Tessory

There was an AI competition we were building toward with a hard deadline in August, and we stalled on it. I couldn't come up with a game I liked, and the entry was supposed to have the business running on AI, which I hadn't done. Then the summer we'd already planned came up against the deadline, and winning the competition at the loss of that summer didn't meet the value of what we wanted to do. We chose the summer we built over a deadline that would have taken it away.Most of us treat retirement like a number. Hit it, and the plan is done. My grandma had it worked out decades earlier, taking occasional shifts at the trading post in Tulameen because she liked the work and liked the people. There wasn't a specific stop, it was a, "Hey, what seems interesting? Let's continue that." The same question belongs inside your company, because sometimes you build things differently if you know what your end goal is. This week's Tessera: name one thing you'd keep doing if you won the lottery tomorrow, then look at your week and see whether any of it is actually there.Read the companion article at https://tesseros.com/tessory-e19-retirementTimestamps:00:00 Retirement as a shape instead of a date01:21 Letting the AI competition go03:18 A porch conversation in Tulameen05:40 Planning a ten-year wind-down07:33 What happens to your company if you stop08:18 Automated e-transfers and keeping your own backups

I'm recording this on August 10th, 2026. There are wildfires all across British Columbia, there's an alert at the edge of our city, our bags are packed and sitting by the door, and today is a normal working day. Technically, nothing has changed. The smoke is the part that really gets you; it doesn't let you forget that there is danger, and the day continues anyway. It's fine and not fine at the same time.Emergency planning is a really strange skill because you build it when you don't need it for a moment when you can't build it. The bag isn't specifically for the fire. The bag is for you standing in a doorway with no judgment left. Every decision that held up under pressure has always been one we made before the pressure arrived. This week's Tessera: pick the future self who needs the hand-off, the one who can't think or the one who checks too often, and build one list or one system for them.Read the companion article at https://tesseros.com/tessory-e18-emergency-planningTimestamps:00:00 Wildfire alert at the edge of the city01:35 Why emergency planning gets built in advance03:06 The fires and floods a few years ago04:36 What the kids chose to pack06:40 Planning while calm as a hand-off07:15 Building a grant finder agent into Notion

In my mid-20s, Simon Sinek's "Find Your Why" video swept through the office, and everyone around me lit up while I quietly panicked. I'd been told my whole life to follow my passion, and I didn't have one. Around the same time, my team read Good to Great chapter by chapter in a work book club, and I remember doing the math instead of feeling inspired: getting from a 90 to a 100 can cost almost a third of the work that the 80 took, and I didn't want to spend those extra hours on a version of great I hadn't chosen.What feels like missing passion can be information. It tells you "not this, not yet," and it points you toward trying the next thing instead of forcing the thing in front of you. Once I started designing my own roles around what genuinely interested me, Good to Great finally made sense. I wanted to be great at things I'd actually picked. This week's Tessera: pick one thing at work or at home that feels stuck or flat, swap it out for something you wouldn't normally try, and pay attention to whether it draws you in.Read the companion article at https://tesseros.com/tessory-e17-passion-as-informationTimestamps:00:00 The passion myth and following your why02:28 A perfectionist's honest math on effort04:45 Rebuilding a retirement plan around what you control09:11 Automating repetitive templated work with AI10:44 Perspective Flip version two and hosting update

There's a spot on the bike trail behind our house where the path drops and then swoops back up, and you can see both the short slope and the long climb right in front of you. My younger son gets nervous at the top because the gravel there is slippery, so if he stops to walk up he slides. But if he kept his momentum down the hill, it would carry him three-quarters of the way up the next section, and one or two pedal strokes get him over the rest. Stopping is what makes it hard. Staying in motion is what makes it easy.That's one of three aspects to momentum I've been contemplating: the physical kind, where staying in motion beats starting and stopping. There's also the design kind where you build a process so momentum can pass from one person to the next, and the redirecting kind for when the exact piece you want to move won't budge no matter how well it's designed. This week's Tessera: Name which of the three you're dealing with right now - starting, keeping, or redirecting, and get that moving today instead of waiting for the whole thing to be right.Read the companion article at https://tesseros.com/tessory-e16-redirecting-momentumTimestamps:01:09 Designing process momentum at an accounting firm03:52 Physical momentum on the bike trail05:27 Getting stuck on the AI game competition06:20 Redirecting momentum into a website audit08:00 Choosing which aspect of momentum you need this week

Growing up, part of my family was into racing, which meant I got direct, specific feedback on how I drove. There were so many trips where my grandma would talk through exactly how I used the accelerator, how much I braked into a corner, how I came out of the exit. It wasn't harsh, it was honest and precise: here's what you did, here's what it cost you, here's what to try instead. I didn't understand at the time how rare that kind of feedback is. Most people never get it, not because nobody notices, but because people don't always say anything.Feedback and reassurance are two different things, and most of the friction comes from asking for one while meaning the other. If you want reassurance, ask for that directly, it's a legitimate thing to need. If you want feedback, mean it, attach a timeline, and be ready to hear something that stings. This week's Tessera: Pick one thing you're building right now, hand it to someone who will tell you the truth, give them a date, and follow up on that date instead of waiting for them to circle back on their own.Read the companion article at https://tesseros.com/tessory-e15-knowing-what-you-needTimestamps:00:00 Feedback versus reassurance00:25 Direct feedback from racing as a kid02:18 Playtesting Perspective Flip and deadlines04:26 The difference between asking for feedback and asking for reassurance05:22 Nice versus kind07:05 The backyard landscaping story

There's a gardening process called hardening off. When you've grown seedlings inside and want to move them outside, you don't just put them out and leave them there. You bring them out for an hour, then back in. The next day, a couple of hours. Then half a day, until they can stay outside on their own. In this house right now, the mantra is attitude and effort. One kid is learning to keep playing a game after he's lost. The other is being asked to show up for gym and track and try, not win just try. And the household rule is that if the kids are being asked to push into discomfort, the adults have to be doing it too, which is part of why this podcast, and Tesseros, and learning AI tools in the open, all exist.You don't build resilience by thinking your way through fear. You build it through small, repeated exposure, the same way a plant hardens off. Cold calls, an uncomfortable conversation, a new tool you don't know how to use yet, all work the same way. If it's your feelings on the line and not your safety, you go out for an hour and you come back. This week's Tessera: Pick the one thing you've been avoiding because it feels uncomfortable, not because it's actually risky, and give it one small, contained practice effort.Read the companion article at https://tesseros.com/tessory-e14-practicing-discomfortTimestamps:00:45 The household mantra of attitude and effort01:54 Practicing discomfort (The sidewalk test)03:19 Shifting from fear to logic at work06:12 The gardening process of hardening off07:38 The web of skills: Harmony over balance10:50 Experiencing one uncomfortable repetition today

We went for a hike over the weekend and my youngest was not into it. He was done before we left the house. Then the grassland changed to forest, streams appeared, the temperature dropped, the air got damp, and the birds started sounding different. He forgot to complain because things got interesting: a small waterfall, caves built into the rock where people had had fires. He stopped counting how long he'd been walking and started getting excited about what was coming next. It wasn't until we were almost back out that he asked if we were almost there. The trail didn't get shorter. He didn't develop more endurance. What changed is what he was looking at, and that changed the whole experience.Perspective is a functional skill, not a personality trait, and it's different from changing the thing itself. Both moves are useful, and choosing the wrong one costs you. This week's Tessera: Pick one thing that's felt immovable lately and run it through three lenses before deciding what needs to change: what would an optimist see, what would someone looking back on this in a year see, and what's the most sideways, absurd angle that could still technically be true?Read the companion article at https://tesseros.com/tessory-e13-choosing-your-lensTimestamps:00:36 The hike and shifting perspective02:18 Perspective as a functional skill04:55 The three lenses behind Perspective Flip06:58 Using AI to reframe and build08:42 Changing the stories we tell about ourselves10:52 Applying the three lenses this week

My fridge died a couple weeks ago, in the morning, right as we were getting ready for school. A power surge took out several appliances across the neighborhood. It still had lights, but the control panel was blank except for a row of eights, and neither compressor was kicking on. I spent about 90 minutes with Gemini working through it methodically before landing on the control board being fried, and the repair not being worth it. That's the moment that pushed me back into an idea I'd been chasing down for a friend a few weeks earlier: the railroad track analogy from episode 154 of Moonshots with Peter Diamandis and will.i.am.The analogy: building a career or a life used to mean choosing a track and staying disciplined on it. Now the tracks themselves get moved, sometimes blown up, while we're still traveling on them, and the skill isn't staying on track anymore, it's developing the agility to jump to another one without breaking everything in the transition. This week's Tessera: Name one thing you're still trying to make work even though part of you already knows the track has shifted, and ask honestly whether you're staying because it's still going somewhere, or because leaving feels like losing.Read the companion article at https://tesseros.com/tessory-e12-knowing-when-to-pivotTimestamps:00:45 The railroad track analogy for resiliency and agency03:10 The broken fridge and troubleshooting with Gemini05:25 Pausing the kitchen remodel to get clarity07:50 Publishing the new Tesseros pages and the fear before hitting go10:20 Using AI as an iterative tool for quick wins12:10 Applying the railroad track idea to work and life

Someone asks you at the soccer field, or school pickup, or a community barbecue, so what do you do? And the answer feels complicated, because you don't want your work to be your entire identity, but it's where you spend most of your time, it's how you pay your mortgage, it's what's turning over in your head at 11pm when you meant to be asleep. For entrepreneurs, your business isn't separate from your life, and it never was. A lot of the friction, the guilt, the pressure to switch off, the sense that you're not doing balance well, comes from expecting otherwise.Harmony, not balance, is the goal. Balance is equal weight on both sides. Harmony is different parts working toward the same thing, because your business and your life are made of the same material, your energy, your values, your time. What depletes one depletes the other, and what fills one can fill the other too. This week's Tessera: Pick one moment from the last week where you felt guilty for thinking about work outside work hours, and look at it through the opposite lens: did it actually cost you something, or was it just the story that you should have been fully off?Read the companion article at https://tesseros.com/tessory-e11-integrationTimestamps:00:46 The integration of business and life01:43 The Tesseros pivot to entrepreneurs03:22 Navigating a shifting AI landscape04:36 Harmony over balance05:54 Externalizing the thought thread08:52 Full, not busy, and this week's challenge

My five-year-old wanted more iPad time, so I told him if he wanted that, he needed to help move the house forward first. I'd asked him to wipe down his bathroom counters. He wanted to scrub the toilets instead. I wasn't going to say no to that. I got the cleanser in, he got the scrub brush, and I went on to other projects while he worked. When he came to get me, I asked if it was all the way clean. Almost, he said, it's as good as I can get it right now. Is that good enough? Of course it is. It's a five-year-old scrubbing a toilet. I didn't go redo it, so he never felt like he'd wasted his time.Coming back from spring break into some hard news and a couple of short weeks that made it difficult to get organized, I keep landing on the same idea: things don't have to be perfect, they have to be better than they were. This week's Tessera: Stop waiting until you have the energy for the full version of something, and instead match the smallest useful version of it to whatever energy you actually have right now.Read the companion article at https://tesseros.com/tessory-e10-progress-when-depletedTimestamps:00:45 A chaotic return from spring break02:15 Leaning on the robots03:30 Maintaining a menu of projects04:45 Minimum viable improvements07:15 Switching modes instead of pushing through09:20 Quiet business administration and automated reports

It's spring break here, which meant a week spent mostly offline, playing games, going swimming. But a few things at work and at home got me thinking about something that comes before what we do with our time: what we let in. The information that fills the gaps between everything else usually isn't something we specifically chose, we just let it fill, and then the algorithm decides what we see next based on what we already looked at. I'd been spending an inordinate amount of time on Reddit and Facebook community groups, and we wanted to be a lot more intentional about when our phones were out around the kids and when they weren't.The fix isn't willpower, it's choosing the signal instead of absorbing whatever shows up. We replaced the scroll with an automated morning briefing built from categories we actually wanted, and it took the pull to keep scrolling down to almost nothing. This week's Tessera: Pick three to five categories of information you actually want, ask an AI to summarize them each morning, and run it for a week to see if it changes how much you scroll.Read the companion article at https://tesseros.com/tessory-e9-replacing-the-scrollTimestamps:00:45 Spring break and intentional scrolling02:40 Building an automated morning briefing05:40 The second report and pirate movie night07:30 The Time Mosaic launch and website updates09:50 Anthropic Academy and clarifying constraints10:45 Brainstorming course three

We had a leaking faucet in our en suite bathroom, and the water was making its way down into the cold room where we keep our freezers and canned goods. The pull thing that switches the water to the shower has a small circular ring inside it, and ours had stretched into an oval, so the seal wasn't sealing anymore and the back pressure was pushing water into the wall and down through the floor. Andrew took it apart and confirmed we needed a new faucet, but I spent hours researching, since the bathroom hadn't been done that long ago and replacing a whole fixture over a seal felt wrong. My default assumption was that there had to be a fix. I sent Gemini a picture and description asking how to fix it, and it confirmed what Andrew already had: the seal had failed and wasn't fixable. What I didn't expect was that a replacement wouldn't cost nearly what I'd assumed. I went in asking how I fix this and came out with a completely different answer.Defaults aren't just habits, they're assumptions we stopped questioning, the entryway scuff marks you stopped seeing six months ago. The most useful thing a tool did for me this week wasn't hand me a new idea, it was challenge my thinking and hand back a clearer version of what was already in front of me. This week's Tessera: Pick one thing you've been looking at the same way for too long, a project, a routine, a tool, a plan, and ask for a second opinion, adding the five words "flag any assumptions I've made" to whatever you ask.Read the companion article at https://tesseros.com/tessory-e8-second-opinionTimestamps:00:36 Invisible defaults01:27 The leaking faucet assumption03:37 A shift in meal planning05:43 Upgrading AI defaults at work08:29 The Time Mosaic and this week's challenge

It’s been a week of "Maintenance Tax." From glitchy game servers to rejected bank deposits and a complete "tech black hole," the messy reality of keeping a household running has taken center stage. When you’re spending all your energy re-syncing your past, how do you find the agency to build your future?In this episode, we explore the finish line mirage - that moment when you’re 90% done and tempted to pivot because completion feels vulnerable. This week’s conversation covers:The Maintenance Tax: Dealing with the high price of mental energy required just to keep existing systems alive.Manual Wins: Finding relief in tactile projects (like sewing office curtains on a 75-year-old machine) when the digital world feels out of control.The Finish Line Mirage: Why we question our direction right before the end and how to use AI as a "reflective mirror" to find your lost ideas.The Kernel of Intent: Stripping away the noise to remember the original, pure reason you started a project.Mini-Challenge: The 5-Minute MetricIdentify one project where you are feeling the urge to quit or pivot because the end feels blurry.Spend five minutes documenting what you have already done. Don't look at the gap; look at the hours invested and the problems you’ve already solved.Let the weight of your investment remind you why the idea mattered in the first place. You’ve done the work, now go and finish!Mentioned in this episode:Google Gemini: Used as a sewing guide and a reflective mirror for project doubts.Suno AI: For creating "Cloud Rap Slushwave" and enjoying the moment.ChatGPT: Used for stripping away noise and honing original thinking.Connect with TESSEROS:Have a question or a "friction point" you want to solve?Email us at [email protected]: tesseros.com/tessory

Our dryer vent hadn't been sitting snug against the base, which meant more lint getting through than it should. Looking down the spring flaps, I found a large accumulation of debris I couldn't reach with the tools I had in such a narrow opening. I started unscrewing the screws that looked different from the rest, pulled things apart a little, and saw more debris than expected, along with a cable switch I hadn't noticed. I stopped, took a picture of the model number and what I was seeing, and ran it through Gemini before touching anything else. Don't take those screws apart, there's a sensor in there. But it also gave me ideas: loosen the solidified lint with a painter stick, then duct-tape a cardboard tube onto my handheld vacuum to guide it down where I needed. A bit of duct tape, a leftover wrapping paper tube, and the vent was sitting flush again.That's the thread running through this whole week: curiosity and play, using the tools already in front of me instead of reaching for something new. It's not about being perfect or hyper-productive, it's realizing how many stuck moments get solved just by playing with what's already available. This week's Tessera: Find one small default in your life, a file, a notification, a creative project, and make one small change to make it a little better.Read the companion article at https://tesseros.com/tessory-e6-solving-with-what-you-haveTimestamps:00:45 Curiosity and custom Valentine's cards03:20 Troubleshooting the dryer vent05:45 Creative energy in work projects09:20 This week's challenge

We'd entered a new stage with our youngest where responsible screen use wasn't quite working, so I went into the iPad settings and set up app limits, a hard one-hour cap, plus downtime blocking screens between certain hours. I felt accomplished. Then in the middle of the night he got up, grabbed the iPad, and still played three games. I'd missed the button that ties a passcode to the screen settings, so he'd just been pressing ignore. I fought it for about an hour, forcing syncs, toggling things, restarting, until I gave up and left it overnight. The settings refreshed on their own and finally took effect. The next morning the kids asked why this iPad was so restrictive when the other one let them press ignore. I thought they had the same settings. They didn't.Digital agency was never about trusting yourself or your kids to have perfect willpower, that's not realistic. It's about building a system that forces a pause, a moment to ask do I actually want this. The win isn't the rule, it's the friction itself. That same week, I was doing the opposite everywhere else, removing friction from grant research, a sourdough side income idea, and a messy database, to make it easier to move toward the things I actually wanted to grow. This week's Tessera: Add friction to one thing you're doing too much of, and remove friction from one thing you want to do more of.Read the companion article at https://tesseros.com/tessory-e5-where-to-add-remove-itTimestamps:00:45 Friction and the iPad permissions fight03:15 Opening up creativity in the kitchen05:35 Using AI for grant research and a Notion database08:35 This week's friction audit challenge

When I set up my new phone, I skipped notifications on most apps and left email off entirely. About a week in, I realized I hadn't heard from my siblings, who I usually reach through Signal. I'd simply forgotten to log back in. Syncing meant opening my old phone, and I was flooded, email, Reddit, news, all of it arriving at once. I'd thought I didn't have many notifications turned on. I didn't realize how many I was still getting until they arrived as a batch. Without them, there was a notable sense of calm, and it was so much easier to actually set the phone down and be present. Notifications create a feeling of urgency that isn't real, and I made the conscious decision to keep them off and leave email off my new phone. Nothing in my inbox is truly urgent. If it is, I'll get a phone call.That's the thread for this episode: the art of the restart, clearing digital clutter the same way we clear physical clutter, so you start the day clear instead of already behind. This week's Tessera: Find one digital friction point, a file you always have to search for, a calendar invite you always type out manually, and fix that one thing with an AI prompt, a saved bookmark, or a simple unsubscribe. Don't fix the whole system. One small change is enough.Read the companion article at https://tesseros.com/tessory-e4-clean-slateTimestamps:00:47 Noise versus signal, taming notifications04:07 Reducing friction with AI assistance05:13 The art of the restart, clearing digital clutter10:01 Building custom Google Gems

My long-term goal for our wall-mounted display was a full digital family dashboard: calendars, per-person tasks, smart home controls, a button to shut off the house lights entirely. I'd started a Linux server over the summer with Home Assistant on it, made some early choices that weren't the right ones, and learned I needed to reinstall the whole thing. So the dashboard I thought I was finally ready to build wasn't where I needed it to be. I still had the display, though, and I wanted it useful now rather than perfect in three months. After some back and forth with Gemini, scaling my own ask back instead of holding out for everything at once, I got it showing exactly what I needed to get the family calendars running.Taming chaos doesn't mean solving the whole system. It means finding the smallest piece that actually works right now, and letting the rest wait its turn. This week's Tessera: Pick one task that feels too big to start, use AI to break it into smaller steps, and finish only the first piece.Read the companion article at https://tesseros.com/tessory-e3-what-you-can-use-nowTimestamps:00:45 Building a digital family dashboard02:50 Streamlining the family calendar05:15 AI calendar integrations and a useful mistake07:20 Visual design and branding with AI08:45 AI music and content brainstorming10:55 This week's challenge

We have a bi-level split entryway with a small landing, a tiny closet, and stairs going up to the kitchen or down to the basement, and it's become the natural collection spot for every backpack the moment everyone gets home. I took a picture and asked ChatGPT for ideas on making it look tidy, and as a follow-up mentioned wanting a monitor-sized touchscreen on that wall for a family calendar and Home Assistant dashboard someday. It offered to sketch a simple mockup of the actual photo, showing where a screen and backpack hooks could go, and seeing it made everything click immediately. The scale wasn't quite right, but even a close approximation of my own space made the plan real in a way description alone hadn't.That's this week's thread: small changes, clearer spaces, and how much a fresh, visual look at something you walk past every day can change what you actually do about it. This week's Tessera: Pick one area, physical or digital, that feels cluttered or awkward, and ask an AI assistant two things: what would a simpler, tidier version look like, and what's the smallest improvement you could make today.Read the companion article at https://tesseros.com/tessory-e2-seeing-your-spaceTimestamps:00:46 AI-assisted phone research03:00 Space visualization and custom mockups05:25 Troubleshooting Minecraft commands08:31 Launching the podcast tab on Payhip10:13 Configuring alias emails in Zoho Mail11:35 Seeing your space differentlyA quick apology the 3D printer noise in the background. I was printing transparent storage containers for Lego organization and haven't mastered removing that sound yet.

My son came home from school convinced he was invited to a friend's birthday party the next day, but he'd never gotten a physical invite, and I wasn't sure whether he actually was. I asked ChatGPT to help frame a text to the other mom, something that could confirm the invite without making anything awkward if the guest list had changed. It gave me three versions, and I picked one and adjusted it: a quick question about whether there was a party, whether he was on the list this year, and no problem at all if not. He was invited. They went bowling.That's the thread for this first episode, five small, real ways AI helped this week, at home and at work, none of them dramatic on their own. This week's Tessera: Pick one tiny task in your home or work life that always feels annoying or time-consuming, write it down, and ask your phone, computer, or AI assistant if there's a faster way. That's the first piece of the mosaic.Read the companion article at https://tesseros.com/tessory-e1-one-piece-at-a-timeTimestamps:00:46 Automated calendar import files02:44 Drafted texts for tough conversations04:22 Dynamic meal planning06:14 Cross-checking ideas with Gemini and ChatGPT09:37 Brainstorming and wireframing course outlines11:39 This week's challenge, pick your piece

The name Tesseros came from way too much introspection and research into names. It was inspired by a mosaic, all the pieces you already have, plus the ones you might still want to gain, and a single piece of a mosaic is called a tesserae, which is where Tesseros comes from. Tessory, this podcast, is the spinoff of that parent company, the forge, the action, the story of actually bringing those pieces to life.I've always been innately curious about how things link together, through every role I've had, accounting, bookkeeping, operations, business analysis, always drawn to how the pieces connect and impact each other. A couple of years ago I started looking into AI and genuinely didn't get it at first, tried it, wasn't convinced, figured I could do most things faster myself. But I kept hearing it was going to matter, so I decided to learn it my own way, starting at home instead of waiting for permission or access at work. That's what this show is actually for: true, practical, how do I get started, with AI and with technology generally, whatever that looks like for your creativity, your organization, your life.Read the companion article at https://tesseros.com/tessory-e0-why-this-podcast-existsTimestamps:00:41 A lifelong curiosity for systems01:52 Bridging the tech gap in everyday life04:12 The meaning behind Tesseros and Tessory05:54 Learning passions and what to expect next