Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough

• Ari Taublieb, CFP®, MBA • Episode 243

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You've run the numbers. You have enough saved. Your spreadsheet says you can retire comfortably. So why can't you pull the trigger and leave your high-stress, high-paying job behind?

This struggle represents one of retirement planning's most challenging psychological hurdles. After spending decades accumulating wealth and building a career identity, many successful professionals find themselves paralyzed when the time comes to actually step away—even when financially prepared to do so.

Our conversation explores this common predicament through the lens of a Root Collective member who knows they're financially ready but can't seem to make the leap. We dive into how our brains process major life transitions, why we tend to see future versions of ourselves as different people, and how this affects our decision-making. Just as starting preschool, college, or a new job feels intimidating, retirement represents a significant unknown that naturally triggers hesitation.

The discussion moves beyond simple financial calculations to examine what we're really sacrificing by postponing retirement. While the opportunity cost of leaving unvested compensation on the table is obvious, the opportunity cost of continuing in a high-stress position—measured in health, time, relationships, and experiences—remains harder to quantify but potentially more valuable. We share perspectives from community members who've successfully made this transition, including practical advice on how to structure your finances and mindset for a fulfilling post-career life.

Connect with our Root Collective community to learn from others navigating similar transitions and discover resources to help make your own retirement decision with confidence. What would your 85-year-old self advise you to do today?

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Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Speaker 1:

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.

Speaker 2:

I will. 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 taken the 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.

Speaker 1:

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 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?

Speaker 2:

Yeah, 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 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?

Speaker 2:

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, 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 wasn't even wet out of the water, but I really know I do wanna go swimming. So it's first starting with that. Hey, it's gonna be a leap. How do we do it appropriately?

Speaker 1:

Yeah, Tomorrow deep. How do we do it appropriately? Yeah, tomorrow morning, my wife and I, we are dropping off our daughter for her first day of preschool and she's gonna be I don't know if nervous is the right word. She just doesn't know what it is yet, but it's gonna be difficult. Yeah, I'm nervous ashton's nervous like this is a big change, and I bring it up because we're not. She's not retiring, she's literally starting preschool.

Speaker 1:

I think what we forget is this is a very normal thing, 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? 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.

Speaker 1:

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, 70, 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, say 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 the latter.

Speaker 1:

So sometimes we have to ask ourselves the question of not, what would I do in this situation? What will my future self do? There is some study and I have no idea where it's from so I'm not going to try to cite it correctly. But 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.

Speaker 1:

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 is 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, that both of those are me.

Speaker 1:

Both of them like at some point we 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 Detroit Lions, dt Lions. What are some other pieces of feedback this individual received that stood out to you?

Speaker 2:

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 going to show up? She doesn't even know where she's going. Like, probably not You're. You're probably told her, hey, you're, you're going to be around other kids. You might even know some of these kids that there's probably some preparation that's occurred that will make that leap a little easier.

Speaker 2:

Now to your point, james. Here we are giving analogies about 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 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 by 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.

Speaker 2:

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 got to make sure you know you won't run out of money and I think this is a very important thing to highlight.

Speaker 1:

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. I had to go back and that was. That was me. So we are making a big assumption. And not even a big assumption.

Speaker 1:

The reason we're jumping right into this is because username Detroit lion 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 want to double check those. I'm going to see that. But there there is this thing that we've observed.

Speaker 1:

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 to 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.

Speaker 1:

But I think the point that we want to make, though, is I don't think I mentioned this enough or reinforce 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 and 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.

Speaker 1:

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. I 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 that face value. 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.

Speaker 2:

Yeah, james, check out to see if there's other comments that you might want to bring up here, cause 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 it's 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, then I'm cool with that. But if you're taking a role to go, you know what I really think financially, I need to keep working. So I'm going to, and I don't really love it, but it's for the health care benefit and you know, without that, I'd have to go pay 800 bucks a month on the marketplace. I don't want to do that.

Speaker 2:

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 need a $10 million and thinking about kind of that morbid of hey, 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? Yeah?

Speaker 1:

there's a few and I think, before I go, Ari, you do a good job of using this example. A lot is to go back to Detroit Lions comment of hey, it's hard Like I should keep just um, 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, neither are good options, but it's about finding that right point where you know that 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.

Speaker 1:

Here's 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 until a certain date and it's yours, and that is very true. 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?

Speaker 1:

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 RSUs 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 side 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 very real 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 already 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.

Speaker 1:

And it's like how much does that person wish they could go back in time. If that person could talk to Detroit Lions right now the username for those of you tuning in late Like, what would they say? How much is money worth? 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 to. 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.

Speaker 2:

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.

Speaker 1:

Were there any others you wanted to reference? Andy Wang had another one. I won't read the whole thing, but he just talks about his experience. 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.

Speaker 1:

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 don't 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 books 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.

Speaker 2:

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 learned things you otherwise didn't know.

Speaker 2:

There are people who are in the collective talking about hey, this feels really weird, but like 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 felt the same thing and I even started working extra because I thought I had to and you don't. 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.

Speaker 1:

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 An example.

Speaker 1:

So when I started Root, someone left this comment that I liked. Let me see if I can go to it. 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.

Speaker 1:

I know so many stories of people like 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 it's like, hey, the boats are burned, go.

Speaker 1:

And 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 a 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 paying 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, rootfinancialcom.

Speaker 2:

Click see if you your fit, but lots of great resources out there to help with that. 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.

Speaker 1:

Awesome, I love it. Well, thanks, ari. Anything else you want to add here? That's it All right. Thanks everyone, and we will see you next time. See ya, that's it All right. Thanks everyone, and we will see you next time. See ya. 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.

Speaker 2:

Past performance does not guarantee future performance 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.

Speaker 1:

Once again, I'm James Canole, founder of Root Financial, and if you're interested in seeing how we help our clients at Root Financial get the most out of life with their money, be sure to visit us at wwwrootfinancialpartnerscom.