities before asking for original content. Success with low-stakes tasks creates confidence for higher-stakes applications. When implementing Slate CRM at work, I discovered AI's real power. Slate's flexibility makes it powerful but challenging to configure. Generic documentation often proved unhelpful. AI provided step-by-step solutions and sourced answers, enabling rapid clarification when I only had vague ideas about what I needed. Lesson 2: AI excels in ambiguous situations. Traditional search requires precise keywords. AI handles vague starting points and clarifies through conversation. This proves invaluable when you know something's wrong but can't articulate the solution. Finding success with research led me to revisit content creation with better prompting techniques. Instead of expecting perfect first drafts, I invested time in prompt development. Now I spend days crafting reusable prompts rather than days creating content. Lesson 3: Context is everything. AI without context produces generic results. Investing upfront time in building knowledge bases and custom prompts creates an "employee" that understands your business values, culture, and communication style. Common Mistakes to Avoid Based on widespread AI adoption challenges, avoid these critical errors: Mistake #1: Expecting perfection immediately AI requires iteration and refinement. Judge initial results against rough drafts, not polished expert work. Mistake #2: Skipping the setup phase Like hiring a new employee, AI needs onboarding. Invest time in context-building and prompt development. Mistake #3: Using AI for high-judgment tasks too early Start with data processing, research, and first drafts. Save strategic decisions and nuanced communication for later. Mistake #4: Abandoning AI after early disappointment Poor initial results reflect approach, not capability. Adjust expectations and methods rather than abandoning the tool entirely. 30-Day Implementation Plan Week 1: Replace search habits Use Perplexity or Claude instead of Google for all research. Practice asking follow-up questions and refining queries. Week 2: Identify one repetitive task Choose something low-stakes but time-consuming: email templates, data formatting, or initial research on recurring topics. Week 3: Create and refine prompts Develop detailed prompts for your chosen task. Include context about your role, audience, and desired outcomes. Week 4: Build a reusable prompt library Document successful prompts for future use. Start identifying additional tasks for AI integration. The Leadership Connection Working effectively with AI requires delegation skills, one of leadership's most challenging aspects. You must clearly communicate expectations, provide sufficient context, and recognize when output meets standards versus needs refinement. Successful AI integration follows the same pattern as onboarding new staff: establishing office culture, setting expectations, and learning each other's working styles. The professionals who master this process will appear almost superhuman in their efficiency and effectiveness (until this becomes the norm). Future Implications and Competitive Advantage AI will replace some jobs, but not quickly for most professionals. Companies with robust technology infrastructure will adopt fastest, but the integration process isn't as simple as "hire a coder and get to work." Effective AI customization requires deep domain expertise, the kind gained through 20 years of experience, not a four-year degree. This expertise enables you to identify what can be automated, recognize when AI works versus when it fails, and guide the technology toward valuable applications. The expectation moving forward won't be universal AI standards but rather that knowledge workers use AI to become more efficient and effective within their existing roles. Those who figure this out will be the most marketable. The In-Between Advantage AI skills prove most valuable during transitional periods. Like when old processes no longer work but new ones aren't ready. Every project has these moments, especially during system updates or organizational changes. Currently, my team faces exactly this situation with transfer credit processing. We've moved to a new CRM system but haven't built the full transfer credit workflow yet. We can't use the old process, but the new process isn't complete. AI provides the bridge, helping us create temporary solutions that maintain productivity during transition. These in-between spaces represent AI's greatest practical value: not replacing entire job functions, but providing flexibility and capability during the messy, complicated reality of organizational change. Conclusion The future belongs neither to AI skeptics nor AI evangelists, but to practical adopters who integrate these tools thoughtfully into existing workflows. By focusing on infrastructure rather than speculation, building competency through low-stakes experimentation, and treating AI as a powerful tool requiring skilled operation, professionals can gain genuine competitive advantages without betting everything on uncertain technological promises. The gold rush mentality will produce a few winners and many disappointed prospectors. The Levi Strauss approach builds sustainable advantage by outfitting everyone for the journey ahead. The average person now juggles 255 different passwords, according to NordPass. 65% of people feel overwhelmed by the amount of information available online. If you've ever missed an important email because it went to the wrong account, paid for three different storage services while still running out of space, or spent 20 minutes looking for a file you know you saved "somewhere," you're experiencing digital sprawl. Similar to urban sprawl it doesn’t take much before it gets out of control.
The hidden costs of digital chaos include duplicate subscriptions, time waste, and security risks. But there's a better way. When Digital Tools Work Against You Digital sprawl happens gradually. You start with Gmail for email, add Dropbox for file sharing, try Apple Photos for convenience, sign up for Office 365 at work, and suddenly you're managing a patchwork of disconnected services that don't communicate with each other. The root causes are predictable:
The real-world impact goes beyond inconvenience. It becomes easy to unknowingly spend $50-200 monthly on redundant services, waste time switching between platforms, and face security vulnerabilities from managing too many accounts with too many passwords. Digital Life Design Think of your digital ecosystem like architecture. You wouldn't build a house by randomly adding rooms without a blueprint. Yet that's exactly how most of us approach our digital lives. Digital Life Design treats your technology stack as an intentional system designed to serve your priorities, not create new problems. The Five Core Principles
4-Phase Digital Redesign Phase 1: Digital Inventory (Week 1-2, 2-4 hours) Create a comprehensive map of your current digital landscape. For each service you use, document:
Phase 2: Ecosystem Mapping (Week 2-3, 1-2 hours) Identify which major ecosystem currently serves you best: Google Ecosystem: Gmail, Drive, Calendar, Photos, Android devices
Apple Ecosystem: iCloud, Notes, Calendar, Photos, iOS/Mac devices
Microsoft Ecosystem: Office 365, OneDrive, Teams, Windows integration
Phase 3: Design Your Ideal State (Week 3-4, 2-3 hours) Use this decision tree to choose your primary ecosystem: Start here: What's your primary device?
Define your architecture:
Bridge solutions that work:
Phase 4: Migration Strategy (Week 4-8, varies by complexity) Prioritize changes using this matrix: High Impact, Low Effort (Do First):
High Impact, High Effort (Plan Carefully):
Low Impact, Low Effort (Quick Wins):
Low Impact, High Effort (Avoid Unless Strategic):
Advanced Application: Family Digital Design Managing digital chaos multiplies with each family member. Here's how to scale your framework: Shared Resources Strategy
Age-Appropriate Digital Skills Ages 6-10: Basic digital hygiene
Ages 11-14: File organization and privacy
Ages 15-18: Advanced productivity and security
Family Decision Framework Before adding any new service, ask:
Implementation: The Next 30 Days Week 1: Assessment
Week 2: Planning
Week 3: Quick Wins
Week 4: Begin Migration
Monthly Digital Health Check Set a monthly reminder to review:
Common Pitfalls to Avoid
Next Step Digital life design isn't about finding the "perfect" setup. It's about creating an intentional system that serves your priorities instead of creating new problems. Start with your biggest pain point. Is it duplicate storage costs? Scattered photos? Missed communications? Choose one area and apply the four-phase framework. The goal isn't to eliminate all digital tools, but to ensure they work together harmoniously. When your digital ecosystem is designed rather than accumulated, technology becomes invisible infrastructure that supports what matters most to you. What's the one digital frustration that's been bothering you most? That's where to start. A zine for improvisors. Here's how to cut it and fold it!She walked past my office seven times that Tuesday morning before finally finding the courage to enter. I watched through my glass door as she clutched a manila folder, stopped at my threshold, then continued down the hallway. When she finally sat across from my desk on her eighth pass, her hands trembled. "I haven't been in school for fifteen years," she whispered. "My youngest just started kindergarten, and I don't know if I can do this with all these eighteen-year-olds." This thirty-something mother had finally carved out time for herself, but the fear in her eyes told the real story. College felt like foreign territory. Assuming it was intimidating, exclusive, meant for everyone else but her. That ten-minute conversation changed how I think about leadership. I realized that going to college could be terrifying at any age, and that my assumptions about what people needed were often wrong. More importantly, I learned that effective leadership isn't about having all the answers but rather about understanding the people you serve. In our increasingly digital world, empathetic leadership isn't soft management, it's a strategic advantage. Leaders who master human connection drive better results because they understand what their people actually need, not just what they assume they need. The Perspective Problem We enter this world with a self-centered perspective. We experience everything through our personal lens. Unless we deliberately widen that perspective to include others and their experiences, we limit ourselves and our potential impact. I learned this lesson during a phone conversation with one of my regional admissions counselors. As an Associate Director, I supervised four recruiters who worked remotely across their territories. I called Sarah, a senior counselor with more recruitment experience than I had, for our regular check-in. Instead of covering metrics, I stumbled into her humanity. "I need to tell you something," she said after we'd covered her recruitment numbers. "It's really hard being off-campus and still feeling connected. I struggle with feeling part of a team when I'm only in the room with everyone a few times a year." That conversation shifted my perspective. I'd called to talk business but discovered I'd been missing something crucial as a supervisor. I'd never been a regional recruiter. I didn't understand the isolation, the challenge of building relationships through screens, the effort required to feel part of something bigger. Sarah opened a door that got me thinking: What is my real work as a leader? Beyond tracking numbers and training for better performance? What did it mean to help people do their jobs better? A Framework for Service Leadership This realization led me to develop what I call "Aligned Service Leadership”. This approach centers on two core commitments:
This isn't about choosing sides between company and employee interests. It's about creating win-win scenarios where personal growth directly advances business goals. The sweet spot lies in the overlap. The intersecting circles of a Venn diagram.  But getting those circles to overlap requires empathy. After that conversation with Sarah twelve years ago, I've discovered five practical strategies that have transformed my leadership approach.
Building Your Empathy Toolkit 1. Cultivate Genuine Curiosity The Strategy: Before any one-on-one meeting, write down three questions about this person's experience that you genuinely don't know the answer to. Not performance questions, curiosity questions. Example Questions:
Time Investment: Five minutes of preparation per conversation Success Indicator: You find yourself saying "I didn't know that" at least once per conversation Why It Works: Genuine curiosity shifts the dynamic from evaluation to exploration. People feel heard, and you gain insights that inform better decision-making. 2. Step Outside Your Comfort Zone The Strategy: Deliberately seek experiences that challenge your assumptions about how work gets done or what challenges people face. Practical Application: Spend a day shadowing someone in a different role, attend a meeting outside your department, or volunteer for a project where you're not the expert. Recent Example: there is confusion around the state for what counts toward academic admissions standards I helped facilitate a discussion with school district representative that classify those courses. We asked process oriented questions, to step inside their role. Success Indicator: You feel mild anxiety. That's growth happening. 3. Practice Strategic Mindfulness The Strategy: Create regular pause points in your day to slow judgment and reaction. These two things make it difficult to connect with others. Simple Implementation: Take a five-minute walk between meetings without your phone. Use that time to process what you just heard and prepare mentally for the next conversation. Advanced Practice: Start meetings with a two-minute check-in where everyone shares their current state of mind. This simple ritual helps people transition from their previous mental space. Why It Matters: Mindfulness creates space for empathy to emerge naturally. 4. Read Fiction Strategically The Strategy: Choose novels or stories that expose you to experiences vastly different from your own. Recommendation: Dedicate fifteen minutes daily to fiction that takes you into unfamiliar worlds, different cultures, economic situations, or life challenges. Leadership Benefit: Fiction provides a safe way to practice perspective-taking. Unlike movies, reading slows information down, giving you time to really consider how others experience the world. 5. Take Empathetic Action The Strategy: Transform empathetic insights into concrete changes in how you lead. After Sarah's conversation: I implemented weekly ”connection calls" with remote team members where we not only covered work metrics, but also talked about their experience doing remote work. Critical Point: Empathy without action is just emotional tourism. The goal is behavioral change that improves people's work experience. Overcoming the Digital Empathy Gap Technology has created barriers to empathy that we must actively overcome. Most of our work now filters through digital interfaces before connecting to another human being. This creates a buffer that dilutes our path to genuine understanding. Research from MIT's Human Dynamics Laboratory shows that face-to-face interaction is 34 times more effective at building trust than digital communication. Yet we're increasingly dependent on screens for collaboration. The Solution: Implement "Empathy Protocols" for digital interactions:
Recently, my team expressed anxiety about artificial intelligence replacing their jobs. A very valid concerns given budget cuts and technological advances in higher education. Rather than dismissing their fears or offering empty reassurances, I designed a hands-on AI training session. I gave them a prompt I'd been working on to extract data from PDFs and convert it to spreadsheets. As they worked through the task, something shifted. "This is actually kind of frustrating," said Maria, one of our credential evaluators. "It keeps making mistakes with the formatting." "It's not magic," added James. "It's more like having an intern who's really fast but needs constant supervision." By the end of the session, their perspective had completely changed. Instead of seeing AI as a threat, they viewed it more as a tool that could potentially handle routine tasks while freeing them for more strategic work. Sometimes the most empathetic thing you can do is help people experience their fears directly rather than trying to talk them out of those fears. Why This Matters Now We're facing unprecedented challenges: remote work, rapid technological change, economic uncertainty. In this environment, leaders who can genuinely understand and respond to human needs have a distinct advantage. My son recently turned sixteen, and we've been discussing his first job search. He's nervous about walking into businesses, uncertain about the process, worried about rejection. It would be easier for him to apply online, maintaining that digital buffer. But the most meaningful opportunities, like the most meaningful leadership moments, happen in person, in real conversation, with genuine human connection. The same principle applies to leadership. We can hide behind email, manage through dashboards, and lead via policy. But the leaders who drive real results are those who take the harder path of genuine human connection. You can manage through assumptions, or you can lead through empathy. One approach maintains the status quo. The other transforms teams, drives engagement, and delivers results that matter. The question isn't whether you have time for empathetic leadership. The question is whether you can afford not to develop it. 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. |