Worst Case Scenario Thinking

Does planning for the worst make you a great Executive Assistant?

I used to think that all great Executive Assistants had to be worst case scenario thinkers - they had to have a back up plan for everything. I still think it's important to have a contingent plan to most things, especially when event planning, but I now know that this whole worst case thinking is a me issue - my personality, my anxiety, my enneagram 6 profile (lol), and my perfectionism.

I recently planned a week long vacation to Puerto Vallarta with my family. I got an insanely good deal on it - $299 for 7 nights, 8 days at a beautiful resort with resort fees waived. We have a vacation club that we are a part of, and as a bonus for signing away our vacation soul (ugh) and paychecks (*sigh* story for another time), we received 8 bonus free-weeks where we only need to pay the taxes and resort fees. 

I booked this trip 6 weeks in advance, so here I am, hand in hand with my anxiety, for the entire 6 weeks, every single day, imagining, yes you guessed it, the worst case scenarios. Like literally every scenario imaginable.

Why was this so cheap? Nothing is "free" in this world, right? This is normally a $1200/nt+ type of resort, why on earth would they include this on a list of resorts offering “free” weeks? The rooms look amazing online, but am I going to get the room that wasn't remodeled, in an older building, with a view of nothing? Will it smell? Oh, I should also tell my brother in law and my sister where our trust is… you know, just in case.

And so went by the weeks - the questions, negative thoughts (aka planning for the worst), expectation setting, wondering, worrying.

When we finally got to the resort, the room we got exceeded our expectations. It made me think, was it necessary for me to worry and wonder about all the what-ifs leading up to this point? Did I do this to myself to set myself up for low expectations so that when I got there, any kind of "normal" room would've exceeded my expectations? And if I did get a smelly room or an old, un-remodeled room, I wouldn’t have been surprised because I was expecting it anyway? Is this my way of protecting myself perhaps?

If I'm planning an event for work, I do think it's critical to have backup plans. But I realized that worrying constantly isn’t something I have to or need to do. It’s actually counterproductive, a waste of brain space, and emotionally draining. What will happen will happen. I am not actually in control of a lot, even though I’d like to think I am. Being as prepared as I can is great and necessary, but also accepting the way things will turn out is important.

Mindset is an interesting thing. So is perspective and how I choose to view the situation.

On a related note, I'm planning a Mexico company offsite in September this year. I tried hard to convince our CEO to avoid September because google says that it is the rainiest month to travel to Mexico and also is hurricane season. I sent screenshots of google searches and data to my CEO indicating these statistics. And you know what he said?

"Google says that it'll rain on average 17 days in places like Cabo or Cancun. This means that for 13 days, the weather could be great!"

What the f? What kind of positivity nonsense is this? Is he not hearing me? Did he not see the stats? What if there are hurricanes and thunderstorms while we're there? What if this September is an anomaly and it rains everyday? What if there are flight delays and our coworkers have nightmare travel stories? What if the weather ruins our company trip? What if we have to stay inside the whole time? What ifffffff????

"But what if it doesn't rain? What if there are no hurricanes while we’re there? What if September is an anomaly and this year actually has the lowest number of days of rain? What if everything will be fine?"

Wow… Touché…

And that’s when I realized, I need to shift my mentality and perspective. He could be right. Or I could be right. If he is right, fan-freaking-tastic. But if I’m right, we could still make the most of our trip indoors, create long lasting memories, and eat delicious food. Some of my biggest travel memories throughout my life are of the times when things didn’t go as planned - in the moment they sucked, but in retrospect, I’m glad it happened the way it did, and I can now laugh about it.

The point I'm trying to make here is that worrying so much and planning for worst case scenarios all the time is exhausting. It's ok for things to not be perfect. It's ok if something goes wrong. It's ok to have general backup plans. And it's ok to think positively and accept whatever comes my way. It’s even ok to think of the worst case scenarios and plan accordingly. It’s just that it’s NOT ok for me to plan for them and then worry about them the whole. entire. time. until the day of the event. It does me no good.

As an Executive Assistant, when I feel like so much of my job requires me to have everything lined up the way I want it to be, is it so bad if things get messed up here and there? (Lol, as I write that sentence out, my anxiety’s like ‘um hello, yeah, it IS bad if things get messed up, are you insane?’. But also like ‘hey anxiety and perfectionism, can you please stfu?”)

Planning is great. Being prepared is even better. But you know what my CEO taught me without teaching me? Going into planning with the mindset of looking on the bright side and making the best of whatever happens is what is truly next level planning and preparation; not planning for every possible worst case and freaking out about it until the day of the event.