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!
