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A
Many of you know, I grew up in Malibu, California, very affluent area. James went to college in Malibu, California, at Pepperdine. And my dad grew up watching his dad as an accountant. And then he once saw the movie the Endless Summer. And he went, my dad's an accountant. I'm watching the Endless Summer and I'm seeing people surf. And he thought they made the same money. So he went, why would someone choose to be an accountant over a surfer? I'm going to be a surfer. Little did he know that didn't come with a ton of financial benefits. Let's just say, regardless, my dad fell in with surfing. And the reason I'm telling you this story is I grew up in Malibu. And my dad said, I'd rather live in a shack in Malibu than anywhere else in the world, even if it was a mansion. And my dad gave me great advice along the way of my journey. And he used to always say, ari, anytime you want something, it doesn't mean you're going to get it. And I would get upset and I'd say, why are you telling me that? He goes, because I'm the meanest dad in Malibu. Now, you can imagine I grew up in Malibu. And a lot of characters. That's me being nice, James. A lot of characters in Malibu. And these characters could be 16, 17 years old, driving the nicest cars, telling teachers, I don't got to do my homework. There was a lot of attitude. A lot of great people as well, of course, but there was attitude. So I even regret to this day a little bit. But I will joke on YouTube and say, I'm the meanest financial advisor, because I'm trying to allude to my dad to say, hey, I'm not just going to tell you you can retire unless you're in a good spot. I'm not gonna. I also don't want you mad at me if you're 85 with $10 million going, hey, Ari, what the heck? You told me I was in a good spot. Like, why didn't you give me more confidence to retire earlier when I had my health, when I had my energy? So my dad's told me a ton of life lessons. So have other family members and friends. But what I wanna talk about today with you, James, is specifically, what advice have we been given that have put us in this position where we have, I don't wanna say, reached success, because there's never a high enough point for that where we are. And I'm asking all of you to contribute as well. I put this as a thread in our community, the Root collective. So if you're in the description of this YouTube video or podcast episode, you're going to see a thread that is a photo of me and my dad. You can see we're both not very tall and I'm talking about some of the lessons that my dad shared with me that I'll be getting into today. But I encourage you all, please. It's one thing if you're hearing from James or I in a YouTube video or podcast talking about, you know, Roth conversion or donor advice funds or whatever it may be that lights us up in our financial nerd brain, but can you all go share with each other? Hey, this was something that I never knew, but turns out my dad wish he retired earlier and he passed away with too much money or they just weren't given this one piece of advice that I wish I would have seen or whatever that may be. Please go in there and it makes it way more fun in that community when I get to see you guys chatting. So appreciate you doing. So, James, is there an advice, a piece of advice from a friend or family member that comes to mind for you?
B
Yeah, and I love this concept because sometimes we hear, well, hey, what's the best piece of life advice? And things are so cliche and whatever, but I love your idea of go to the community, share the best piece of advice that you learned from a parent or whatever, because they're. Almost everyone has a piece of life advice they've been given that's just. That does kind of hit you differently when you hear it because there's context, because there's stuff behind it. So I, I like this. The thing that first came to mind when you asked, this was not a piece of advice that was verbally given as much as it was, I guess, messaged. I was a freshman in high school. It was my second year or second semester, and I had a history final coming up. And the way that it worked was like the final exam, for whatever reason, was weighted very lowly in terms of your overall score. You know, sometimes like the final exams, 40% of your grade or 30, some big number where if you don't do well, you're not going to do well in the class. I can't. It was something like 5% of the grade or something. And I remember I was squarely in A minus territory where I was thinking through like, I could do really well on this exam where I could totally flunk it. I'm still going to end up with an A minus. And I think this Was my last final exam. So I was tired, I was exhausted, whatever. As a freshman, I'd rather be doing other things than studying. And it was, I remember getting home from, I think a previous final and my dad asked me what, you know, what I had next. And I said, oh, just my history final. I don't need to study. Here I am like, I mean, get a minus no matter what happens. And I remember he didn't just say, no, you're going to study, Go study and do it. He said, no, that's not how. Like, that's not how. I forget the exact words, but like, that's not the attitude we take towards things. We are going to give it our all regardless of what the outcome was. And that's easy enough to say like a parent to tell their kid, go study, I'm going to go watch TV or I'm going to go relax or I'm going to go do. But he, I remember he sat down with me for, like hours at the kitchen table studying for my history exam, which had in my mind zero importance because it was not going to change the final grade one way or the other. And I remember that so vividly because I ended up, I must have done pretty well on it because I remember it moved my grade from an a minus to an A. Which when I was looking at the math, I was like, there's no way, like, I think that I. I'm at an a minus regardless. But the lesson I learned that my dad didn't just tell me as much as he exhibited it was, we don't do things for the outcome. We do things for the character building. Like, we do things for who it makes us kind of become along the way, which can be so cliche. But it's like, if you're just attached to the outcome, sure, give up, go to the park with your friends, go do whatever, go watch tv. No need to study because the outcome's there versus if it's not about the outcome, but it's about you being the best you can possibly be. Who cares if you get a B and who cares if you get an A as long as you are doing everything you can to be excellent here in this pursuit, in this studying for your final exam, that's what we're going to focus on. So focus on what you're putting into it, not what you're getting out of it. And I think even as that relates to root, like you mentioned, yeah, we've had some success. That's great. But, like, that's not what we're focused on is not that. It's not just how many team members do we have, how many clients do we have, how many, whatever do we have? We're what we've built, I think is really cool, But I think there's so much more that we can keep doing. What are the inputs that we can focus on? How can root be the best it can be? How can we view this as like the place for even Ari's personal expression? My personal expression advisors put like, this is where everyone gets the opportunity to be excellent. And it's that. It's that input that we're so hyper focused on. How can we make this the best? It can be less focused on what growth rate is. How do we compare to the rest of the industry? Those are kind of cool things, but they can quickly become addicting and make you lose sight of what actually matters. So that wasn't like, verbal advice that my dad gave me, but for whatever reason I remember that stuck with me as a freshmen in high school. The importance of doing your best in disconnecting from the outcome.
A
You said cliche a few times because this could be cliche. This could be a valueless episode if we just said, hey, carpe diem, you know, go seize the day. It's like, hey, everyone says that. The reality is, it's very different. The fact that your dad spent the time to sit down with you knowing that it might literally not change your grade, but reframe your brain. Maybe he wasn't even thinking that, but he just said, that's the right thing to do. Shows who he is. The biggest moment for me was my dad used to say, no means get to work. And I just didn't understand what he said. I went, that sounded nice. He said it with conviction. But I thought no meant no, so I would go. And I remember I once wanted my first job. I wanted to make money. I already was interested in that because my parents struggled by not having financial savviness growing up. So I wanted to help and I went to get a job and I applied. I had an interview, and they said, no. I said, okay, so no onto the next job. My dad said, no means get to work. What didn't go well? And I said, okay, I get it. He's trying to be a good dad. He wants me to look at what I did in my interview and what could I have done differently? And he was saying, no, this will not. You did not succeed here if you don't get the job. And I said, dad, they already declined me and he said, that doesn't mean anything. That does not mean that's not available anymore. That just means you're now beginning and go start. And so then I was thinking, okay, what are creative ways that I can get in front of them? And I started coming up with new ideas. I don't remember what they were, but I remember I once actually, it did eventually relate to you, James, in a far away where I had an AOL email address was a dumb idea at the time, but I thought maybe they're going to think I seem more mature or older if I'm, you know, have an AOL email address even if I go in and I still look like I've got all my zits on my face. So really didn't apply. It wasn't thought out well, but it was the thought of, oh, just because someone said no doesn't mean it's over. It's, hey, go fight for what you want. So with that being said, a lot of comments we'll see on YouTube of people who say, oh my gosh, I wish my spouse would have told me earlier that they didn't want to travel because I was planning my whole retirement to travel. Or I wish that I had spent more time not sitting at my desk because I found out that that wasn't going to be great for my health, which then relates to my hiking and retirement, whatever that may be. So want to certainly say, guys, please go in the community. It makes it way more fun when you do comment. So thank you for doing that and then touching back, James, on that success piece and people say, oh, did you reach success? The first thought is, how many million of people have we underserved? And people would say, well, you haven't done anything wrong. They just maybe don't know about you. I go, well, that's us not serving them. We feel we have a solution to a lot of people's problems and it's not always working directly with us. Maybe it's tuning into a piece of content, looking at something differently. But how many messages have you received from people going, wow, if you didn't say this one thing, I would have thought differently about this for the rest of my life. And we get these notes from team members internally. We just had a really fun meeting today. It's our staff meeting where people are sharing how a team member who just got married, the whole team came together and put together a little custom video for them and they didn't have to do that. But we're around these people, which personally motivates Me to do it even more. So, I think surrounding that culture, which a lot of people use as a buzzword today, but putting real intent behind it goes a long way.
B
Yeah, agreed. And then even with the feedback people give, I know I am guilty of this. There's a tendency where feedback seems too cliche, it's too trite, it's too whatever. Focus on what you can control, let go of what you can't. Kind of like, yeah, it's almost so simple. We just dismiss it, almost get upset when people say, because it's like, gosh, so lame. Who cares? I've heard that a million times. And then we like. It takes sometimes a life experience for us to realize, no, that was the feedback that I needed. Sometimes we look for the more complex feedback. We look for the thing like it's just a firm form of procrastination, where the feedback for people listening, hey, prioritize your health, prioritize. What are you going to do in retirement?
A
Whatever.
B
I need something more complex. I need, like the most efficient Roth conversion, flip crut, charitable remainder gift. Like, we look for the complex because it gives us something new to put our focus on as opposed to addressing the simple thing, which is sometimes a difficult thing, which is, oh, that lesson is actually really profound. Maybe there's a reason I've heard it 10 million times in my lifetime. Maybe it's a 10 million first time that I should actually pay attention to it. So I think that that is, again, something I know I am guilty of. But as people share their lessons here, don't dismiss something because it's trite, because it's cliche, because you've heard it a million times. Really think through how do I apply this? Because I think so much of the work that we do, I think so much the work that I even do personally is like, how do I minimize future regrets? How do you live fully in the moment and minimize future regrets? Which typically means you. You were kind of living by default. You were living in automatic mode, you were living in whatever's easy, whatever's in front of you, whatever's urgent. As opposed to, I'm going to shift to intentional mode. I'm going to shift to manual mode and kind of start doing things on my terms. But that takes embracing the simple questions that are really difficult to answer sometimes and applying them in a way that maybe we haven't thought of before.
A
I've told your story many times, James. I think it's worth finishing today's episode with it. When you were on the Jet Ski and how you didn't hesitate and just went right back to your friend's dad and told him what? I'll let you tell in just a second. But I know a lot of you will say maybe it's really hard to retire because. Not because I'm not excited, I am excited, but because this is what I know. And the idea of going to something, I don't know is scary because I don't know the last time I did something for the first time. I mean, I remember, yes, I got married or I went to school, or I. Whatever, I had my grandbaby, whatever that is. But when's the last time you personally said, I am making a big shift to my life where I might. I mean, you guys can be very honest. You know, I'm very honest and a transparent person. It might feel weird to go up to your co worker and say, hey, so I'm gonna stop working. And we might, like, not see each other by the cooler. And we both haven't ever said it, but we both, at 10:37 every Tuesday, go and hope that one of us is there. When we're not there, we're sad, but we don't look sad. And that's weird to bring up. You need to initiate that, which can be difficult if you've been in a role where that really hasn't. It's been unspoken. You know you're gonna see them and you know you're gonna miss them, but you don't wanna say it. And all these little hidden things that we can all talk about, but unless we actually do take action, which is what we say in our videos of if you walk away and go ask your spouse one question. Hey, spouse, have I ever said that I'm moving back my retirement? I've had people say, yeah, you, like, a hundred times, like, what's new? That's just every Friday. And they're like, oh, I just thought I was just telling you about my day. Or, oh, my gosh, I had no idea that you didn't want to travel around the world. I thought that's like what we were going to do in retirement. No, I'm more of a homebody. You're like, okay, well, that really changes things because I was about to work 10 more years so we could do this thing that turns out you don't even want. So on that Jet Ski story, I just think it's powerful, James, if you don't mind sharing it, because it was a moment where you just did it. And that seems like it comes from experiences like the one your dad had with you about building character.
B
Yeah. I don't know where I learned this initial lesson, but the story was this was my senior year of high school, got invited out to a friend's place on the river and this friend had some jet skis, which was awesome. I don't. Maybe I'd written jet skis once in my life before, a couple times. But anyways, it was like this very big, fun, exciting thing to do. I get to ride a jet Ski on the river and I get to go hang out with my friends while we do it. And we were riding and it was myself and my friend were riding one. So I was driving, he was sitting on back. And then two other friends were on another jet Ski, you know, both on the same one, riding behind us and we were going down the river as fast as we could and I wasn't paying attention. I know how close they were behind us. I forget the exact circumstances. But you know, it's fun to whip those jet skis around and see if you can throw whoever's sitting on back off the Jet Ski. So you, you know, you go full speed, you whip it, you try to stay on by leaning forward and not being where the, you know, the, the Jet Ski whips around. So we were doing that, we were going, I flipped, I, you know, I, I turned as hard as I could. Thankfully my friend flew off the back. And then I do the 180 in the water. Water splashes. You can't see anything because it's just misty. Water settles. I'm now looking backwards 180 degrees to where I was. And then my friends on the jet Ski right behind us are now very, very close, kind of beelining right towards us. So I have about a split second and I jump off the jet Ski right as they're hitting the other side of the Jet Ski. So thankfully it wasn't like a head on collision, but it was still almost head on to where, you know, the sides kind of hit. And there was serious damage done to the jet Ski. Thankfully I jumped off, my friend had flown off. So neither of us got hurt or anything, but swam back to the jet Ski, saw the damage done and obviously immediately felt this pit in my stomach of get invited by my friend, take out her dad's jet ski, crash it and how dumb am I? Like I, I just feel so dumb. So anyways, I remember getting back on the Jet Ski as fast as I could, driving it as fast as I can back to the house and going right up to her dad. Saying, I crashed the jet Ski. I'll do whatever, I'll pay for it. You know, just like, I kind of blacked out. Just so nervous telling him all this stuff. My friend comes up to me later like, wow, I can't believe you just, like, went right up to him and said, you crashed the jet Ski. And in my mind's like, yeah, that was the easier thing to do. And it kind of separated my mind the difference between pain and suffering. And, like, the pain was the actual telling him that hurt. It stung. But the worst part was, like, that suffering, the anticipation, the making up in your mind what's to come. I hate the suffering. Like, give me the pain, let me get out of the suffering period as long as possible. I think the takeaway is so many people are there, and there's so many different forms this can take of the pain of retirement. I don't know what I want to do. It's the unknown, there's the uncertainty, so they put it off, but there's the suffering that now they're sitting with. And suffering can maybe like, be an overly dramatic word in this case, but. But not always. Like, you're sitting there too afraid to make the decision, too afraid not to. And so that you just create this life of unnecessary suffering where, yeah, there is going to be some pain in some decisions. There are going to be some things that don't go perfectly according to plan. There is going to be newness, but that can also be part of the adventure and the fun and the experience of it all, depending upon how you frame it in your mind. But embrace the pain, avoid the suffering, I guess, is some of. Is the takeaway from some of this. I love that story.
A
I get more goosebumps on that. I'd say equal to the manifesto that we put out. And if you guys haven't seen that, make sure to check that out on our root YouTube channel. So that's it for this episode. Please, as always, like this video, comment below if there's something you learned. Whether it's, I'm now scared of jet skis or oh, my gosh, no, I really do see the value of finally talking to my boss or my partner or my spouse about, wow, what do you want your retirement to look like? Because here's where I'm at here, here's what I'm thinking. Please go to the community and be as. Be a participant, but also go through there and be a little bit of a detective and go, okay, what are other people really doing? And like James said, there's so many cliche things, and they're cliche for a reason. So hopefully you guys can take those to heart. And Maybe it's the 10,001 time that it finally hits you. So that's it. Please finally share this with someone who you think might resonate with it. I said that's it about four times there. So my. That's. It doesn't really have a final ending there other than I appreciate all of you guys for tuning in, and we'll see you next time.
Podcast: Ready For Retirement
Host: James Conole, CFP®
Date: October 2, 2025
Episode Theme: Reflecting on the life and financial advice that, though seemingly cliché, holds genuine value—especially as it relates to retirement, personal growth, decision-making, and building a meaningful life.
This episode digs into the oft-repeated but undervalued advice and lessons that shape our financial and life choices. James Conole, joined by guest Ari, encourages listeners to not just acknowledge cliché advice but genuinely internalize it, sharing personal stories about work ethic, responding to setbacks, character building, and facing pivotal moments. Listeners are invited to share their own foundational advice within the Root community.
Ari on Parental Advice:
"Anytime you want something, it doesn't mean you're going to get it." (00:44)
James on Effort Over Outcome:
“We don't do things for the outcome. We do things for the character building.” (05:11)
Ari on Perseverance:
“No means get to work.” (07:26)
James on Cliché Advice:
"Maybe there’s a reason I’ve heard it 10 million times in my lifetime. Maybe it's the 10 million and first time that I should actually pay attention to it." (11:51)
James on Facing Mistakes:
“Give me the pain, let me get out of the suffering period as long as possible... Embrace the pain, avoid the suffering, I guess, is the takeaway from some of this.” (18:07)
The episode is direct, personal, reflective, and laced with humor. Both Ari and James keep it candid, using storytelling and vulnerability to connect. They emphasize that while popular advice often sounds trite, revisiting and sincerely applying it can be transformational—whether you’re planning your retirement or navigating life’s other major decisions.
Summary Takeaway:
Cliché advice—about effort, persistence, communication, or self-care—endures not because it’s trite, but because it’s true and essential. The challenge is not to find something new, but to finally practice what we’ve known all along.