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-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