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James Knoll
This is another episode of Ready for Retirement. I'm your host, James Knoll, and I'm.
Ari
Here to teach you how to get.
James Knoll
The most out of life with your money. And now onto the episode. All right. You and I know there's a big difference between being financially ready to retire and actually being ready to retire, which of course extends beyond just financial. And that's what we're going to talk about today. We actually have a comment from someone in the root collective which is asking that exact question of look, I've run the numbers, I'm ready to go, I have enough, but I can't bring myself to not just leave my job, but leave my high stress job that also happens to be very high paying. And this is a predicament we see time and time and time again of we work all our lives thinking that as soon as we have enough money, we're going to call it quits. We finally get there and it becomes very difficult to actually pull the trigger and call it quits. Will you read for us the question? Not the question, but the comment that's in the root collective? I will.
Ari
And for those who do not know what the root collective is, it is our free community. So you can go join this and see exactly what we're looking at under the tab that we call the what I wish I knew earlier. And this comes from DT Lyons, who says taking the big leap. Curious to hear from others that have stepped away from high stress, high paying career and retired early, but continue to work doing something they're passionate about at the fraction of the salary I'm in that situation. My analysis says I can do it, but it's hard to take the leap.
James Knoll
We see this a lot and as I just alluded to, the reasons why is it's not just a math problem. It's not just a spreadsheet problem. There's a lot that goes beyond that. So I'm curious, Ari, you see that question? You see that comment? We've got some really good comments, people responding to that from the collective, which we're also going to point out. Where does your mind go first?
Ari
Yeah, mine. My mind first goes to. It would be really weird if you were to be like, oh my gosh, I can retire. I have no worries, no political concerns, no economic concerns. I know exactly what I'm going to do in retirement. That would actually concern me as an advisor because I'd be like, look, how could you really know? You haven't done it yet. So, yeah, you can ask friends and you can kind of see on some online forums, even like this root collective, and see what people say. But there's always going to be probably some piece of you that goes, look, how could I really know? Like, this whole concept of retirement, having income for 40 or maybe 50 plus years, it's weird. It's like you're living off this portfolio for so long you've been adding Money to your 401k and now all of a sudden you're supposed to pull from it. It's like, no, no, no, I'm never going to pull from it. I just add money to it. So I would start by saying the big leap, it's always going to be a leap. But how do you make it so when you jump in the water, not a perfect analogy, but you jump in the water, it's not this crazy splash where now all of a sudden it's, oh, my God, who can you hang out with? And how much income could you really support? And it's more of a perfect dive where you're in and you're like, yep, I'm in the water. I was more comfortable out of the water because I was even wet out of the water. But I really know I do want to go swimming. So it's first. Starting with that, hey, it's going to be a leap. How do we do it Appropriately?
James Knoll
Yeah. Tomorrow morning, my wife and I, we are dropping off our daughter for her first day of preschool and she's going to be. I don't know if nervous is the right word. She just doesn't know what it is yet, but it's going to be difficult. Yeah, I'm nervous. Ashton's nervous. Like, this is a big change. And I bring that up because we're not. She's not retiring, she's literally starting preschool. But I think what we forget is this is a very normal thing that, like, what, your first day of school, maybe you remember, maybe you don't. Like, was that scary? Probably. Are you glad you took the leap and went to your first day of school? Maybe. Maybe not. Being coerced into it by parents. First day of high school, was that scary? Probably so. First day of college, was that scary. First day with a real grownup job, was that scary? First time you asked out your maybe now spouse, was that scary? Ask them to marry you, was that scary? Starting a family, all of these things are scary. And I think we forget that because sometimes, not always, but sometimes, by the time that we're 60, 65, like in those retirement years, we haven't done one of those new things in quite some time. We're in that position where like this commenter said, hey, I'm in a high paying job, which probably means you've hit your stride, you've been there for a while and you haven't. Maybe you're not remembering what it was like to be in that job for the first time. And so I think that one thing that we have to do, I always think like this. Some people might think this is morbid, but I always think through, I'm going to die one day. Am I going to be, if I have the opportunity, when that happens, if I'm looking back on my life and if I'm this individual, am I going to be looking back at myself, kicking myself for retiring because I could have stayed in that high stress job and I could have put more money in my portfolio, which means as I am going to my grave, I probably could have had more money that I'm going to die with. Or am I going to be kicking myself because I'm saying, look, you stayed in that high stress job too long. It literally took years off your life. Not just these extra years of working that you can no longer do the things that you wanted to do, but the years of your health that it took off because your blood pressure was out of control, because you couldn't go to the gym, because you couldn't eat healthy, because you couldn't prioritize physical health, mental health, spiritual health, friendship health, all those things because of that, I don't know. But my guess is going to be it's latter. So sometimes we have to ask ourselves the question of not what, what, not what would I do in this situation? What will my future self do? There is some study, I have no idea where it's from, so I'm not going to try to cite it correctly. But when, when psychologic, when psychologists look at our decision making frameworks, one of the reasons people procrastinate, which I think this in large part is maybe procrastination, is our brains literally think of ourselves like James right now. When James has something important that he doesn't want to do in front of him and says, oh, I'll do it later, it's because my mind is registering future James as a completely different individual. So it's almost saying that person's going to do it. I'm not, because it's uncomfortable for me to have to do. But the problem is that never changes. It's always that person, that person, that person, meaning later, later, later. And if we could disconnect from that and try to think, no, both of those are me. Both of like at some point I'm gonna need to make that decision. Is now the time to do it? And a lot of times the thing that helps me is thinking through the version of 85 year old James, 95 year old James sitting there hopefully in those later years being able to reflect on a life and saying what would I have been glad I did? And then trying as best as possible to make the decision that future me would have made. So that's my thought. Now we have some other good comments I think in here to this username is dt. Well, Detroit Lions. DT Lions. What are some other pieces of feedback this individual received that stood out to you?
Ari
Yeah. So first of all, you're not going to pass away for much, much later and I can only imagine how you're feeling right now with your daughter starting tomorrow. But my first thought is, is she starting tomorrow? And there was no prep, was it just, hey, you're gonna show up. She doesn't even know where she's going. Like, probably not. You're probably told her, hey, you're gonna be around other kids. You might even know some of these kids. There's probably some preparation that's occurred that will make that leap a little easier. Now to your point, James, here we are giving analogies about, you know, your daughter jumping in a pool. It's not likely as applicable to a lot of you who are going, hey, this sounds great, but like you guys really aren't hearing me. I'm about to retire. What do I do? And so here's the cool part about this collective. You get to hear from people like Tommy C. Who says the following and there's a little longer, but there's a few things I want to read in here, so I'm not going to read all of it. But here's someone who says, I took this leap 11 months ago at age 56 and thought I would need to find something part time just to keep my engineering mind busy. Honestly, I haven't even missed work. Omg. The reduction of stress and the increase of time is so liberating his guidance to once again this Detroit Lions. This big football fan says, here's what I would do. I'd set up a plan to pay yourself on the same schedule as your current paycheck. It'll feel like vacation plan to keep yourself engaged with your field and then go back if you want to, but you probably won't want to. And then the third one is just do it and my only issue with this, as a financial advisor, where I want to bring your thoughts in here, James, is I love the idea of just do it. Nike's a cool brand. I get why they started just do it. But it's really hard to do it if financially you don't know you're going to be okay. And so, yeah, we're always going to make sure people are dreaming and think about retirement. Because the worst thing is you retire early and go, yep, I did it. I was over it. Work was high stress, high paying. But now you can't really live your retirement. Now you're retiring on eggs and top ramen and that's probably not ideal for most of you. So, yeah, I like just do it. But the financial brain is going, I gotta make sure, you know, you won't run out of money.
James Knoll
That's good. Is step two. And I think this is a very important thing to highlight. Most people should not just do it. Most people would do, hey, this is awesome. I loved retirement for six months and then I ran out of money and it sucked and I had to go back. And that was. That was. So we are making a big assumption and not even a big assumption. The reason we're jumping right into this is because username Detroit Lyons says, in my situation, my analysis says I can do it. So he's run the numbers, run the projections. I don't know to what degree. I might want to double check those. I want to see that. But there is this thing that we've observed, another version of, I'm going to call it procrastination, is I worked with clients before where it's, hey, you're in a position retire. Awesome. And it's cool, let's run one more analysis. So one more analysis and one more analysis, one more and it becomes this form of distraction because it's easier to address that, to address the thing that we know, which is the financial side. Way easier to do that than to say, what do I actually want to do when I'm retired? Who am I going to become? What's life going to look like? And I think that that's why step one has to be, are you financially ready? If you're not financially ready, do not just do it. Work the hours you need to work, save the amount you need to save. Like, those things are not just things you can leapfrog and go right to the enjoyment phase. But I think the point that we want to make though is I don't think I mentioned this enough or reinforced this enough is I actually think that a perfect life is one that you don't really retire from. In some ways, like a perfect world is, you have a job that you love and it fills you with so much purpose and enjoyment and fun that you can keep doing that for the rest of your life or at least until health no longer permits. Unfortunately, a lot of people, especially in high stress corporate jobs, you just don't have that freedom. You can't make it something that you want. You have to pay your dues. You have to trade your time for money so you can invest that money the right way and ultimately live the things that you want to live. But that's not to say retire into nothing. It's saying, okay, let's get away from that thing that was high stress and preventing you from the life that you wanted to live. And now let's create that life that you do want to live. And in many cases, like some version of work, whether or not it's for money, should be part of it. Work can be something as simple as everything from I know some people that very successful careers and they're now working at Trader Joe's just because it creates this structure and the sense of community and it's a fun environment. You know, a lot of people that go work down at the golf shop, you know a lot of people that work and they volunteer with the local parks and rec because they want to just be part of that and that's important to them. So keep doing something. But to your point, Ari, make sure the financials are in order first. We have plenty of podcasts where we discuss how can you tell if you're actually in a position to retire. We are just making the assumption or we're taking at face value Detroit Lions comment where he says that he is in a position to do so, but it's hard to take that leap.
Ari
Yeah. James, check out to see if there's other comments that you might want to bring up here because I'm curious and I'll tell everyone it's going to be a little tough love for all of you. And the reason I'm bringing this up is I'm going to ask you not to lie to yourself. And it's going to be hard because some of you are going to go, you know what? Yeah, I'm going to do a part time job and going to cover my healthcare costs. And you're really still in that mindset of, hey, I'm taking this role because financially I need it to do this or that. Now if you're taking a role because financially you just think, wow, this is going to add more bonus money where I can enter more pickleball tournaments and just show my neighbors how much better I am than. I'm cool with that. But if you're taking a role to go, you know what I really think financially I, I need to keep working. So I'm going to. And I don't really love it, but it's for the healthcare benefit. You know, without that, I'd have to go pay 800 bucks a month on the marketplace and I don't want to do that. Well, it starts with that and then it becomes, okay, what next? And what I'll see is people go, yeah, well I have this part time job but now I'm not going to buy appetizers because I was making 200,000 a year before and now I make like 30,000 a year. And it just doesn't feel right because I just, I don't think I have it in me. And then the real problem is you're 80 and you go, I don't really think I needed $10 million. And thinking about kind of that morbid of him, I'm not going to be here forever. It's also the reality. So are there other comments that you're seeing in there, James, that resonate?
James Knoll
Yeah, there's a few and I think before going, are you, you do a good job of this. Using this example a lot is to go back to Detroit Lions comment of a. It's hard like I should keep just working and saving and investing. Let's play that out. If the goal is to keep improving the financial situation, why not always, never retire, never stop saving fully delay Social Security, cut out all the extra discretionary spending on fun stuff, cut out all the giving that you do. Cut out all. Just keep. And obviously we hear that and say, okay, that's absurd. And obviously that's absurd. And you could also be extreme in the other direction, which is why not just retire at the age of 24 right after you started your career? Well, you neither are good options, but it's about finding that right point where you know that you're in a good financial situation to do it. I think that Andy Wang shout out Andy, he had this comment, he said, look, it's even harder when you look at how much more money you're leaving on the table if you haven't invested in RSUs. I'm in that boat. But I've decided enough is enough. Enjoy your retirement is another comment I want to touch upon. But that what he's essentially saying, look, it's so hard when you say, here's the opportunity cost. The opportunity cost is there's money, a carrot that's dangled in front of you that all you have to do is stay employed till a certain date and it's yours. And that is very true. And that's very difficult because money is so tangible, it's so quantifiable. You know exactly what you're leaving on the table. The reframe we'll try to encourage people with is there is absolutely an opportunity cost to leaving money on the table. And that's apparent. You know it and it's painful. The thing that you don't see, the thing that's not apparent, the thing that's just not obvious, is the opportunity cost of continuing to work. What's that year of health worth to you? What's that year of travel worth to you? What's that year of adventure worth to you? And by the way, there's not a right or wrong answer. In some cases it is the better option to work one more year to get that extra bonus, more RSU vesting, more contributions to your 401k. That is the necessary and wise answer sometimes. But other times it's not. And you have to be able to say it's not just a one sided equation. If it was just one sided and just about the money. Never stop doing this. But when you realize it is a balance and there are other things you need to consider, there is a variable trade off there. It's just we don't see it. And what makes us see it is this. Comments that we get all the time, Ari, on channels, on podcasts and whatever it is, is, hey, I saved and saved and saved. I finally retired. I had all these dreams my wife and I were going to do this. And then she passed away a year into retirement. And it's like, how much does that person wish they could go back in time? If that, if that person could talk to Detroit Lions right now, the username for those of you tuning in late, like, what would they say to how much is money worth it? It becomes the thing that drives all of our decisions until. And this is why I think about like, wait, your future self, what are they going to think at that point? Money is not a top 10 factor anymore. So it just comes by looking at this from all different angles, all different sides to say, yes, money is important and we never want to discount that. But so too is the life that you want to live and the things that you want to do, and what's the cost of sacrificing those things just for. Just for more money? And at some point it's just no longer worth it.
Ari
Yeah, you always say that the sign of a good financial plan is a life well lived. And I know there's more comments that you saw in there. Were there any others you wanted to reference?
James Knoll
Andy Wang had another one. I won't read the whole thing, but he just talks about his experience and he says these podcasts from Ari and James have been helpful along with reading Die with Zero. So that's a great book that I just like to recommend to people to read of this concept of what is money really? How do we translate that into its true value, which in large part is helping us to have the experiences and do the things that we want to do. So just for someone that's on that edge and looking for that sense of. I even want to say that push, because we shouldn't be looking for a push if we're not financially ready yet. But if we are financially ready, we need that push first and foremost. Join the root collective. It's free. There's a link in the show notes here. Go check it out. Lots of great things you can take away there. But then that book's a great perspective along with just trying to put yourself in the shoes of your future self, because your future self is going to have a more objective, a more disconnected perspective on this than you will in the moment.
Ari
And by no means do James or I go, yeah, so everyone's going to listen to this and just feel the comfort to go to their first day of school or to go retire. That's not what we're expecting. But to join this collective and see what other people say. And it's completely free, by the way. Just go hear from others. You might take some ideas and you might even feel that you learn things you otherwise didn't know. There are people who are in the collective talking about, hey, this feels really weird. But, like, I, I think I'm in a spot to retire. But like my neighbor, I know they have way more money than me in a way bigger house. And like, I heard them talking about working till 65. And so now I'm thinking, like, did I just miss something entirely? Because I don't think I'm anywhere close to retiring. But I also know that, like, our values are different. And then someone else was in here saying, oh my gosh, I, I felt the same thing. And I even started working extra because I thought I Had to and you don't. It. It's all custom based off the life you want to live. So certainly check out that community called the Root Collective and you'll see it in the description of this episode. Anything else for today, James?
James Knoll
I don't think so. I think that that's a very normal feeling to have. As much as we say do it, as much as we say, here's the perspective, it's going to be scary. And an example like so when I started root, someone left this comment that I liked. Let me see if I can go to it. Of Evan commented, my job stepped away from me a year ago, so I retired early. You know, somewhat tongue in cheek, just saying, look, I got terminated. But I know so many stories of people like, hey, I got released from my final job. That was the best thing that could ever happen. Like the boats were burned for me. I didn't have to make the decision. I know when I started Root that was the same thing. It was. I got let go from my previous job and I was like, hey, the boats are burned, go. It's like, oh my gosh, how scary was that? Well, it was less scary because someone else made the decision for me, it's the decision that's the scary part in many cases. And once you make it and don't make it ill informed, don't make it if you're not prepared. But once you make it, there's so many good things on the other side. And one of the things we try to help people do is how do you live better lives? Well, one way that you do that is you get out of this high stress job, no matter how high pain it is, assuming you're a good financial spot and you start living. And it starts with that decision. So join the collective. Reach out to Root if you need an advisor to help you do so. Rootfinancial.com Click. See if you're fit. But lots of great resources out there to help with that.
Ari
I, along with others, am so grateful that that boat burned which brought you to join and create Root and allow us to have this community. So to that one boat, I'm grateful.
James Knoll
Awesome. I love it. Well, thanks, Ari. Anything else you want to add here?
Ari
That's it.
James Knoll
All right, thanks everyone and we will see you next time.
Ari
See ya.
James Knoll
The information presented is for educational purposes only and is not intended as an offer or solicitation for the sale or purchase of any specific securities, investments or investment strategies. Investments involve risk and are not guaranteed. Any mention of rates of return are historical and illustrative in nature and are not a guarantee of future returns. Past performance does not guarantee future performance.
Ari
Viewers are encouraged to seek advice from a qualified tax, legal or investment advisor professional to determine whether any information presented may be suitable for their specific situation.
James Knoll
Hey everyone, it's me again. For the disclaimer, please be smart about this. Before doing anything, please be sure to consult with your tax planner or financial planner. Nothing in this podcast should be construed as investment, tax, legal or other financial advice. It is for informational purposes only. Thank you for listening to another episode of the Ready for Retirement podcast. If you want to see how Root Financial can help you implement the techniques I discussed in this podcast, then go to rootfinancialpartners.com and click Start Here, where you can schedule a call with one of our advisors. We work with clients all over the country and we love the opportunity to speak with you about your goals and how we might be able to help. And please remember, nothing we discuss on this podcast is intended to serve as advice. You should always consult a financial, legal or tax professional who's familiar with your unique circumstances before making any financial decisions.
Ready For Retirement: Episode Summary
Title: Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough
Host: James Conole, CFP®
Release Date: April 3, 2025
In this compelling episode of Ready For Retirement, host James Knoll, alongside co-host Ari, delves into the often-overlooked emotional hurdles that accompany financial readiness for retirement. Titled "Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough," the episode addresses the paralysis many face despite having the financial means to retire, particularly when considering leaving high-stress, high-paying jobs.
James opens the discussion by highlighting the critical distinction between being financially prepared to retire and genuinely feeling ready to take that step. He introduces a poignant comment from DT Lyons within the Root Collective community:
"I've run the numbers, I'm ready to go, I have enough, but I can't bring myself to not just leave my job, but leave my high stress job that also happens to be very high paying."
[01:01] James Knoll
This scenario is a common predicament many face—achieving financial milestones doesn't automatically translate to emotional readiness to retire.
Ari elaborates on this fear, emphasizing that retirement isn't purely a mathematical decision. The uncertainty of long-term financial stability and the abrupt shift from actively contributing to a 401(k) to drawing from it can be daunting.
"The big leap, it's always going to be a leap. But how do you make it so when you jump in the water, it's not this crazy splash... It's first. Starting with that, hey, it's going to be a leap. How do we do it appropriately?"
[03:14] James Knoll
This analogy underscores the suddenness and discomfort associated with transitioning from work to retirement, even when finances are in order.
James introduces the concept of procrastination rooted in psychological behavior, where individuals perceive their future selves as entirely different beings, making it easier to delay retirement decisions.
"Our brains literally think of ourselves like James right now... both of those are me. Both of like at some point I'm gonna need to make that decision."
[07:12] James Knoll
This mindset fosters continual delay, making the leap to retirement more challenging as the decision perpetually moves into the future.
The episode features insightful comments from the Root Collective community, providing real-life perspectives on overcoming retirement fears.
Tommy C.'s Experience:
"I took this leap 11 months ago at age 56 and thought I would need to find something part-time just to keep my engineering mind busy. Honestly, I haven't even missed work. OMG. The reduction of stress and the increase of time is so liberating."
[07:12] Ari
Tommy's journey illustrates the profound positive impact of leaving a high-stress job, emphasizing liberation and enhanced quality of life post-retirement.
A Thoughtful Strategy:
"I'd set up a plan to pay yourself on the same schedule as your current paycheck. It'll feel like vacation plan to keep yourself engaged with your field and then go back if you want to, but you probably won't want to."
[07:12] Ari
This strategy offers a structured approach to transitioning out of a high-paying role, maintaining financial stability while gradually adjusting to retirement.
James cautions against the simplistic advice of "just do it," highlighting the necessity of ensuring financial readiness before making the leap.
"But my financial brain is going, I gotta make sure, you know, you won't run out of money."
[09:22] Ari
He emphasizes the importance of not only dreaming about retirement but also meticulously planning to avoid scenarios where one might have to return to work prematurely due to financial constraints.
Ari expands on the concept of opportunity costs, urging listeners to consider not just the financial gains of continuing to work but also the intangible losses associated with remaining in a high-stress environment.
"What is life worth? What's that year of health worth to you? What's that year of travel worth to you? What's that year of adventure worth to you?"
[13:31] James Knoll
This perspective encourages a holistic evaluation of retirement, balancing financial benefits against personal well-being and life experiences.
James advocates for a retirement that doesn't equate to complete withdrawal from work but rather a shift towards fulfilling, passion-driven activities.
"A perfect life is one that you don't really retire from... Create that life that you do want to live."
[12:03] James Knoll
Whether it's volunteering, engaging in hobbies, or part-time work for personal satisfaction, integrating purposeful activities can enrich retirement life.
Listeners like Andy Wang share their positive experiences with the podcast, crediting resources such as Die with Zero for reshaping their understanding of money and life's true value.
"These podcasts from Ari and James have been helpful along with reading Die with Zero."
[17:00] James Knoll
Die with Zero is recommended as a transformative read that challenges traditional notions of wealth accumulation, promoting a life rich in experiences over mere financial success.
Both James and Ari underscore the importance of community support in navigating retirement fears. The Root Collective serves as a platform for individuals to share their journeys, gain insights, and receive encouragement.
"Join the Root Collective. It's free... Just go hear from others. You might take some ideas and you might even feel that you learn things you otherwise didn't know."
[17:53] Ari
This collective approach fosters a sense of belonging and shared purpose, mitigating the loneliness and uncertainty that can accompany retirement decisions.
James concludes by sharing personal anecdotes and reinforcing that making an informed, prepared decision to retire can lead to a fulfilling and healthier life.
"Once you make it, there's so many good things on the other side... how do you live better lives?"
[18:56] James Knoll
He encourages listeners to leverage available resources, consult with financial advisors, and engage with the community to ensure a smooth and satisfying transition into retirement.
"Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough" offers a nuanced exploration of retirement beyond financial metrics. By addressing psychological barriers, emphasizing the value of life fulfillment, and fostering a supportive community, James Knoll and Ari provide listeners with a comprehensive guide to overcoming the fears associated with retiring. This episode serves as a valuable resource for anyone standing at the crossroads of financial readiness and emotional uncertainty, aiming to achieve a retirement that truly maximizes their return on life.
Notable Quotes:
"How could you really know? You haven't done it yet."
— James Knoll [01:52]
"When psychologists look at our decision-making frameworks... it's comfortable for me to have to do."
— James Knoll [03:14]
"The reduction of stress and the increase of time is so liberating."
— Tommy C. [07:12]
"What's that year of health worth to you?"
— James Knoll [13:31]
"Die with Zero is a great book that I just like to recommend..."
— James Knoll [17:00]
"Joining this collective and see what other people say... it's all custom based off the life you want to live."
— Ari [17:53]
This detailed summary captures the essence of the episode, presenting key discussions, insights, and actionable strategies for overcoming retirement fears. By incorporating direct quotes with proper attribution and structuring the content into clear sections, the summary provides a comprehensive overview for those who haven't listened to the episode.