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

Why It's Natural To Be Worried To Retire (And What To Do About It)

• Ari Taublieb, CFP®, MBA • Episode 245

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Retirement anxiety is normal and healthy, even for people with solid financial plans—it shows you're taking your future seriously and want to make thoughtful decisions about your life transition.

• Understanding why retirement worry is natural despite having financial security
• How joining a retirement community can provide perspective and reduce anxiety
• Balancing financial needs with personal purpose and meaningful activities
• Learning to differentiate between necessary caution and excessive worry 
• Finding comfort in flexibility and dynamic planning during market changes
• Recognizing that uncertainty is normal in major life transitions
• Defining your personal measures of retirement success rather than comparing to others
• Taking action by exploring new ideas from peers rather than just passively consuming content

Join our free retirement planning community to connect with others navigating the same challenges and discover new strategies to improve your retirement confidence.


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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.

“Early Retirement – Financial Freedom” is a podcast produced by Root Financial Partners, an SEC-registered investment adviser. The content provided is for informational and educational purposes only. It should not be interpreted as investment, legal, or tax advice. I may reference planning situations based on real client experiences, but they’ve been simplified for clarity. Always consult your own financial advisor before making decisions.

Listening to this podcast does not create or imply an advisory relationship with Root Financial. Investing involves risk, including the potential loss of principal. Past performance does not guarantee future results. Testimonials and endorsements do not reflect all client experiences and are not compensated. Learn more at our website or by reviewing our Form ADV at https://adviserinfo.sec.gov.

Speaker 1:

If anyone were to come to me and say, look, I'm just not worried about retirement, I'm sure it's going to be fine. I have a plan for purpose fulfillment financially I've never worried about anything at all I'd be like kudos to you, you are the anomaly, because most people they're not worried, like am I going to be? Okay? I mean, there is an extent of that to everyone. But most people are like, look, I want to make sure I don't miss something, or look back with regret of why didn't I spend more time with family or friends? Or how do I make sure I don't die with like 20 million, cause I don't need 20 million, but I also don't want to run out of money, and I feel like that's a hard line to kind of understand. And so the point here of today's episode is really going to be about like why it's natural to be worried and how to plan around that in a way that decreases your anxiety, and that is my goal of this episode. So if you're like, hey, I am that anomaly, I just don't worry, because I just I don't know what to tell you. I feel like I have a good plan, I'm not worried about anything, nothing Great. This might not be the episode for you. I never want to waste someone's time, if you're like, no, I just want to kind of hear your thoughts on it. Anyways, even if I'm not worried, I'll try to make it entertaining for you. So thank you, as always, to listening to the Early Retirement Podcast. Bad transition right there, but you're getting the raw transparency here, as always.

Speaker 1:

My name is Ari Taublieb, I'm a certified financial planner and I'm the host of the Early Retirement Podcast. Finally, I am the chief growth officer at Root. What the heck does that mean? Well, my job is to help as many people as possible retire with confidence, and sometimes that means I have to institute a minimum, meaning how many people my advisors can take on in a single month. Sometimes it's regarding an asset minimum, sometimes it's me going how do I expand? What services look like as an industry? So it's one of the reasons I created this Root Collective, this community that's free, that anyone can go join, to go see new ideas about retirement planning, which I'd encourage all of you to join if you're not already in it, and you can see that in the description. That's my job.

Speaker 1:

So today's episode why it's natural to be worried and how do you plan around. That was prompted by something someone said in the community, so I'm going to read it aloud. You can see it If you're watching on YouTube, if you're listening on the podcast app. Please keep doing that. And this comes from hi fi, who says I feel for your clients, I'm sort of in the same boat. Now, real quick disclaimer on that. I posted saying hey, any of you worried about retiring? And if you are, like, what specifically are you worried about? Because I think if we all talk about it publicly and in a really open, transparent manner, other people will go hey, so I'm not alone, other people feel this way. So this person says that I feel for your client, I'm in the same boat.

Speaker 1:

I'm 45 years old, entering recreational employment. Entering recreational employment Recreational employment is the phrase I made up instead of what a lot of people will call the FIRE movement, which is Financial Independence, retire Early, where people are getting multiple jobs, sacrificing health, all to try to retire at 35 and they don't know what they want to. Or because you have to, great. If it turns out it's because you want to keep doing it. If it's because you have to, when could that possibly stop? Okay, no more interruptions.

Speaker 1:

Let's finish this point here. Many of my colleagues have left this portion of the profession to move on to a different area. I have no plans to do so. I live in a rural area that doesn't afford me the luxury of most meetup groups or activities that are available to others, but here's my thought. I'm going to use the drive and mindset that allowed me to run a successful business and become financially independent to fuel a successful retirement, whatever that may be. Yeah, I'm a little worried, but I'm up for the challenge. It is a challenge. It is a fun challenge. It is real life, though, and what I mean by that it's like some of you are like what do you mean? It's not.

Speaker 1:

I do have people that go well, I'm just going to retire and it's just going to work out, right. No, it's almost. It's something you have to be really intentional with and practice because and I'll do these exercises with my clients I'll go. Okay. So you want to retire where, I don't know, maybe Hawaii. I go, great, what are you going to do? They're like well, I'm going to have time with family and friends, and that's what I'm so excited. And then I have clients that go you know, I'm going to play golf and I go great, like if you're at your back, what are you going to do? And they're like I don't know, like I was going to golf, that's what I put all my marbles in and I go well, you could do that, but I also don't want you to all of a sudden go. Hey, I feel like I put all my kind of effort and energy into family and friends and like they're busy because I'm retiring so early. Who the heck am I supposed to hang out with and what am I going to really do? Am I going to have purpose?

Speaker 1:

Some of you are like, omg, are these real problems? Like just go volunteer. Do you know how many different you some of you are like listening, going, how are people literally bored? Like I have a laundry list of things I want to get to. But this sense of worry, I find stems from the financial side. So at first it's like, hey, do I really know I can retire, which is why I encourage people to at a minimum use the software I talk about in that academy, get confidence from an advisor, whether one at Roots or another firm, to go okay. So financially I've worked through all of that, I'm in a good spot.

Speaker 1:

But what prompted this episode, why I wanted to record it is because there's a lot of people that financially, feel, yeah, I'm in a good spot, but I still am not confident, and I don't know why. Why is it that I could be shown hundreds of graphs and numbers and I have a degree of confidence, but I still don't feel like I can take the leap. Why is that? Well, I'm going to use a personal example and then you'll be able to hopefully take some insight from it.

Speaker 1:

And so when I was proposing before I proposed, should I say to Alice Alice is my fiancé, we have been together for over six years and I proposed last August and we're getting married in August, this upcoming August and I went to a therapist and I said, look, this just feels weird. I know this is my person, I couldn't live life without her, she is my everything. But like I'm committing for like life here and so like, is there something I'm missing or overlooking? Like I don't know, like maybe there's not, I don't think there is but like I just have this feeling, not like it's not my person, but a feeling of like, hey, it's like you're a professional, you talk to people that like get married all the time and people that get divorced, and like what are the best tips and strategies? And can I just like give you my thoughts so you can give me a gut check as to whether it seems like you think I should do this or if there's something I'm overlooking? And they were like this is a common case of you trying to have everything figured out. I'm like, well, I am a planner at heart, so I do believe that. And they're like look, some of this is. And when they said this, they go some of this is you're not going to know and you've got to be comfortable with that, but is this the person that you want to figure it out with? And right when they said that, I said I'm good, totally good, doing doing it. It was about a 12 minute call that I paid 50 minutes for and I was like more than happy to do it. So the idea here is some of you just might need to go.

Speaker 1:

Wow, a lot of other people are also kind of worried, even though financially they're in a good spot. And I just like my anxieties got lifted because I saw one thing someone said in this community that is making me, for some reason, like more confident, like I know maybe I shouldn shouldn't pay off the mortgage, but like they just talked about how great it is, how much better they sleep when they do pay off the mortgage. That's been something that I've been debating, or a common one is hey, I just I'm really worried if I travel extensively from 55 to 65. Am I going to run out of money because I'm spending so much more at the beginning, like when markets aren't doing well, and I'm also traveling? Am I screwing future me later?

Speaker 1:

And the reality is, I'll give you the financial answer, but the reality is, hey, these are the years you have your energy and your health. I want you to spend time doing this. I want you to prioritize those things. I also don't want you mad at me when you're 90 with $20 million going. Why didn't you give me confidence that I could have spent more money? So the point here is you're going to go if you're in the community and you're going to see what people say about. Hey, yep, I'm actually in the community right now and I actually stopped taking five trips when markets weren't doing well and I instead only took three trips because I could see on my portfolio if I just kept taking five trips while markets were going down. It really would have changed how much I could spend the rest of my life. So I'm still traveling, but I'm taking three, not five.

Speaker 1:

Some of you might go wow, that hits. That resonates with me. I get why I would want to take less when markets are doing well, and maybe then I ramp up when markets are doing well. It's about being dynamic. And so some people come to me and I've given this example a lot.

Speaker 1:

They'll go look, I just want you to tell me, am I going to be okay? Just like will I be able to meet my legacy goals? Tell me I'm not going to run out of money. I'm like look, I'm sorry I can't do that, but a thousand other advisors will. And they're like why not you? And I'll joke that I'm the meanest advisor Not really, but because I don't want you mad at me retiring too early or too late. And my dad growing up used to say I'm the meanest dad there is because I would go hey, why can't I have Cheetos? My friend does? He'd be like life isn't fair, too bad. And so I'm like look to all of you guys hey, life isn't fair in the way of like, not like. You're not going to be okay.

Speaker 1:

Most of you watching, listening, you're going to be okay. You are taking the time to reflect on your retirement plan and you're choosing to casually listen to this instead of watching some reality TV or other things that I think a lot of that is head trash anyways. But regardless, my point here is I want you to go wow, I'm not alone. I do see what I'm on track for and I see what I can manipulate, like I see my trade-offs. You might go. I really want to take five trips per year, no matter what. That's my thing. I'm traveling and your software might show you. If you're using it correctly, it might go hey, john, you can do that, but it means you're working one more year, so you're going to work till 56 instead of 55. So, whether markets do good or do bad, you can still do your five trips a year.

Speaker 1:

Other people are going to be like I'm more of a. I'd rather stop working now, and if that means I take a few less trips, fine, because I just don't want to work. Okay, that's you. You're different people, but you can still gather ideas from each other. So I want everyone, hopefully, to take some sort of action from this, and that action can be like I see, when I'm on track very clearly, where I will not have to work ever again using software, working with an advisor, whatever that may be, or going.

Speaker 1:

I'm going to go in this community and learn what other ideas are out there that I don't know, and this could be ideas regarding I changed my umbrella insurance, I moved my 401k to these investments, I started using this rule of 55. I decided to optimize my withdrawal strategy. Whatever it is. Let this be the tough love meanest dad, whatever analogy you want to take and take some sort of action. Because if you're just listening to this casually awesome, but a lot of you guys do listen to this casually, which, look, I love more people download the show Helps it grow. But my mission is to make sure as many people as possible can retire early or at least know when it's possible. So if you're casually listening and enjoy it, but not taking action, at a minimum join the free community so you can see what other ideas are in there. You can be silent, don't use your real name, just go in there and kind of look around to be a fly on the wall and if there's a few ideas you take that really resonate with you, awesome, and if there are some that you think are terrible, you can put those thoughts in there as well. But that is just that's this episode.

Speaker 1:

This is not my normal episode of case study, conversion, withdrawal health care. This is like, hey, you're a human, it's okay to be worried If you are not worried at all. I would be more worried because, as an advisor, I talk to people. It'd be as if, like, I went to surgery with a doctor and I just, hey, doc, just, you know, open me up. You know, just go for it. Don't even worry whether it's the right leg, left leg, just go for it. No, obviously not like that. But I would say, look, that would be weird. If I was the surgeon, I'd be like, hey, don't you have more questions for me? Like, don't you want to really make sure you're about to get surgery? Like, yeah, I want to be asked questions.

Speaker 1:

I, we are given comfort as advisors At least I am. When someone goes, ari, I'm really worried. What if I live till like I'm a hundred? Great, let's plan for that. Oh, at a minimum, let's do it. Oh.

Speaker 1:

But also, what if my friends don't retire at the same time as us, but I still want to travel with them. Can I afford to pay for my friends to come on trips with us as well? Absolutely, let's see if we can do that. So go dream to the nth degree and then play around with the trade-offs to go. You know, yeah, I do love my friends, but if that means I have to work three more years just to travel with them, they can pay for their own ticket. You might go. No, what am I doing? It turns out me working one more year would allow my spouse to have unlimited you know whatever golf trips. Okay, that's something that's valuable.

Speaker 1:

Define what you view as success. Don't let other people go. You know, I'm going to tell you how much you need. You need $2 million, and the biggest head trash that I see is people will go. Oh, you know my neighbor, they have $2 million, we have $3 million, and they say like they're nowhere close to retirement.

Speaker 1:

I feel like maybe we can make it happen, but I don't really know. And so we just feel anxiety, and it's one of those things of are we going to like, create, like what? Is it? Not anxiety, but create havoc? I don't think that's the perfect word either, but havoc on the street of like oh, they're the retired couple, retired so early, they're going to regret it later, cause what if they spend too much too soon? I'll have people come to me with those thoughts and conversations. And so all of this is to me just truly to say hey, you're normal, you're a human, you're not normal. I'm not normal, I'm weird, I am pro-weird. By the way, that's going to be one of my t-shirts. I'm going to have cauliflower shirt, pro-weird. And then I'll do you guys think if I were to say, hey, you can go get some merch, some early retirement merch, what would it look like? Those are the two I'm thinking Cauliflower, pro, weird, and that's it.

Speaker 1:

So obviously I try to keep these fun, entertainment, lighthearted, educational. If you like this style, great, let me know. If you're like no, I'm more of the technical person. I want a little more hard hitting, hit me with the facts and awesome. I have way more of those types of videos and I like doing those equally as much.

Speaker 1:

I love doing different types of content podcasts, videos, live shows. If you're unaware, I do live shows every Wednesday on YouTube, so if you wanna check those out, you can even see all the previous live recordings. Those are different than this. This is, you know, 10, 15 minute. Here you go. Those are like hour, two hours of me going through lots of case studies, lots of terrible jokes in there, which I'll apologize for in advance. I love getting to do them and that's all I got for you guys today. See you next week.

Speaker 1:

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, earlyretirementpodcastcom, 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.