Michelle O'Brien Michelle O'Brien

2022 Beer Can #1

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This is a late entry because I had to help my bestie roll in 32 with an excessive amount of laughs (and wine) this week. Wednesday was our first official beer can of the season! It’s now Monday (whoops) and I’m writing this from the passenger’s seat on hour fucking ELEVEN of our drive to CT to hopefully, finally, officially close on selling my dad’s house which is whole different post. Seriously people can we please normalize flying with well behaved dogs? Ok back to beer can.

I mean what can I say. It was a perfect evening. Checked predict wind <put link in here> ahead of time and I’m not going to lie, I was not a believer that we’d actually race. The conditions looked like shit. It was foggy and cold and the only model I checked (ALWAYS check them all) showed less than 5 knots all evening. Considering last week the poor race committee was literally BLANKETED with bugs I did not have high hopes for the night. Luckily I was 100% wrong and conditions were perfect. A solid steady 14-16 with calm seas. What a dream.

Our start was super rusty. We were distracted getting out there and only had time to make one pass at the start line which was error number one. Error number two (a biggie) Is that we completely misjudged the starting horn. We thought the one minute warning was the start and had to tack at the line. When you’re in green fleet you’re the first start so while you’re about to start a lot of the fast boats are trying to check in. A mistake here not only fucking blows for timing purposes but also can be a god damn mess. Somehow Dan always remains cool calm and collected during these trying times.

Anyway despite this our start was ok for first of the season. The rest of the sail was heavenly. Sailing with the new sails feels like we are just gliding through the air in the most beautiful way. Where we used to struggle to even punch upwind at 60 degrees we now can do with ease up to 40. First leg we pinched hard but would have had to tack either way. We were able to just jibe the job around the mark and on the downwind leg we ended up going wing on wing with the whisker pole on the jib. We then trimmed up for the last leg. Tried pinching but knew we were going to make it so we tacked once and then tacked over the line FIRST IN FUCKING FLEET with Success (literally the boat name and figuratively) right on our tails.

All in all- quality first race. Dan on the helm. Jeff and I swapped back and forth on the jib and I mostly did the main. Jeff did the foredeck work.

Goal for next race: read up on main sail trim.

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Michelle O'Brien Michelle O'Brien

Columbia Yacht Club presents: Skipjacks

I participated in the Summer 2019 Skipjacks session. In case you missed my intro, here’s a quick overview of how I became involved in this program. In the winter of 2019, my husband and I spent a lot of time deciding what our next step would be to become more involved in the Chicago sailing community. We figured the Chicago Boat Show would be a good way to gather information. We spent a lot of time at all the booths looking into buying a boat, being part of a timeshare program, or joining one of the local yacht clubs. We also had friends that belonged to Columbia Yacht Club (COLYC) so the scale was already a little unbalanced, but one thing we weren’t aware of was the Skipjacks program. If you gain nothing from this article, hopefully you will take away this little secret. COLYC typically offers perks when you join the club and sign up for Skipjacks at the same time. These perks change yearly, but it’s a fantastic way to be introduced into the club and here is why. 

Skipjacks is a really great program geared towards the beginner sailor or someone with some sailing experience that needs a refresher on the basic skills. If you feel like you are more advanced than this, there are still other courses for you which you can find here. I would still call myself a beginner when I signed up, but I had a few summers worth of on the water experience. I had taken lessons elsewhere a few years prior and spent some time cruising around and racing (not very well) with a friend. My husband, however, had grown up living the pontoon life, wake surfing, and water skiing. He was familiar with being on the water but had literally never been on a sailboat. This is a really great course that was set up not only to introduce you to sailing in general, but also to introduce you to what the sailing community is like at COLYC. Aside from this, THE MOST valuable thing you could ever EVER be given as a new sailor is the ability to connect with people with sailboats that enjoy the same aspects of sailing as you do. This course provides with you with an insane amount of opportunity to do just that as well. 

Quick overview of the Skipjacks course breakdown. The program itself is 7 weeks long and runs from Mayish to Julyish. It involves two classroom sessions and five on the water sessions. There is also a party at the end of the course with free food and booze (heyyyoooo) with a very competitive “Skipper of the Season” award where you get to show some love for your favorite skipper (telepathically communicating Dan Cooley-Bloody Mary).There is a lot of debate in the sailing community about the value of classroom sessions. Personally, for this course, I find them to be extremely beneficial. First off, I’ve been there in the beginning, and if you are someone that’s never stepped foot on a sailboat it can be extremely intimidating to find your way down the dock and figure out where to step and what to hold onto without plummeting to your death in 45 degree Lake Michigan water in mid-May. The classroom sessions are a great way to be introduced to the course, the club, and sailing in general, and in my opinion, I think it’s a great way to start out. The two classroom sessions not only focus on topics geared towards getting you ready to get out on the water, but also give you an opportunity to explore Columbia Yacht Club, which is super cool in itself. Some of the things I learned during my classroom sessions were boat safety, knot tying, physics behind sailing and how to make the boat go, what to wear, gear, and an exclusive tour of a few of the Skipper’s boats. Afterwards, the best part is hanging out in the member’s bar. The food and drinks are amazing and most importantly, you get to spend time and share battle stories with others that love sailing as much as you do.  

After two weeks in the classroom, it’s time to practice being the salty sailor you’ve always dreamed of being. One of the coolest parts of Skipjacks is that every week you are on a different boat with a different skipper. To me, this is completely invaluable. There are so many different ways to enjoy a sailboat, and this gives students an opportunity to figure out which is best for them. Some examples of what I was on during my lessons were:

·      Beneteau First - a modern, light, hybrid (can race or cruise) style boat that is quick and exciting on the water

·      Catalina- a fat cruiser built for stability and designed for a live aboard lifestyle

·      Express - rigged for racing. Fast, fun, and competitive  

Each boat will have one crew member (say hey to me on Bloody Mary if you sign up), an experienced sailor that’s on board to help out the skipper. During each on the water lesson, you are encouraged to participate in each role of maneuvering a sailboat, including being at the helm (don’t worry, we’re here to bail you out just in case but I promise you’re going to be so good you won’t need it). You’ll really get to put everything into action that you learned in the classroom, and your last week there is a super fun race to get you ready for beer can Wednesday's if you’re not ready for your season to end once the course does. 

Even better than getting to see a bunch of different boats, you also have, at the very least, five opportunities to learn on the water from a different skipper every week. This group of people has a HUGE wealth of knowledge to share. Every skipper and crew member does this on a voluntary basis, so you KNOW they love what they do, and some of them have been sailing for many of years. I can truly go on forever about how much you can learn here. This is also the perfect setup to be able to connect with those who enjoy the same type of sailing you do (racing vs cruising). Most skippers in the program either race in the Beer Can series on Wednesday nights or enjoy the weekend cruising series. You will quickly find out that sailors love nothing more than getting other people to also love sailing, and they are frequently looking for others that are interested to help out on Wednesday nights during the Chicago Beer Can races. In case you need any more persuasion, my husband and I met our current Captain during the Skipjacks program, and have been sailing with him for three years now. Last summer we even gave him the honor of marrying us (at the club obviously). On top of learning (or refreshing) the fundamentals of sailing, this program also holds a special place within me because of the ability to be able to connect with other like-minded sailors. 

 When you sign up for Skipjacks, you are also given member access to use Columbia Yacht Cluboutside of your lesson time. This is such a steal and really kills two birds with one stone. If you’re interested in sailing, now you get lessons AND an eight week interview to see if our home is also a good fit for you. I know I’m biased, but in my opinion, COLYC is the best of the best. There is A TON of educational opportunities both on and off the water. Each summer I try to get involved in at least one course on the water, and in the winter there are several seminars which is a fun way to stay involved even when it’s too cold to feel your face. The club is housed inside the Abegweit, a 372 foot former ice cutting ferry boat that has been renovated, but still holds a lot of its original luster. As cool as this is, what makes this club in particular so special is the sense of community that it holds. It’s completely unpretentious and always welcoming to anyone who shares the same love for the water, including (but not limited to) sailors, power boaters, cruisers, or even just those who might enjoy the view alike. 

All in all, Skipjacks is more than just sailing lessons. Whether you just want to try out something new, learn more about something you already know, or just need a refresher, this program truly has something to offer sailors of many different types.  Hope to see you here this summer!

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Michelle O'Brien Michelle O'Brien

Welcome

MY SAILING STORY 

Live Breezy is a real-life modern sailing adventure. My husband and I watch a lot of YouTube channels where main characters have saved all the money, quit the jobs, sold the house, fixed the boat, and sailed off into paradise. We still work full time, but are obsessed with this hobby. While we absolutely love and support these channels 100%, we found it hard to relate. This story takes place when all of that is still just a daydream at work. 

I’m Michelle! The first spark of my love for sailing starts in 2016 when I said, “fuck it,” and moved across the country from a small town in Connecticut (where I’d spent my 26 years of life at the time) to Chicago, IL, where the only souls I knew were my new craigslist roomies and built in besties, and a work family that I was introduced to by a recruiter. I don’t think anyone actually believed I was going to do it. “Oh you’re actually moving?!” Dad, two days before leaving with my Uhaul parked in front of our family house. I spent my entire life loving the water and waiting for summer, so why I picked the COLDEST place ever, I have no idea. Must have been fate. Sailing was something I was always fascinated by, but in Connecticut, I always felt like it was way out of my tax bracket and status ranking. Shout out to my central CT peeps that understand that even though it’s only 30 minutes away, the shoreline towns seem like the Maldives in comparison to where we live. 

Chicago felt like such a glamorous new world and I felt like a freaking queen. Not only could I order literally WHAT EVER food I was craving that could be delivered in 30 mins and probably was one of the best in its category in the country, but I was meeting people from all over and being introduced to so many new things. It was a fresh start where no one knew me and I didn’t have to be afraid to try something new and fail. I could always go home! (LOL spoiler alert- six years, marrying my best friend, and adopting the best dog ever later). I decided it would be my Summer of Yes. Que googling “sailing lessons” one Saturday morning while try to hydrate away a vicious hangover and the haunting memory of a skinny dude in a pineapple shirt from the night before. I stumbled across 3rd Coast (Hey Captain Jim!) and since pineapple shirt dude bought all my shots the night before and it was the “Summer of Yes,” I said “fuck it” again and signed up. 

On the day of my first class I felt like such a bad ass. Driving down Lake Shore Drive with my windows down probably in some cute lululemon outfit thinking I was going to meet a hot 20 something with a job I didn’t understand in finance. Well, I rolled up to the dock feeling like a rock start and immediately deflated with intimidation when I hopped on the boat and realized the average age was about 60 and I was the only chick on board (I PROMISE there were young people in other lessons. This is just one time and it’s hilarious so I’ve been told I can’t leave it out). I was SO NERVOUS. I was obviously the only one on that boat that had never even stepped foot on a sailboat before, but that day lit the flame and I learned so much from those salty sailors. I spent every week looking forward to my next time on the boat. This is totally endorsement free right now but if you’re looking for a real sailing experience- HIGHLY recommend 3rd Coast. Captain Jim definitely pushed me out of my comfort zone. I got to sail in tons of different conditions in each role on the boat. I could go on for several more paragraphs… maybe I should write a full review?

Next up in my sailing history was meeting my first sailing/work partner in crime Kirsten, likely my first non craigslist friend in Chicago. We worked together at the time and when she heard I was taking sailing lessons she admitted that she had just bought a boat from her friend and “didn’t know how to sail it.” Lies by the way, Kirsten and her husband Michael are awesome co-captains of an occasionally comically terrifying boat. This led us to several super fun adventures and a handful (or two) of near death experiences on “Always Heelin.” Kirsten also introduced me to Columbia Yacht Club (COLYC). Insert my second home and future wedding venue. OH MY GOD I loved it there and immediately felt like it was home (still do). 

Somewhere along the way (only months after moving to the city) I met Jeff. My coworker at the time, and an avid wake surf boater (since recovered and turned sailor) and just a good ol’ “up for anything guy,” who went perfectly with my “summer of yes.” Well now we’re married and live with a mutual sailing obsession. A few years back, we were toying with the idea of buying a boat, joining a yacht club, or participating in one of the time share programs. We made it our mission at the Chicago Boat Show that year to explore all options and see which would be the best fit for us to start out. We decided to join Columbia Yacht Club and participate in Columbia Yacht Club’s Skipjacks program that year. Jeff had hardly any experience sailing and we thought that if we were to buy a boat, we wanted to get some more time on the water through networking – AKA sail on other people’s boats. Through Skipjacks, we met the fifth addition to our sailing family, Dan, and his girl, Bloody Mary, a 1986 Pearson 303. She’s just a fat old cruising boat that Dan has rigged for single-handing and racing, yet beloved by those who she carries through the waves under her sturdy care. 

 

WHY AM I WRITING THIS?

What business do I have starting a sailing blog when I don’t even own a boat, haven’t sailed the seven seas, and don’t crew on a fancy 1st place team you say?! Well back off haters. This is about the spark and the day dream and *the process* remember? Maybe you’ve already made it to paradise. Maybe you’re daydreaming about the process like me. Either way, this blog is for you. 

In all seriousness, like the rest of the world, the last two years have been a completely TRYING experience for me. I spent six months working as a provider in the covid ICU, and my dad died four days before my wedding. Need I go on? Back up to the covid ICU part. I am a physician assistant that has worked in orthopedic surgery for the last eight years (my whole PA career). However, I’ve spent approximately the last 15 or so working as a lifeguard or as an aid in the hospital, so essentially, always in healthcare or first aid. When the Covid-19 pandemic hit in March of 2020, the big boss came into work and told us we better start relearning medicine or we could all lose our jobs. I was 30 and broke (a product of the 2016 Summer of Yes), so I studied my ever expanding butt off and volunteered to work in the Covid ICU. Numbers went down, and then back up. I got out of the ICU, and then was voluntold to go back. Life is “back to normal” and quite honestly, I am burnt the fuck out. Healthcare worker burnout is real people, so please be nice to us. Maybe it’s left over grief from mourning my dad, or maybe working in healthcare during a global pandemic sucks. My therapist (HEY LISA!) has advised me not to do anything manic and that I need a creative outlet to express my feelings so why not share them for the entire interwebs. I’ve always enjoyed writing so for a third time, I said, “fuck it.” 

More driving than all of the above, one of the most valuable things I’ve learned over countless hours of therapy and meditation is the power of gratitude. In a world that has been shaken and divided by politics and fear over the past two years, when the sails are full and I’m on the water all of that disappears. Would I rather have a hot 40 ft center cockpit with six pack filming a youtube channel on some beautiful tropical island? I mean obviously, but sailing in the city is another side of beauty that really doesn’t get enough credit. Inside this city I’ve found this little microcosm that represents everything I love. A community of normal people that go to work by day, and then eat, breathe, and dream of sailing year-round. I still can’t believe I found this passion and I’m so grateful I’ve had this opportunity. I can’t wait to build this life. 

 

CONTENT

What wisdom do I have “for sail” you say? 

1.     I’m REALLY freaking good a going down the rabbit hole researching something I’m curious about. Stay tuned boat nerds. #adhdproblems

2.     My captain (HEY DAN) comes from a long legacy of sailors. Not only is he one of the coolest guys ever, but most of the wisdom will probably come from him and be paraphrased by me. Stay tuned racers and cruisers. 

3.     My husband, Kirsten’s husband, Michael, and Dan are all super handy (Kirsten and I kind of are too). Again, most of the fix it stuff will also come from them and be paraphrased by – me. This one is for you boat nerds again.

4.     I am a full time working, thirty-something female in a male dominated healthcare specialty that ignored that stereotypical intimidation both in my career, and when I decided to explore this passion. I have a soft spot for inspirational bullshit, and maybe you’re looking for some cynical, self-depreciating humor to remind you to say, “fuck it,” and go for it too! Whattup millennial ladies!

5.     My sailing family and I have A TON of fun. We race, we cruise, sometimes we swing from a spinnaker. We kind of do it all. In the summer we spend as much time as possible getting our fill of our salt-less sea. In the winter, we reminisce about our summer adventures over a good barrel aged stout or a complex glass of cab at the club. Maybe you live nearby, maybe you’re thinking of moving here, or maybe you are just like I was and are looking for something new to get into. As a pretty hip thirty-something chick who follows a couple Instagram of influencers, I think this just might be a detail oriented, well researched (lol), and hopefully hilariously inspiring place that captures your attention. 

 

Stay tuned! Next up, read my article on my experience on Columbia Yacht Club’s Skipjacks program!

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