Stoicism in Action Build a Life You Never Want to Retire From | Ryan Cadwell
25 Jun 2026 · 47 min
Ryan Cadwell, co-founder of Resolute RDM Properties, uses Stoic philosophy to guide business and life decisions. He asks "why" up to seven times to strip away ego and uncover true motivations, a practice he applies to negotiations, deals, and annual reviews. Daily habits like Transcendental Meditation and morning pages keep him present and clear.
Chapters
Hello and welcome to this episode of The Inner Estate with your host, Bridget Stewart. My guest today is Ryan Cadwell. Ryan, welcome to The Inner Estate and thank you for being our guest.
Thanks for having me, Bridget. Glad to be here.
Well, Ryan, there's so many things that I know we are going to go into today, and it's a broad range. I think we're gonna go into leadership, business building, philosophy, stoicism. There's so many things that you're passionate about, and I'm excited for us to dive deeply into it with What you've built so far, just to give people a perspective, you are a co-founder, co-owner of Resolute RDM Properties and specializing in all areas of real estate or nearly all areas of real estate with the services that your company provides. And I believe you pride yourself on being a leader that is continually growing and working to be your best each day in each situation. So when we first started chatting, you were mentioning how what and why really drives a lot in your life. Could you share with everyone how that impacts what you do?
Sure. What, what and why became the main thing as, as we kind of, as I started going through a few of our investments that didn't pan out the way that I'd planned, jumped into a few things quickly. Tried to scale a couple different businesses. And then when the, you know, when things didn't go well, I started, I started to look back at things that how decisions were made when they were made. And the big thing that kept coming back was what did I want? And then why did I want it? And then, so for us, for us, when we get into an advisory role, we try to stay, I mean, a lot of what we do does a lot of different things in real estate from residential to commercial to asset management development. We step into the advisory role a lot and really trying to help people narrow down what do you want. And as easy as that question sounds, when you really try to do it, it's quite hard.
Yes.
There's so much to it. There's so much in it. And then after you define it, then you need to ask yourself why 7 times. What, why do you want it? And there's usually the reason we do it, the reason I do it. Is I'm trying to strip away ego from everything. I don't want ego to have any type of influence in decisions, in reactions, in responses. I mean, as Ryan Holiday puts it in his book, Ego Is the Enemy, it never, it's never served me very well.
Right. Right.
It's usually always made things worse. And Holiday says that too. It doesn't matter what the situation is, you can always make it worse.
Stuart says that too.
Oh, okay.
I will raise my hand. Yes. That has also happened for me.
Yeah. So yeah, I mean, what, and then like from the real estate perspective, what matters when you're negotiating with the other side? What's important to them? Why is it important to them? You start understanding all of that. It makes transactions a little easier. So just try to stay in that. If, you know, if as a company we're sitting down and we're, we're going to try to implement some system and process updates. Okay. What do we want? Why do we want it? Make sure that we're very clear on that. When you, when you're— one of the things I'm learning about AI is if you really want to get good at prompting it, you need to know what you want, why you want it, and tell it exactly how to respond to you and how to interact with you. So it really applies almost everywhere.
Right.
Especially if you're going to get into real estate investing, you're going to do it at a high level. I mean, I recommend, even if it's not at a high level, I recommend And do you always do that? Because otherwise you're probably gonna get sold a product that's not gonna be what you actually want. Yeah, that's, I mean, that's the real driving force behind it. It's life lessons of ours as well as, um, helping clients navigate, um, some decisions that didn't pan out. And then even having other ones where they made money, but they didn't make as much money as they wanted.
So, right. Yeah. You know, I wanna highlight something that you said, uh, there, asking why 7 times. So in my experience, not only with my own self, but also with my coaching clients, oftentimes very driven entrepreneurial people and leaders, it's like, all right, here's what we want and here's why. And we might get to 3 reasons why, and then we're like, all right, that's good. Let's go. And then we just go. So could you share a little bit of the power of asking why 7 times? Why is that a measure and what does that achieve?
So, I mean, understanding the essence probably helps understand. 7 is just the number that I think when I've done it, when I've done it, when I'm trying to avoid, like if I'm trying to force something, if I ask it 3 times, it's easy for me to hide behind, like my answers will, my answers will be easily like, oh, we want to do it because it's going to add this much revenue. Okay.
Why does the revenue matter? And then you ask it enough times, you need to drill down and make sure it's not based on ego, again, ego or some other driving force that has nothing to do with your mission or goal.
If you gotta expose that early, if you do, you're gonna save yourself heartache and, you know, burning resources you don't need to burn. So 7 is like, I would say it's probably between 5 and 7. But if you don't get to something that is kind of like very enlightening, very vulnerable, a lot of times by the time you get to 5 or 7, you feel naked.
Mm-hmm.
So, because that's, I mean, it's kind of like the clothes we wear and the way we present ourself to the world. The first 1 or 2 or 3 things are gonna be, sometimes you're gonna say them for other people.
So, right.
If you're talking about, so like sometimes when I teach classes, uh, to investors and, and, and I, and I talk about what you want, a A lot of them are like, well, I want to give back. Okay. Why do you want to give back? And then what do you want to give back? Why do you want to give back? And the first thing is it's usually noble, but it's usually also very geared towards them. And then when you keep drilling down, you got to get vulnerable about it to where you're admitting there's nothing wrong with doing something for yourself.
Just don't lie to yourself about why you're doing it.
Like that's the biggest.
That's the biggest thing that catches us, catches all of us off guard is don't lie about, don't lie, especially to yourself about what you're doing and why you're doing it, because you're taking away the good parts of what you're doing. And that's when it becomes not necessarily bad, is not good or bad, but that's when it loses the luster and it can easily become something that's just okay. And maybe you wouldn't have spent your life doing that.
Right.
Yeah.
And you can fall into a default position.
Yeah.
Because, you know, yeah, there are traps there that you can fall into. I have one other question in this area for you. So in this conversation so far, we've really been talking about using the What and the 7 Whys in terms of launching something or starting something. Have you ever used the same process with yourself to make a decision to stop something? Or get out of something.
Yes. Yes. For the same reason. And you also, I also say to use that same what, whys on annual reviews. Like, I mean, if you, if you want to do, so we're in real estate. If you want to do a real estate thing, it would be, you're gonna buy a specific property. You're gonna create a business plan. What, you know, what am I buying? Why am I buying it? You establish all that, but you need to review that every year. That's part of the asset management side, side of that work. I, that applies in everything. If it's— I mean, if it's where you're living, if it's the job you have, if it's— it doesn't matter if it's the church you go to or whatever the choice is, even how you eat, like— is how you're eating, is, is that, you know, why are you doing it? Is it, you know, are you trying to gain weight or everybody's trying to lose weight?
He's trying to gain weight.
Some people, I mean, I, my son, You know, he, he, he was skinnier, so he was always trying to gain weight while everybody else was trying to lose weight. But like any of those things, like having an annual review, I know it's so cliché to do it like at January, on January 1st. I recommend you do it in Q1, like do it in February. Don't do it whenever, don't do it when you're supposed to do it. Like do it when you can specifically focus on you, just change your annual reset, but yeah, I mean, plugging the what, whys in, um, even it's just healthy to help. It's kind of like spring cleaning. It's kind of like just cleaning the mess away, making sure you're clear. Yeah.
And I do think that I love that you mentioned that it ripples out into and can be used in all areas of your life. So one example that I think is critical is How much are you sleeping? How do you go to sleep? When do you go to sleep? When do you get up? You know, like that whole arena around that. Apply the what and the whys to, to what you're doing with sleeping.
Yeah, it's well, and with sleeping, like one of the things that I think people overlook is if you had a bad day, your day technically starts the night before.
Agreed.
So if, if you had a bad day or the day wasn't great, like when did you go to bed?
What did you do before bed? Did you watch some intense thing?
You didn't get a whole lot of sleep and then you woke up in the morning and you're groggy and dragging ass and you know, it, that has a major impact on how your day is. I mean, even that, like what time is bed and then what, and you know, my wife always gets onto me about, about like sometimes I'm too committed to my, you know, to my regimen. She's like, you gotta have more fun. And she's not wrong. She, she is right about that. But in that moment, I, you know, the why is okay, learn, learn to go with the flow. Life is funner. Funner. Life is more funner.
I like funner.
Funner. Life's funner when you, when you actually have, have a little bit of the flow going on and it's not just, you know, always what's in your control.
Right. Well, I think that I have used that process of what and why in making big business decisions, switching back to business for a minute. In terms of deciding to shut down an enterprise that frankly, I probably didn't answer all the whys before I started it. So I've used it in that process. So it is not, if anyone's listening to us and they're thinking this is just for when you're planning, it's not. It can be when you need to make a tough, any, any big decision, take the time, stop yourself, do the what and 7 whys. And it's going to allow you, in my opinion, and I love your opinion, Ryan, to have more confidence in your decision and less of a feeling of, did I make a mistake? Because you will know that you thoroughly investigated it and removed the ego and made a strong decision.
And a lot of times, I mean, I even, like, one of the things that I, that I've tried to take some of the, some of the real estate, like the real estate application of this into life. And if you do that, like specifically to your example, like if you take a business decision you made and you, and in your gut, it feels uncomfortable. Maybe I shouldn't have done it. Well, instead of ruminating on that, get a piece of paper and a physical piece of paper and write it down. Like get it outta your head, put it on paper, think it through, like, and have a relationship. Like what's the saying? Paper's more patient than people.
Yes.
So like have that conversation with yourself, even, even where it's outside of your head, you're able to look at it from, you know, from an independent third party. Because one of the things, the most dangerous thing with real estate, and I, and I, and I think it pertains to everything, is when we make a decision, when we justify a decision by accepting standards that we wouldn't accept. So most of the time, if you go into a real estate deal and you say, these are my standards, I have to make this return. I'm only going to have my money to work for 5 to 7 years. Maybe 5 years on this particular deal, the numbers are going to tell you whether this deal works. It's not an emotional decision.
Correct.
So when you, when you start getting that emotion, that's really where you want to apply that to pull the emotion out because then it's going to really expose. I mean, maybe, maybe you feel like that was a bad decision. You go through it and you're like, no, I'm right on track. Like we're right where, or it's yeah, you shouldn't have maybe done that and it's time to free your energy up to go do something else.
Yeah. Or you will creatively get the clarity of another solution that you hadn't thought of before.
Yeah.
So it's, it's a, it's really a good tool to use. Now you mentioned emotion and as I mentioned at the top of the call, introducing you, that you are intrigued by and study not only philosophy, but also stoicism. And, uh, could you share, cause when I, when I think about— the power of the Stoicism movement is it's allowing you to manage emotions in a way that will not hinder you. So I like to express it that way, cuz some people think that it just means, oh, Stoics, they just shove it down and hide it. Uh, no, I don't believe that's the case, but I feel like it allows you to have the skills and the habit of removing emotion. Could you share with everyone, how do you incorporate that? Into your life with the practice and the study of Stoicism? Sure.
I mean, Stoicism, the interesting thing about it is the word to be stoic in today's language doesn't really, doesn't really define what it is, where it, what it actually, how it originated. And, and, you know, its true intention is to, its true intention is really to bring you into the present moment and to be the best version of you in that moment by removing all the stuff that you just don't need. And most of that stuff is the worries about what may or may not happen. Everything that's outside of your control. What do we control? What decision can we make? What can we know? What can't we know? Do the, do the whole known and unknown risk analysis, but don't overdo. It's not about shoving it down. It's really, it's really just kind of, I always just say, it's really kind of like you're just going to get out of the way of some of it. Some of it just doesn't matter. Just get outta the way and let it go past you like a stranger in the crowd. Like the, you don't have to grab onto everything that passes you. In a lot of ways you don't, like driving home from work, you're not, you know, you don't care what everybody around you is doing. It's the same, same focus when you apply stillness. When you, when you get into like what its real intention is, it's really about freedom. Like if you, one of the worst things in life I've ever done to myself was when you bury, when you bury emotions or you, you bury the things that you need to deal with. Stoicism just made it to where you don't need to bury them. Sometimes you just, hey, sometimes the best part is learning that you don't even have to let go because it was never yours to begin with. You're totally worried about something that's, it's not even yours to worry about. I mean, And I know we said we weren't gonna get political. The only political reference I'm gonna make is I have friends that get so worked up about whichever side's doing what, and it's like, you don't control any of that.
Like, why, why mess with your day? Like at all?
I know, right? Like we all have our own world. You mentioned the cars on the road. Every car on the freeway is going somewhere different for a different reason. And they all have their own world, the people in it, and how they impact the people in it. The more we focus on being the best we can be in the world we've created— I'm not saying to be exclusionary, but have power where you have power.
Yeah.
And impact people where you can have an impact. And that can be worldwide. We both, we, if we thought about it, we both know people that have started charities that are impacting people in all the continents, right? So I'm not saying to be limited, but know where you are going to bring the biggest benefit every day.
Yeah.
And it's measuring the proper use and understanding of stoicism. It's more measuring like you've got 24 hours in a day and X number of years.
We don't know how long that is. How are you gonna use that one limited resource and in the best way possible? And if you only focus on, you know, that one person in the coffee shop You were kind to, or the way you treated your server. Those moments are the moments of your life. And really it's about being present in that moment.
Stoicism just has more to do with learning how to let go and let go of that nervous energy that permeates so much of social media. I mean, unplugging from social media for me, like I'm, I'm on it like a tad bit, but I'm there for a specific reason.
Right.
And then every time, you know, if it starts pulling me in for 10 minutes, I'm like, oh, I'm done.
Done. Yep.
I don't, I don't need this. Like it's algorithms are grabbing hold of my attention. But yeah, it, and a lot of times, like you, you, you mentioned people that have major impacts. If you look back at their life, most of the time it started very small and they just showed up over and over and over in the biggest way they could. In each of those moments and it snowballed.
Right.
Um, and that's how they got where they are. Like we all have these moments of FOMO that goes through the brain. You know, the evolutionary is always worried about not surviving. And we have these moments of FOMO or, well, they're, you know, they're more popular than me. And, and, and you worry about that. And it's really like, well, do you, did you go on the journey that they went on to get there? Because And would you even want that life?
Would you want that? Right.
You know, so embrace what we have, embrace what the opportunities that are in front of us. I had somebody ask me, you know, for like new real estate investors, what would you, what would you suggest?
And I, off the cuff, I just thought there's most of the time there are, there are opportunities right in front of us. We're, we're too busy feeling like, I gotta go find the right one. Maybe the right one is, is literally the guy next to you in a coffee shop. You just need to strike up a conversation or, or, you know, something like that. It's being aware and open and present.
And then taking that time to go through the process of evaluating it.
Yeah.
And especially in the example you just gave, look at the numbers. The numbers work or the numbers don't. And make sure that, and you can correct me if you disagree, but, and make sure that your expectation of return is something that is possible and probable, right? So don't miss out on a great opportunity because it's not going to give you some sky-high, you know, not probable return because you'll just miss out on opportunity after opportunity.
Yeah, that's the danger. That's the danger of financial modeling. That's the other reason why being honest, being brut— if you can't be brutally honest about things that are emotional, about your ego, you run the risk of become— making very bad investment real estate decisions, cuz you're always, you're looking for the dopamine hit. This feels good. Like this deal feels great. And it's like, it's, you shouldn't feel, it shouldn't feel anything. It should, it either fits my profile or it does not.
Right. Yeah. The only time you should feel anything in real estate is with your primary residence, you know? And then that's different. That's different for everyone.
Yes.
Yeah.
But you're exactly right. If it's in the investing world, really check in with your 7 whys. If you're feeling emotional, Ryan, how often do newer investors get hung up on wanting to have the story to tell? They want the big story, the big, you know, it was listed for this and I got it for that. And then I did this and the story is driving them rather than the numbers.
I always say, did you buy, are you in real estate investing to tell people on a bar or Are you, like, do you do it because it's a business and, you know, if somebody says, what do you do? And you say, well, I'm in real estate and you just kind of leave it alone. Or are you deep diving every conversation?
Because the, if, if you're in it for the bar conversation, mm-hmm. I, if you're in it for the bar conversation, you're probably a person that I wanna be on the other side of the table with.
Yes.
So I'm gonna probably make money off of you. Yes. Um, mostly because you haven't cleared the, the emotional part of it. And which, which means that you're, you're gonna probably make a, you're gonna, you're okay fudging the numbers a little bit to make it feel okay when you buy it, even though like what's actually gonna happen is, is probably not as great.
And then.
When you get to the end and you're like, well, I didn't make as much money, but it's okay. Like, so you've literally justified every move the entire way instead of staying disciplined, hitting your numbers and/or exceeding them.
Right. And the other flip side of that is I'm sure you and I both, we've had sellers that don't take great offers because the great offer isn't their story that they want to tell. Like, that's true. You know, they let a great deal go over $5,000 or, you know, 1.5% of the list price and then end up having the property longer. All of that, we don't have to get in the details of that, but it can show up kind of like we were talking about before. It can show up in business planning and business decisions to move forward, but it can also bite you in the butt when you're selling or divesting.
Yeah.
That's a great example of ego, you know, the seller that's like, And I'm not selling it for less than blank. Yeah. Really? If every other term was perfect or more than you wanted, you still would be hung up on that. It can crop up on the way in and on the way out and all spaces in between.
And that, and they, I mean, it even kind of goes back to the foundation. And if you take the time to build the right foundation and you understand what you did, why you did, why you were doing it, when you go to sell, you're making a decision because of what we wanted to do, why we wanted to do it. Then it keeps your decision-making kind of in a straight line and your trajectory through the— and I even say, you know, that even goes for even the personal residence. Like some of that's emotional and that's okay. That can be the why that we're doing it. We want X amount of space because we're going to house, you know, or that's just what I want. And that can be just what you want. It's easier when you go to sell it, if it's not emotional, but, and a lot of times I always think it's interesting. A lot of times in those deals, it's just interesting that you could talk yourself out of something and then the next deal, and I've done this to myself, the next deal that comes along, you're like, damn, I should have, I should have taken that one. You know, even if it was, even if it was like $2,000, you know, maybe I lost $2,000, maybe $5,000. It doesn't feel good to lose because of the loss aversion in our brain, but it The bigger lesson has to do with if your ego just wouldn't have been involved, you wouldn't have even had to do this extra work.
Right. Or even the extra thought process and feelings over losing out. Right. Yeah. It would've prevented a lot. So I have to ask, how did you get here? So when did you start having an interest in philosophers? I believe you've shared with me that on a daily basis, you study Marcus Aurelius. Um, you know, like when did this all start for you? Were you just born this way or did an event happen? Was it something in school?
Growing up, I was always a reader. Um, I mean, my mom, my, my mom had always put stuff in front of us to read at breakfast every morning and going through life and I got away from it.
And Stoicism, that just reading that stuff just kind of started 3 years ago.
Okay.
I was, I was in a much more stressful place. I'd started a meditation practice. I started doing Transcendental Meditation. That helped me through, that helped me through other stressful stuff. I mean, we had some business ventures that didn't go well, so I was under a lot of stress, but none of it, I mean, Transcendental Meditation helped it, it, it, that was life-changing too, but the Stoicism part and the philosophy part, I was always into reading, reading other perspectives, seeing it from a different angle, try just learning. Learning has always been part of my, part of my world. And when I wasn't doing it, I had more anxiety. I had more, I just wasn't processing life very well.
Right.
And I'm trying to remember the first, the first book would have been I'm trying to look at which one. I think it was The Obstacle Is the Way.
Yeah.
Was my first one. And super easy read. And then I grew up in a Christian home, got a degree in, two degrees in, in like religious studies, Christian, uh, Christian ministry and Bible.
Mm-hmm.
And then once I started digging into that, I started seeing the similar correlations and then that leads me into how are these the same? How are these similar? So then I start studying the, you know, the history of basically like Stoicism and Christianity were coming up in Rome at exactly the same time.
The same time.
Seneca, Seneca was alive when Jesus was alive. So that, and then that intrigued me. So then it just started, okay, what, you know, who were these guys? What did they teach? Who was Zeno? The fact that he lost everything in a shipwreck and then, and then he, and then he dives into Well, you know, deal with what you can control. You couldn't control the storm. Right. Now what can you do? So, and then he's the founder of it all.
And then it's not a religion. It's just a way that you approach life. It's a philosophy of how you apply, apply it with life. So then you have correlation between, it's an ism, Stoicism, but it's not the same thing as, as a full-fledged religion, cuz there's no like rituals or anything.
Right.
It's more of just when you interact with life, you're gonna be present. I'm gonna worry about the things I can control and that's it.
Well, it's funny that it shows up more places than you may think. So for example, uh, one of my major influences, so I've been in real estate since November 1998, and in February '99, I discovered the Mike Ferry organization and got coached there and I went there for 16 years. And so Mike Ferry would often say from the stage, keep your emotions between the lines, leave your ego at the door. You know, in hindsight, later when I read The Obstacle Is the Way, it was funny. I started connecting dots and not just from Mike, other mentors that I've had in these years in real estate. I realized a lot of what they were saying actually overlaps and enhances everything in the stoicism belief system. Yeah. And It almost was like a confirmation of what I had learned over the course of my career in real estate, even though it's not real estate specific, what is part of my faith. So it's funny, it's this overlapping of concepts. It almost gives weight to it.
Mm-hmm.
Not that it needs it, but if you're looking, you know, it can give you some confidence that there's substance behind implementing this for yourself.
And when you, and like for me, I, like I nerd, I, I nerd out on the, on the why, like, okay, what did he do and why did he do it? And if I, like, sometimes it's a curse if you ask that about everything in life, but, but for me it was like when you started digging into like, okay, Roman culture, what was it like? Greek culture, what was it like? How, like, how hard was the struggle to survive? Like, I mean, you had pestilence, you had disease, you had, you had all these things and that are a little bit different than us. I mean, we, we have some of that, but You know, our life expectancy is far longer than theirs. And so you got, you got people whose life expectancy is like half of ours now. And their whole thing is control what you can control.
Right.
And it's just like so simple. Like it's, well, you can't control whether you get sick, just you can control not going around sick people.
Yeah.
Like, but yeah.
And just trying to simplify life to where it wasn't, I didn't have to be in control of everything. Cuz at the end of the day, I'm not, but I would make myself anxious over, oh, I can't control that. I need to, you know, yeah, that was always the more I dove into it. Like I started on the Ryan Holiday. The only books I haven't read of Ryan Holiday so far are just the two kids' children's books. Planning on reading those someday to my grandkids.
Nice.
Yeah.
I mean, The Obstacle Is the Way is where it started. I think I read Ego Is the Enemy and I saw so many mistakes in my life. In that book. It's like, man, this is— I'm grateful for it, but I was like, wish it would've been earlier. Don't know if I would've heard it though. That's kind of the thing.
That's what I tell myself. I believe that the message, the material, and the awareness comes at the right time for each of us.
When the student is ready, the teacher appears.
There you go. Thank you for putting it far more smoothly. Yes, that you're exactly right.
I stole that from somebody else.
Yeah. It's, uh, but the, anyone that's listening to you and I talk right now, which I would imagine that there may be people that were drawn to this because maybe they are feeling anxiety or overwhelmed, or they are feeling disconnected from the path they're on. What would you recommend as a very small, very achievable, what's like a first action step someone could take to start moving in the direction they want to go?
For me, I mean, I, that, that just takes me back into a, into moments where I was in that place. The advice I had to give myself is slow down, slow down. And that's easier said than done. But when your mind is spiraling, you know, there is an actual thing that I just learned from Tim Ferriss on his most recent podcast I saw, and it's called Morning Pages. You ever heard of doing Morning Pages?
No, tell me.
So Morning Pages is just this exercise where when you get up, you just start writing everything down in your brain, no matter what it is. There's no judgment that it's not good, it's not bad. You just write it and write it and write it. It's a brain dump in the morning. And he called, he refers to it as spiritual windshield wipers, but it basically just like clears your day to where then you just start showing up and the stuff that was worrying you, because our brains are just like, they're amazing, like computers and they, and they process so much information. And there's stuff going on. We call it the subconscious, but there's stuff going on. And once you start that habit, some days you're going to have a bunch, other days you're not going to have as much. What I've started noticing, and I've only been doing this for like 3 or 4 weeks.
Okay.
But I've like, I've noticed that there's days where I don't have that much and I'm like, oh my gosh, I've actually started to hit a point to where I've cleared so much out from inside. That anxiety, the stuff that creates anxiety, that's nonsense. I don't remember what the statistic was, but I think Seneca or one of those guys even talks about like the majority of the disasters we create in our mind, like only 2% of the time does it ever even come to fruition.
Right.
So that's basically what morning pages is, is dump all that stuff and then just show up. I mean, that's the biggest thing. Show up for your kids, show up for your job, show up in your relationship in the best way possible. Show up for yourself.
Yeah. I'm very neglectful of that part. I like that. So he's taking free writing and he's taking free writing in the morning, brain dump style with no editor and no filter. Nothing's right or wrong. It's just coming out. You're making the connection. I hope everyone listening knows there's a stronger connection between handwriting and our subconscious mind than keystrokes, right? So that's a known. And, um, I'm very intrigued by that. I'm going to dig up his, that episode. It's taking, it's taking things that I coach to and things that I do myself, but putting it in a different time and a different manner. And so I'm very intrigued by that. And I think I'll be having a March experiment playing around with that. So thank you for sharing that.
Yeah. It's, yeah.
When you finish writing it, does he recommend that it's all in one book and you keep it? Do you fold it up and put it in a box? What do you do after you're done writing? Is it journal style or is it?
You know, I don't, I don't know whether or not he goes back through it or not. Cause I, cause I do a couple things for my own. So I do a one line a day. I have the 5-Year One Line a Day Journal.
Nice.
And then, but I do that afterwards now.
I was, I've been doing that for a little bit and that one is, you know, that one's made to look back at how far you've come.
Right.
The brain dump, because I, I just started, I, I don't, I'm planning on looking at it. I always, I always notice, I can notice when I look at my writing how I feel based on my penmanship. So if, if my penmanship is very clear, I was very calm. If my penmanship is, looks like a doctor writing a prescription, then it's usually coming out of a place of like stress.
So I, I haven't really gone back for me. It's, I do it on an I do it on a reMarkable.
Um, okay, cool. Okay.
Yeah, I, I started that like in November.
I, I got a reMarkable and I started actually using that cuz I had a, I, I had a regular notebook and, and like you said, there's a lot to, even in this day and age, big AI guy, there is a lot more to writing things down and the brain connection and your brain actually has to process it, put it out. That's right. As opposed to typing.
Well, I wanted to ask you, you mentioned feelings there again. So some people, because some, believe it or not, I get into conversations with people about Stoicism and some people think that if you are Stoic that you're not passionate or you're not energetic. They have this belief that Stoics are the dead fish on the ice, you know, laying out in the fish market. Like, could you address, have you ever encountered that? Has someone said like, oh, well then you must not have any fun or you must not That's not what it means. In fact, I think it means the opposite because by staying present in the day, the hour, the moment, staying present and connected to your own self and your own spirit and energy and that of anyone who's around you, knowing that you impact them just by your being, right? Um, I actually think sometimes for me, there's been more joy, but have you run into that belief where, or, you know, misconception that people have, and would you address that in any manner?
Yeah.
I mean, the, I was accused of being, I was accused by even in conversation with my wife about just kind of being even emotionless before, before I got into stoicism. But it, but even in that, like, I, I still have moments of outbursts. I still have, it's not like you just completely eliminate emotions entirely. It's the understanding that usually, so like, Passion, passion and hope for me, like, like when you, when you dive into those things, hope and fear are two sides of the same coin.
Yes.
You ever read Viktor Frankl's Man's Search for Meaning?
Absolutely.
The people who didn't make it, they're the ones who had hope they'd be, they'd be home after, you know, like December, like by January 1st, we're going to be out of here. And then they would just give up.
So it's, it has more to do with how you interact with your day. And I've, for me, I actually have way more of a connection to the to the present moment.
I think sometimes when we talk about passion and we talk about that, the energy of, you know, of doing things like we, we get too attached to, and I'm guilty of this, we get attached to the outcome.
So we're always focused on the future.
So our passion is about the destination, not the step we are on right now in today's journey.
And, and most of the time it's because people are like, well, that's not exciting. Well, actually the whole, that was the whole point. The whole point was who are you walking with today? Who was the person you interacted with today? There's so much value in our days. If we just learn how to squeeze life out of the day, I think you, most people that I've heard say that either know me really well and know that I need to lighten up or, or they're usually talking about themselves and it's It's the way they interpret how they interact with life. And it's typically get into the what, why conversation again. Okay, well, that sounds interesting. Why do you think that? And when you start listening to them, it's probably not even about you. It's about them. It's about something with them. And if you get them talking, get them, then they're going to end up in the present moment. They're going to be extremely like, that's almost like one of the most life-giving things you can experience is just a positive experience in the present moment and just a smile comes over your face, whether it's the Grand Canyon or cherry blossoms on a tree in a park. Like some of those things can just be absolutely breathtaking. And if you're, if you're too worried about having this energetic experience, you totally missed an awe-inspiring moment.
Agreed. Yeah. And if you are having anxiety and thinking about things 20 years from now, you can actually walk through cherry blossoms and really not see it or feel it or smell it or have the experience at all.
Yeah.
Yeah. We've all had times where we are driving home and we get so wrapped up in our thoughts that we pull in the driveway and we're like, to quote the Talking Heads, how did I get here? We're like, you know, you don't really remember the drive. Like how often is that happening and you're missing out on the cherry blossoms or your child seeing a butterfly, or, you know, you're missing that out because you're not, you're thinking about something that's 20 years away. It happened this weekend and we did talk about it. One of my, one of my clients has just been almost obsessing about how am I gonna pay for my daughter's wedding? They're 2 and 6. I'm like, take out a line of equity on your home that you're gonna own 20 years from now. You know, like, I, I don't know, but is that something you need to solve for today? No. I gave her like 3 options and I was like, let's get back into today. So it, it's funny. And by the way, brilliant woman, you know, it's all of us can fall victim to it. We can all, all of a sudden be like, wait a minute, what about when I'm 81? Okay. Well, A, hope you make it to 81 and you're living how you wanna live. You don't need to figure out anything else about that today. Right.
Most 81-year-olds worry about the next 12 hours.
Yes.
Yeah, that's right.
Yeah. So today start living like an 81-year-old and start thinking like someone from thousands of years ago and everything will be better. Right.
And I, and I, you know, I shouldn't pass judgment on 81-year-olds. I haven't reached that, that yet point to do that. But yeah, it's, it's one of those things where it's like, how many things did you assume? To that example about, you know, your daughters are 2 and 6, and if you have that anxiety and it's, it's not that, that's even one of those things where you can just like sidestep the anxiety, let it brush past you.
How do you even know that those two are going to get married?
When they're going to get married?
I know it was something that created just this stumbling block for her that was, you know, just not— it's funny. It's an example that happened recently. So it can happen to any of us. So just be on alert.
It happens to us all the time. I mean, we all have that stressor.
That's just an example.
We all have those stressors. I mean, it, like in those examples, like one of the things I've found is the most Is the thing that, that alleviates it. Like my thought would be, okay, do the math. They're 2 and 6, they're gonna get married, call it 28. That's, you know, 26 and 22 years. Do the time value of money.
That's what I did.
How much is it gonna cost?
That's what I did with her. And, and I even said like, well, what about schooling? They've got that covered. So here's what's funny. Like she is confident about college options. Yeah. And this got in her mind. And so yeah, it's very funny. But it's, um, the tying back to that first question I asked you, what's gonna steal more joy? Being worried about something that far off that we have no idea that that's so far off. We have no idea of what is going to happen or what they would want, or even what society's gonna be like then. We don't really know.
Right.
Which steals more joy, that worry she had in that, and she's excited that she got over it. Now she's laughing at herself in a powerful way, a joyful way. Right. Yeah. Um, or being present in the moment. So it's, it is something that I am hopeful that more people in our society will take the time to, A, if they're not familiar with what you and I are talking about, they may decide to pursue it. I do think that Ryan Halliday's books are a wonderful digestible first step into checking this out. If you have some other recommendations, I'd love for you to share them. And you did mention some other books that you're currently reading. I'm going to put those in the show notes as well. Anything you would recommend if someone's like, what are they talking about though? I wanna dive into this. Do you have anything else that you would recommend?
One book that is written by Kate Bakewell, it's, it's the, it's about the life of Montaigne, who was a French philosopher and French philosopher, Stoic. It's along those lines, but it's called How to Live or The Life of Montaigne. She basically. Has studied Montaigne and I didn't know who Montaigne was until I heard this book suggestion. I think it was from Holiday. It was on a podcast. And she takes 20 questions and answers the question, different questions about life from the perspective of Montaigne, how he did it. It's, it's just a, it's a great book because it just approaches life in all these different ways. And it just kind of, I'm only like, I think 13 chapters through it, but I, I pick it up and just read a chapter maybe once every 2 weeks and mostly just to digest it, just to kind of enjoy it as opposed to crank, you know, crank through what I, what I read for work.
But, right.
That's one. And I mean, if you haven't read Holliday's, the, the Four, the Stoic Virtues series, I recommend that. It's an easy read. It's got tons of, tons of applicable stories. I always promote that as things to read. What is another one of the books that I've read? I love, uh, I love history books. I'm reading a book on Roosevelt called River of Doubt right now. That's Teddy Roosevelt, not FDR. Okay.
I was just about to ask which one, which Roosevelt.
Yeah.
Yeah.
Ted Roosevelt, more of the exciting, I mean, FDR was cool, but more of the exciting guy that, you know, hunted bears and—
right.
But the river, the River of Doubt's about his expedition when he, he lost the race. He lost the presidential race when he was trying to go for his third term and he ends up going on a trip down in the Amazon. Almost, I think he almost dies. I've only read like half of it, but that's a really good, quick digestible book. I need a growth book though. If you know, one of the things that I like about Seneca's Letters of a Stoic is it's digestible and he's writing back and forth to someone. So it's almost like you're reading, you can read it in a way that he's like, he's writing to you. Kind of.
Right.
And if you haven't read Epictetus' Discourses, I, those things are, those things are so good at just putting you into perspective, especially if you know who Epictetus was and he was a slave and his slave master broke his leg and he suffered so much. And then he becomes a free man after 31 years of being enslaved. And, and you just listen to this guy address life the way he does and you're like, wow. Like, wow. I wish I had that patience.
Well, thank you for sharing all of those. I was thinking you and I could probably talk about this for quite a long time.
Oh yeah.
Because even as you started talking about Ryan Cadwell's book and started referencing French philosophers, then I was thinking, ooh, you and I could have a conversation about existentialism versus stoicism. We could probably have a great time talking about that. I want to And extend to you now, invited to return to the inner estate if you would like to, because that could be really interesting. I actually, on occasion, which is funny, cuz I'm a, I'm a woman of faith. I do embrace and love the power of Stoicism's approach to life. But honestly, every once in a blue moon, I do have a bout of existentialist crisis or whatever, you know, so. Proving I'm a human and not a robot. So this, I, I found this very intriguing and I love that you shared with us that this has shown up in your business, business decisions, investing decisions. Your clients are benefiting from it. Your family's intrigued by it from what you've said and also benefit, right? And I just wanna thank you for being our guest today on The Inner Estate and being vulnerable and sharing those things. And if you are listening to this episode of The Inner Estate, I hope you will also come back and join us again for another episode. Ryan, thank you so much.
Thank you for having me, and I will gladly come back. That sounds like a great, a great episode talking about that.
That would be a fun conversation. I would really enjoy that. Again, wherever you're consuming this podcast, you can connect with Ryan by going to the description. What is your best way for people if they do want to reach out to you? Do you have a platform you prefer?
LinkedIn is usually the fastest way to grab me or, or our website, resolutrdm.com. My name is Ryan Cadwell.
Thank you so much. All right.
Yep.
Thank you and have a great day.
More from Ryan


Multifamily Investing in 2026: How Smart Investors Create Cash Flow and Wealth | Ryan Cadwell
Part 2 ft. Ryan Cadwell - Exit Strategy First: Why Most Investors Build Backwards: Exit Strategy First: Why Most Investors Build Backwards
FLA 213 - Ryan Cadwell - Top Lessons From $100 Million Real Estate Investor and Developer
POWC # 860:From 150 Flips to 252 Duplexes: How Not Overpaying Drives Success | Ryan Cadwell
Ryan Cadwell on Real Estate Development, Property Management, and Why Relationships Matter Most
The $100M Mistake: Why Investors Confuse Market Price with Investment Value with Ryan Cadwell