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Lessons Learned: Spring Break or Spring Broken?


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I’ve spent a lot of time lately thinking about my investment decision-making process as I’ve read books like “The Behavioral Investor,” “Principles,” and “Thinking in Bets.” The Farnam Street blog also has a strong focus on improving decision-making, and I just read their post The Anatomy of a Great Decision.

These books encourage you to focus on your process and not on outcomes, to use principles and not tactics, etc. As a result, I have principles guiding my overall investment approach, the resulting investment process, and a checklist of criteria a new investment has to meet.

I recently realized that I need to expand this thoughtfulness about investment decisions to other areas of life. Here’s why.

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Spring Break or Spring Broken?

My kids had spring break last week, and we went somewhere warm to relax and rejuvenate. I usually like to read or exercise when not entertaining the kids, but I also sometimes like to tackle small housekeeping items that I generally have less time to get to during the day-to-day grind.

One such housekeeping task was to shut down our old server after our successful migration to AWS. It’d been a few weeks and things were running smoothly, so no sense paying for that old server, right? Thus, on day 1 of our vacation, I hit the “destroy” button on that box.

Within moments, I realized I’d made a mistake. Suddenly, our blog was down. It turned out there was a single connection to that old box still lingering from our blog, buried in a config file, which stored our posts. It was easy enough to point this to the new database, but all the posts we’d written between the server migration and then were gone.

Of course, I had backed up the server before getting rid of it entirely. But I hadn’t tested the backup, and it turned out it was incomplete and unreadable. Our separate daily blog backups were of no use; because of that one bad configuration, they hadn’t even been running. Those posts were gone.

Then I noticed that traffic between our blog and our new AWS database was through the roof. Previously, when these had been hosted side-by-side, this traffic didn’t matter. But now it was going across the wider internet, and it was both costing money and making the blog really slow. So then I realized I had to migrate the blog server into AWS ASAP, too. This took a bunch of time, obviously.

My point is: with the click of a single button, I ruined the first few days of my vacation. Not just for me, but for my family, too. And even after I wasn’t frantic, I still used my free time to get things optimized instead of getting to read and exercise.

New Principles and No Shortcuts

All in all, this seemed like a decision that is well worth learning from.

I initially wrote down a bunch of takeaways, but if I really simplify it to the core decision-making principles, here’s what I learned:

  • Don’t make highly committing decisions when you don’t have the time to deal with the repercussions.
  • Use dry runs, dress rehearsals, or simulations when possible.
  • Make decisions less committing/more reversible. Preserve optionality.

These are things I knew, so maybe what matters is the reinforcement of the idea of not skipping steps in my process. There are no shortcuts.

Having a checklist helps with that. Atul Gawande’s book, The Checklist Manifesto, makes that abundantly clear. We need checklists to deal with the complexities of life and to help make our decision-making principles actionable.

So, I’m also turning these principles into a tech infrastructure deployment checklist:

  • What does a bad outcome vs. a good outcome look like? What are the costs and benefits (expected value)?
  • Do I have time to deal with all outcomes?
  • Am I tired, stressed, hungry, or otherwise impaired?
  • Have I completed an end-to-end dry run of some kind?
    • Turn server off temporarily or stop all traffic to/from it
    • Test complete migration/deployment on development
  • Have I backed up?
  • Have I verified the backup and tested it?

This may seem pretty off-topic for an investing blog. But it’s not.

This checklist will indirectly help your investing process, because it’ll help us deliver a better investment software tool for you to use, day in and day out.

It’s also an example of how to improve your own decision-making process. If we can all become better decision makers, in all aspects of our lives, we’ll have more time and wealth to intentionally live the way we want. That’s the real goal.

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