The 5 Regrets of the Dying
Hosted by Mike DeHaan, Dan Austin, Dylan Koch
In this episode
In this Friday Focus solo episode, Mike DeHaan shares an exercise from a GoBundance event in Tahoe: reflecting on the five most commonly repeated regrets of people at the end of their lives. He walks through each one and connects them to how investors and entrepreneurs structure their lives while chasing business growth.
Key takeaways
- The five regrets covered: not living true to yourself, working too hard, not having the courage to show feelings, losing touch with friends, and not letting yourself be happy.
- The regret of having worked too hard showed up across all income and success levels, not just among high earners.
- Staying connected with friends now takes deliberate planning — Mike added an annual reunion with college friends to his one-sheet goals after hearing this.
- Being open about feelings and finding communities where you can be transparent can lead to deeper relationships and more opportunities.
- Happiness has to be pursued intentionally; Mike notes he knows financially successful people who are unhappy, and that suicide among very successful people is not uncommon.
- Mindset events and rooms full of like-minded people have, in Mike's experience, changed the course of decisions he made over the following year.
Show notes
EP 111 - The 5 Regrets of the Dying
On today’s Friday Focus episode, our host, Dan Austin will be discussing the top 5 regrets of the dying. You’re probably asking yourself, “what does this have to do with real estate investing?”. The correlation might not be so apparent, but these five regrets are the main reasons we invest in real estate.
Most of our lives are spent chasing money or careers and less time is spent doing what is actually important to us. The point of investing in real estate is to build wealth for you, your family, and your community, so you can live a full life.
Hearing what people have to say on their deathbed is an important piece to understanding why you’re in this business and what you want out of it. Our “why” is the driving force for mostly everything we do, and almost all of us share a few common ones. It’s safe to say, if we deduce it down, as real estate investors, all we want is to create wealth and passive income so we can do the things we love with the people we love.
So, tune in to hear the top 5 regrets of the dying and how you can upgrade your life to live more holistically to not only gain more wealth, but enjoy it while you’re here.
Topics discussed in this episode:
Living authenticallyWorking lessCourage to be vulnerableMore connection with friendsAllowing more happiness
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Frequently asked questions
What are the five regrets of the dying?
As discussed in the episode: living a life expected by others instead of one true to yourself, working too hard, lacking the courage to express feelings, not staying in touch with friends, and not letting yourself be happy.
What does the five regrets of the dying have to do with real estate investing?
Mike frames building a business and chasing wealth as something that can become all-consuming. The exercise is meant to help investors check whether their pursuit of success is costing them time, relationships and happiness.
Why does Mike say staying in touch with friends will be a bigger regret for younger generations?
Because constant on-demand entertainment — Netflix, video games, Kindle — removes the need for social interaction, so friendships now require real intention, especially once people are married and in their thirties.
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Transcript
Read the full transcript
Mike DeHaan: [0:01] Welcome to the collecting keys Friday focus. What is going on collecting keys fans? Today, you have me, Mike DeHaan, here to talk to you about my thoughts for the week. So if you listen to this past week episode or you follow me on social media, you're probably a little bit sick and tired of hearing me talk about the GoBundance event, the Millionaire Tribe event that I went to last week in Tahoe. But, I'll be honest, I talk about it a lot, and I enjoy it because it is a group that has been extremely impactful on both Dan and myself. And the events, I mean, when you're surrounded by so many like minded people, you know, it just sort of reframes your mind, you know, both in the short term and then sometimes big picture as well. I've had some of those events that I've gone to, and the takeaways that I've had have, like, literally adjusted the course of my life and the ways that I have, you know, moved on things and and reacted to things and put things in motion over the following year. So, you know, I get excited about them. And if you guys, you know, are kind of, not super interested in in mindset stuff, I apologize because I do think it is very important for people to consider these things, especially if you're trying to do big things with your life. So, anyways, on this episode of the Friday focus, I wanted to dive into another sort of topic of conversation that came up during the GoBundance event.
Mike DeHaan: [1:29] This was brought up by a speaker, and they spoke about the five regrets of the dying. And, you know, it's based off of a book where they went and interviewed all these people that were kind of on the deathbed. They're at the end of their life and asked them what exactly had they regretted in their life. You know, what, looking back, had they wished they had done differently or had they had changed. And, you know, there's lots of various answers, but there were five things in particular that were repeated. And, you know, the the guy wrote his book on it. And then the speaker, the exercise that we had at the event, basically had us write these down and kind of reflect on them and see, you know, which of these things we might be guilty of as we are working on building out our businesses and building wealth and chasing success, which can become kind of all consuming. So it was a little bit of a meditative practice, and I just wanted to share what these five regrets are with you. And, you know, maybe you can have a same sort of reflective thought process on these just like I did. And then they sort of framed me for the way that I'm gonna be approaching things over the next little bit here.
Mike DeHaan: [2:36] So, anyway, so here's the five regrets of the dying. Number one regret was they lived a life that was not true to themself, but they lived the life that was basically expected by other people. So, you know, they failed to live up to what they really wanted to do, but they instead lived their life in a way that other people expected them to do so. And I think that one is extremely relevant, especially for a lot of the younger crowd out there, the millennials, the Gen Zs. A lot of us are kind of resisting the corporate sort of push, the expectation to go to college and get this corporate job. You know? But those people that are a little bit older and, you know, were raised more in a society where that's the only option, I think this is a super relevant thing. So, you know, when you get to the end of your life, you wanna make sure that you are you know, you have lived true to yourself and you are not living a life of you know, in a way that's truly expected by others. The second one was that they hadn't worked so hard. And one of the things that was interesting about this was that this response was mirrored across various levels of people's success. So it was a mutually shared thought amongst many dying people, whether they had been very successful or not, you know, or they had been just like a lower income earner. But the emphasis on having worked so much that they hadn't enjoyed their lives appropriately was something that stuck with a lot of people at the end of their So number two is they hadn't worked so hard. And I think that that's, you know, as you're going through everything, you wanna make sure that you are indeed setting time aside to do things that you enjoy. Number three was that they wish they had the courage to show their feelings. And I think that this one, you know, varies.
Mike DeHaan: [4:24] I've actually thought about this one quite a lot because I think it does vary culturally, and it does vary by demographic and age group as well. You know, I think that with this, a lot of the people that were interviewed were likely older, right, where sharing feelings and things like that were more frowned upon. But with the younger crew, I think it's going to be a little bit less of an issue. But either way, I think that, you know, finding people in communities where you can have more transparency and have more openness with your life, you know, does lead to a more fruitful life. And, ultimately, you know, you never know how that could affect things bigger picture. Right? You can have deeper relationships. You can establish more friendships. You can get invited and involved in more opportunities if you're open with your feelings. And a lot of people, when they were older and they were reflecting on their life, one of the big regrets was that they didn't share that. Right? They weren't open with their feelings, and they probably spent a lot of their life kind of bottled up and that led to some regret. Number four, and I think that this one is extremely relevant for right now. Number four, the fourth regret of the dying was that they wish they had stayed in touch with their friends more. This one really stuck with me, especially right now in this virtual world.
Mike DeHaan: [5:43] It's so easy to just constantly have entertainment that's right in front of you. You know, whether that's Netflix, video games, even books. If you're a big reader, you can go on Kindle. You can download a book instantaneously. All of a sudden, you get into a lifestyle where you're not around your friends. Right? You don't need to. You can constantly entertain yourself. And, you know, different lifestyles aside, you know, that people have families, people are, you know, have different careers, things like that. One of the things that I think is so different from in the past is that we don't aren't necessarily encouraged to have these sort of social interactions. So this is one of the ones that I think will probably be more of a regret with the current generations as as we start to get older is those connections to friends because it's something that, you know, it's difficult to do and it does take intention. And actually, after hearing this one, I I set a goal on my one sheet to try and establish a an annual setup with a lot of my friends from college because I'm out of age right now. You know, I'm in my early thirties. Everyone's married. We don't we're kind of like out of excuses to get together, so it's going to require intention now.
Mike DeHaan: [6:55] And I know that when I'm older, I don't want to be I have to look back at my life and say that I'd wish I'd stayed in touch with my friends more. The fifth one, and this one is kind of the most meta and bigger picture, I guess, was that they wished they had let themselves be happy. And this one is extremely, I guess, that kind of like deep and and challenging if you if you think about what exactly that means. And, you know, where this stems from is hard to fully say, but I think it's kind of tied to the first one where they're, you know, not letting themselves be true to themselves. But, you know, being happy, you know, it is something that you have to be intentional about a lot of the time, right, for a lot of people. Like, most people aren't just walking around, you know, just happy all the time. You have jobs that cause you stress. You have family drama. You know, you have kids that are keeping you up at night. There are bad things in the world, especially right now. Everyone's always focused on how the world is collapsing. There's all this tragedy and all sort of stuff. But if you think about how you can structure your life, how you can do the best for yourself, how you can make sure that you're taking care of yourself and you are enjoying the little things and you are doing that with intention, then you can encourage happiness in your life. And I think that this is something that humankind has probably struggled with forever and will continue to struggle with, especially, you know, as we get into these years of extreme transparency where there's just FOMO and there's all these, you know, rose colored glasses that people seem to look through, right, of different sort of things. Right?
Mike DeHaan: [8:29] I guess that's not the right term. Rose colored glasses would in turn that they see the good things. I think it's the opposite. I think people tend to see the bad things in everything right now. Where people's definitions of happiness comes from is, you know, seeing, like, the influencers and stuff like that on social media, which isn't an accurate representation or hearing other people's stories. But I think that, you know, being happy is something that you need to be intentional about trying to pursue. And if anything, I I would say should dictate the vast majority of the decisions you make in life. More so than money, you know, more so than success, more so than fame. Even though those things will bring you happiness, I can tell you what, I know plenty of people that are very, very well off that are unhappy people. They don't do well in their marriage. They have mental health issues. I mean, even look at some of the biggest names out there. Suicide amongst very successful people is not uncommon. So it's important that you make sure that you make happiness a priority. Anyways, guys, that is the five regrets of the dying. So just a quick recap. Five regrets of the dying. Number one is they wish they had lived a life true to themself and not as was expected of others. Number two, they wish they hadn't worked so hard. Number three, they wish they had the courage to show their feelings.
Mike DeHaan: [9:47] Number four, they wish they had stayed in touch with friends. And number five is they wish they let themselves be happy. So, anyways, guys, do with that what you will. I found it very meditative, and I really enjoyed pondering those things as I am marching towards trying to live a whole and full life. So, hopefully, you got some buy out of those the same. Anyways, guys, follow me on Instagram at Mike underscore Invest. Please shoot me a DM, and, let me know what you think of these. I'm always curious when we do these Friday folks episodes if people have thoughts on them. We sometimes get feedback, sometimes we don't. And when we go into some of these different conversations, honestly, Dan and I, we put ourselves out there a little bit. So any sort of feedback, I would love to get. On top of that, if you would like a free collecting keys T shirt, if you leave me leave us a five star review wherever you listen to your podcast and you DM it to me on Instagram, I will send you a free collecting keys T shirt. And we've been sending a handful of those out and I'm hoping to get a bunch of photos of people that have received them so I can run a story with that. I think that would be pretty cool. On top of that, guys, please share this podcast with anyone who's interested in business, real estate, or just the ramblings of a couple, you know, guys that are sometimes entertaining.
Mike DeHaan: [11:01] Sometimes we're just full of ourselves, whatever it is. But it's the easiest way for us to grow. So if you enjoy anything that we do, please share this with those people in your life that might also enjoy it. And aside from that, thanks so much for listening. We'll talk to y'all next week. Thanks for listening to this collecting keys Friday focus. Be sure to subscribe wherever you listen to your podcasts.
Transcript generated automatically and may contain errors.
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