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The 3 P’s of Reducing Common Financial Regrets – Episode 164

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Will You Regret Not Saving Enough Money for a Good Retirement?

On this episode of Dentist Money™ Reese and Ryan get philosophical as they discuss a list of typical regrets people feel when they get older. No one wants to feel regrets, but somehow everyone ends up with at least one or two. With so many people experiencing disappointments tied to finances, Reese and Ryan offer their advice on why it’s crucial to have a good savings plan in place as you prepare for your future.

Listen to learn how to live your life free from financial regrets. 

Podcast Transcript:

Reese Harper: Welcome to the Dentist Money Show. I’m your host, Reese Harper. Ryan and I spent some time today talking about the five biggest regrets of the dying. It was interesting to see about how people felt when they were at their death bed about things they wished they would have gotten around to in life. We tried to take these perspectives, and couple them with financial habits that can actually help you overcome those regrets. We hope this episode serves you well for the upcoming year, and helps you see some financial habits that’ll reduce your level of regret as your life passes.

Reese Harper: Make sure and visit us at, and check out our education library. You’ll find a lot of videos, podcasts, and new articles that we’re releasing every week. Also, when you go to the website, don’t forget to book a free consultation, clicking the Book Free Consultation button, where you’ll be paired with one of our dental specific financial advisors on a day that works for you. We book appointments on off days, lunches, even on some Saturdays. Just check out the calendar and find a time that’s convenient.

Reese Harper: Call us anytime at 833-DDS-PLAN. You can also text us at the same number. Don’t forget to submit your financial questions on our free Facebook group at We take the questions from the Facebook group and use them in the podcast. Thanks again for listening, and enjoy the show.

Speaker: Consult an advisor or conduct your own due diligence when making financial decisions. General principles discussed during this program do not constitute personal advice. This program is furnished by Dentist Advisors, a registered investment advisor.
This is Dentist Money. Now here’s your host, Reese Harper.

Reese Harper: Welcome to the Dentist Money Show, where we help dentists make smart financial decisions. I’m your host, Reese Harper, here with my trusty old co-host, Sir Ryan Isaac.

Ryan Isaac: And I do not regret being here today.

Reese Harper: You never do.

Ryan Isaac: I never regret being here. Regret being here.

Reese Harper: Is that a segue because that was a quick segue? I like it.

Ryan Isaac: Today we’re going to talk about regret, but I’m going to ask you a question. I did some polling on my massive social media networks. I have pretty extensive networks.

Reese Harper: Going viral.

Ryan Isaac: Yeah. I’m always going viral every time. So, I asked this question, what type of regret do you feel like you regret more in your life? I’d be curious to hear what you say. Is it the regret of something you did, or something you never did, but wish you had done? What do you think is a stronger regret?

Reese Harper: For me, it’s definitely the things I wish I would have done, but-

Ryan Isaac: You regret a lot of things you’ve also done.

Reese Harper: Well, I was going to say I feel like every time I have something I want to do, I tend to do it, and then they don’t always work out.

Ryan Isaac: Yeah, that’s fine.

Reese Harper: So, I regret some things, but it’s not because I haven’t done anything I’ve ever wanted to do that I didn’t do.

Ryan Isaac: Okay.

Reese Harper: It’s because if you actually play out that logic and do all the things that come into your mind that you wish you would do,-

Ryan Isaac: Yeah.

Reese Harper: -you realize after you’ve done them, some of them end up being bad ideas.

Ryan Isaac: They weren’t all great ideas. And then you have that regret.

Reese Harper: Yeah, I think that that’s the interesting thing.

Ryan Isaac: Yeah.

Reese Harper: I mean, I can’t… There’s not anything I’m like, “I wish I would have done that, but didn’t,” but there are things that used to feel that way, and I did them, and I’m like, “Oh, never mind.”

Ryan Isaac: But you crossed them off, though. Until you had, you felt that way.

Reese Harper: Yeah, and then I’m like, “I don’t really need that.” Or, “That wasn’t as cool as I thought it would be.” Or, “That didn’t actually help me,” or-

Ryan Isaac: Well, that’s… which is fine. I mean, then you got to experience it, or you did them and you’re like, “Oh, that was-”

Reese Harper: That’s a pretty strong driver for me, is to not have… I like to try things I’ve always wanted to do, or think about doing, or wish, wonder if I could do that. I like to do those things, and I typically don’t have… like if it comes at the cost of maybe experience, like money or success can wait, as long as I get to experience more stuff.

Ryan Isaac: Okay, so are there any you’re sitting on right now, like something you haven’t done, and you regret not having done that? Or have you crossed a lot of those off so far? You sitting on any, like waiting?

Reese Harper: No. I mean, not any huge ones right now. No. I mean, I think I wish I would have spent a little more time developing my song writing skills during college, because that would be fun right now. I feel like I’m-

Ryan Isaac: I’ve heard songs you’ve written.

Reese Harper: I feel like I’m working on that right now.

Ryan Isaac: Aren’t there videos on our website that you wrote the music to it?

Reese Harper: Yeah.

Ryan Isaac: At least there were at some point.

Reese Harper: No, there’s… the one on the elements page has a whole… I did like a Blade Runner, like the new Blade Runner, composition using doepfer synths.

Ryan Isaac: I don’t know-

Reese Harper: It’s really cool, like an old synthesizer?

Ryan Isaac: That’s on there?

Reese Harper: Yeah.

Ryan Isaac: It’s, elements, go to the elements page and it’s the elements video.

Reese Harper: Yeah, and the top video, I think it says, What is your financial-

Speaker 4: We’ll put it in the show notes.

Reese Harper: -It’s like what is your financial melody or element or something.

Speaker 4: Yeah. We’ll find it.

Reese Harper: It has me actually playing the piano, and I wrote all the music for that.

Ryan Isaac: Everyone go check that out. But, so you wish you would’ve… now I’m curious about this, because I’ve heard music you’ve written that’s poppy or fun or symphony or film scores. What would you have worked on?

Reese Harper: Probably choral arranging.

Ryan Isaac: Oh, that’s [crosstalk]

Reese Harper: I really, really wish I… because I like music that stands the test of time and that lasts.

Ryan Isaac: Okay.

Reese Harper: And like big orchestrations, choral pieces, they last a long time. And I like pop music too. I think lyrics and song, or like Bob Dylan songs that last forever –

Ryan Isaac: Post Malone –

Reese Harper: Yeah. He’ll be around for a long time.

Ryan Isaac: He’s a Park City resident, and he’s a Jazz fan.

Reese Harper: Yeah, I mean shout out –

Ryan Isaac: Yeah, shout out, for sure.

Reese Harper: But anyway, it’s not a huge regret, but it’s something like I think it would be –

Ryan Isaac: You wish you would’ve done that. Spent the time –

Reese Harper: I don’t know, like I did do that, though, I mean, but there’s… I wish that there’s some… I don’t have a lot of aspirations in my life, and the ones that I do have, I typically follow through with them and go do them –

Ryan Isaac: That’s cool.

Reese Harper: Because I don’t have a long list.

Ryan Isaac: Do you think that’s unique? Do you think that most people do that, like, I have aspirations and I just go after them, or do you feel like that’s kind of [crosstalk] most people don’t –

Reese Harper: No, no. Well, I don’t know. I don’t know.

Ryan Isaac: I don’t think most people do. I think most people remain –

Speaker 4: That’s not normal. That’s incredible, but that’s not normal.

Ryan Isaac: Yeah.

Reese Harper: That’s not normal?

Ryan Isaac: It’s not normal.

Reese Harper: Because for me, I feel like there’s been many times where I’m like, this is probably not a good idea, –

Ryan Isaac: But I’ve always wanted to try it.

Reese Harper: But I want to do that, and so the experience of having done it is more important than whether it’s a good idea or not.

Ryan Isaac: Cool. Yeah.

Reese Harper: When I was at Northwestern Mutual working financial services there as like a life insurance agent in 2003 –

Ryan Isaac: Yeah. Call it what it was.

Reese Harper: Okay? They get… my card said financial advisor, but I was not that.

Ryan Isaac: Yeah, yeah.

Reese Harper: All right? And I remember feeling like the primary driver for me to want to leave and start this business… what became this business –

Ryan Isaac: Yeah.

Reese Harper: Was I didn’t know what it was like to carry someone else’s payroll. I was so… I wanted to know the feeling of like, what does it mean to not get paid and pay someone else.

Ryan Isaac: Oh.

Reese Harper: I just wanted to feel that.

Ryan Isaac: Wait, you wanted to feel that?

Speaker 4: I was going to say, that’s also not normal.

Ryan Isaac: That’s also not normal.

Speaker 4: Yeah.

Ryan Isaac: That’s also very abnormal.

Reese Harper: But I was like, what if you go your whole life, and you never know what… I mean, I just, for me –

Ryan Isaac: Gladly. Sign me up.

Reese Harper: Yeah.

Speaker 4: I have no desire to do that.

Reese Harper: I was like, I just wanted to know what it felt like to say like… It felt so scary to me, and it felt so risky, so uncomfortable –

Ryan Isaac: Yeah, I like that. That’s cool.

Reese Harper: I was worried about it. I just thought, I don’t want to spend my whole career not knowing what it felt like, so I thought –

Ryan Isaac: I can relate to that.

Reese Harper: I can’t… and I couldn’t do that at Northwestern, because –

Ryan Isaac: That’s not the business model [crosstalk]

Reese Harper: It wasn’t the business model.

Ryan Isaac: Yeah, you can’t do that.

Reese Harper: And it grew into other things. But I guess I just saw a friend of mine who left college and got a loan and did that, and I thought –

Ryan Isaac: Oh, cool.

Reese Harper: Man, I could never do that! That would be so scary! And I was writing music for the time, making like $500 a week, and I thought, what if I could hire another person to help me write music, and what would that feel like? Would that be scary, and how would that change my life?

Ryan Isaac: Crazy!

Reese Harper: You know? And I guess I just wanted that experience because I knew that if it was that hard and that scary for me, then it would probably actually be a positive thing down the road. I would learn a lot from that.

Ryan Isaac: Yeah, you totally… So, I was actually, I don’t know why, at a stoplight last night thinking of the name of your media company.

Reese Harper: Do Re Media.

Ryan Isaac: Yeah, that’s what it was, right?

Speaker 4: That’s so good.

Reese Harper: I worked on that logo for a while. Nate Dyer [phonetics] right now up in Oregon, best friend from high school, worked on the logo with me.

Ryan Isaac: Do Re Media.

Reese Harper: Yeah.

Ryan Isaac: Is it still in existence?

Reese Harper: Yeah, and shout out to my friend Russel Jack [phonetics], who was kind of… I guess we were partners at the time. We made a few music songs together.

Ryan Isaac: That’s so cool!

Reese Harper: So –

Ryan Isaac: Okay, so I’ve just been really interested in this subject of regret. I’m 39 years old in a few months, four months. Jeez! I’m getting close to 40. I’ve been calling myself almost 40 for a couple of years now.

Reese Harper: You’ve had some regrets I’ve heard you express, but then I told you that you actually realized those things, and you were like, oh, yeah! I don’t have that regret anymore. Do you remember this?

Ryan Isaac: Yeah. This was when we were talking about dream career stuff?

Reese Harper: Yeah. You said like, one day I want to be on… I wish… it would have been so cool to be a writer, like on Conan –

Ryan Isaac: I want to sit on a team of smart, funny people and write things for like shows.

Reese Harper: Yeah. It was like, you threw out like Conan, or you threw out like a late night show –

Ryan Isaac: Yeah, Conan and Jimmy Fallon, yeah.

Reese Harper: Colbert, and –

Ryan Isaac: He’s too smart for me.

Reese Harper: And I was like, Dude, that’s what you do.

Ryan Isaac: Isn’t that what this money show is?

Reese Harper: You write funny stuff with a team of smart people and you deliver it every week.

Ryan Isaac: That’s really cool.

Reese Harper: And I was like, that’s awesome.

Ryan Isaac: And it’s not a regret.

Reese Harper: You see, your subconscious like played out and it became your reality, and you didn’t even know that you were like –

Ryan Isaac: Didn’t know.

Reese Harper: I was happening.

Ryan Isaac: I’ve been really interested in this. I think it’s my midlife crisis. I think it’s having my oldest daughter be a teenager. I still see her as this little chunky-faced 4 year old in a Tinkerbell tutu that used to dance around and color pictures at the table.

Speaker 4: Aww!

Reese Harper: Except she slaps you around now and tells you what to do.

Ryan Isaac: She’s a very sweet girl. No slapping around. But instead of Tinkerbell tutus, there’s bras on my floor, you know?

Reese Harper: Okay, yeah.

Ryan Isaac: And there’s like math homework that’s hard, and it’s just like this point in my life I think a lot of people you get to it and it’s like, all right, I’ve still got some time, but I don’t have all the time, and am I on a path where, am I going to regret anything? Am I on a path… Am I doing things right now that I’m going to regret, or I’m not doing things I’m going to regret not doing? I’ve been really fascinated with that subject for a few years now.

Reese Harper: Yeah, yeah.

Ryan Isaac: Anyway, along that kind of path, I found a book that came out, it was probably about five years ago. There were some articles that got written about it that were really famous, and it’s called The Top Five Regrets of the Dying. If you ever read this book, I would highly recommend listening to it. The author has the most serene Australian accent. Her name’s Bronnie Ware, and she narrates the book.

Reese Harper: That’s cool.

Ryan Isaac: And it’s a collection of stories. Her own story’s amazing. She was a… she lived in Australia, grew up on like farms. She’s a vegan that grew up on a meat farm.

Speaker 4: Ouch!

Ryan Isaac: Her family business was meat.

Reese Harper: Did she know… How young was she when she knew she was a vegan?

Ryan Isaac: In her young 20s.

Reese Harper: Oh, okay.

Ryan Isaac: And she even kept working at these jobs. Anyway, she was in banking, and she’s a musical artist, but eventually she ended up taking a job in, they call it palliative care. You just go live with people who are in their last months of their life, with terminal illness and diseases. She did that so that she could sell all her possessions and not have a mortgage and work on her musical career, –

Reese Harper: Uh-huh (affirmative).

Ryan Isaac: Which she eventually one day produced an album. But during this time, she just got to know… she would just sit in the house with these dying people and would get to know their stories, get to know them like extremely personally, you know? And so the book is about the collection of these five top regrets that she kept hearing get repeated from people over and over. And it’s interesting, as I’ve seen these, I don’t relate to all of them. Not all of them are regrets I could see myself having, because it’s not my personality, but some of them I could, and as I read this book, I was like, yeah, that’s really interesting. I wonder which ones I’m on a path to regretting in the future.

Reese Harper: Yeah.

Ryan Isaac: And so I’ll read these top five here. I’m curious if you relate to any of these.

Reese Harper: I’m sure I will, personally.

Ryan Isaac: The number one most common thing that her patients said to her was that I wish I’d had the courage to live a life true to myself and not the life others expected of me. And the stories behind these… these aren’t just like, she didn’t just list these. She tells the stories of these people personally. It’s pretty heartbreaking, actually.
Number two is –

Reese Harper: Well, let’s pause at this one. Let’s take them slowly –

Ryan Isaac: Okay, great.

Reese Harper: Because, the first one you’re saying, in other words, people wish they would’ve done what they wanted to do or be who they wanted to be. Like, I do think… I would imagine that that’s a large regret for the majority of the population, you know?

Ryan Isaac: Yeah.

Reese Harper: I do think that as humans we have a tendency to not appreciate the present –

Ryan Isaac: For sure.

Reese Harper: And embrace what we do have.

Ryan Isaac: Oh, yeah.

Reese Harper: And we tend to put a higher priority on what we don’t have –

Ryan Isaac: Yes.

Reese Harper: So that this whole idea of like, I wish I would’ve lived a life that’s true to me, part of me sometimes wonders what the alternative would have looked like for people, because –

Ryan Isaac: What could you have done about it?

Reese Harper: I feel like there’s a… like the Book of Joy, the Dalai Lama book that I really like that he published with Desmond Tutu last year, it talks a lot about embracing… like letting gratitude kind of be like your primary filter for how you see all the experiences that are happening around you, and I don’t know that our lives are… I feel like at least in my own life, I could look at my life and have consciously… you could have two points of you on it.

Ryan Isaac: Oh, yeah.

Reese Harper: Either I’m living the best life that I can, given all the choices I’ve got, and I’m making these –

Ryan Isaac: Circumstances, yeah.

Reese Harper: – choices to be true to myself on an ongoing basis, or there’s always this kind of like –

Ryan Isaac: It could’ve been better.

Reese Harper: This could’ve been something totally different. Like, what if I just chose to be a professional musician?

Ryan Isaac: Yeah.

Reese Harper: Or what if I just chose to be a writer?

Ryan Isaac: Be a surfer! I wanted to be a surfer my whole life.

Reese Harper: Yeah.

Ryan Isaac: I just wanted surf hair. I clearly failed that [crosstalk]

Reese Harper: I’ve thought like, I love design, so what if I should’ve just been a software engineer, or maybe, why not be an attorney, like, because you know –

Ryan Isaac: I like to debate things!

Reese Harper: I love debating!

Ryan Isaac: Yeah.

Reese Harper: Like, you could allow yourself to drive yourself crazy about who you’re not as well.

Ryan Isaac: Yeah.

Reese Harper: I just think it’s a normal regret to have, I think, is like, I wasn’t true to myself. I’m just not sure that’s objectively true.

Ryan Isaac: I have a quote from the author that touches on that point, because I think that’s totally true. There’s this fine line between having hope and optimism for something in the future that you’d like to become or achieve, right?

Reese Harper: Yeah.

Ryan Isaac: But, at the same time, not discounting what you have today, because you might not have tomorrow.

Reese Harper: Yeah.

Ryan Isaac: It might not be there.

Reese Harper: Yeah.

Ryan Isaac: There is no promise of that.

Reese Harper: Yeah.

Ryan Isaac: And so there’s this fine line between like having optimism for something else, but not feeling… you know, not lacking gratitude for what you currently have.

Reese Harper: Yeah, and like at the end of every day, it’s important to be able to put your head down on the pillow and kind of feel like what you had was enough.

Ryan Isaac: Yeah.

Reese Harper: Like, could you… And I don’t often find that it’s the achievements that lead you to a place –

Ryan Isaac: No, no.

Reese Harper: – where you’re like, now I’m successful.

Ryan Isaac: No.

Reese Harper: It’s just usually that moment of gratitude where you’re like, man, this has been really good. And it usually takes comparing… seeing all the things that you do have and recognizing that, you know, probably the majority of the population doesn’t have those things that you do have at this point.

Ryan Isaac: Yeah, right.

Reese Harper: Some people… I mean, it’s amazing how people in poverty-stricken circumstances in third world countries carry a higher sense of measurable happiness than a lot of the people in the United States. I think it’s just an important thing.

Ryan Isaac: Yeah.

Reese Harper: So anyway, that’s your first point.

Ryan Isaac: First one. And the second one is, I wish I hadn’t worked so hard. And that was a sad story. It was this guy named George and Margaret. This couple, they raised four great kids and had grandkids. They were in their 60s when their kids left their house, and they were a very, very wealthy family. He was a very successful guy that owned his own business. He was kind of addicted to his working, though, and she begged him for like 15 years, all through their 60s into their 70s to just finally give it up so that they could… They had all this money, and they lived in this giant house that was empty now that they could like sell and they’d be fine, and for 15 years, and then finally one conversation just happened to be a little bit more emotional. He was getting older. He said it was the first time he ever realized that he actually didn’t have a lot of time in front of him, so he was like, okay, one more year. I got one deal in the works right know, one more year, and seven months later his wife had passed away. She got sick like three months after that, and then she was in critical care, and then died three months shy of that goal.
Then he kept living. He was in really good health, and he lived the rest of his… kind of just always… you know, he kind of got to a place of acceptance, it was what it was, and they were who they were, and they just did the best that they could, but he kind of lived through his retirement thinking like, man, we could have been laughing or traveling or having fun, or all these things I could’ve done that we… you know? That was his regret.

Reese Harper: Yeah.

Ryan Isaac: Wish I hadn’t worked so hard.

Reese Harper: That’s interesting. So, wait, so –

Ryan Isaac: And he… I’ve got some…

Reese Harper: Go ahead.

Ryan Isaac: I was just going to say, this is from him, these are his words. He said, there’s nothing wrong in wanting a better life. Don’t get me wrong. It’s just that the chase for more and the need to be recognized for our achievements and belongings can hinder us from the real things, like time with those we love, time doing things we love ourselves, and balance. It’s probably all about balance, isn’t it?

Reese Harper: Yeah, I mean that’s the trick is… I think this can be an extreme condition, and I do think the majority of the working population suffers from the challenge of turning work off –

Ryan Isaac: Oh yeah.

Reese Harper: – because it is a [crosstalk]

Ryan Isaac: It follows us everywhere.

Reese Harper: Well, you have 168 hours per week of time, right? I mean, that’s your weekly allotment of time.

Ryan Isaac: Yeah.

Reese Harper: Now, the bulk of that has to be spent –

Ryan Isaac: Sleeping.

Reese Harper: Sleeping. I mean –

Ryan Isaac: Yeah, shout out to sleeping, though.

Reese Harper: Let’s say eight times seven, you have 56 hours, so roughly like 100 discretionary hours. 50 hours –

Ryan Isaac: 50 hours are eating.

Reese Harper: 50 of those hours you’re –

Ryan Isaac: Work.

Reese Harper: – working, and the other… Let’s say you have two to three hours, maybe two hours a day of eating, you know, between… Not me, [crosstalk] I’m like 10 minutes a day, but

Ryan Isaac: [crosstalk] like five hours.

Reese Harper: – I eat while I work.

Ryan Isaac: Yeah.

Reese Harper: But you know, what I’m saying is there isn’t actually a lot of discretionary time for anything but work and eating, and then basic home cleaning and keeping up with your crap, and then going to bed.

Ryan Isaac: Yeah.

Reese Harper: And so, what I’ve found in my own life is I’ve had to… as my life’s gotten more complicated and busier, I spend kind of an insane amount of time planning for the balance thing.

Ryan Isaac: Yeah.

Reese Harper: So the balance… Like, if I don’t schedule, like I’ve scheduled a trip to go with my kid tomorrow and Friday to Jackson Hole, and it’s been on the calendar for a year.

Ryan Isaac: Yep.

Reese Harper: And then I have to do one thing a month like that well in advance and block it out, or it won’t happen.

Ryan Isaac: Or else it won’t happen.

Reese Harper: And the same thing with like if I want to go to a Jazz game, or I want to go to a PAC-12 championship game, or I want to go skiing, or anything I want to do –

Ryan Isaac: Gotta be on the calendar.

Reese Harper: – if I don’t plan it in well in advance and be protective of that, it won’t happen. Because there’s just a constant pressure… like every day I say no many times to things that will jeopardize those things that are scheduled that are my balance kind of things.

Ryan Isaac: Yeah.

Reese Harper: And I don’t get out a ton, but I travel on a schedule, and I try to… and it’s something that I barely started, like maybe a few years ago.

Ryan Isaac: It’s pretty recent.

Reese Harper: And I don’t think I have –

Ryan Isaac: Same with health –

Reese Harper: Yeah.

Ryan Isaac: Prioritizing health and scheduling health and activity.

Reese Harper: And I don’t… I think it’s… It really is hard to get to that point, though, and I still don’t do it really well.

Ryan Isaac: Yeah.

Reese Harper: But I’m just saying it wouldn’t have even happened ever in my life without scheduling. I don’t know that people prioritize scheduling that stuff in.

Ryan Isaac: No, I agree with that, and it’s the double-edged sword of success, too, because the more success you have and the more means you create to enjoy those things, the less time you have to actually enjoy those things.

Reese Harper: Enjoy them. Yeah.

Ryan Isaac: And if it’s not scheduled and it’s not regimented, it’s not going to happen.
Number three was, I wish I’d had the courage to express my feelings. I don’t think I’ll ever regret that. I don’t think you’ll ever regret that. It wouldn’t be a regret you’d have.

Reese Harper: It might have I think 10 years ago.

Ryan Isaac: Huh.

Reese Harper: I think I –

Ryan Isaac: I feel like you’re a pretty expressive person.

Reese Harper: But I think it takes a lot of practice. Like, I see a lot of people who struggle to communicate what they feel and say what they feel and –

Ryan Isaac: The stories of this one were heartbreaking, too, because they were stories of parents and children and parents who regret that –

Reese Harper: That’s where I think it –

Ryan Isaac: – never having said like, I love you, or I’m proud of you.

Reese Harper: Yeah. I think that’s a big challenge.

Ryan Isaac: Those were tough stories, many.

Reese Harper: And I don’t think you… Again, that’s a practice thing. Like, it felt kind of artificial to me to have to start to develop that skill sometimes. I mean, it wasn’t super natural for me to compliment. They say you’re supposed to compliment five times for every one time you give constructive criticism, and I was definitely swapping that. I was like –

Ryan Isaac: Five to one?

Reese Harper: Yeah. I was criticizing five times and complimenting one time. And I found myself like, man, that’s a lot of like… because I think of constructive feedback a lot –

Ryan Isaac: Yeah, how do I fix something.

Reese Harper: – but I don’t think to compliment as often, and it takes –

Ryan Isaac: It’s practice.

Reese Harper: – an effort. You have to be like, okay it’s compliment time.

Ryan Isaac: Yeah.

Reese Harper: And it’s sincere, but you won’t naturally compliment as often as you think –

Ryan Isaac: Yeah, you do less than you think you will.

Reese Harper: Yeah, especially with parenting.

Ryan Isaac: I was just going to say, since I live in my house with five women, my life is very verbal.

Reese Harper: Uh-huh (affirmative).

Ryan Isaac: That’s actually felt like something I’ve learned from being around verbal people is constantly just like expressing something that you think like, oh, they probably know about that, but saying it? Because they don’t, and they’re like, oh, thank you. You know?

Reese Harper: Yeah. It’s important. What’s number four?

Ryan Isaac: Number four is I wish I had stayed in touch with my friends.

Reese Harper: Okay.

Ryan Isaac: And number five is I wish I had let myself be happier. And I think that goes back to your point earlier about, like look, have optimism, have hope, have goals and dreams, but you might not even get tomorrow.

Reese Harper: Yeah.

Ryan Isaac: So, how do you be happy about what happened today, and it’s probably not your things, and it’s probably not your achievements and your recognition. It’s probably like little moments with people you care about that actually will create that happiness. And letting yourself be happy is just maybe more just recognizing that it was a good moment with a person you care about.

Reese Harper: Yeah. I like number… Dude, honestly, of all those five, I think number four to me resonated the most.

Ryan Isaac: I wish I had stayed in touch with my friends.

Reese Harper: Yeah.

Ryan Isaac: You feel like that’s a regret you could have?

Reese Harper: Yeah. Like –

Ryan Isaac: Because you haven’t maybe made time for that. It’s been hard to do.

Reese Harper: I don’t know that I have friend regrets. Friends to me are like… Friends are difficult to maintain relationships with unless it’s convenient sometimes.

Ryan Isaac: Yeah. Well that’s adulthood.

Reese Harper: And adulthood is –

Ryan Isaac: It’s tough to do all the time.

Reese Harper: I feel like I’ve always had good friendships, but they’ve changed over time. Friends tend to be –

Ryan Isaac: Yeah, ebbs and flows and –

Reese Harper: But the people that I wish I would’ve stayed in touch with are more family.

Ryan Isaac: Hmm.

Reese Harper: Like extended family –

Ryan Isaac: Oh, interesting.

Reese Harper: – or people that really did have a meaningful impact on my life, even like peers, mentors, people that have helped me, people growing up that maybe helped me a lot.

Ryan Isaac: Yeah.

Reese Harper: It’s sometimes difficult if they don’t live close to you and they’re a far ways away, it’s easy to let those kind of people fade, and I kind of… I feel like it’s sad to me that they might not know how grateful I am for what they did to help me get to where I’m at today –

Ryan Isaac: Interesting.

Reese Harper: – and I just hope they know that, you know?

Ryan Isaac: Interesting.

Reese Harper: And the town I grew up in and the high school teachers I had, and like I worry sometimes that a student comes and goes, and you wonder if you had an impact.

Ryan Isaac: Yeah. You’re one of hundreds, yeah.

Reese Harper: Yeah. And I think a lot… like for me, I carry a lot of gratitude for all those people.

Ryan Isaac: So that might be mixed in with the other one, too. I wish I had maybe not the courage to express my feelings. Maybe it’s just more of like the act of –

Reese Harper: It’s just time, man.

Ryan Isaac: – deliberately staying in touch with –

Reese Harper: Like, I don’t have time to plan for family time, and you know, having no regrets about time off and spending time with kids and all that and incorporating the extended people in your life that you want to build –

Ryan Isaac: It’s hard.

Reese Harper: It’s hard, I think. And I think I’ve just consciously said, until I get the family done, until I’m not sacrificing my close friends and my immediate network –

Ryan Isaac: Yeah. I’m going to pay attention to my child and my spouse first before my high school teacher.

Reese Harper: And if I have time, I’ll go back to the other people, but I just don’t… I never have really gotten to it.

Ryan Isaac: Yeah, that’s a really interesting thought. I’m thinking of a couple teachers that I really liked, like my English teacher.

Reese Harper: So those are the five regrets.

Ryan Isaac: Hey, I got a poem published when I was in seventh grade about a window washer.

Reese Harper: Really?

Ryan Isaac: Yeah, in a poetry magazine.

Reese Harper: I knew that. [crosstalk] future in poetry.

Speaker 4: Can we include that in the show notes [crosstalk]

Ryan Isaac: I got a link to it in the show notes. Okay, so the whole point of all this… It’s a very interesting discussion, though. I appreciate it.

Reese Harper: Yeah. Once a year we’re going to have a philosophy discussion like this. It’ll still have a financial tie –

Ryan Isaac: Oh, they’re coming. Here we go.

Reese Harper: But we just want you to let us be able to have a moment of like –

Ryan Isaac: We just want to reflect.

Reese Harper: – being able to reflect, and hopefully this has some impact, you know?

Ryan Isaac: Well, you know, money… I mean, money’s a part of our lives. It’s a tool, right? It’s a part of our lives that either will give us freedom to pursue a life we really want and a life regret-free as much as possible, or money becomes a thing that’s like a burden and a stress and an anxiety to us, you know? And there’s a lot of parts of our lives that… We’re very complex people, so there’s a lot of parts to our lives that you have to work on to make a happy, grateful, optimistic life that’s free of regret. But money’s a part of it, and that’s our job, right?

Reese Harper: Yeah.

Ryan Isaac: So, I thought today we could offer just having over the decade plus that we’ve been watching dentists make financial decisions and seeing the outcomes of those things, let’s just talk about… I came up with three habits or three key areas of dentists who seem to have less stress and anxiety and regret about their financial decisions, okay?

Reese Harper: Mm-hmm (affirmative). I think… and I want to hear those. I think some things are coming to my mind, too. I’d be curious. I haven’t seen your list, but there’s some financial principles or habits that I think help make these regrets less likely.

Ryan Isaac: Yes. Less likely. Yeah, that’s what we’re getting at. Like, three financial habits that’ll make your regrets less likely.

Reese Harper: Okay, let’s hear what yours are. We’ll see if maybe they’re all of mine, too.

Ryan Isaac: Okay, my number one was processes. I actually call these the three Ps of reducing financial regret.

Reese Harper: Okay, cool.

Ryan Isaac: Very catchy title.

Reese Harper: Yeah, I’m intrigued.

Ryan Isaac: I was a published poet, so…

Reese Harper: I’m intrigued.

Ryan Isaac: Okay. The first one is process, and the thought is that dentists who create processes in order to make important decisions, make important decisions, and they make smart decisions. They make better decisions. So, following a process to make a decision multiple times over your career life will result in better decisions than trying to use a strategy or a tactic individually to, you know [crosstalk]

Reese Harper: So, give me an example of that.

Ryan Isaac: Let me give you an example. Actually, I found a great example from our good friend Ben Carlson [phonetics] who had a wealth of common sense.

Reese Harper: Okay.

Ryan Isaac: He was writing an article on New Years’ resolutions, and he was talking about resolutions, but this still applies. He was saying resolutions don’t stick usually, because they’re tactics, not systems. They’re strategies, not philosophies. And he gave a few examples. He said a goal of losing 15 pounds is a tactic, but figuring out how to live a healthy lifestyle, that’s a system. A goal of running a single marathon requires a strategy, but becoming somebody who runs on a consistent basis requires a change in philosophy. You know, a goal of getting your finances in order is a nice idea, but automating your whole financial ecosystem requires a change in mindset. So, there’s this strategy or a process, you know?
For example… This is a great example, actually. We just got done running insurance rate for all of our clients. So last month, we helped analyze how much life insurance does someone actually need based on their spending and their debts and all their other assets, how much disability insurance they need, how much liability they should have if they ever got sued, and we gave them kind of like a formula, or a way to look at it from a formula.

Reese Harper: Yeah.

Ryan Isaac: Now, deciding on insurance is something that people do all the time, and usually when they buy insurance, it’s done in an isolated one-time event. Like, how much premium do I want to spend per month, and that’s kind of where it ends, right? So, like last month, we got to see for hundreds of people, give them like a process to analyze how much insurance they should carry, not a… what’s the limit of pain you feel paying a premium every month, and then we’ll just stop there. Is it 100 bucks? All right, we’ll see what that can get you. Like, here’s the process for determining what you actually need, and then implement it according to that.

Reese Harper: Yeah.

Ryan Isaac: That’d be a process. Another one would be, as we talked about recently, we’re in an investment market cycle that we’re seeing more volatility than we’ve seen in a while. So, how are you making decisions with your monthly savings? Are you withholding monthly savings because you’re worried about it? Are you continuing to save money? Have you pulled money out of markets? Are you leaving money in markets? Are you using a strategy just to react to something that’s happening now, or do you have a process that like when the stress and the pressure gets really high and you might tend to make bad decisions, you have a process to check yourself and run through a system instead of just like a tactic, you know?

Reese Harper: Yeah. I think that’s great. I mean, I think that’s really critical.

Ryan Isaac: Okay.

Reese Harper: I would –

Ryan Isaac: I was curious what you were going to say. Like, you had your list of things that were coming to mind for you.

Reese Harper: Well, I’d like to hear the rest of yours –

Ryan Isaac: Want to keep going?

Reese Harper: – before, yeah, I hear them. But I think as it relates to process, I would just say it can get difficult to understand how to implement a process when you don’t know how to design one.

Ryan Isaac: Yeah.

Reese Harper: I’d just say, something is a process if it is something that you have habitually implemented in your life that is repeatable, you know? That’s a process.

Ryan Isaac: Okay. That’s repeatable. And I was going to point in to episode 156, if you go to, episode 156 is Three Critical Ingredients For Your Decision-Making Recipe.

Reese Harper: Yeah.

Ryan Isaac: We did a whole episode on processes.

Reese Harper: Yeah, and I just think there is going to be a… you have to kind of put some ground rules in place that are repeatable and that you can stick with. That’s a process, you know?

Ryan Isaac: Mm-hmm (affirmative).

Reese Harper: And I just feel like most people don’t have that with financial planning.

Ryan Isaac: Yeah.

Reese Harper: They tackle it when it’s urgent. They tackle it when there’s pain, but it’s not like they’re… they haven’t fully tackled all of the jobs and all of the tasks in a process-oriented way. And by… The reason we have this on a regrets episode, and I think the reason you brought up process is that will throw off… that will increase the likelihood that you have regrets is when you’re reacting to things and you’re not following a process –

Ryan Isaac: On an individual, yeah, case-by-case basis.

Reese Harper: – you’ll just constantly be putting out fires [crosstalk] throw you off.

Ryan Isaac: Well, especially when the, yeah… when pressure and stress is on, decision making gets even more difficult, and we’re more likely to make poor decisions during that.

Reese Harper: What’s number two?

Ryan Isaac: Number two is preparedness. So, I was thinking about what are some characteristics of dentists that feel like they have less stress and anxiety in their life? And by preparedness, I mean liquidity.

Reese Harper: Mm-hmm (affirmative).

Ryan Isaac: That’s what I’m talking about. We’ve done, episode 159, if you go search for that too, was on… we talked about how having liquidity allows you to slow down and take your time when you make a decision and leads to better decisions, so we’ve been able to see dentists with a lot of debt and no debt, and a lot of liquidity and no liquidity. We’ve been able to see the difference in someone’s psyche and emotions and decision making that liquidity brings.

Reese Harper: Yeah. I think that you’re right on there. That’s probably one of my top ones that would have hit if you said, if you want to live a life –

Ryan Isaac: Reduce future regret.

Reese Harper: Yeah, reduce future regret, well you’ve got to have the flexibility in your finances that only liquidity can provide you with. And too many people just don’t have patience to build up liquidity; they want to implement something quickly. They want to pay down a debt, they want to invest in property, they want to… I mean, and there’s some good… that’s a good desire we have, but if it comes at the cost of liquidity, then we’ll start to see these regrets pop up more. Half the reason people work too hard or don’t reach out and talk to friends, or they end up, you know, having these top five regrets is because they’re so inflexible with how they have to react… they’re paycheck to paycheck, they’re month to month, they’re quarter to quarter, and they’re… you’re doing this to yourself. Like, you know, no matter what income you make out there, you don’t have to be a liquid and be on quarter to quarter. You know, you can say no to the house that you wanted and get the house you can afford. You can say no to the car that you want and get the car you can afford.

Ryan Isaac: The Christmas you wanted, and yeah.

Reese Harper: The vacation you want and the one you can afford. Like, you can do that, and the result will be the more you say no, the more liquidity you build up and the more you’ll be able to live more purposefully –

Ryan Isaac: And more flexibility.

Reese Harper: Yeah. I think liquidity is key.

Ryan Isaac: As far as being prepared with liquidity, I was thinking that there’s three maybe categories of liquidity in a dentist’s life. You have business liquidity, right? Do you have enough liquidity to last a couple of months’ worth of your business expenses? Do you have personal emergency quick access to money liquidity? And then, do you have kind of long-term, bigger picture liquidity?

Reese Harper: Well, yeah. Like, without that longer term, bigger picture liquidity, there’s a lot of problems that crop up later on in life. Like, today I’m dealing with a case where there’s an opportunity to get a several-hundred-thousand-dollar tax deduction from one of my clients, but if they didn’t have this long-term liquidity available –

Ryan Isaac: You mean outside of like 401K, like it’s in accessible, nonpenalized money –

Reese Harper: Yeah, they’ve got a trust account that’s accessible that I would consider liquid, and without that large pool of money, they would miss this opportunity for a big tax deduction.

Ryan Isaac: Because you can take that money and shift it somewhere, is what you’re saying.

Reese Harper: Yeah.

Ryan Isaac: Okay.

Reese Harper: And so, by having more liquidity, you have flexibility to be proactive on taking advantage of good investments. You can take more tax deductions when they become available to you at opportune times.

Ryan Isaac: Yeah.

Reese Harper: And I just think that that is critical.

Ryan Isaac: So, an action set for this section, I would say pick one of these areas. Is it business liquidity? Is it short-term emergency liquidity? Is it long-term, big picture liquidity that you feel like you’re lacking the most, and focus on that this year, and put it on someone’s calendar to fix that problem.

Reese Harper: Yeah.

Ryan Isaac: I like that, all right.
Number three, this is my third one here is progress. People who know their progress in life, where they’re headed, how fast they’re headed there, tend to have fewer regrets because they knew where they were going to end up. You know, you don’t just end up somewhere and be like, oh, crap, I wasn’t planning on it. There’s this saying, you know the saying, ignorance is bliss, you know? Because I was trying to think, why do more people not want to know where they’re headed? You hear that a lot. Like, if you asked the average person right now in any room, do you want to know how much you weigh right now and compare that to how much you weighed a year ago and how much you weigh a year from now, most people… you just don’t want to know those things. Or spending, you know? Do you want to know how much you’re really spending every month? There’s just certain things we tend to feel like it’d be better to not know.

Reese Harper: Uh-huh (affirmative).

Ryan Isaac: And so I was curious, actually, about the psychology of this. I found this study where they were trying to determine if it’s better, or if it’s less stressful to know that the outcome’s going to be negative, or just to not know the outcome at all. What would you say is probably more stressful?

Reese Harper: No, you just don’t want to know.

Ryan Isaac: So it’s less stressful to just not know than if you knew the outcome was negative?

Reese Harper: Yeah.

Ryan Isaac: So, there was a study. What they did was they put people in this room and had them play this computer game, and this computer game was, is really simple. There were rocks in this computer game, and under certain rocks there were snakes, and your job was to uncover rocks and see if there was a snake. If there was a snake, you got an electric shock that was hooked up to your hand. They’d shock you and it kind of hurt, okay? And then they were monitoring like their sweat glands and their pupils and their heart rate and all these things. So they were trying to figure out, because after a while playing the game, you could kind of predict when there was going to be a snake under a rock. So they were trying to figure out if people were more stressed when they had no clue what was going to be under there, or if they kind of knew for certainty that it was going to be a shock, and it turns out, people are more stressed when they actually don’t know what’s going to happen. They’re more stressed than if they know it’s bad.
So, the participants in the study had more stress and anxiety not knowing than they did knowing, eh, there’s a snake under that rock and I’m going to get shocked.

Reese Harper: Interesting.

Ryan Isaac: And so I was trying to think like, I think a lot of people in their finances… I know this is the case, because I hear this so many times, and I felt this way before… Sometimes you don’t want to know where you’re at and where you’re headed, because you know it’s not great right now, and you just don’t want to know that it’s not great, and so you’d rather just not know about it at all, and it turns out, like from this study and from the things that I’ve seen, that it’s actually better… even if you know that it’s not great, it’s good to know it’s not great.

Reese Harper: So you’re saying… That’s how I would have said it. You’re saying people don’t want to know the truth –

Ryan Isaac: Because it feels like that would be better than knowing that like, I actually don’t have a lot of savings right now. My savings rate’s way too low, and I’m not very liquid.

Reese Harper: Yeah, but the truth is, if they did know, they would feel more relaxed.

Ryan Isaac: You would feel more relaxed.

Reese Harper: Yeah.

Ryan Isaac: And it’s better to just –

Reese Harper: Get the bad news.

Ryan Isaac: – get the bad news and know what it is, because then you can even know what to do about it, and then you’re not even wondering if it is bad news or not.

Reese Harper: I see what you’re saying.

Ryan Isaac: So my last –

Reese Harper: That’s a long study there, trying to get me to figure that thing out.

Ryan Isaac: Yeah.

Reese Harper: So basically, summary is –

Ryan Isaac: It’s a snake and a rock study.

Reese Harper: – bad news is good for you –

Ryan Isaac: Bad news is good news. Ignorance is not bliss, it turns out.

Reese Harper: Yeah, okay.

Ryan Isaac: As they say. So, I was just thinking, like, I feel like from experience that a dentist who, even if it doesn’t feel like there’s a lot of progress being made, even if you know, like, I don’t have a lot of cash flow, I’m not saving a lot of money, I’m not generating a big net worth that’s growing, it’s better to record that and know it, and know how that’s tracking over time than not know it at all.

Reese Harper: Yeah.

Ryan Isaac: So that’d be my third piece of advice for a dentist to avoid future possible regret is to just start tracking where you’re at today.

Reese Harper: Yeah.

Ryan Isaac: Know where you’re headed and know the things that are contributing to your progress or your lack of progress.

Reese Harper: Yeah. I think that’s great.

Ryan Isaac: And the action step, I would say, to that is we have… you can see it on our website, in the elements section, it’s a little brick that we measure called TT that’s someone’s progress. But there’s a free download someone can go get that’ll help them track this. If you go to you can download this free guide that’ll show you how to start tracking your progress today and at least know what’s happening in your situation.

Reese Harper: I think that’s great, man.

Ryan Isaac: Okay.

Reese Harper: I would’ve said the top two for me… the first one I would’ve said is if you want to have no regrets, give yourself a lot of options, and the only way to get options is through liquidity, so that would’ve been my first one.

Ryan Isaac: Okay, cool.

Reese Harper: If you don’t want any regrets, you’ve got to give yourself the ability to be able to follow what you want to do.

Ryan Isaac: Yeah.

Reese Harper: And the only way you can have choices like that is with access to cash, so you’ve got to save up some money, build up some liquidity so you have some choices.

Ryan Isaac: Cool.

Reese Harper: The second thing I would’ve said is… I mean, I would’ve said you have to have… you have to be pursuing something in your life that is growth oriented, a growth-oriented goal.

Ryan Isaac: Hmm. Okay.

Reese Harper: Like, you have to be heading towards something that you haven’t done in the past, that you’re pushing towards achieving something.

Ryan Isaac: Okay.

Reese Harper: I think people… It’s kind of… There’s some element in this progress kind of spin you’re talking about –

Ryan Isaac: Yeah, I was going to say… Yeah.

Reese Harper: – but I think it’s a little different in that I think everyone wants to be doing better than they did before, and I think that really helps people have no regrets, is when they’re achieving new things and becoming someone that is better than they were last year. I just think there’s a really critical kind of component to that –

Ryan Isaac: I like that.

Reese Harper: – because if you’re changing and you’re evolving, it’s difficult to beat yourself up too much.

Ryan Isaac: Mm-hmm (affirmative). [crosstalk] But what if you don’t know that you’re changing and evolving? Because some things are obvious, like I got a master’s degree (which I didn’t, I’m just saying). So, you got a master’s degree, that’s an easy one because you’re like, before I didn’t have a master’s degree, now I do. But some things are not obvious. You might not know that your net worth increased 100 grand in the last 12 months.

Reese Harper: Yeah.

Ryan Isaac: It might feel like you’re in the… It might even feel like you’re –

Reese Harper: Progress measurement and this idea of growth goals, they’re critical.

Ryan Isaac: Yeah.

Reese Harper: I mean, yeah. They’re related.

Ryan Isaac: And that’ll spur more growth if you’re recording and tracking progress [crosstalk]

Reese Harper: I think you just have to achieve things that for you are a step further than where you were before. Do a little better with what you had to work with. That’s going to make you feel great.

Ryan Isaac: All right.

Reese Harper: And regardless of how objectively you compare to others, like progress for your own self is going to feel awesome, and the best way to get there is by having access to cash and not being too strapped. So I think too often, people feel like by pursuing a concrete thing like putting their… instead of building more liquidity, their long-term savings, business liquidity or personal, they feel like they’re kind of like burning up their cash, they’re not… they should be investing it more, and I kind of feel like, yes, you should be investing it. I mean, you shouldn’t have more than necessary in your business or personal –

Ryan Isaac: Yeah.

Reese Harper: – but there really probably isn’t more… there’s not an excessive amount of long-term savings that you could have.

Ryan Isaac: Mm-hmm (affirmative).

Reese Harper: It just… so, you know, I just think access to cash allows people to have flexibility and freedom, to pursue growth goals, but track them, right?

Ryan Isaac: But track them, like know what they are. Thanks for kicking in some ideas –

Reese Harper: Yeah, this is great.

Ryan Isaac: – on this podcast about regrets and having no regrets. When I’ve thought about this regret story… I don’t know if you ever have anythings like this… I remember being in like a… speaking of regrets, I was like 10, I was in the middle of a soccer game, and I was the forward, and I had the ball like on a breakaway, and I heard a whistle on another field, and I thought like maybe that was my whistle, and if I kicked the goal I was going to get in trouble because I kicked it after the whistle, and I just stopped the ball. It wasn’t even our whistle, and I’ll always regret not kicking that goal because it was wide open, man. I’d faked the goalie out.

Reese Harper: Oh boy.

Ryan Isaac: And I stopped, grabbed the ball.

Reese Harper: You dimble.

Ryan Isaac: Don’t have regrets, man!

Reese Harper: That’s a tough one. Have to go back to freaking third grade for that one.

Ryan Isaac: It was, it was like third grade, man!

Reese Harper: One down from the archives.

Ryan Isaac: Yeah, we’re pulling them down.
Thanks for listening everybody. I’ll give you two invitations today. If you’d like to schedule an appointment to speak with one of our dental-specific advisors, do it on a day off, do it on a lunch break, on a Saturday… we have advisors with Saturday availability on our calendar, don’t we?

Reese Harper: 833-DDS-PLAN.

Ryan Isaac: Call us or go to, hit book free consultation and schedule an appointment today to chat with us, or join our Facebook. Not or, and.

Reese Harper: And.

Ryan Isaac: Please and, yes and. Join our Facebook group. We have discussions and polls, and Reese and I jump in there every week and answer questions. That is Love to see you in there. Thanks for listening.

Reese Harper: Carry on.

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