5 Deathbed Regrets

About the Episode:

In this episode of ALL IN, I dive deep into the five most common regrets people experience at the end of their lives and how you can avoid them today. I explore why living true to yourself matters more than meeting others’ expectations and why “working too hard” isn’t really about work—it’s about missing important moments with the people who matter. I share my personal experiences, including turning down a lucrative speaking gig to be present for my kids’ 16th birthday, and why expressing your feelings is crucial for authentic relationships. I discuss the importance of maintaining meaningful friendships and why “letting yourself be happy” might be the most powerful choice you ever make. This episode is all about making choices today that your future self will thank you for, because where you are now is not where you’re meant to stay.

Listen to the podcast here:

What’s shakin’? Hey, I’m Rick Jordan. Today we’re going all in. One of the things you’ll see in articles all the time is around, like, regrets when you’re on your deathbed or regrets when you’re old. You see these things posted all the time, and there’s some truth to them, and it’s something that I try to think about a lot is, hey, when I’m 70, when I’m 80, and I’m looking back at my life, and I’m looking back at my contribution. I’m looking back at how I raised my kids, how I showed up as a partner, all of these things. There are a couple of things that come to my mind, and I’m going to go through, really five of the most common things with you today, and walk this journey with me, because these are some things to think about as we go into this second half of this year. Is just to maybe make some shifts, maybe give some consideration to some of these things, because where you’re at right now is likely not where you’re meant to be. And what I mean is that you actually could be in the exact right place right now, but six months from now, heck, even six weeks from now, where you’re at right now should not be where you’re at six weeks from now, because you should always be growing. You should always be moving that way. You don’t have any of these to experience that. There are some of these.

 I’m going to give you my take on today and really how I see them, because there’s all these quotes that are posted out there about, don’t regret this when you’re on your deathbed and all that. But I’m going to give some context and some color to them today that is actually straight from my heart. Okay, here we go. The first one is, I wish I had the courage to live true to myself, not to what others expected of me. I wish I had the courage to live true to myself, not the life others expected of me. Now, when I say these two phrases here, right? Because they’re kind of contradicting, it’s like the courage is something because we’re squashed that way. And in many books that I’ve read, I’ve always read around, Hey, be your true self, you know, let yourself shine through. There’s a but all of these things that I’m looking at, it’s like nobody actually grasps the emotion of what you go through. Because if you’re a good person, at least what I would call a good person, you understand what I do, and you feel that you’re on this earth to really be around for other people. Now, that’s a lot of people that could be the general public, like how this is broadcast right now. This could be you as a parent, you as a spouse, you as a partner, around for those people. And of course, you want to do things that makes them happy, but at the same time, you have to be true to yourself, because if your glass is already empty, there’s no possible way that you can give any of yourself to anybody else, and you have to constantly be refilling that now. 

The other thing is that you have to truly examine where you’re at today, because if you place yourself right, maybe you’re maybe 30 right now, or 31, and you place yourself when you’re 70 or 71, and you’re looking back and you’re thinking about all these things. It’s like, do the reverse right now. You’re 30 years old. Look forward. Maybe you’re 40 years old. Look forward and be like, What am I looking at down the road? Because your choices today are affecting who you are becoming tomorrow and the following year, your choices today are affecting exactly what your potential is going to be, because your potential can shift any given day because of the choices that you make. You can either grow it, you can either raise it, or you can squash it. So when you’re staying in any kind of situation that is not right for you, that could be toxic, or maybe you’re not going after something that could be the best possible thing for you, either one of those two things my friend David Meltzer always talks about today, about having compassion for yourself today, and making the choices that you need to continue to move forward and grow, to let things go that you need to let go and to continue investing into things that will help you grow. He says, Be kind to your future self. I love that. I love that. 

The second one, which is very near and dear to my heart, is that people will say, Oh, I wish I hadn’t worked so hard. And when they say something like this, I kind of scratch my head a little bit, because really, that’s not what they mean. What they mean is that they wish they were around more with other people. Because outside of sleep, your job, your your your company—if you’re growing a company, if you own a company, whatever you put work into is it’s called work, for most people, that is really the second place that you spend your most time in life, sometimes even the first with that other one just being sleep. Okay, so if it’s sleep and your job, that really. Means that everybody else kind of gets what’s left over from you. You tracking me on that, but at the same time, here’s what I want you to really think about, because that sounds super dark and dismal, doesn’t it? Here’s what I want you to think about, because all of that is a symbiotic relationship, including sleep. You have to sleep. And if you have kids. This is especially important. I have kids. My kids are turning 16. 

Okay? And I look back, and it’s like, there are times where I wish I had been there more with them, and those were choices that I had to make. And at the same time, I think about Carly Fiona, Carly Fiorina. I’m sorry, there’s an R in her name. Carly Fiorina. She was the first female CEO of Hewlett-Packard, and I was reading an article about her on how they asked her, it’s like, what about all the time away from your kids being the CEO of a multi-billion-dollar company? And what she said really resonated with me. She’s like, I don’t regret it. She’s like, Yeah, I made mistakes. I’m human. There are times that I should have been there that I wasn’t, but what I did is I made it a priority, because everything in life has priorities. And my kids, of course, are one of my top priorities, just like me, just like Rick Jordan, my kids are one of my top priorities. And when she talked about this, she was like, but still, I made sure that I was there for every single important moment, because that’s something that you can still carve out time for and still fulfill your responsibilities, your obligations to where you work, and also pursue your own passion. 

All of this stuff can flow and function together. This is not a give-and-take scenario. This is not an if-then. This is a simple matter of putting time down for all of these things and being a student of your calendar. There are going to be times when you mess up with this. There are going to be times when things happen. In fact, even this week, right I am passing up a very lucrative speaking engagement at a large event because it’s my kid’s birthday. I changed my flight because I’m like, You know what? And I told him, like, if you can shift my slot, that would be awesome. If you can, I understand, because it’s my kid’s 16th birthday, and it’s one of the biggest opportunities for me to spend time with them, because that, to me, is an important moment. I will spend the time with what’s important to me, and sometimes you have to make those hard choices. Sometimes you have to pass up on something else. But you know what? Because your intentions are good, because you’re going to try to make it for all those important moments, for whoever or whatever it is, those things will come back around. I have no doubts. I have no doubts, life. It can be hard, choices can be difficult, but at the same time, when you’re good intentions, things are always going to turn out exactly the way they’re supposed to, and exactly in a good way, because it’s all going to be okay. Number three is, I wish I had the courage to express my feelings. You know, so many people bottle this stuff up, and this actually is, I’m going to be straight. 

This is actually a form of manipulation. When you don’t express your feelings, you’re actually manipulating the other person’s emotions. That’s what you’re attempting to do. When you don’t express these things and you don’t tell somebody how you feel, it’s actually a scenario where the other person will not have even the opportunity to respond to you. This is something I’m hitting hard on right now, because you should always express how you feel, even if you think it’s going to upset the other person. Now there’s a way to do this. There’s a way to do this respectfully. There’s a way to do this with compassion for the other person. There’s a way to do this so that you’re not blowing up at the other individual, because they might not have even done anything in a bad way. Maybe they have good intentions, too. Now, some people are very manipulative. They can be, and that’s a form of self-preservation. Okay, so I’m not talking about those individuals, but the other ones that you interact with, if you withhold your feelings from them, you’re actually attempting to manipulate their feelings and their emotions by not allowing them, not respecting them, the opportunity to respond when you just pass up the moment to talk about it. You bottle it up inside. 

Eventually it’s going to burst like a pressure cooker, and at the same time, that’s not fair to the other person either, because all of a sudden they’re getting flooded with all this stuff, and they don’t even know what hit them or where all of this came from, because it wasn’t discussed over the years. This is something that kills jobs, kills relationships, kills your life, and makes you die inside because you’re holding up all of those emotions. So it’s not even just giving respect to the other person. It’s respecting yourself. Remember, be kind to your future self, express how you feel in a way that is articulate, in a way that is passionate, in a way that is respectful. Full of the other person. The fourth one that people say on their deathbed, right, is I wish I had stayed in touch with my friends. Now there’s friends that I absolutely wish I had stayed in touch with, and there are other ones that have kind of fallen away. Right? When it comes to relationships, there are three things: there’s feed, there’s fall away and there’s fire, meaning get them out of your life. Fall away is just kind of letting the separation take place, because those kinds of things, those last two, are really for toxic scenarios. So I’m not talking, I’ve done on the podcast before, around your circle of friends, today might not be your circle of friends tomorrow, because you have different viewpoints. 

You guys have gone different ways. That’s not what I’m talking about right here. What I’m talking about and staying in touch with your friends are the ones that you probably resonated with. There are two people I can think of right off the top of my head that I wish I had done this with, and now looking back, I can actually learn from those choices, which I would consider to be poor choices on my own self, and understand that at this point, that’s not something that I’m going to do anymore. I recognized this several years back at this point. That man, I wish I had stayed in contact with this dude and that dude, two dudes. Now I make it a point and prioritize important people. I feed those relationships. There are certain relationships that you can let go of, that you can fall away from, and certain friendships that you can do. So there are other people that you need to get out of your life right now. I mean, completely gone as much as you can anyway. But then there are those relationships that you need to feed because all relationships, in order to grow, you have to feed them, and you have to feed them good things, like I was talking about in number three, expressing your emotions and allowing those individuals to express their emotions back. This is one specific regret that a lot of people say I don’t want you to fall into. I’m sure you can think of people right now that you wish you had stayed in contact with who could have been like your allies, gotten your back all these years. Change it and make it right right now. 

The last thing, which is a heavy hitter, number five, is that I wish I had let myself be happier. Now, hear my phrase on that. It’s not that I wish I was happier. It’s I wish I had let myself be happier. Because when you look back at things and you look at the way that you responded to certain situations, because no matter what, no matter what, if you’re in any kind of a disagreement or you feel like you’ve been wronged in some situation, there’s always a part that you had to play in that. But even more so than this, and I want you to hear this today, because you may have gone through a period of life where you were unaware of something with yourself, absolutely unaware of it. But then there comes this moment where, whether it’s by your own realization because something has hit you like a lightning bolt—this happens a lot with relationships—or maybe you’re speaking with a counselor, and the counselor finally is able to notice something in you, and it just hits you again because they called it out and said, This is what this is. And now you become aware, or you do some work on yourself with a coach, and you come to a recognition of some things that you want to change in your life because they are keeping you from being happy, and you recognize that you’ve been in that same place for so many years. This has happened to me before, in many different areas. 

And when you’re kind to your future self, what you choose to do in that moment is you choose to go a different direction, because once you become aware, once you become aware of who you are and what you’re doing and what’s around you, you don’t want that anymore. When you do not change that now, you are accepting the role of a victim. That’s the straight truth, and you will continuously live that role of a victim. And the worst part is, the shittiest part is you are not a victim to that other person. You are not a victim of that other person who might be doing something to you. You are a victim of yourself at this point. You are abusing yourself. You are not allowing yourself to be happy because you are choosing to stay in the shit. I’ve had this many times in my life, and some of these choices are hard; they suck, but coming through on the other side is where you find happiness. So allow yourself to be happy. Stop playing both the role of the victim and the abuser in your own life. These five things are things that I don’t want you to experience, but that last one is hard-hitting. It’s time to be happy. It’s time to move forward with whatever it is—maybe your dreams, maybe your purpose, maybe your vision, maybe something new you wanted to try this last one. Allow yourself to be happy and be kind to your future self.