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“It still is a choice,” O’Conor told Patch.

But that choice is always without reservation, intentional.

Now in his fourth winter of lake jumping, O’Conor builds on the experience gained from recent years. While winters, in general, have been more on the mild side since 2020, Mother Nature has offered up her fair share of conditions when either wind chills or air temperatures didn’t make the Lake Jumper’s daily plunge ideal. That has been the case since Sunday when, despite harsh wind chill warnings that have canceled school and made the most routine of tasks seem impossible, O’Conor has continued to make his way to the waterfront and leap.

In such dangerous conditions, O’Conor is keenly aware of the consequences of what could happen. Given the early hour at which he jumps and the lack of people around that area, O’Conor has thought about what could happen should something catastrophic take place but learned long ago that at that moment, positive thinking remains among his best allies and that it must overtake thoughts of what could go wrong.

“You have to block everything out,” O’Conor said. “I know it’s a difficult situation, but it’s like, ‘Here I go’ and just have to be as safe as possible when the goal is to get in and get out.”

More times than not, though, the goal is one of gratitude and not survival. O’Conor thinks back to where he was from a mental health standpoint when he first started jumping in 2020. The pandemic was just beginning, he had become stressed and upset with where the country was politically, and the anxiety of raising a family in the midst of all of it had gotten to be too much.

Admittedly hungover from his son’s high school graduation party the night before, O’Conor was particularly cantankerous on a June morning when his wife, Marge — tired of all of her husband’s roller coaster mood swings — told him to do something. To go jump on his bike and then just go jump in the lake. So, in the middle of June 2020, the daily routine began.

It hasn’t stopped since.

There was never a longevity goal in mind when O’Conor began. He thought that maybe the streak would reach his wife’s birthday in November. But when city officials began closing public areas like the Lakefront path down to residents and visitors because of the surging pandemic, the motivation of going somewhere someone told him he could not, took over.

He would arrive at his destination just east of Lake Shore Drive and find himself alone with his thoughts. As the streak went from days to weeks and then from weeks to months, O’Conor began to see his mood improve, and he also found that he had a new appreciation for what was happening around him.

His surroundings played a major role in his transition from darkness to light. His fellow lake jumpers say there is a sense of gratitude that comes from a place when an urban setting and nature magically come together, especially when one feels they have it all to themselves, if only temporarily.

“That’s why I return —for that glorious moment,” O’Conor told Patch. “(That moment) of seeing the beautiful skyline, being able to use a great natural resource like Lake Michigan. When I started doing this in 2020, there was a lot of crap going on in the world and it was somewhere I could go and wipe everything off the mind, off the slate, and just block everything out.”

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Marge O’Conor jokes that other than ruining the family collection of beach towels, her husband’s daily trip to the lakefront unlocked something within him. The “glorious moment” moved Dan O’Conor out of the darkness and into the light mentally. For years, O’Conor — a former college football player — has lived off the message of one of his former coaches who always preached the need for a positive attitude and the belief that anything is positive if one puts his mind to it.

For O’Conor, the daily jump provided a chance to reflect and free himself from any negativity or stress he may be feeling that day. The trips allowed him to mentally wipe off the deck and to focus on being in the moment and allowing the gratitude he felt as soon as he hit the water to wash through him and provide him with a proper mental attitude to deal with what life would bring.

“You hit that water and, especially in the winter, the endorphin rush is amazing,” O’Conor told Patch. “I found in just a simple act of jumping in this natural resource that is just a couple of miles from my house, I’ve found some lightness, some positivity. I could forget about everything else and knowing I needed to forget about everything else because it is a dangerous lake.”

But since O’Conor’s jump in solitude began, a funny thing began to happen. O’Conor, a former advertising executive with Spin Magazine and lover of all things local music, began to invite others to join him as COVID restrictions began to loosen. While many of his daily jumps and flips into the lake are done solo, O’Conor has an open invitation to others who may be looking to purge feelings and to experience that moment of gratefulness to begin their day.

On his 365th consecutive day of jumping, O’Conor hosted a party that included local musicians and fellow lake jumpers. Another party was held for his 1,000th leap when he and a long line of jumpers leaped one-by-one into the waters below, accompanied by the musical stylings of a local performer. Other friends and fellow lovers of the lake have joined him, each bringing their own reasons for plunging into the water to the ledge.

Others have joined O’Conor in spirit, taking in his daily social media posts from afar. Sometimes without even knowing the back story of why O’Conor began lake jumping, admirers have used his daily video posts as their own moment of joy or serenity. Marge O’Conor says the couple has heard from military veterans in Florida who watch the video just to find experience and a temporary break from their stress, anxieties or fears.

Couples struggling with marital issues or strangers coping with personal grief of the loss of loved ones have also taken solace in O’Conor’s daily jumps and have, in their own way, resolved to find a better place. Outside of a following on both Instagram and X (formerly Twitter), O’Conor has done little to market himself, choosing instead to use the daily jump to keep him in a good mental health space. But while the daily exercise has helped O’Connor, his reach has ended up helping others.

Saskia Hofman considers herself among that group. Since first encountering O’Conor in the winter of 2020 — wondering what was happening as she saw O’Conor climbing out of the icy waters as she walked along the lake with her husband — Hofman has become a regular jumper herself.

Through O’Conor, Hofman says she realized that they shared mutual friends and common experiences that link them together. What started as a one-off opportunity to wash some of her anxiety away with two other friends, has become a ritual for Hofman in her own search for peace and tranquility.

Inspired by O’Conor’s journey, Hofman and others have begun their own.

“He’s not some Huberman bro, he’s not some ultra-high-performance athlete who says, ‘I want to do this after my hard-ass workout’ or “I want to do this to show how macho I am,” Hofman told Patch. “That’s not why he is doing this. That’s what made me want to do this. He’s so accessible and so he’s so quietly encouraging.

“He gets it. He knows that there is a reason that someone is going to keep coming (even) when it’s this cold out and voluntarily get into 36 or 37-degree water — whatever it is. He’s just this gentle guy who senses things in people and quietly supports them in that way. … Again, this isn’t about anything athletic. It’s about supporting each other’s mental health and doing something scary and being brave and working through it.”

The more she has jumped herself, the more aware Hofman has become increasingly aware of the personal issues people bring with them to the waterfront. Whether they only jump once or become regulars like she and her friends have, the lake waters have proven cathartic for those who enter them, bringing healing for those who need it and a moment of peace and accomplishment for others.

Like with O’Conor, Hofman says she appreciates the ability to leave her troubles in the waters as well as the daily reset that comes from her plunges into Lake Michigan. But it is the sense of community that Hofman says she has seen build up around her that perhaps she appreciates the most.

A fair amount of attention has come to him. O’Conor has been featured on various Chicago TV stations and other media outlets, including the New York Times. Since the 1st anniversary of his first jump, much of the media coverage has died down. It often returns in extreme weather like in recent days before the daily jumps are only chronicled on social media. The stories, along with O’Conor’s social media feed, have made him what his wife calls a “local ambassador of craziness.”

“He’s become this ambassador of how Chicago really strives to be a strong city and that’s a positive thing,” Marge O’Conor told Patch. “I don’t think he will get formal accolades for that, but we’re just an ordinary family.”

“It’s never going to be this high-brow thing. I mean, how could it be? It’s jumping in the lake.”

Without intending to do so, O’Conor got out in front of the cold-water immersion craze that has led others to seek out the cold to help their muscles relax and to bring other physical benefits. While many have found happiness either in joining O’Conor at the lake or have chosen to live vicariously through him, O’Conor balances the positivity with the naysayers who call him out for putting his body in danger in treacherous weather conditions like the city has experienced in recent days.

Even with more than 1,200 jumps under his belt, O’Conor has no timeline for when he will stop jumping. His streak includes jumps into the other Great Lakes as well as local lakes, rivers, and streams in Wisconsin and other parts of Illinois as well as the Atlantic when he has been out of town.

On a daily basis, he allows his love of the water and the positivity it brings him to keep him motivated even on the days when getting to the lakefront is tougher or when people say he’s crazy for going. Marge O’Conor insists she will never join such negativity, choosing instead to support her husband in any way possible.

Marge says that her husband has never allowed the “haters” to stand in his way and will continue to carry on the tradition as long as he sees fit. Marge and his other band of followers will continue to support his efforts, knowing the good the daily jump in the lake has brought — not only to himself but to countless others who share in his joy as long as the Great Lake jumper continues to do what he does each morning.

“Until there’s a real reason — aside from logic — not to go,” Marge O’Conor said, “I wouldn’t frustrate myself by pushing him to do something that I know he’s not going to do.”

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