The hardest times to get back into the boat are after an incident like this. I've been dismasted twice but thankfully have never had a MOB or near-sinking incident.

In the summer of 2021, I purchased a Vanguard 15 sailboat to race with my significant other. We were entered into a casual regatta in late August 2021, might've been Labor Day Weekend.

Either way, we're racing out of Montrose Harbor in Chicago, likely not far from where you're sailing. The forecast is 15-25 knots out of the North.

Our racecourse was just beyond the point fully exposed to the 6-8 foot rollers from the north. We're both competitive sailors, sailed in college, and both have dozens of nights and thousands of miles offshore even at our junior age of 24. Both of us have sailed in these conditions, in boats this small, but not together, and certainly not on a 15-foot dinghy. Despite this, we were stoked for the event and didn't give the weather much thought.

The wind increases by about 5-10 knots as the afternoon sun turns on the sea breeze. 20+kt consistent gusts to 30kt. We are a combined 305 lbs, significantly underweight for the conditions and our boat setup, and not nearly enough rig tension for our combined weight and the breeze.

We end up capsizing the boat, we can right it successfully the first 3 times. But not the 4th time. My body is shot, the water is cold, and the mast has begun to fill with water such that getting it upright is a Sisyphean effort with my 200 lbs of cold shaky muscle. In the breeze, the mast being full of water makes it so heavy the moment I get the boat upright, the weight of the mast and the mainsail take it the full 180 back in the other direction, back to a capsize and we continue to drift southwest away from Chicago toward the water intake cribs.

Thankfully, as this was a dinghy regatta in a heavy breeze on a wavy day, the club had a safety boat on the course. There were some Chicago Corinthian Yacht Club junior sailors (teenagers) in power boats who thankfully came and helped me keep the boat up one last time while we got the main down and rig a tow line.

We're still together thankfully and the boat had no damage. But it was a good lesson and it changed me as a sailor forever. I am much more cautious and less seat of my pants, on all-sized boats. I still get some wind anxiety, checking windy.com even when I'm just going for a drive or a walk I'll get anxious if I see a breeze over 25. With time and hours on the water those anxieties lessen, and now, like 18 months later, I only get those jitters when there's a storm in the forecast. I went sailing on Lake Michigan just this Saturday (water temp 37F, wind 22 gusting 30+ out of the north). Even 20kts out of the north in the same location a year later was no big deal since I had 75 sailing days since the incident.

My advice, get back out there, there's no better therapy for a bad day sailing than a bunch of good days sailing. If you're ever back in Chicago let me know, I'd love to take you sailing. I sail with a bunch of nerds here and we usually race shorthanded so we have space for a couple of guests. Wednesday and Thursday nights just gimme a shout to the email in my bio.

Obligatory big breeze big waves Chicago Sailing footage. https://www.youtube.com/watch?v=0ibSzKNxk08