Biweekly stories for the entrepreneurially minded.
Tessory is the forge of Tesseros, where the experimenting happens. Time, energy, money, and AI tools do not stay separate from the business, so we try things, break things, and figure out what actually sticks. Work projects, household fixes, family routines. No tech background required. Honest tests and the small shifts that come from them, so the skills you build apply across your work and your home.
New episodes every other Tuesday. Start anywhere.
hello@tesseros.com · https://tesseros.com/tessory
Retirement: Shaping It Before You Reach the Number
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-retirement
Timestamps:
00:00 Retirement as a shape instead of a date
01:21 Letting the AI competition go
03:18 A porch conversation in Tulameen
05:40 Planning a ten-year wind-down
07:33 What happens to your company if you stop
08:18 Automated e-transfers and keeping your own backups
11 Aug 2026
Emergency Planning: Deciding While You're Still Calm
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-planning
Timestamps:
00:00 Wildfire alert at the edge of the city
01:35 Why emergency planning gets built in advance
03:06 The fires and floods a few years ago
04:36 What the kids chose to pack
06:40 Planning while calm as a hand-off
07:15 Building a grant finder agent into Notion
14 Jul 2026
Passion as Information: What to Do When Nothing Is Lighting You Up Yet
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-information (https://tesseros.com/tessory-e17-passion-as-information)
Timestamps:
00:00 The passion myth and following your why
02:28 A perfectionist's honest math on effort
04:45 Rebuilding a retirement plan around what you control
09:11 Automating repetitive templated work with AI
10:44 Perspective Flip version two and hosting update
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