September 22, 2022
I love special occasions. I love getting dressed up and going out, especially to shows. It doesn’t matter if it’s a musical or a play or an opera. If I can put on a dress and some heels and drink cocktails for a night out (preferably with a good friend or a handsome man at my side), I feel like such an uptown girl. I really look forward to these things. When I’m looking forward to things, I typically over-plan and overprepare, and imagine the way said things will go in my head. Last week, I had a visitor from out of town. He was here for one night, and I was so excited and determined to make the evening memorable. I plotted with a girl at work about what we should do and followed her solid advice – a reservation at a nice restaurant (but not too nice because he’ll almost certainly insist on paying), and tickets to Hamilton at the Kennedy Center (which I managed to keep a secret until 30 minutes before the show!). I did the mental gymnastics to see what time we needed to leave dinner to get to the Kennedy Center on time and made the dinner reservation accordingly.
On the day of the event, I kept looking at the weather and stepping outside to see how hot it was so I could make the call about whether we should do dinner and drinks outside on the patio or not. Around noon, I made the decision that it was way too hot to sit outside so I called the restaurant and asked them to move our spot to inside. Then of course when I arrived at the restaurant, the temperature outside felt so lovely, I had to be ‘that person’ who sweet talks the host into changing the plan at the last minute. I got my nails done the weekend before and went to this magical place called a DryBar on the day-of during my lunchbreak at work where this wonderful lady named Nadia washed and dried my hair and made it shiny and fluffy and beautiful. I tried on three dresses the night before and asked some friends which one they liked best. In true girl scout fashion, I packed a bag the night before with cash, extra panty hose (which I ended up needing!), a pair of flat shoes (also needed those!), lipstick, the printed Hamilton tickets, masks, Tylenol, deodorant, and a phone charger. As one does. All in all, all of my over-planning went off without a hitch other than some minor logistics things I didn’t consider. It was everything I wanted it to be. It was a wonderful evening and I felt like a beautiful, uptown girl treating someone to a really nice evening out. He even showed up with roses! A fun time was had by all, and I don’t think I’ll ever forget it. Then I woke up the next morning and thought “Now, what?”



I always feel this way when the thing I’ve been looking forward to and fretting over is…well…over. I usually mourn the end of Christmas well into January, not because I want it to be Christmas all the time, but because all that build up toward something wonderful can sometimes feel more exciting than the memory of something wonderful. Isn’t that strange? Most of the fun experiences we have in life are centered around one concept – making memories. I ran in a 5k race at Six Flags in July, and after the race I rode roller coasters with my friend Amanda all day. We rode the same Superman themed coaster about six times that day. The trip down the big hill at the beginning of that ride is worth the full price of admission – that’s the fun part. In front of that fun you have the slow climb to the top of the big hill, and on the backend you have the memory of the fun you had going down the hill. While the memory of the fun may be great, it’s not as intense as that anticipation you feel on the way up the hill. Once that anticipation is gone, you feel a moment of relief and exhilaration as you fly down the hill, followed by inevitable sadness that the ride is over.
What can I say? I’m a planner. Planning is that climb up the hill on the rollercoaster. Planning something out meticulously (especially when it’s something fun or meaningful) is this special combination of anxiety and excitement that I love. You try to put all the pieces in place, leaving no detail unconsidered, while imagining how it’s all going to play out in real life. Will the ride down the hill make me scream with joy? Scream with fear? Swallow a bug? Throw up in Amanda’s lap? Throw my hands in the air? That’s up to the universe, and that’s the part of planning that can drive you mad – you don’t have as much power over things as you like to pretend you do when you’re making plans. You might have some power, but for the most part you are at the mercy of all of the outside forces of the universe (weather, traffic, other people). After the plans have been made and executed to the best of your ability within the constraints of this thing called life, all you can really do is sit back and enjoy (or not) the ride. And boom! Good or bad, a memory is made.
I mentioned in my last post that I can be a little insufferable intense. I can give off an intense “I’ll love you so well, no one can love you as well as me” vibe. It can be a lot. I’m like that at work too. “I won’t just do a good job, I’ll do the BEST job.” I come in to the office first thing every morning and make my to-do list in my notebook. I can only imagine how much my teammates start to shudder when they hear the scratching of my mechanical pencil against the paper in my moleskine notebook because as soon as my list is finished, I’ll start adding things to their lists. Some of the strongest criticism I’ve gotten from my boss over the years is “Rebecca is excellent at burning through a list of action items each week and driving her team to success, but sometimes fails to see the bigger picture.” Boy oh boy, if that isn’t the truth. That big picture is what gets me. It drove me crazy that my plan to review that proposal draft from 10:30-12:30 on Monday was thwarted by my client who wanted me to remake all of the maps in our PowerPoint deck with a different background map layer. Sometimes the small picture kills me. How am I supposed to think about the BIG PICTURE where derailed plans go from “possible” to “all but certain” and the stakes are high?
When has big picture planning ever worked out for me? When I was a teen, my big picture plan was to be married by 25 with 2 kids by 30. HAHAHA. Small detached home, big yard for the dogs (yes, plural). Last year, my big picture thinking caused me to buy a house to be closer to a man who was so NOT INTO ME that even the blind dog that lives next door could see it. The day he dumped me, I had been angry with him because he wouldn’t go with me to see Little Shop of Horrors at the Alamo Drafthouse. I had been telling him for weeks that I wanted to go, and he would say “I’m not sure I’ll be able to get off work in time.” Then the day of the show, he made last minute plans with a friend instead. I acted like a brat about it, and when he broke up with me later that evening he said something like “I don’t like to make plans more than three days in advance!” and then the floodgates of all of his grievances opened – grievances about me and how I made him so unhappy. At the time, I blamed it all on my stupid, intense, plan-making nature – YOU PLANNED YOURSELF RIGHT OUT OF A RELATIONSHIP! ARE YOU HAPPY NOW, REBECCA? TAKE YOUR DATEBOOK AND SHOVE IT RIGHT UP YOUR… Of course, that wasn’t it. This incident was just a symptom of a hard truth. I was making big picture plans in my head about marrying him, and he couldn’t commit to Rick Moranis on a Tuesday night. That wasn’t his fault or my fault. We just had different plans.
Big picture stuff is so scary. I had the nerve to think about the future with my ex and I landed right on my tail with another door slammed in my face. And it’s not just the romantic stuff that’s scary. I want to get promoted next year and become a partner at my firm by the time I’m 38. I want to save enough money to buy that little detached house with a yard for Maudie. I want to run a marathon before I’m 35. I want to find a partner who will take me to see Little Shop of Horrors and buy me some popcorn. I’m taking steps toward all of these things- well except for the Little Shop of Horrors partner thing, because I refuse to go on another date with a stranger in 2022- but eventually I’ll start working on that again too. Because not only will failure to do big picture planning cause you to get negative feedback from your boss, but it will also keep you from looking forward to the future. You know how last Tuesday I was looking forward to my Hamilton date and made thoughtful plans for it? Even if that whole evening had been a disaster – if I had showed up with lipstick all over my teeth and dropped the tickets to the show in a puddle and had an allergic reaction to my shrimp dinner like that guy in the movie Hitch and spent the evening with my face swelled up like a balloon – that wouldn’t change the joy and excitement I had from looking forward to it and planning for it. I should be looking forward to all this big picture crap in the same way. It might not work out the way I want it to, but I can still look forward to these things, and try to plan for them as best I can and feel that anticipation of going up the big scary hill.