Win Today

#231 | Demonstrate Genuine Care: Check-Ins May Save Lives

• Ryan A. Cass • Season 5

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This episode starts with a simple truth: the holidays hit everyone differently. What unfolded during a long training run on the Ravenel Bridge turned a routine “how’s it going?” into something heavier—something that demanded presence, not performance. When the night later connected to a reported suicidal person, it became clear that endurance didn’t matter nearly as much as paying attention. You may not control the outcome, but one real question, asked with care, can change the direction of someone’s story.

Takeaways:

  • Stop asking surface questions—ask ones that invite real answers and listen long enough to hear them.
  • Leadership and trust grow when people feel seen, remembered, and safe telling the truth.
  • Keep resources ready and be willing to help someone take the next step, even if it’s uncomfortable.

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SPEAKER_01:

Two hard things. Help one person. Be good and do good. Live a life of discipline and you will always win. You have all the tools that you need to succeed. Welcome to win today.

SPEAKER_03:

Thank you so much for tuning in. My name is Ryan Cass and I'm your host. My purpose in this world is to help push people further and harder than they believe possible and become unshakable in what matters most to them in their lives. Every week you're gonna learn from either myself or renowned expert in their field, and we're gonna unveil pieces of our playbook to help you win today. Please, if you love this show, subscribe and share it with somebody that will benefit from it. Let's dig in. Have you ever had somebody in your life, or do you have somebody in your life that they seem to be so invested and interested in in what you have going on that it makes you feel better, it makes you feel valued, it makes you feel like life is even more worth living than it is right now. Somebody that they know when your birthday is coming up, they know your recent milestones, they know even what's important in the lives of others that are close to you. Somebody that genuinely, I mean genuinely cares about it. It's my wish that even by saying that, that made you reflect on at least one person that represents that in your life. And that's such a beautiful thing to have. This episode has been on my heart for a few weeks now, and I believe it's the right time to get it out, especially as we're in the holiday season, and for some that can be a very difficult season while others are celebrating and being joyous. This can often be the time that a lot of folks also reminisce on memories with loved ones, or a time where they tend to isolate because this could be tied to an anniversary or something special that they once had with somebody that is no longer here. And it's the intent with putting this out that this helps serve as a tool, as always, but also that this helps spark a this helps spark positivity in at least one life and perhaps the one life that really, really needs it right now. So we're gonna talk about the importance of genuine care and a genuine check-in, not just for the holiday season, but as we're going into the new year, if there's one thing I wish that we all made a norm in society, is that we all performed a genuine check-in with people. Not the, hey, how's it going? I'm good, okay, I'm gonna keep walking, I did my civic duty. But that we all really invested in what is going on in the lives of the people we serve, our friends, our family, the people at work, the people that we lead. Imagine what this world would look like if every person that walked the face of this earth could tell you not just about their life, but three to five things about the lives of at least one person that is close to them. I see this a lot in the corporate world as well. That if there's one thing I wish I could change, not wish I could change, if there's one thing that I'm focused on influencing, is challenging people to really get to know the person to their left and their right besides what they do for work. There's so much more to our lives than the titles that we carry, the three letters after our last names, et cetera. And those things are way more meaningful than our occupations. And that's often what drives how how we perform, how we show up to the things in our lives, whether it's work, whether it's social events, et cetera. So this is how we can do a better job with checking in. And I'm gonna tie it to a recent story that has sat heavy on my heart, a recent experience with what I'll call as a close call in my life. So, with that, going back a few weeks, as we're now beyond the run across South Carolina, training for that effort required a lot of long runs at various points in the day. I would often go and do a marathon before work starting at 2:30 a.m. and also do some efforts starting late at night. So this particular effort was going on a 40-mile bridge run here in Charleston, South Carolina, back and forth across the Ravenel Bridge, which is the uh two and a half mile span of bridge, so five miles round trip that connects downtown Charleston, the peninsula, to the neighboring town of Mount Pleasant. And it's a beautiful, beautiful bridge that going up, you ascend roughly 200 feet, and you're looking over the Charleston Harbor, picturesque views. You get to see cargo ships coming in, you can see cruise ships coming in, you can see miles and miles and miles out into the ocean on a on a great day. And there's thousands of people that walk and run this bridge on a daily basis because of the views that that it offers. Unfortunately, this bridge also, with it being as high as it is off the water, is a destination for, I don't even want to call it a destination, but it is a way for people who are struggling in life and depressed. It is it is unfortunately also an outlet for those over the years who have gone to the top of the bridge and and chosen to end their lives uh by by jumping into the water and you're descending at terminal speed at that point. Uh recently there was a student at College of Charleston, Owen Kenny, who on Halloween night went missing and ultimately decided to go to the bridge and uh take his life at, I believe, 19 years old, uh so much life ahead of him. And this made a lot of headlines across the across the state, across the nation that somebody so young who has so much life ahead of him, you know, how how could this happen? And it's a question that I believe a lot of us will scratch our heads on. How, how, how is this possible at 19 years old? And really, how is this possible ever? How can we prevent these things? And on the bridge that evening, as we started this 40-mile run at about 8:30 p.m., we were going to be out there for about six, six hours. So it was myself, uh, friends Edwin and Jake, who recently completed the run across South Carolina. As we were going up and down the bridge, we saw the ribbons for Owen commemorating his life and a lot of information about how to be there for somebody in a difficult time. And it was tough seeing those things and just picturing what Owen could have been going through as he was making that final walk up the bridge. And what if somebody had just been able to speak to him, speak some life into him? Would we be in this situation right now? Uh we we don't know, but we can imagine, I would imagine, that maybe if there was that one person there at that right time that we wouldn't have this situation. And Edwin and Jake and I were talking about this, and what would we do if someone that we knew made that same decision and how heartbroken we would be and how personal we would take it, that man, what if there's there's something that we we could have done? So at about 10:30 p.m., we've been running for roughly two hours now. There was a uh kid that I would say was around 20 years old, that as we're now descending back up from the Mount Pleasant side, going back downtown, is is sitting crisscross applesauce in the in the pedestrian lane on the on the bridge. Which I've seen a lot of things, having run the bridge at literally every hour of the the day over over various days and stretches that I've been out there at 12 a.m., I've been out there at 4, I've been out there at 6 p.m. Seen a little bit of everything. You it typically late at night, you'll see some folks that choose not to drive home, thank God, that are stumbling on the bridge. I've seen folks that are just going up there to enjoy life and enjoy the view at 3 a.m. and in the breeze and just be there when no one else is there. I've seen folks that are going up there to take their sunset photos, their engagement photos, literally everything. And what I haven't seen is somebody that is just sitting the way that this kid was. And it seemed odd to me. There was something that just in my heart, right there in that moment, said, Go talk to this kid. Something's not right here. So we I told Ed and Jake, I'm I'm stopping to talk to this kid. And when I stopped and chatted with him, I asked him, How is he doing? And he said, Good. And it wasn't a convincing good. And I said, No, tell me, tell me what's going on, bud. Like, how what how can I how can I be of service? Are you sure you're okay? And he very softly said, Yeah, I'm okay, no problem, man. And I knew just back to my mind this this is not good. So I continued to press and just offer support and offered one more time, you know, is there anything that I can do for you? He said, No, but you know, thank you. And I said, Alright, brother, I'm praying for you. God bless. Kept running. Now, the second thought that I had in my mind, just because this kid was about 20 years old and and knowing what Owen had just done, and I had this thought, well, what if what if what if this kid does it? What if this kid chooses to to end his life right here and I was the last person to talk to him? I I would take it personally upon myself as if it was my fault. So I did have a thought for a half a second that I'm gonna rip this kid off the ground and throw him on my back, and we will run, and I'll take him down to the less inclined part of the bridge, back basically back down the ground. And I could be wrong and could get myself in trouble, that hopefully the the law enforcement would understand, or I could be right, and that could change a life, that could save a life right there. But we keep running, and we get back to the bottom, we refuel, and we're going out for another lap. Since we had eight laps to do that night, we were starting our fourth lap. As we're coming back up right to where that kid was, he's no longer there anymore. And I figured, okay, he could have gotten up the second that I stopped talking to him, but I didn't look back and started moving. He would have had to move rather quick or walk somewhat fast to get back to the other side of the bridge before we ran there, but it is possible. Didn't think much of it. As we're going up now for another lap, the police show up. And the police are responding to a call of a kid that they got a tip was suicidal and was going to the bridge. The description that they gave matched the description of the kid that I just spoke to. And my heart absolutely sunk in that moment.

SPEAKER_02:

That holy smokes, I was right. And this kid jumped right after I spoke with him.

SPEAKER_03:

And I start to become an emotional wreck there in that moment. And I'm at the end of the bridge, we get I start crying, and I'm telling I'm apologizing to the police officer and helping him look around. Not that there's many places you can look on the bridge, but I'm offering my support and really just at this point have a very heavy heart, and my stomach is just not sitting well. It kind of sinks. I told the police officer I was going to be out there for the rest of the night, regardless. Now, even if I didn't want to be, I was definitely going to be because I know that he he was going to be coming back and checking in and monitoring the area, and I felt that it was my responsibility to be there as well. Run continues. The police officer comes back about an hour after now, and this is about midnight. And no news, but he was was very gracious in that again and comforting me, knowing that, hey, you did what you what you could do. But in the back of my mind, I'm still feeling absolutely horrible. The rest of the evening goes by and finish up the 40 miles around 4:30 a.m. And I called the police to then speak to the responding officer who was still on duty at the time. And again, once again, offer my support. And fortunately, they were able to identify the location of the kid's cell phone that was no longer on the bridge anymore. I remember when I went to go speak to this kid that he had his cell phone in his lap and he was looking out at the water. And so his cell phone was no longer near the bridge, meaning that he was, in fact, at least, at the very least, had not made the decision to end his life right there in that moment. They had not found him yet, but going back, going ahead a few days, uh, there were no there were no issues where investigators or detectives called, which would have been the case had he made that decision that night. So that was a a huge sigh of relief, but a very scary and real occurrence that holy smokes, you were right there when somebody was considering, at the very least, considering ending their life. And that following Sunday, that next day, I remember staring at a wall for a very long time, a lot of thoughts of taking personal responsibility for this, etc., which I understand now is not fair to put that weight on my shoulders, but caring so deeply about humanity and people living their best lives and helping provide tools so that people can do that, it did feel like it was my personal responsibility in that instance. Now, I'll never know. I don't want to say I'll never know, but I likely won't know if that conversation and speaking to that young kid that day was what made him get up and go down the other side of the bridge and not make the decision. What I do know based off the decision, the conversation with the police officer, is this kid was contemplating taking his life and either had informed somebody about it or somebody else knew about it and tipped off the police. What I can believe in my heart is that perhaps speaking to that kid at least injected some sense of positive life into him in that he was clearly in a bad place and there was somebody that came up to offer care and support.

SPEAKER_02:

People make choices.

SPEAKER_03:

One of my mentors at Boeing had a list of leadership rules, and that one is number four. People make choices, meaning that uh we can have the best check-ins, the best processes, the best everything in place. But somebody is still going to make a decision. We can lead a horse to water, but we can't make it drink. We can have all of the tools and everything in place, but we cannot force people to do the things that uh we ultimately want them to do. But I suppose the question is are we, are you, uh, doing things in your life that uh promote positivity into the lives of others and your life too?

SPEAKER_02:

How you live your life is often an invitation for the people to your left and right, forward, back, on how to live their life as well.

SPEAKER_03:

I understand that not everybody is gonna be as forward-facing as as me, and you don't have to be. You don't have to be on a microphone putting out your message. You don't sometimes showing people the way is simply showing people the way. It doesn't have to be spoken, it's just done by your being, your presence, how you approach life, what you do.

SPEAKER_02:

How you treat others, how you greet others, how you check in with others. But here's one thing that as I share that story that I challenge everybody to to do.

SPEAKER_03:

And this is the one thing that this is one thing that I see as such a massive, massive opportunity to create a more positive world.

SPEAKER_02:

All right.

SPEAKER_03:

Think about how many times throughout your day that this Is your conversation with somebody in passing? Or even at their desk. Whatever. Think about how many times during your day is this does this conversation occur? Hey, how's it going?

SPEAKER_02:

Good. Okay, cool. Hey, how was your weekend? Oh, it was good. Oh, cool. How was yours? Oh, it was good. Meanwhile, you have no idea what's behind that good. Maybe it is a bunch of goodness, but maybe it's not.

SPEAKER_03:

Sometimes the word good is used to mask whatever is actually going on, but that's our societal way to avoid further questioning.

SPEAKER_02:

Oh, if I say good, I know this person's not gonna ask me a follow-up. Right?

SPEAKER_03:

So one thing that I do at work, especially at work, but in normal life, I'm gonna share two things. Two things that I believe we can do to create a more genuine check-in with people in in this world, in our in our families, in our work lives, etc. Everything. Okay, one we can do the standard check-in. Hey, how's it going? Oh, it's good. Okay, well tell me tell me what's good. What makes good? People know at work, especially on my team, that as soon as they say good over the last couple years now, I always say, what makes good? So part of them, part of them, I feel like they were doing an experiment that if they changed the description to, oh, I'm I'm great, that I wouldn't ask and just assume that, oh, they must be great. But now I always ask, well, what's great? So what I'm working to influence in the team is to share, one, to be op to openly share how they're feeling, whether it is good or not. And two, to highlight why, because I believe it's important to celebrate those things. Oh, I'm good because my son just turned nine and he had his T ball, well, not T-ball, he had his third grade graduation this past week.

SPEAKER_02:

Awesome.

SPEAKER_03:

How cool is that? Now I can follow up on how's third grade going when I see this person next week or the next day. What play do they have in the third grade, etc.? Right? So one thing that we can do if we want to break this societal norm of hey, how are you? I'm good, okay, cool. What can we do? Two things. One, when you're giving your check-in, go a little bit deeper. Don't stop it good. Hey, I'm good, and here's why. Dot dot dot. Now I'm creating an invitation for you. Maybe you're a little more shy. And when I'm not good, I also will share that too. I'm not doing so, I'm not feeling so great right now, man. Had a tough weekend at home with my with my family. Could have been a tough evening with the girlfriend, but at least that person now is more aware of what's going on, and they can be more cognizant, more gentle with you during that day. So this goes both ways, folks. This goes both ways. Secondly, is consider asking a different question that doesn't generate a binary response, meaning, how are you doing? Typically, that's a binary response question. I'm good, I'm not good, I'm bad, I'm great, I'm amazing, I'm somber. But if I ask you, what is your what is your day looked like? What is your day consisted of? What is your week? Tell me about walk me through your weekend. Now we're getting more descriptive. Now we're gonna open people up a little bit more. Now we might get the non-binary responses. Now we might get some of the details that we're really craving. It's interesting. I read a a paper in the American Psychological Association. The paper is titled, How Does Perceived Social Support Relate to Human Thriving? And it's it was an interesting stat here that people that just believe that support is available to them feel less loneliness, reduced anxiety, less stress, etc. So even by going one step further on a check-in, I believe that that's what can create belief in that person's life that, oh wow, there is actual care for me. Someone really cares. Someone asked me how I'm doing, and then they they asked me why I'm why I'm good.

SPEAKER_02:

Wow. Like they were they're really there for me. They really care. So go one step further on what makes good and or ask non-binary questions.

SPEAKER_03:

And I believe that that's what will also build more trust, whether it's if you're in a leadership role in the workforce and you have people that report to you, or you've got friends, new group of people that you're that you're connecting with, just show them that you care. I believe this is how you show them show somebody your heart and make them feel like wow, there's somebody that that that has a heart for me.

SPEAKER_02:

The next thing is become familiar with some resources that you can offer to people. Have those in your back pocket.

SPEAKER_03:

Whether it's something that you've used personally, something that you've recommended, or do a little bit of homework on resources that are out there. One thing that we have at work, we have an employee assistance program, we have an office on site. And I often will walk people there with their permission. I'll walk people there and introduce them to the therapist, which I've used myself so that they can have somebody to talk to. Because I understand as well that not everybody has wants to talk to, may not want to talk to you, or especially if you're their boss, they may you might not be the person. But again, them seeing that you're making the effort to connect them to a resource, to provide them a resource, could make all the difference. One, another one that I've used that I love to recommend to people is spring health and telehealth counseling. I understand that folks maybe want in-person connection, but sometimes just having someone to vent to. Now I'm speaking from personal experience, just having someone to vent to has been an absolute game changer and helped me release a lot of weight that I'm carrying in the backpack. We're all, I believe, carrying a theoretical backpack in life that's filled with experiences. And I see the negative experiences as bricks, and we all have negative experiences, but it's a matter of, you know, how long do you do you carry it for? How long do you choose to hold it for? A lot of people that I believe end up making these decisions about their lives, it's because they're tired of carrying the rucksack full of bricks. And by checking in with people and by being that person that really cares, you can help somebody shed a few bricks from their backpack and start walking around feeling like they've got a stronger sense of purpose connection.

SPEAKER_02:

Somebody that cares.

SPEAKER_03:

What makes a good leader? And this Marine General, at first, I was preparing for a long answer. This Marine General had maybe this 10-step routine and this very in-depth philosophy. He told Simon, the sign of a good leader is somebody who asks you how they're doing and follows it up with, and I and I care about your response. Meaning, somebody that says, Hey, I want to know how you're doing, and I really care about what you've got to say to me right now. The sign of a good leader, the sign of a great leader is somebody that asks how you're doing and genuinely cares about your response. So my challenge to everyone right now is that this week you make it a point to take a conversation further than I'm good, you're good during a check-in. Find out why somebody's good. Ask a different question that yields a different response. And by doing so, you're also planting a seed in that person to do the same thing. We change the world one person at a time. And so I wish that we we improve our check-ins, we make our check ins great and win today. Thank you so much.

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Ryan Cass

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