Happy August y’all.  So it’s 10:22 as I begin this blog post.  I’m at my local coffee shop eating the most ridiculously decadent peanut butter cookie.  I swear it has three times the requisite amount of butter, the outside is crisp, and the inside is perfectly undercooked.  I’m also sipping a $5 caramel macchiato that I got for free.  I come here far too often, and my, eighth coffee, no matter how expensive, is free.  I usually get a small dark roast coffee, so this is a real treat.  In case you are wondering – none of this is going to serve as a metaphor.  I’m just feeling really thankful for my life right now, and I’m exquisitely aware of the fact that two weeks from now, I will already have been up for nearly six hours and will have taught 3 ½ classes with no peanut butter cookies or caramel macchiatos in sight.  That shock to the system begins a week from tomorrow with meetings, but I’m not ready, and that’s ok.  In fact, I’m never ready to start a new school year, just as we are almost never ready for a new challenge, and that my friends, is the metaphor for today.

Many of you know that every Wednesday in the summer, my mom and I spend the day going on a city adventure.  We started this tradition four years ago by seeking out free activities like museums, cultural events, farmer’s markets and city parks.  By our second year, the activity for the day had become simply a means to an end – the lunch and wine we would treat ourselves to post-adventure.  We’ve exhausted many of the free options over the years, and have begun to pay for our fun.  I assure you, no matter the price, Chicago summer never disappoints.  Yesterday we took on stand up paddleboarding (or SUP) at North Avenue beach.  I’ve been paddle boarding twice before in my life with varying degrees of success, and by varying degrees, I mean varying amounts of time toppling into the water followed by dragging myself gracelessly back onto my board.  This time I insisted that we take a lesson so I could learn the basics – thus hopefully staying on the paddleboard and out of the water. 

I don’t know if any of you have ever taken a lesson in some sort of outdoor sport (skiing, snowboarding, rock climbing, kayaking, surfing, paddleboarding etc.).  If you have, you will likely agree with me that the instructors of said sports are, almost universally and regardless of gender, total smoke-shows.  Their bodies are ripped, their teeth are straight and white, they’re seemingly effortlessly really, really good at a sport most people have never tried, and your safety is in their hands.  Sign me up for a lesson, and I will crush hard.  No question.  Yesterday was no exception.  While up to eight people can sign up for a lesson at a time, my mom and I were the only two to sign up for our 1pm time slot, so we had Eli’s undivided attention.  He was charming, smart, skilled at his craft, and really, really ridiculously good-looking. He was also married with children, but that didn’t stop me from enjoying the view and the conversation. Eli taught us the basics on the sand, and then got us leashed to paddleboards and pushed out onto Lake Michigan.

Paddleboarding is hard. It’s even harder when you don’t want to disappoint your incredibly patient, alarmingly attractive instructor.  Instinctually, every cell in your body wants you to stop moving, stand up, and shift your feet until you find your balance.  Turns out doing that is a one-way ticket to a dunk in the lake.  Instead, you have to build speed, plant your feet, stand up, and keep your feet glued to the board while you try to remember how to balance, paddle, and turn the behemoth piece of plastic as waves from nearby jet-skis rock beneath you.  The first time I stood up, my legs shook like a cartoon character anticipating an anvil drop on my head.  I couldn’t stop them, but I didn’t fall.  Over the course of the half-hour lesson and hour on my own, I spent more time kneeling than standing on the board, but by the time I docked and hobbled onto the sand on shaky sea legs, I felt fairly confident in my skills.  In fact, I was already planning when I could come back and rent a board on my own.

Learning an unfamiliar and challenging sport is no different from taking any other chance in life. It’s scary, it’s hard, and even with all the advice in the world – you never feel ready.  Eli was an incredible instructor.  He was thoughtful, patient, and knowledgeable, but no matter how much I practiced on dry land, there was no way I was learning to paddleboard until I was wobbling on the waves on my own.  The same goes for taking risks in my dating life.  I could read all the advice columns, self-help books, and dating manuals in the world – but nothing is going to happen until I get out there, steady my shaky legs, and take a chance. 

The metaphor extends even further, though, because generally speaking, our fear of the unknown is far worse than the worst-case scenario.  Barring some sort of bizarre jet-ski collision – the worst that could have happened yesterday was that I fall in the water and drop my paddle (something that may or may not have happened to my mom).  The only thing to do in that situation is to climb back on the board, wait for your hot instructor to bring you a new paddle, and start over.  Again, and again, and again.  Each time it gets easier, each time you’re a little bit stronger, and each time you’ve learned a little bit more.

I’m planning to get back out on Lake Michigan at least a few more times before the end of this season.  It’s almost exhilarating as talking to strangers.  If anyone wants to join me, let me know.  I could always use a buddy.

 

Until next time…