🌲 On prioritizing problem-solving over perfection

The value of preparing to handle curveballs with confidence

May 11, 2024

Last month was the Readwise biannual offsite — we stayed at the absolutely incredible Juvet Landscape Hotel in Norway1. In much the same way that my ‘babymoon’ to Germany’s Black Forest helped me really get the atmosphere of fairy tales like Hansel & Gretel, a week in Norway gave me a visceral understanding of why hungry young men went raiding to escape the fjords.

It was in some ways the most productive overseas trip of my life — but in others the most brutal, mostly in terms of travel. I missed two connections, got caught up in what seems to have been an electronic warfare exercise on the part of Russia (?), there were the usual airport security shenanigans… I also had a remarkably difficult time finding outlets with which to safely recharge either my American-made portable electric breast pumps.

Other things that went wrong — it is the nature of things to sometimes go wrong — but that was the scariest. I was able to manage to avoid mastitis — a painful inflammation that can happen if you don’t get enough breastmilk out for whatever reason. It can lead to infections, complete with ‘flu-like symptoms’ aka fever, aches and pains, headaches, sweating, etc. I got through by the grace of helpful people in my life and because I had backup plans and contingencies in place — but ultimately the key to keeping my emotions on kilter was the knowledge that I am good at problem-solving, and the confidence that I would solve this problem too.

The value of front-loading stress

When it comes to travel, some folks (like my husband 🙈) prefer to put all the stress upfront, meticulously planning and preparing for every possible contingency. Some folks I know end up in anxiety spirals, making sure that they have everything they could ever possibly need. I liken this to the sorts of folks who need to have a perfect system before they feel comfortable writing, whether it be a novel or a note.

My approach is generally more laid-back. I think things through, get them “good enough,” and then stop worrying about them. While my husband’s method is objectively better at ensuring we don't forget anything, I tend to forget things that would be convenient to have rather than necessities.

I take a more flexible, adaptable approach and believe in solving problems on the go. If I forget something, my instinct is to think I can either buy it at a local store or order it online if I really have to.

For example, I was planning to take my pram to Santa Fe for the last work event, but realized at the last minute that the pram attachment wouldn't fit in my carry-on bag. My husband was worried about how our baby would sleep without the pram, I was confident I could find a solution, even if it meant asking the hotel's concierge service for a crib. My husband, however, wanted to call and confirm they had a crib, because he’s a “find out and adapt in advance” kind of thinker. It’s a useful skill in a developer, I’m told… but I spent most of my professional life as a teacher. There’s just remarkably little planning you can do to pre-empt the multitude of things that go wrong in an environment with that many variables. You try, of course, but you also learn pretty quickly to roll with the punches.

It’s not always easy! Turns out it’s nigh-impossible to get ahold of pseudoephedrine in Norway, even if you’re in a major city — which I mostly wasn’t. Decongestants like pseudoephedrine (aka Sudafed) are a hacky way to dry up milk supply if you’re worried about mastitis.

The value of brute-force solutions

Another fundamental difference between my husband and I, aside from personality and life experiences, is our physical strength. This has a huge impact on how much travel preparation we do.

My husband can easily carry multiple bags and the baby at the same time — he's in great shape. In contrast, I've faced postpartum pelvic problems and cannot manage heavy loads. If something weighs three pounds and fits into his suitcase, my husband is perfectly happy to pack it, even if it only has a 1% chance of coming in handy. Me? I'm willing to take a risk leaving it behind, because if it turns out I need it, I’d rather risk solving a future problem with money than risk causing myself a new problem being able to carry all my gear.

Trade-offs are different for different people. The example I come back to time and time again is a time when I helped a friend move. The particular social group I met him thru biased toward young, healthy, athletic people; the core of the group met via a college dance club. These guys think nothing of picking up a couch and carrying it hundreds of yards… but I was the only person who happened to be available on the random weekday afternoon in the summer (at the time, we were both teachers).

I have not been capable of carrying a couch hundreds of yards at any time in my life, so I suggested maybe moving the truck closer to the door would help…?

My point here is not that I am smart and he was dumb. My point is that different people have different backgrounds, different advantages, and different things they are optimizing for.

Your average developer thinks that whipping up a quick python script is as obviously useful as moving the truck closer to the door. But if my friend had six guys at his disposal that day, instead of just me, it probably would have been faster and easier to just carry the damn couch over to where he’d originally parked the truck.

Passive learning is a form of preparation

There’s a metaphor here for optimizing systems in general — note systems, email workflows, whatever. Many people want to perfect their system upfront, and worry about everything that could go wrong. Software issues, corrupted files, compatibility problems, and workflow changes can indeed disrupt a system (I work in quality assurance now; believe me, I know things can go wrong). But I find that, for me at least, it’s more effective to live life, go ahead and use the system I’ve got time to create, and have the confidence that I can address difficulties as they arise.

Passive learning plays a vital role in building this confidence and problem-solving ability. I spent a lot of time as a kid in creative problem-solving competitions. I spend a lot of time reading stuff that feels relevant to my future — parenting books, professional development resources, newsletters about the economy, whatever. My habits have, so far, given me the context and knowledge needed to handle unforeseen issues, knowing that I’ve got ideas for solutions in my back pocket, latent and undeveloped, but ready to go if I need them. It may seem less efficient in the long run, compared to avoiding issues in the first place, the reality is that absolute perfection is impossible. The world is constantly in flux, and there are more things that can go wrong than solutions that can be prepared.

When I travel, I’m going to keep assuming that unforeseen circumstances are going to disrupt my plans, and that I’ll be able to handle it. I’m going to fight the temptation to beat myself up for failing to properly research what countries my breast pump batteries had been tested in.

Front-loading stress has its place, but my personal threshold for it is pretty low. What works for my husband is not unreasonable; it's different because of his unique experiences and the heuristics he’s developed because of them.

In the end, how you approach establishing your systems is about striking a balance between planning and adaptability, and that balance varies from person to person.

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