Context Comes Before Learning

Day 73 of 280 | The 7-40 Challenge

A few years ago, my wife and I decided to go see a movie at the theater. We hadn’t heard anything about it. Didn’t read a review. Didn’t watch a trailer. Just picked one and sat down.

It was horrible. We walked out in the middle of it. I wanted to poke my eyes out.

That’s what happens when you consume something without context. You don’t know what you’re getting into, you don’t know why you’re there, and you have no framework for deciding whether it’s worth your time. You’re just sitting in the dark hoping something good happens.

I don’t pick up books that way anymore. I need to know what I’m diving into — what it’s about, why I’m reading it, and what potential benefit it has for me before I start. At work, when I sit down with a dataset, the first thing I do is figure out what I’m looking at. What system did this come from? What business purpose does it serve? What am I trying to answer? Even if the point is just discovery — just trying to understand what I have — that’s still a point. There’s still a reason I’m sitting down.

Context comes first. Learning comes second. And when you flip that order, you waste time, money, and energy consuming things that never stick.


I read Atomic Habits years ago. Good book. I could recite the habit loop: cue, craving, response, reward. The concepts stuck with me, at least on the surface.

But here’s what’s different now. Seventy-two days into the 7-40 Challenge, with a daily data management career running alongside a personal transformation experiment, I can see that habit loop everywhere — and not just in habits. I see it in bad data flowing into systems. In process failures that repeat because nobody defined the steps well enough. In shortcuts people take because the workflow was never designed properly.

Those associations didn’t exist for me before. Not because the book was lacking, but because I was. I didn’t have the professional and personal context to hang the framework on. The book was the same. I was the variable.

Todd Henry put it simply today: we learn best in the context of what we already know. Building context is key.


I’ve watched this play out in corporate settings for eighteen years. Companies train people on new systems and tools without ever explaining why the system exists or what business problem it was built to solve. Six months later, some of those people are using the tool well — the curious ones, the ones who started asking questions on their own. And the rest? They’re clicking buttons. Doing exactly what they were told and nothing more. No enthusiasm. No skin in the game. No growth.

The difference isn’t intelligence. It’s context. The ones who thrive went looking for the why behind the tool. The ones who stagnated never had it and never sought it out.

A data architect looks at a table and sees the system it came from, the business purpose, the relationships to other data. A regular user sees rows and columns. What the regular user misses — because they don’t have the context — is whether they’re even looking at the right data. Is this the source of origin or a reporting copy? Can you trace the lineage? Is it reliable? I’ve heard people call Excel a database. It mimics one, but it has none of the governance, procedure, or protocol that needs to sit on top of real data.

Without context, you don’t know what you don’t know. And you make decisions based on that ignorance.


A kid in college takes a class on personal finance. They learn the principles: spend less than you earn, pay off debt, invest early. Five years later, they’re drowning in credit card debt and living paycheck to paycheck.

The principles were sound. The education was delivered. But nobody connected the spreadsheet to the Saturday night. Nobody showed them what “spend less than you earn” looks like when your friends are all going out and you’re twenty-two and the credit card company just handed you a $5,000 limit. The knowledge was there. The context for applying it to their actual life wasn’t.

This is the same thing happening across every “how-to” space right now. The AI crowd skips to the prompts. The self-help crowd skips to the habits. The fitness crowd skips to the workout plan. All three are chasing the shortcut past the same hard work: Who are you? What do you value? What do you want?

That’s not a warmup exercise. That’s the foundation everything else is built on. Lifting weights is great — but understanding what you want your body to do is even better. Prompts are useful — but you have to know what you want before the tool can help you get it.


So how do you build context for someone who doesn’t have any? Someone with no data background, no self-help reading, no system for their life?

You start with one question: Are you happy?

Are you living the life you want to live? Yes or no. If it’s no — what are the things you’re unhappy about? You start picking out the points of dissatisfaction and look for the common theme. Is it because you don’t have the habits? Is it envy? Is it a lack of direction? What’s the reason behind the frustration?

Find the common theme. Work through the pain points. Build context from the inside out — starting with who they are, not what they should learn.


My son is seventeen. He’s watching me transform in real time. And one of the things I’ve learned as a parent is that you’re constantly building context into your kid’s life so they can understand why you bring them the things you do. You’re trying to help them see the world with more wisdom, but you’ve got to find the balance between letting them explore and just doing it for them.

They don’t learn anything if you do it all for them. But it takes forever if you just let them figure everything out alone.

Here’s what I love about my boy: he asks why. And once you satisfy the why, he’s generally pretty good at coming along. That’s the whole argument for context-before-learning in one kid.


I’ve been in church my whole adult life. I’ve heard sermons from the same passages dozens of times. But the clearest example I have of context changing everything about how you receive information comes from a story I’ve known since I was a teenager — one that only broke me open this year.

These people saw the Red Sea part. They saw the pillar of fire by night and the pillar of cloud by day. They saw Mount Sinai. The Spirit of God lived in the camp with them. And yet — when God said they could go into the promised land, they said no. A trip that should have taken eleven days took forty years. And everyone who said no didn’t get to go.

I’d like to believe I would have had the faith to go. But truth be told, I’m no better than them. There have been opportunities in my life where I knew God was opening a door, and I still said no.

It means more to me now because I’m actively trying to pursue what I think God wants from my life. I’m not sitting on the sidelines anymore. When I see something I need to do, I want to go do it — because I don’t want to be standing right on the edge of the promised land and not get to go in because I was a bonehead.

My life context finally caught up to a passage I’ve heard since I was a teenager. Same words. Different reader. That’s what context does.


If context comes before learning, then most education systems have it backwards. They deliver the learning first and hope the context catches up later. Sometimes it does. Most of the time it doesn’t.

If I could design it from scratch, I’d start with aptitude and self-knowledge. Not “what do you want to be when you grow up” — but what do you enjoy? What are you good at? What do you find yourself doing when nobody’s making you do anything?

I never knew at eighteen that I’d be an IT professional who loved data. It made no sense to me. I didn’t find data management until I was twenty-eight — eleven years after I graduated high school. I had to learn about myself first. I had to understand what made me me. And when I finally had the context of who I was and figured out where education could help me become more of who I was — that’s where I landed. And that’s when I really started to take off.

Context comes before learning. Always has. The question isn’t whether you’re smart enough to learn — it’s whether you’ve done the quieter work of knowing yourself well enough for the learning to land. I spent twenty years skipping that step. The last seventy-two days have been what happens when you stop.


Day 73 Scorecard:

✅ Bible study and prayer
✅ Walking and Lifitng
✅ Reading (Die Empty — Todd Henry)
✅ Calories tracked
✅ Water (100 oz)
✅ Gratitude
✅ BiblePictures365 (Deuteronomy 21-23)
✅ Creative hour


740Challenge #ContextBeforeLearning #DIKW #PersonalDataModel #Agency #Transformation #LivingProof #DayByDay #LifeOnPurpose #ToddHenry

A Tomb or a Library

Day 71 of 280 | The 7-40 Challenge

I’ve spent nearly twenty years working in data management. It’s my day job. I think about how data flows through systems, how it gets organized, how it turns into something useful. I think about the architecture behind it — the tables, the databases, the business processes, the people who care enough to enter things correctly and the people who throw things at random into places they don’t belong.

And about ten years ago, I started seeing the same framework everywhere — not just at work, but in life.


In my field, there’s something called the DIKW pyramid. It works like this:

Data is raw. It’s the unprocessed facts of your life — the events, the numbers, the experiences piling up with no context.

Information is data with context. When you start to organize what’s happened to you and see patterns, you’ve turned data into information.

Knowledge is information you’ve absorbed. The books you’ve read, the lessons you’ve been taught, the principles you can recite from memory.

Wisdom is knowledge tested against your own life — wrestled with, questioned, and earned through action.

Most people stop at knowledge. They read the book. They save the post. They listen to the podcast. They can recite the principles. And they stay stuck. Because knowledge without action is just a shelf full of books you never opened twice.


I didn’t learn this from a textbook. I learned it the hard way.

I was lying in a hospital bed during my second bout with cancer. I had time to think — more time than I wanted. And I started seeing the connections. The way data moved through my company was the same way information moved through my life. Raw inputs get processed into something contextual. Context builds into understanding. Understanding, if you act on it, becomes wisdom.

And I realized: if I control the inputs — what I read, how I eat, how I exercise, what I feed my mind and my spirit — I can, in a lot of ways, influence the output. That’s true in data management. And it’s true in life.


Here’s the question that keeps coming back to me: What’s the difference between someone who reads Atomic Habits and changes their life versus someone who reads the same book and puts it on the shelf?

Same book. Same information. Same knowledge available to both.

The variable is agency. The willingness to act on what you know. The realization that nobody is coming to save you, nobody is going to do it for you, and the information sitting on your shelf is useless until you decide to apply it.

That’s the leap from knowledge to wisdom. Not reading more. Doing something with what you’ve already read.


My data management brain sees things in a different way. I see systems. I see related sets of information that join together. I see frameworks and architecture. I think about how things connect — and more importantly, I think about what happens when they don’t.

And here’s what I notice about how most people organize their lives: their inputs are at odds with their stated goals.

Someone says they want to be a writer but never sits down to write. Someone says they want to get in shape and fills their body with garbage. Someone says they want a strong marriage and spends their energy tearing their spouse down behind closed doors.

A data architect would look at that and flag it immediately: you have a structural problem. Your inputs don’t match your desired output. No amount of motivation will fix that. You need to redesign the system.

That’s what healthy habits do. They redesign the system. They align your daily inputs with the life you say you want. And when the system is aligned, the outputs start to change — not because you’re trying harder, but because the architecture finally supports the goal.


So if you’re sitting at your desk right now, with a shelf full of books behind you and a head full of knowledge that hasn’t changed anything — I have one question for you.

Is that shelf a tomb or a library?

A tomb is something that’s never opened because it’s full of dead bones. Decay and rot and silence live there. The information inside has stopped moving. It serves no one.

A library is alive. It’s rich with possibility. It’s full of words that want to guide you somewhere better. It’s waiting for someone to pull a book off the shelf, open it, and do something with what’s inside.

If you’ve been collecting books the way I collected books for twenty years, I have a feeling you want more than you have right now. You want to be more and do more than you are. But you’re stuck on this word: agency. You don’t feel like you have any. You feel like every time you try to move forward, something pushes back.

Here’s what a data architect would tell you: that pushback is a system conflict. Your old architecture — the habits, the patterns, the defaults you’ve been running on for years — is fighting the new inputs you’re trying to introduce. That’s not a sign that you’re failing. That’s a sign that the redesign is working. Every system resists change at first. The old processes don’t want to be replaced. But if you keep feeding the new system with the right inputs, consistently, the old one loses its grip. The architecture shifts. And the outputs start to change.


So I’ll ask you plainly: what do you want?

And if you know what you want — what are you willing to do to get it?

I spent twenty years with a shelf full of books and a head full of knowledge that wasn’t going anywhere. I had data. I had information. I even had knowledge. What I didn’t have was the willingness to put it to work — to wrestle it into wisdom through daily, unglamorous action.

Don’t let your shelf be a tomb. Turn it into a library. Take what you know, apply it to your life, and start the climb from knowledge to wisdom. Do it today. Do it again tomorrow. And pretty soon, you’ll look in the mirror and barely recognize yourself — not because you became someone new, but because you finally became who you were always supposed to be.


Day 71 Scorecard:

✅ Bible study and prayer
✅ Walking
✅ Reading (Die Empty — Todd Henry + Keep Going — Austin Kleon)
✅ Calories tracked
✅ Water (100 oz)
✅ Gratitude
✅ Exercise
✅ BiblePictures365
✅ Creative hour


740Challenge #DIKW #DataToWisdom #TombOrLibrary #Agency #Transformation #LivingProof #DayByDay #LifeOnPurpose #ToddHenry #SystemsThinking

The Robbie Hart Insight

Day 70 of 280 | The 7-40 Challenge

I went to college on a full music scholarship. Bass baritone. Show choir. The whole deal. Singing and dancing literally paid for my education.

I sang in everything I could find — college choir, a professional chorale that was just starting up, church worship teams, a summer-long ministry tour where I sang at a youth camp for over two months. By the end of that summer, I was sung out in ways I didn’t even know were possible.

And when I got back to campus that fall, I realized something had shifted.


It wasn’t that I couldn’t sing anymore. I could. It was that the environment around music had started to change me into someone I didn’t want to be. The music department had started a critical spirit in me — a snobbish perfectionism that I was fighting without realizing it. And I didn’t have the tools at that age to separate the pursuit of excellence from the culture of superiority.

If I’d had the work ethic I have now — the ability to self-assess and improve — I probably would have excelled. But at nineteen, I didn’t have that in my toolbox. And honestly, I didn’t need to stay. That path wasn’t going to serve me. I just didn’t have an adult come alongside me at that moment to help me figure out what should come next.

So music faded. Gradually. Not with a dramatic exit — just a slow drift into other things. I even spent a season as a music pastor, where singing was my entire job. And it took the fun out of it completely.


Years later, I found my way back to performing. Not as a career. Just for the love of it. I joined a theater group in the DFW area and ended up playing Maurice in Beauty and the Beast — ten shows, not an empty seat in the audience.

Something was different this time. I was just there to do my best and enjoy the ride.

In the version of the show we performed, the original script had included a duet between Belle and Maurice. But the musical’s writers had replaced it with a short solo that Maurice sings as he gets lost in the woods. The removed the duet completely. They did it because the duet weakened Belle’s character — it undercut her agency in the story.

Would I have loved singing a duet with the actress playing Belle? Absolutely. She was an incredible singer. But it’s not what the story needed. It’s not what the character needed. It told a better story without it.

And I was completely okay with that.

That’s when I knew I was a different person. The younger version of me would have been devastated. This version understood that the talent exists to serve the story — not the other way around.


I’ve been thinking about this because I just started reading Todd Henry’s Die Empty, and he talks about identifying your through line — the thread that runs through everything you do and connects it into a single coherent purpose.

My through line isn’t singing. It never was. Singing was a tool. A resource. A gift I was given that served me well for a season and still sits on the bench ready to be called up when the moment is right.

But it’s not the thing.

The thing is what I’m doing right now — writing, creating, documenting, building something that helps people see what they already have and use it on purpose. That’s the through line. Phase Defiant, the 7-40 Challenge, BiblePictures365, this blog — they’re all expressions of it. The singing, the thirty voice impressions I can do, the odd jobs I do around my house — those are resources. They’re talents. They just don’t run the show.


There’s a moment in The Wedding Singer where Robbie Hart, played by Adam Sandler, realizes something about himself. He used to play in a band. He performed at weddings. But what he really wanted wasn’t to be the guy on stage. He just wanted to express the feelings and create the things. He wanted to write songs people loved. He didn’t have to be the one up there singing them.

That’s me.

I’ve written over fifty songs. I’ve performed on stages large and small. I can sing, and I can do it well enough to hold my own. But I don’t need to be the guy on stage. I need to be the guy at the desk — writing the story, building the framework, documenting the journey, creating something that lasts longer than a performance.


If you’re reading this and you’re in that spot — talented at something, maybe even genuinely good at it, but sensing deep down that it’s not your thing — here’s what I’d tell you:

There’s a difference between what you’re talented at and what matters to you.

Start with what you value. Your family. Your faith. The work that makes you come alive. The problem you can’t stop thinking about. Then ask yourself which of your talents actually serve those values — and which ones are just things you can do.

Your talents are resources, not assignments. The through line decides which ones get deployed. And having a real gift sit on the bench isn’t waste — it’s wisdom.

Let the story decide what it needs. Not your ego.


Day 69 Scorecard:

✅ Bible study and prayer
✅ Walking
✅ Reading (Die Empty — Todd Henry)
✅ Calories tracked
✅ Water (100 oz)
✅ Gratitude
✅ Exercise
✅ BiblePictures365
✅ Creative hour


740Challenge #DieEmpty #ToddHenry #ThroughLine #TalentVsCalling #TheWeddingSinger #RobbieHart #ShowYourWork #Transformation #LivingProof #DayByDay #LifeOnPurpose

Flow and Stock

Day 65 of 280 | The 7-40 Challenge

I started reading Austin Kleon’s Show Your Work today. To me, he sounds like a modern-day Seth Godin — an artist who’s figured out how to say, very poignantly, not just how he found success, but how he built it. And he shares it in a way that’s both relevant and timeless.

Three things hit me today.


Maintain your flow while collecting your stock.

My flow is what I do every day. The habits. The routines. The framework. The stream of ideas, creativity, and writing that comes from showing up and doing the work. Flow is the engine.

My stock is what I produce over time because I stayed in the flow.

What have I produced over the last two rounds of the 7-40 Challenge? I edited one novel and got it published on Amazon. I wrote another novel and took it through its revision passes. I’ve blogged every single day this year — not just on challenge days, but during the assessment weeks too. This blog has become my daily creation habit — my response to how the habits are affecting me, how the reading is impacting me, and how I’m starting to put things together and see the world in ways I never have before.

Some of the visions and thoughts I’ve had over the years are coming back to me now and making more sense in the context of where I am and what I’m doing. The ideas didn’t change. I did.

Maintain your flow. The stock takes care of itself.


Small things over time get big.

We know this. If you’ve ever put money into a bank account and watched compound interest work, small additions over time can get really big.

If you’ve ever thrown your clothes down in a room and kept throwing them down, something as small as a single shirt on the floor can end up being something as big as your wife not being happy with you and a whole lot of cleaning to do because you let it go too long.

There are so many examples. But here’s the one that matters to me right now: if I proactively practice my habits every day — if I put in my time writing, put in my time creating, put in my time connecting on social media — then I will see those things get big. The same is true for exercise, eating well, drinking water. As I put in the repetitions, my body is getting more fit. The pounds are going down.

Sixty-five days of small things. And they’re starting to get big.


Your website is your own little corner of the internet.

I’ve heard this before. But Kleon added something that turned on a light bulb for me: your social media platforms — Instagram, Facebook, TikTok — can be taken from you. If the overlords of those companies decide to change the rules, your content lives on their land, not yours.

Your website is different. It’s yours. It’s where your content is stored, where your central hub lives, where you’re building the brand of you so you can speak on anything you want — and it’s a place you can lead people back to so they can see exactly who you are and what you do.

I saw a Gary Vaynerchuk video the other day where he said one of the things that’s working in social right now is making content about everything — not boxing yourself into one lane. I identify with that. I have interests in many different areas. I have many different things I want to work on. And having my own corner of the internet where all of that comes together? That’s the hub. The social platforms are the megaphones. The website is the house.


Maintain your flow while collecting your stock. Small things over time get big. Your website is your own little corner of the internet.

Three good nuggets from today’s reading. And every single one of them confirms I’m on the right track and doing the right things.


Day 64 Scorecard:

✅ Bible study and prayer (finished Numbers!)
✅ Walking
✅ Reading (Show Your Work — Austin Kleon)
✅ Calories tracked
✅ Water (100 oz)
✅ Gratitude
✅ Exercise (Workout B with Trey)
✅ BiblePictures365
✅ Creative hour


740Challenge #ShowYourWork #AustinKleon #Flow #Stock #SmallThingsGetBig #Transformation #LivingProof #DayByDay

You Showed Up

Day 64 of 280 | The 7-40 Challenge | Thank You Campaign

Last night, I knocked on a door I’ve been refusing to knock on for quite some time.

The door of telling people what I’m up to and inviting them to be a part of my creativity.

I don’t know what I thought would happen. I don’t know if I thought I was by myself, or that nobody was paying attention, or — honestly, I don’t know what I thought.

But I was more than pleasantly surprised.


People I haven’t had the opportunity to talk to in several years reached out to me today. To congratulate me. To buy my book. To give me immediate feedback on a few things that need to be corrected — which I thought was awesome. Real feedback from real people who took the time to read what I wrote.

I’m overwhelmed. Because the support that came out of just putting myself out there — just trusting that there are people who care about who I am and what I do — was amazing. It was really, really good.


So this isn’t a long post tonight. It’s a simple one.

If you’re reading this — know that I’m thankful for you.

Whether you bought my book, or left a comment, or shared a post, or just sent me a message — thank you.

Thank you for hanging out with me long enough to read the words I’m saying. Thank you for the feedback. Thank you for the comments. Thank you just for being you.

I spent a long time convinced that nobody would care about what I was creating. I was wrong. You showed up. And that means more than I know how to say.

I really appreciate it.


740Challenge #ThankYouCampaign #Gratitude #PhaseDefiant #DMTWillis #IndieAuthor #Community #LivingProof #DayByDay #YouShowedUp