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

The Shocking Reason Most People Work Past 60

• Ari Taublieb, CFP®, MBA • Episode 289

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Retirement doesn’t come down to a magic number, it comes down to your number. This episode gives you a simple, personalized framework to decide when you can truly retire based on the life you want, not generic benchmarks.

First, get clear on monthly spending (baseline needs + lifestyle wants). Then reverse-engineer your target by layering in taxes, a sensible withdrawal strategy, guaranteed income (Social Security, pensions), and the one-time costs people forget—like cars, remodels, weddings, or big trips.

Beyond the math, we tackle the emotional side: purpose, identity, and designing days that feel meaningful, so the plan funds a life you actually want to live.

What you’ll learn

  • A simple framework to find your number, not “the” number
  • How to translate monthly spending into a retirement target
  • Coordinating Social Security, pensions, and portfolio withdrawals
  • Planning for taxes, RMDs, and estate basics without overwhelm
  • Budgeting for big one-time expenses (and avoiding nasty surprises)
  • Stress-testing returns and inflation—without getting lost in complexity
  • Building purpose and rhythm in the first 1–2 years of retirement

If this brought clarity to your timeline, follow the show, share it with a friend, and leave a quick review—so more people can retire on purpose.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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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_00:

Having worked with hundreds of early retirees one-on-one so that they can retire with confidence, I've learned the shocking reason people work past 60. And it's not just, well, you know, they didn't save enough or they didn't think about their purpose. Number one, it's health care. Number two, it's the Social Security timing. And number three, it's the tax traps that are associated with withdrawal strategies. And that's what I'm going to go over in today's episode. This is a fun one. This is going to be jam-packed with just little hints and tips and hacks and tricks that I've gathered from working with clients that hopefully you all resonate with. Now, are things constantly changing? Yes. That's why I say I don't do financial plans. I do planning because healthcare is changing and subsidies are going to be shifted based off of income and how you withdraw that income. And if you don't have a superhero account and you're pulling all your money from a 401k, you're going to be paying way more in taxes because that's taxed as ordinary income versus capital gains. So the reason I bring that up, and I'm already getting into it, because you can tell I get so excited, is there are people that want to retire early so bad and they feel they're on track, meaning they feel they've saved enough. Where if they were technically 65, they'd have enough money to last from 65 to 95, but they're 57 or 58 today, and they're worried I'm going to need to pay for healthcare. So I feel like I should keep working to stock some more extra money away into this superhero account, which is going to help me keep my income low so I can either get healthcare subsidies or do Roth conversions or pay less on Social Security in terms of taxes from let's call it 62 to 70. So I see a wide range of people that retire. And the fun thing for me is I get to see and learn from these situations and tell you all about them. So my request is if you're watching this on YouTube, let me know what is your plan to retire. How did you come up with it so that we can all learn from each other? If you're listening on the podcast app, there is a way to rate and review the show on Apple. It's a little difficult. I think you have to scroll down and you will see where you can leave a star review based off how you enjoy the show. And then on Spotify or iHeartRadio, wherever you listen, you'll see an option there. And if you want to leave your feedback and what you're planning to do for retirement, that helps more people find the show. So thank you in advance for doing that and taking a second. My goal is to help you all retire early with confidence. My name is Ari. I am the chief growth officer here at Root Financial. I am a CFP that stands for certified financial planner. And I love helping people, just like you, make sure that when you're retiring, you don't have that little thing in the back of your head going, Oh, is there something I missed? Should I work one more year? Or why didn't I do those conversions? Or you're always talking about this cauliflower stuff. Do I need to be eating that? So I have all these little simple analogies and examples that I like to share because it what I find helps people actually relax and go, okay, once I get a plan, I'm in a good spot. So the way I like to start these episodes oftentimes are with little stories. And the one I'm going to use today is a true story with me and a soccer injury I had. And I'm going to connect the dots here. So when I play soccer, I'm over the moon. That is my flow state. When I get injured, I am not fun to be around. I am hangry. Worse than hungry and angry. Put together, I am hangry. Now, I am not fun to be around when I'm hangry. That's what she says. So she says, all right, you need to go get an MRI. So I go get an MRI, and you're thinking I'm going to be miserable because I'm going to see the, oh my gosh, am I hurt? How long am I out for? I'm actually at peace. I now have the severity of my injury. That's like your financial plan. You're going to see, got it. This is what I'm on track for. Whether I like it or not, this is the truth. Then I get to see my physical therapy. I can see, got it. So I'm going to need to do this procedure, then I'm going to have to do this PT, then I'm going to be back on the field. Once I have my plan, I'm actually pretty calm. At this point, I'm not thinking what's the worst case scenario, what's going to happen. I've got a plan. So I know that plan's going to change because if I'm doing well, I could get on the field sooner, and vice versa. Same thing for you guys. You need to know, oh my gosh, are you on track to retire right now? Like, imagine you went and ran an analysis and you saw that based off what you want to spend and when you know you want to retire, that it was actually doable. I mean, think about what it would be like going to work every day. You'd be like, oh my gosh, this is way easier. I'm going to work and like I'm on track, like, versus what can feel like a pipe dream at times. So hopefully you guys resonate with that. And if you're going to work now, after listening to this, running your plan, going, wow, it does feel different. Let us know because this is what helps inspire us all to keep adding money to our own 401ks, myself included. I want to be working as long as I enjoy what I do. And that's the cool thing about getting to run a business with my partner James and all the amazing team members here at Root, is our job is to make sure our clients have an awesome experience and that our current employees that are internal love their jobs, that they keep wanting to work here and therefore service clients better and have career opportunities, and we all win. So I am taking my work very seriously, not because I have to, but because I I want to. My life is better by doing that. And at the same time, I want to save and invest for my future. What if all of a sudden all of our clients turn out to be terrible and which would never happen, but pretend they're all super mean to me for whatever reason and my employees are saying, hey, we don't respect the work you do. Well, I wouldn't feel very fulfilled. I would ask myself, what am I doing wrong? But then I would go, okay, let me look into what I need to do here. And what if it got so toxic? I want to have the financial freedom to do what I want to do. So I'm in the same spot as all of you. So let's go into some of these examples here. So health insurance, retiring before 65 means you're paying for health care. Okay. Now it can be a significant cost, but it's not enough to scare you away. I have clients that spend a few hundred bucks a month and I have clients that spend$30,000 a year in health care. So I don't want you to hear that and go$30,000 a year, how on earth am I going to pay for that from$60 to$65? Like, where am I going to magically come up with$180,000 a year? That's not what I'm expecting. I'm expecting you to go, okay, let me look at the reality. How am I going to withdraw income in retirement? And if you see you have the option to do it in an effective manner and keep a subsidy in a reasonable state where maybe you're paying$300 a month. So yeah, that's significant. Maybe it's$3,600 for you and your spouse. So now you're at$7,200. Is that doable? You might find it helps a lot to work two more years so that you're in a spot to do that. You might find you need to instead of maxing out your$401K, you just want to get the company match and defer the rest into a savings account so that you have enough money to travel the first year of retirement because you haven't set enough money aside for that. Or you want to do a home remodel or you still have kids in college. These are things that you need to make sure you're planning for. Because if not, healthcare can be one thing that can derail your early retirement. But when I say derail, it's not like you won't be okay. Most of you, if you're planning well and you retire, it's not like you're not going to eat. It's more of you're going to look back and go, well, I can't really go out to eat and get everything I want. Or I can't travel and if I want to stay longer, extend my trip because that wasn't in the budget. You don't want to be thinking like that. It's just not fun, trust me. So that's number one is plan around healthcare. I have tons of videos and podcasts where I go into great detail on that. But it's surprising because I'll, I'll, you know, I used to think someone come to me, I go, look, you're on track for retirement. And it looks like from 65 to 95, you're great. Like, what's the holdup? And they're like, well, no matter what you say, no matter how many times you say it, it feels weird. I have kids in college. And what if they want to go to grad school? Like, am I going to pay for that? And I'll say, Do you want to? And they'll say, Yeah, I want to. I go, okay, well, let's add that in. I'll say, what about uh helping them with a wedding? And they'll say, Well, I never had help. And I'll say, okay, so do you want to help them? They go, yeah, because that's something I didn't have. I go, great, let's layer that in. We keep layering in things. Home remodels. Are we going to downsize? Downsizing is a big one. I'll see people who go, Yeah, I kind of want to plan for it. I go, well, that's tricky. And they go, why? I said, are you going to plan for it or not? Because if you plan for it as if, yeah, we're going to downsize, and that's going to really help our plan. And then all of a sudden, you're like, we don't want to downsize because emotionally we love this home and it's where our kids grow up and they just told me they never want me to sell, but you already retired. Well, if we didn't seriously plan around that, and I had assumed you were going to do that, you might have to go back to work, which we don't want you to have to do. So a large reason people work past 60 is not just financial in terms of do we have enough money? It's okay, well, we're in a good spot, but we could be in a way better spot if I worked one more year, or if I work six more months. And that's what I often hear is oh, why don't I just we call that goalposting, moving the goalposts back. Yeah, one more project, one more year, two more years. In fact, I hear that so often. What I'm gonna do, I'm gonna close my eyes, I'm gonna ask you to do it with me. Unless you're driving, don't get in trouble. Don't make me get in trouble, don't sue me. Okay, don't crash. But if you are thinking, just like I'm thinking, yes, have I pushed the goalpost back? Let me know in the comments. In the comments, say, you know what? I just went and asked my spouse, and they said I've done it 10 times. I just thought I did it once, or you know, I kind of known I've always been pushing it back one year, but it's not financial. I just don't really know what the heck I'm gonna do. And that's scary. My partner James has a great quote. He says, When's the last time you've done something for the first time? And I think about that a lot. I'm like, well, I just got married for the first time, and hopefully the last time. Before that, I guess I graduated college or I passed the CFP. Like these are things that come into my mind. So it's worth thinking about. Okay, when's the last time you've done something truly for the first time? And when's the last time you've not had income hit your bank account? Like, that's a scary thought. Now it's coming from your account. So that's number one. Number two, Social Security timing and pressure around that timing. Oh, I hear this all the time. Here's most of you, ready? Most of you are like, yeah, I know I should retire at some point. I don't know when, but Social Security, I paid into it for so long. I know it looks at my 35 highest years of earnings. I've worked that long. I'm gonna turn it on at 62 because I don't want to look back and if Social Security gets cut, wonder why didn't I turn it on earlier and you know collect as much as I can? But then there's another part of you that's like, well, what if I do live till like 95 and it turns out I, you know, pass away? I want my spouse to make sure they get the largest amount. And if they were at home with the kids or just didn't have as much of an earnings record, you're gonna regret if you turn it on and you get$2,500 a month when if you would have waited to get$4,000,$4,000 is what they would receive for the rest of their life. So there's that sense of, okay, yeah, I I know maybe I'm, you know, let's call it 59 years old. I know I could retire at 60, but it really is gonna help bridge the gap because I don't have a ton in the portfolio and 162 hits, I'm turning on Social Security. So I'm just gonna work one more year. So you can see how we keep coming back to that theme of goalposting. So if that resonates, let me know in the comments because these are things that I hear from my clients. And if you guys don't chat below, I just am doing a weird TED talk here right now. So that's number two. If I don't want to hear number three, all these tax traps. Oh, what do I call the tax window? The tax window is the time from when you retire until Social Security turns on until RMDs begin. So pretend you retire at 60 and you turn on Social Security at 67, and RMDs, required minimum distributions, begin at 75. We've got a seven-year window here where we've got to do those Roth conversions. When would we do Roth conversions? And what is Roth conversion? Well, that's called eating cauliflower. You're paying a little bit of taxes to avoid eating a lot of taxes, or paying a lot, obviously, in the future, which is what happens at that RMD age. That's when you're forced to take out 3.8% as a starting spot from your portfolio that is pre-taxed. So some of you are like, big deal. I've got like 200,000 in my IRA. That might not be something you got to deal with. Other people are like, well, if I have 2 million and that grows to three and then 4 and then 5, I'm gonna have to take out 3.8%. That's a significant amount on top of Social Security, on top of inheritance. Like, am I gonna get taxed at like 40, 50% on like millions of dollars? Yeah, sometimes that's the case. So what do we do about it? From 60 to 67 until Social Security gets turned on, that's where your income can be manipulated as you see fit. We can decide to turn on a level of income when we do a conversion that increases your income. So if you retire at 61, well, we've got six years to do really good conversions. Because once Social Security is on, maybe that's 40,000, 50,000 bucks that's now helping us out on the portfolio side where it's not fully up to your portfolio to create income for you. But now that's 50,000 as a starting spot for Social Security. So in terms of income, your modified adjusted gross income. So now we don't have as much room in terms of tax brackets to do conversions at the best possible brackets. Meaning if we have no income, theoretically, we could go do Roth conversions and pay taxes at 10%, 12%, how great would that be? But if Social Security is coming in, we're already in the 12% bracket. So maybe if we do a conversion, we're gonna have to pay at 22 or 24 or 32. So what we want to do is be really effective with how we withdraw income. So I find a lot of people are retiring after 60 because they go, wow, I didn't even know about this tax window thing. I just thought if I kept working, it would be better. In a weird way, the earlier you retire, the more of a tax window you have, the more opportunity to do more of these conversions or harvesting. Now, don't just go retire for the tax window. Make sure you're in a comfortable financial position where you know it's gonna help, but it's not driving that. You don't want the tax tail to wag the life dog. So hopefully, some some cool tips and tricks from today's episode. If it resonated, please let me know. I love getting to do this. And then finally, this is what we specialize in here at Roost. If you want to work with a team that loves this stuff, the tax planning, the estate, the healthcare, the withdrawal, the Roth, the insurance, this is what we love. And we want to help you. So you can reach out to us at rootfinancial.com. See you guys next time. Thank you all, as always, for listening to the early retirement podcast. I love getting to host these shows and make different content for you guys every single week. I've not missed a single week in years, and that is because I love getting to do this. Now, please be smart about this before you actually execute any strategy that you see me talk about or hear me talk about, should I say, please talk to your financial advisor, your tax preparer, your estate attorney. Please be smart about this. None of this should be construed as financial advice. This is for fun, educational, informational purposes only. Once again, just quick disclaimer here, guys, please be smart about this. Appreciate you listening as always. And you can, of course, submit a question on my website, early retirementpodcast.com. If you, of course, want me to address a specific case study or topic. I will not promise I can get to it, but I respond to every single person. And if I find it will be helpful for a lot of people, I will absolutely make an episode on it. At the very least, give you some insight. That's it. Thanks, guys.