Tag: agile

Expert First, Trusted After

Expert First, Trusted After

JakeLeave a comment

I have been thinking a lot about the word expert lately.

It is a strange word, because most people do not become experts while looking like experts. They become experts while trying things that are half-working, while fixing something that broke for the third time, while realizing the elegant idea from yesterday does not survive contact with the real world.

That has been true for most of my life.

I have always been drawn to systems. Old computers. Software projects. Business problems. AI ideas. Robots. The little details that make something feel alive instead of just technically functional.

Lately that has shown up in a few places at once. I am building Transcendent Software full time. I am working toward CoffeeBreak as a bigger product vision. I am reviving Jibo through Open Jibo Cloud. I am thinking about websites, blogs, videos, podcasts, social posts, consulting, product work, and whether any of this can become a real engine instead of a pile of good intentions.

The funny thing is that the work itself is the clearest argument.

If I want people to trust me as someone who can help with AI systems, software modernization, automation, architecture, or technical leadership, I probably do not need to pretend I have a perfect machine already humming in the background.

I need to show the work.

Show the thinking. Show the decisions. Show the messier middle. Show the way a robot comes back to life one capability at a time. Show the way a consulting business becomes clearer by solving actual problems instead of polishing slogans. Show the way a product like CoffeeBreak emerges from real operational pain, not from chasing whatever AI headline is loudest this week.

That is the kind of confidence I trust in other people too.

Not the confidence of someone who says they have it all figured out. The confidence of someone who has been in the weeds long enough to know where the roots are.

So maybe that is the content plan for now.

Keep building. Keep writing. Keep showing the reasoning. Keep sharing the progress before it is perfectly packaged.

The expertise was built over years. The trust will probably be built one useful piece at a time.

More to come. ☕

Growth Happens Before You Feel Ready

Growth Happens Before You Feel Ready

JakeLeave a comment

This weekend felt like one of those moments where you realize life is changing while you’re still trying to keep up with it.

My son suddenly wants to help with everything outside. Not just ride along on the mower for fun, but actually help mow the property, do weed eating, and be part of the work. We spent part of the weekend working on the land together and somewhere along the way it hit me that he’s growing. He’s starting to become capable.

That sneaks up on you.

We also spent time planting flowers, working around the property, and dealing with spring projects. I hatched a few more chicks this week too. Some made it, some didn’t. That’s just part of raising animals and living a little closer to nature. Things grow, things fail, and you keep moving forward.

Mother’s Day was good too. Family time, good weather, slowing things down for a minute. Watching everything my wife does for our family always reminds me how much growth happens quietly in the background while everyone else is focused on bigger, louder things.

At the same time, the technology world feels like it’s changing faster than ever.

Every week there’s another AI announcement, another new model, another prediction about how everything is about to change. Some of it is hype, but some of it is real. You can feel the shift happening underneath everything now.

That’s part of why I’ve been so focused lately.

CoffeeBreak is evolving quickly. My thinking around orchestration, memory, smaller expert systems, and long-term AI behavior is changing almost weekly right now. Jibo keeps improving little by little too. New versions, new features, more personality starting to come back into the system.

It feels like a lot of things are growing at once.

Some of it is exciting.
Some of it is uncertain.
Most of it is happening faster than expected.

I think that’s just life sometimes.

You make plans, and then growth changes the shape of them.

Your kids grow.
Technology changes.
Your priorities shift.
New opportunities appear before you feel fully prepared for them.

And somewhere in the middle of all of it, you realize the future isn’t some distant thing anymore.

It’s already showing up around you in small ways every day.

The trick is noticing it while it’s happening.

☕

Cozy farmyard reflections at golden hour

Working Through It

JakeLeave a comment

Lately I’ve been focused on making progress.

Not the kind you see in demos or announcements. The kind where you’re just trying to move things forward a little at a time. Fix something. Improve something. Keep things from drifting too far off course.

That’s been true across everything.

Work has been steady. I had a good onsite with a client. Productive, grounded, the kind of work that reminds you why experience matters. At the same time, I’ve been pushing forward on my own projects. Jibo has mostly been regression testing. Fixing things, breaking things, trying to get to a version that feels stable. Versions don’t mean much without users, but they help me stay disciplined. They give me something to work toward.

CoffeeBreak has been a different kind of work. Less visible, more foundational. Thinking through user experience, agent loops, how systems should behave over time. Not just what AI can do, but how it fits together. I find myself thinking more about structure than features. Planning for things like memory, cost, how to use smaller models effectively instead of just reaching for the biggest one available.

It’s a lot of thinking. A lot of iteration.

And then there’s everything outside of that.

We’ve been spending time as a family, which has been good. A few days off helped reset things a bit. Spring is here, so we’ve been working outside more. Planting, tending to the land, adding more chickens. It’s work, but it’s a different kind of work. Slower. More tangible.

Not all of it goes the way you want.

Today was one of those days. We lost a few baby chicks. One didn’t make it out of the shell. One probably got trampled. Another overheated. That’s just part of it, but it doesn’t make it easier. You try to do everything right, and sometimes it still doesn’t work out.

That’s nature.

I’ve still got others at different stages, more eggs in the incubator, so it’s not a loss that sets us back. But you feel it anyway.

Same with the dogs. They’re getting older. You start to see it in small ways at first, and then more clearly. It’s part of the cycle, but it’s not something you really get used to.

Mother’s Day is coming up next week. That brings its own mix of emotions. Losing my mom still feels recent, even though time keeps moving forward. At the same time, I see everything my wife does every day for our family, and it puts things in perspective.

All of it together, it’s just life.

Messy, sometimes frustrating, sometimes really good. Rarely clean or predictable.

I think that’s why I don’t get too caught up in perfect outcomes anymore.

Whether it’s building systems, raising animals, or just trying to take care of a family, progress usually looks the same.

You keep showing up. You keep adjusting. You take the wins where you can, and you learn from the rest.

And you move forward.

☕

Cozy workspace with a lakeside view

What Building AI Actually Feels Like Right Now

JakeLeave a comment

There’s a lot happening in AI right now.

Every week there’s something new. Smarter models, faster responses, better benchmarks. If you just follow the headlines, it feels like everything is accelerating perfectly.

But building with it feels different.

It reminds me a little of when I first started working with computers. Back then, nothing was polished. You didn’t just install something and expect it to work. You had to figure things out, piece by piece. Manuals, trial and error, late nights. When something finally worked, it wasn’t because the system was perfect. It was because you understood it enough to make it work.

That’s where AI feels like it is right now.

I’ve been spending time bringing Jibo back to life. It’s been fun, a little nostalgic, but also a reality check. When you move from demos to something that lives in the real world, everything changes. Timing matters. Context matters. Small failures stand out. Things don’t just need to work once, they need to keep working.

And that’s where things start to break down.

Not because the AI isn’t good. It’s actually impressive. But because everything around it is still rough. Getting systems to talk to each other, keeping them aligned, knowing when to step in as a human. That part is still messy.

It’s kind of like working in an old shop. You’ve got great tools, but they’re scattered everywhere. Some are new, some are worn down, some don’t quite fit together. You can build something solid, but only if you know how to use them together.

That’s the part people don’t see in the demos.

The demos are clean. Controlled. One path, one outcome.

Real life is not like that.

Real life is interruptions, edge cases, things that almost work, things that work until they don’t.

That’s what building AI actually feels like right now.

And honestly, that’s what makes it interesting.

Because this isn’t the end state. This is the phase where things start to become real. Where the difference isn’t just who has the best model, but who can actually make it useful.

That’s the part I keep coming back to.

Not just what AI can do, but how it fits into real life. How it works with people. How it holds up over time.

That’s where the work is.

And it’s also where the opportunity is. ☕

Serene sunset by the winding driveway

Mowing, Momentum, and Building Something That Works

JakeLeave a comment

I spent a good part of yesterday on the mower.

Fifteen acres gives you a lot of time to think.

I had a podcast going the whole time, listening to everything happening in AI right now. Models, agents, orchestration, tools, memory, workflows. It’s all moving fast.

Really fast.

And I’ll be honest, as I listen to it all, there’s a part of me that feels it.

A lot of the ideas I’ve been working toward are showing up.

Multi-agent systems.
Orchestration layers.
Different runtimes.
Memory strategies.
Security and governance conversations starting to take shape.

The big players are moving in that direction.

And they can move faster than I can.

More people.
More resources.
More reach.

That can get in your head if you let it.

But sitting out there on the mower, going back and forth across the same lines, I kept coming back to something simple.

There’s a difference between building something fast…

…and building something that actually works.

Not in a demo.
Not in a video.
In real use.

Something that produces useful output.
Something that guides you.
Something that doesn’t leave you wondering what to do next.

That takes a different kind of effort.

It’s not just features.
It’s not just capability.

It’s how it all comes together.

I get why companies move fast and figure they’ll clean it up later.

They probably can.

But that’s not how I’m wired.

I want something that feels right when you use it.

Something that makes sense.
Something that helps, not just impresses.

That means spending more time on the details.

On the flow.
On the foundation.

It might take longer.

But I believe that’s where the real value is.

So yeah, things are moving fast right now.

But I’m still focused on building something that works.

And getting it into people’s hands soon. ☕

Easter stroll in a sunlit field

Easter, Time, and What Actually Matters

JakeLeave a comment

As I sit here on Easter reflecting on the day, a few things are on my mind.

For me, Easter is about faith. About resurrection. About the idea that something new can come from what felt finished.

But even outside of that, there’s something about this time of year that everyone can feel.

Spring. Growth. New life.

And time.

Time is the part that keeps hitting me.

My son is three and a half now.

I can still remember when he was born like it was yesterday, and now he’s running around the yard, talking, laughing, figuring things out in his own way.

My mom passed away last year.

My dad passed when I was 18. He was 50.

I’m 48 now.

That gets your attention.

It makes you look at things differently.

Today was a simple day.

We had family over for Easter lunch.
We went out in the field and flew kites.
We walked around the chickens and the garden and talked about what might grow this year.

Earlier in the day I took a walk with my wife and son and the dog out in the field.

Nothing big. Nothing complicated.

But those moments stick.

They feel different.

At the same time, life keeps moving.

I’m building CoffeeBreak.
Working with clients.
Still at TFL.
Fixing things when they break.
Working on bringing Jibo back to life.

A lot going on.

And somewhere in all of that is a simple thought that keeps coming back.

I want more of those moments.

More time in the field.
More walks.
More afternoons that don’t feel rushed.

That doesn’t happen by accident.

It means making changes.

It means deciding what matters and actually acting on it.

In a way, that ties back to what I’ve been building.

So much of what we do in technology is about speed. More output. More systems. More everything.

But if it doesn’t create space for the things that actually matter, what are we really optimizing for?

That’s been on my mind today.

Easter is a reminder that things can change. That new life, new direction, new priorities are always possible.

I’m thinking about what that looks like for me.

Not someday.

Soon. ☕

Impressive Isn’t the Same as Satisfying

Impressive Isn’t the Same as Satisfying

JakeLeave a comment

I watched the Super Bowl last night.

It wasn’t big or bold. It was boring.
Clean. Technically solid. Well produced.

I even watched both halftime shows at the same time. They were fine.
The commercials too. A few were funny.

The whole thing just didn’t stick with me.

Maybe it was because the Chiefs weren’t there this year. That probably played a role. But it was more than that.

That feeling has been showing up a lot lately.

In sports.
In technology.
In AI announcements.

There’s no shortage of impressive things right now. New models. Bigger numbers. Clever demos. Even an AI-generated compiler that can play Doom.

It’s cool. I appreciate the engineering.

But impressive isn’t the same as satisfying.

Satisfaction comes from coherence. From purpose. From systems that do something meaningful over time, not just once on a stage.

Lately I’ve found myself drawn more to quiet work. Marching towards a CoffeeBreak beta launch. Restoring old systems. Building things slowly. Making sure I understand what I’m creating end to end.

Not because I don’t value progress.
But because I want the progress to matter.

That’s where the real work is.
That’s where it has always been.

☕

Why I’m Waiting for One Thing to Work Really Well

Why I’m Waiting for One Thing to Work Really Well

JakeLeave a comment

This is probably overdue, but here we are.

The thing I’ve been indirectly writing about for the last few weeks has a name. It’s called CoffeeBreak. It’s an AI teammate designed to support the software development lifecycle, end to end.

I haven’t named it until now on purpose. Not because it’s a secret, but because the name isn’t the important part yet. The work is.

Over the years, I’ve learned that most software failures don’t come from ambition. They come from shipping something that almost works and asking users to fill in the gaps.

I’ve been feeling pressure lately. Not from investors or timelines, but from peers. People asking when they can try CoffeeBreak. That’s a good problem to have, and it’s also a dangerous one.

Right now, CoffeeBreak doesn’t need to do everything. It needs to do one thing, really well, end to end, without excuses.

I don’t want to ask people to imagine how it will work. I don’t want to say “ignore that part for now.” I don’t want users doing invisible work to make the system feel useful. And I certainly don’t want people to feel, “Pay no attention to the man behind the curtain” vibes.

I’ve shipped software fast before. I’ve cut corners before. And I’ve paid for it later with trust, rework, and long nights debugging or explaining why something behaved the way it did.

This time, I’m waiting until one workflow can stand on its own.
One task. One path. One outcome that doesn’t require hand-holding.

I’m close. I can see the shape of it now. But “close” isn’t the same as “ready,” and experience has taught me not to confuse the two.

When CoffeeBreak is ready to share, it won’t need caveats.
That’s the bar I’m holding myself to.

The Most Valuable Skill I’ve Seen Engineers Lose, and Why It Matters Now

The Most Valuable Skill I’ve Seen Engineers Lose, and Why It Matters Now

JakeLeave a comment

This time of year has a way of slowing things down.

As winter settles in and we all spend a little more time with family and friends, there’s often a moment when the noise quiets just enough to think. For most people, I’m sure it’s about the magic of the holidays, time with family and friends, or maybe even a warm-weather vacation. For me, my head wanders to my work. Not the next sprint or the next feature, but what actually matters over the long haul.

This year, that reflection keeps coming back to a simple question:

What really makes a great engineer?

After decades in this industry, I’ve seen tools change, paradigms shift, and entire job descriptions come and go. But I’ve also watched one critical skill slowly fade into the background.

And right now, that skill matters more than ever.

It Isn’t Coding Speed or Tool Knowledge

The most valuable skill I’ve seen engineers lose isn’t typing speed, language fluency, or familiarity with the latest framework.

It’s not PR velocity or anything measured by DORA metrics. It’s definitely not who has the deepest front-end framework expertise.

All of those things are valuable. But something else is more important.

It’s the ability to reason through ambiguity.

When I was coming up, we didn’t have the luxury of abstraction layers everywhere. If something didn’t work, you traced it. You reasoned about it. You figured out why.

I’ve mentioned before that I used to test on algorithms in my hiring assessments. They mattered. Not because engineers would be implementing them every day, but because algorithms expose reasoning, tradeoffs, and comfort with uncertainty.

The final part of my assessment was a four-question story titled “One Bad Day.” In it, engineers were faced with real-world problems and incomplete information. There were no right or wrong answers. What mattered was how they handled uncertainty when confronted with it.

Those questions revealed how someone thinks when there isn’t a clear path forward.

As software evolved, we got very good at assembling systems. We got much less comfortable sitting with ambiguity.

Abstraction Is Powerful, But It Has a Cost

Modern tools are incredible. They let us build faster and bigger than ever before. But they also hide complexity, and when complexity is hidden long enough, people forget it exists.

That’s how we end up with engineers who are productive, but uneasy the moment something doesn’t behave as expected. When the happy path breaks, the thinking muscle hasn’t been exercised.

AI accelerates this trend if we’re not careful.

Why This Skill Matters More Now, Not Less

There’s a fear that AI will do the thinking for us.

I believe the opposite.

AI is very good at producing output. It’s much worse at knowing when that output is wrong, incomplete, or misaligned with intent. That gap is where human reasoning becomes invaluable.

The real present in this new era isn’t faster code generation. It’s the opportunity to refocus engineers on judgment, evaluation, and problem framing.

Those are learned skills. They compound over time. And they don’t disappear when tools change.

The Gift That Actually Lasts

As you head into the end of the year, maybe while you’re opening presents or just enjoying a quieter moment, this is the thing worth investing in.

The greatest gift you can give yourself as an engineer isn’t another tool or certification. It’s the willingness to slow down, sit with ambiguity, and reason your way through it.

That skill never goes out of style.

What Yoda taught me about being a mentor

JakeLeave a comment

Like I mentioned in my blog post, What I’ve Learned from Mr. Miyagi, the elderly, wise, green alien creature from the Star Wars saga, Yoda, was another model for how I learned to be a great mentor. I didn’t know it at the time, but while I watched The Empire Strikes Back when I was a young boy, I was learning many life skills while I dreamed of being Luke Skywalker flying an X-Wing, commanding the force, taking on the bad guys, and learning to overcome the dark side, and in particular, Darth Vader.

Yoda was introduced into the story when Luke Skywalker crash lands into Dagobah, a swampy forest planet. After a moment trying to gather his surroundings, Yoda arrives in scene as a quirky, curious, alien creature who speaks in broken english, but still shows some sarcastic and quippy wisdom when he speaks. For instance, when Yoda asks Luke why he is there, after some banter, Luke states, “I’m looking for a great warrior.” Yoda immediately in his broken english language states, “Great warrior? War’s not make one great.”

You can watch the entire dialog above, but the truth of the introduction is that Luke is overconfident, and almost cocky. He has many thoughts about how everything works, how he is supposed to become a Jedi Knight, how his destiny is supposed to pan out, and in reality, he has much growing up to do. Luke is like many of us when we start out on our career paths. We have a small education and maybe some bits and pieces of real world experience, but in practice, we don’t have much experience at all.

Many of us, when seeking mentorship, are ready to receive it. Luke, on the other hand, was not. He argues with Yoda and Obi Wan Kenobi’s force ghost about whether he is ready to be a Jedi Knight or not. Eventually, they all agree he will finish what he starts and become the Jedi Knight he is meant to become. This submission of will is important, because being a good mentee is about submitting to the process, knowing that in the future you’ll be able to expand your wings and fly on your own.

Yoda trained Luke on calming his mind and approaching challenges in a clear frame of mind and to stay focused. He also taught Luke small concepts and allowed him to build upon them later, even though he didn’t know why he was doing them in the first place. This idea of foundational building was something I explored with how Mr. Miyagi trained Daniel in The Karate Kid. This was the same with Yoda. He started by having Luke move small objects with the force. Later in the training scenes, he had Luke try and move his X-Wing from the swamp as it began to sink. He utters some of his best lines during this scene, “No. Try not. Do or do not, there is no try.” or Luke saying, “I don’t believe it,” when Yoda uses the force to move his X-Wing from the swamp and Yoda replies, “That is why you fail.”

I use these same techniques when I mentor. I often only give out bite size pieces of information which are enough to get the job at hand completed. This allows my mentees to become masters of that technique faster, and later one we can connect the dots. Keeping things simple is a core value of mine. Not only is it the best way to keep things progressing, but there are many times I learn new techniques as well. As I have explored in many of my previous posts, including Teach a Man To Fish, I point out that the best leaders and mentors surround themselves with smart people, and allow them permission to fail. Everyone gets an opportunity for growth this way.

In conclusion, Yoda and many other wise sages in many movies taught me much about how I mentor today. Lessons such as keeping things simple, staying focused and submitting to the process are all key to growth. We will explore this more in the future, but for now, venture out and try these things out for your teams.  May the force be with you.