Preparing for rain

This essay initially appeared in the Monday morning newsletter on 9/18/23.

I’m so excited to be back to writing this morning after a trip to Ireland (!) for fun, followed by quick turnaround trip to New York for work. Some very high highs these past two weeks, but I’m also very happy to be home and settled. I do love a routine!

Ireland was incredible. I included some of my favorite pictures from the trip below – but wow! What an amazing country. I hope I’ll be back one day!

One thing I really couldn’t get over?! The WEATHER! We seriously had blue skies and sun every day. I didn’t expect it to rain the whole time, but the forecast called for the majority of days to be rainy, so I was prepared to walk, bike or navigate around in the rain at least once or twice. But as it turns out, I didn’t take my cute rain jacket (which I’d purchased specifically for this trip) out of my bag once.

I think because I’d accepted rain would be involved, every time it didn’t rain, it felt like such a bonus. It was an unexpected surprise and something I was grateful for, both when things went accordingly to plan and when things naturally went awry (well, hey, at least it’s not raining!).  

I wanted to find some way to bring this sentiment with me back to Chicago. I guess you could say the old adage “prepare for the worst, expect the best” rings true, but that doesn’t feel like the whole story. I don’t want to just focus on what could go wrong… I don’t want to spend every day looking for the rain.

But I think what I learned in Ireland is that there’s a difference between staying in a state of rumination about what could go wrong (it will probably rain most days) vs. acknowledging what could go wrong AND coming up with related strategies (it will probably rain most days. So, I will be practical about what I pack to wear and invest in a raincoat I actually like.)

After doing some Googling, I’ve discovered this is actually a thing. It’s called the theory of defensive pessimism and it suggests that imagining—and planning for—worst-case scenarios can be more effective than trying to think positively.

Sure, there are many worst-case scenarios one could focus on, but where I see this idea being most helpful is for things like a rainy day – those minor annoyances that are bound to happen and out of our control.

For example, a few places where I’m thinking of applying this “defensive pessimism” idea include…

• A commute contingency plan. For those days when something goes wrong, and the bus doesn’t show or is extremely delayed. What’s my back-up plan? Probably a ride-sharing app, but I can take this preparation a step further and eliminate a potential “freak-out” moment by thinking about where my bus stop is located and determining the best place to call the ride from. And since it would probably be a pricey ride (rush hour), maintaining a small slush fund for situations like this could take care of potential stressors. 
• Overflow slot. Over the course of a work week, some things naturally take longer than anticipated and unanticipated urgent things pop up. Taking a look at my schedule recently, I noticed that Thursday mornings were magically meeting free. So, I’ve now been thinking of that time as my “overflow slot.” When I have to shuffle things around, I have a go-to time to bump things to. 
• Go-to freezer dinner. Having a reliable, go-to dinner on hand in the freezer comes in handy when you’re in a pinch and just need to eat something. So many options here, but I think my favorite is probably having frozen meatballs, frozen broccoli and marinara sauce (in the pantry, not freezer  ). All can be heated up and served together for a good enough meal when you really need one.  
• Replacing the back-up. This is something I’ve learned from my mom. Of course, it’s not the biggest deal when you use the last roll of toilet paper or last bit of toothpaste and realize you’re completely out. But it is a minor annoyance that can be easily avoided. So, as a tip from my mom, I’ve gotten in the habit of having one household item in use and another ready to use as backup. Then, whenever I finish using something, I replace it with the back-up and add the item to my shopping list for that week. By buying the back-up immediately, instead of waiting until I’m out, I avoid possible stress or inconvenience later on.

All small things, but all things that could make a bad day just that bit more bearable, which I am all for. But what do you think?

Where would you apply this “defensive pessimism” idea?