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

When Is The Ideal Time To Hire An Advisor?

• Ari Taublieb, CFP®, MBA • Episode 298

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Hiring a financial advisor isn’t about credentials alone, it’s about timing. And for many people, getting that timing wrong can cost years of freedom.

Ari explores when it doesn’t make sense to hire a financial advisor, when it absolutely does, and why the decision often has less to do with intelligence or interest in finances and more to do with stress, life stage, and opportunity cost. Drawing from personal experience, real client conversations, and a story from his own life, Ari explains why pushing back, asking questions, and trusting your instincts matter just as much as spreadsheets and projections. 

The discussion reframes financial advice away from credentials and rules of thumb and toward partnership, value, and peace of mind. Some people genuinely enjoy managing their own finances and are well-equipped to do so — until complexity, time constraints, or major transitions enter the picture. Others reach a point where the cost of doing everything themselves quietly becomes higher than the cost of professional help. 

Rather than offering a one-size-fits-all answer, Ari breaks down the signals that matter most: losing sleep, worrying about missed opportunities, navigating retirement timing, tax strategy, healthcare decisions, or coordinating finances with a spouse. The goal isn’t to convince anyone to hire an advisor — it’s to help people make the decision intentionally, with clarity and confidence. 

This conversation is for anyone who has ever wondered whether they’re doing just fine on their own, or whether having the right partner could help them work less, worry less, and live more.

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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_01:

When should you not hire a financial advisor? Well, I just thought this would be a fun topic to discuss at the beginning of the year because I get this question often. Not just when should I not hire an advisor, but when should I hire an advisor? What's the right time? And to me, hiring an advisor is all about timing. It's not just competency and value. Yes, those are things that need to be discussed, obviously. There's people who have said, well, you're a CFP, you're a certified financial planner, so I should start working with you. I'm like, don't work with me because I'm a CFP. How many doctors that are MDs would you never let touch your body? Probably a lot of them. And I bring up doctors because I'm gonna tell you a story right now that hopefully is gonna help you decide when does it make sense for me to hire a financial advisor? I try to do all these stories in fun ways because this actually happens to me, so I'm gonna tell you a real life story, and then you'll be the judge to see if this helps you. So I am a soccer player, I love playing soccer to an unhealthy degree. I like to play five nights a week. Should I? No. Many physical therapists have told me if I played three days a week, I might be able to last longer or recover better. And I get that, but I love playing. So it would be like someone telling you, if you love cookies as an example, or reading, whatever it is, you can't do it as much as you want. You're like, dang, that sucks, and maybe you do that. But it's just not something I have in me, okay? So I play soccer so much that my hip is in a bad position. So I got an MRI scan, and they said, Yep, this right hip, it's not good. And this left hip, it's also not good. So we should probably just do both surgeries at the same time. And I said, How bad is the one that you say is not as bad? And they go, Well, it's bad enough, your left hip, that maybe we should just get it done at the same time. And this was a surgeon I trusted, and he's doing what he thinks is in my best interest. Why do a surgery on your right hip when you're gonna have to do one on your left hip so shortly after? And I said, Hey, respectfully, doctor, I hear what you're saying, but this is my call here. It's my body. I know that you think this makes most sense, and if there's something I'm missing, please tell me. But it sounds like if I just do my right hip first and see how I do, the downside is I have to come back and get another surgery, and maybe the recovery is even worse. But the potential upside is if I just do the one hip and I'm okay, I just avoided doing my left hip at all. Is that right? And they go, that's right, but I really think you should probably just get them done at the same time. That's what I would do if I were you. I said, Okay. And there's nothing to say that this doctor was wrong, okay? But I only did my right hip, and I've never had to do my left hip. So the reason I tell you this story is I am the weird person that will push back in life. I am just naturally, I'm not doing it to be mean. I'm not, I never want to be rude, but this is my body, just like your finances are important, obviously, because this dictates how long you need to work. Many of you like what you do. Great, keep doing it. But know that if you don't want to go to work, you don't have to. So I'm gonna bring this back to finances now. My parents were burned by four financial advisors. Not burned truly in the sense that, oh my gosh, they stole their money or anything like that. Nothing crazy happened. They just didn't receive great advice and they had to work much longer than they needed, and some of the fees were insane where they were. And so it wasn't justifying the value. And so when you hire an advisor, the reason I say it's all about timing is if both of my hips were bad for that surgeon showed me, look, you're gonna, I'm telling you, not be able to play soccer next week unless you get both of these done. Obviously, it wouldn't be a week recovery, so bad example, but you get my point. It wasn't that clear-cut, should I say. With advisors, the time to hire an advisor is number one, if you are losing sleep about anything. If you're like, oh my gosh, I'm losing so much sleep. I know that I need advice, I just don't know where to go. I don't know where to go. I don't know what I should be focusing on. I'm so busy doing my job. I want to hire a professional to help me with my finances. So that's the number one gut check. Number two is going, okay, do I feel an advisor can add significant value? Because if they can add value, great, that's not the sole reason to hire someone. I've spoken to many people who go, I believe that you guys could add value. I've seen the videos, the tax strategy analysis, the healthcare management, the insurance, investing, all that I see, but I actually like doing it. And there's a time where I find certain people like doing it because they're a year out from retirement, they're two years out, they're really starting to dial it in. But there's also another part of them that's going, could I be missing something? And there is that sense of if I had a third party tell me I was okay and maybe enlighten me on things I otherwise couldn't have known about because I'm not doing it all day, would that make me feel better about my decision to retire? Many of you are like, Yes, that would. Many of you are like, Well, I actually like doing this stuff. I enjoy, I'm listening to a financial podcast for fun right now. Awesome. You might not be the person that needs an advisor until, and this I say often, uh, my rebalancing story, I had someone who reached out and they were really wanting to know about rebalancing and how we do it. And I said, I don't really believe in a let's do it quarterly or monthly. It should be on an as-needed basis. What if markets fluctuate wildly in a week? We should rebalance. What if you have 100% equities? Well, you should rebalance still. What if domestic did really well and international did poorly? You should rebalance. And so I'm giving all these examples and they're like, what's your point? Would you just get to it? And I said, My point is, is this something you're gonna want to do in retirement? Because many people want to golf or play pickleball. And if you're doing all these things or hanging out with friends, that's less time rebalancing. So you are missing out on opportunity. And it's not always competency, it's just do you have the software or means to do it? Do you have a desire to do it? So I bring this up because timing is key when it comes to hiring an advisor. They're already retired and they wish they hire someone earlier to five years out. That's generally the sweet spot. Now there's there's big differences, okay? If you have significant equity and you're 10, 15 years out, or if you're 15 years out and you're like, oh my gosh, I inherited a ton of money, I just don't even know what to do. But the fact that this is a lot, I don't want to squander it, yeah, there's more reasons to hire an advisor. But the ultimate thing it should come down to is that feeling. It's that feeling, and I relate it to love. You could do all the pros and cons in the world. If your partner, let's just say it has the worst breath, which my wife, if she's listening to this, she might be like, oh my god, did you say that because I have the worst breath and you haven't told me? No, that's not what I'm saying. Okay, my wife has a lovely breath. Okay, it's actually don't even really can't even tell she has breath, which is good because that means it doesn't smell. So, bad bad joke here, obviously. But my point being, you can do all the pros and cons you want. Oh my gosh, are they tall enough? Do I have sexual attraction? Do I find that they're actually someone that I like hanging out with when I'm in the car and no one's even talking? Is it weird? Is it ever awkward? There's a gazillion things, right? But at the end of the day, it's that feeling. You can pro and con it all you want, but you get that feeling, and that's the same feeling I want you to have with your advisor. Not on the sexual front, okay? But just six strictly on the front of do I trust them? Is this a feeling where I go, oh my gosh, this person, just by talking to them, I feel they're gonna work harder to manage my money than I would on my own. I feel they have a greater ability to do so. I feel they have a desire, I feel like they actually care. And you can't really ever know until you speak to someone first. So most people that I speak to that go, yeah, I just don't know if an advisor can help. I go, how could you? You haven't spoken to one yet. So what I invite people to do is have a conversation. You might speak to us at root or whatever advisor firm that you think resonates with you, and they might go, you know what, you're awesome, you're a really cool person, but I don't think you can help yet. Most of your money's in a 401k. You don't want to retire for 10 years based off X, Y, and Z. I think you'd be overcharged working with us. And I would hope the advisor you speak to would say that. The reason that I like to be this transparent is to me, it's just honest. There are times when I'm like, oh my gosh, what the heck are you doing? Hiring an advisor, we can't even help. To be honest, sounds like you love this stuff. Yeah, go our separate ways. Like, thanks and keep watching the videos. There's other people that go, Wow, I just didn't even know what was involved. And my spouse, it's hard to ask my spouse these questions financially. But when a third party does it, I now find that we're having better conversations. And now I find that the dividend investing that I used to love researching, although it was fun, maybe wasn't the most optimal. And now I can spend more time with my spouse and redate them in retirement. Well, that's cool. So there's so many different ways of looking at this. There's, okay, am I losing sleep? Do I feel that there's something I'm missing? If you're like, I'm really losing sleep, okay, skip that one. Go to the value. Do I feel an advisor can add value just financially? Whether I like them or don't like them. Do I feel that they would make me more money? That's something to consider strongly. There's one conversation you might have with an advisor that could shift your entire plan. That might justify the fee in one chat of, hey, you didn't know that you can massage your income to do this? Yeah, that's going to save you$20,000 this year in healthcare and for the next 10 years before Medicare kicks. Or, hey, you didn't know that you should not do a Roth conversion because you were about to, because it sounds cool and the software told you you should. Well, did you know how these assumptions work underneath that? And did you know how Monte Carlo actually connects to the withdrawal rate? And how if you don't have the right insurance and something, God forbid occurs, now you're in a lawsuit of whatever it may be. I've seen so many wild situations at this point that there's just too many directions. What I find is the ultimate reason to hire an advisor is so you don't have to do it. Now, the one caveat to that, and I'm gonna be very honest here, because I say often, when does it not make sense to hire an advisor? I'm just gonna use root as an example because that's our firm. If you were to reach out and say, I only want to talk to someone once a year, I want them to tell me that I'm doing fine, and I want them to just tell me, hey, never be too harsh, and just kind of give me some a little light encouragement, we are not the right firm. I can do that right away. Tears are coming out in the first few meetings. We're asking you, hey, did you have a lemonade stand when you were a kid? Why is it that your spouse is nervous to talk about finances right now? What's the relationship been so far as to how you both manage finances? Or if you're single, what's the legacy plan when you don't feel that financially, or should I say mentally, you have the ability to manage your finances? There are so many directions, once again. The greatest fear, I think, is you look back and you go, Wow, so I could have actually worked less, I could have spent more, and instead I do the rough conversion, even though I don't have a legacy goal. Or these things that on paper can look like they make a ton of sense. For example, paying off a mortgage. There are people that go, I'm not paying off the mortgage, I have a 4% interest rate. If I invest the rest and get 8-9%, it's way better. Yeah, but what's gonna make you sleep better at night? Okay, well, it doesn't mean you do it, but it means you factored in. So the right advisor should give you a level of, oh my gosh, my shoulders are down. I have a partner. There's someone that I can consistently reach out to who's always looking out for my best interest so I don't have to do it. And the reason I bring this up, and I'm so honest here, is the first few months, emotions are going all over the place. We're starting with purpose. We want your dreams, we want your fears. We're talking every single week for the first six weeks. Some people they're like, that sounds like going to the dentist. Great, we should not work together. It is not gonna work out because we want to talk to you. You are hiring a family member. Some people say that cliche, like we're part of your family. My brother played professional soccer for 10 years, and his pet peeve was whatever they do at team huddle, it was always one, two, three, family. That's what they would say. And my brother's like, look, we're not a family. We're all acting as a family in a fake way, but we all don't want to be on this team. We all are playing at a level that isn't happy. The coach is kind of stabbing us behind the back and says we should be family, but it's because he thinks that's the best way to motivate the team. It's not actual family. He was saying it felt like fabricated. So with us, it's actual family. It's not just, okay, we're gonna talk and tell you that you're doing great. Well, we might tell you, hey, I know you want to retire next year. We think you should retire in five years. And you might go, Well, what am I paying you for? And we're like, we're paying, you're paying us so that we give you great advice so you don't look back and run out of money. At the same time, you might be paying us and we might go, hey, markets are down this year. Are you willing to take three less trips? And you're like, what? And we're like, well, this is so that you can save on taxes when it matters most before Social Security comes on to optimize the taxation of how that's gonna connect to your withdrawal rate. And you might be like, what the heck did you just say? And then we'd be like, oh, let me tell it to you in English. When you bring in income through Social Security, that increases your overall income. So if you have Social Security and you do a Roth conversion, that's bumping you to a new higher bracket. Well, that's gonna change things. If you already have Social Security coming in and you're pulling money and you don't pull it from the right account, we might pay more in taxes than we need to. Let me show you three examples and you tell me which one resonates most. That's what real planning looks like. It's not about making sure the advisor's right or showing off how fancy they are with big words. It's about making sure that you feel, yes, value is being added and you have a true partner so you don't have to do it. You are paying for your time, which to me is the most valuable resource. Now, this is something that once again, if you're gonna try to black and white and you get the Excel spreadsheets out and you try to map it perfectly and go, does it make sense? You're gonna drive yourself nuts. And I tell people not to hire us or any firm when they're in that headspace. It's when you're in a spot where you go, okay, do I feel that there's something I don't know? Is there true expertise? And the only way to know, in my opinion, is to find out. So if you've ever wondered, it's the beginning of the year, if you want to reach out to Root Financial, you can do so and have a conversation with one of our advisors whose role is to show you if they can help. They might say that they can't. They might go, you're lovely, but you asked too many questions, and you know, you're gonna be my biggest hassle of a client. And they're not gonna do that. I'm just trying to be silly here. But my advisors, I they they adhere to a strict calendar policy. And what does that mean? Some of you go, oh, so they're like really dialed in working all the time. Strict calendar policy, like a quota. No, no, no. It's the opposite. They must look at your name on the calendar and go, I'm excited to talk to John and Jane next week. Because if they don't have that feeling, then they're not gonna run through a brick wall for you, which means it's gonna be a problem. And I want you to feel, oh my gosh, every meeting with your advisor is truly like going to Disneyland. Now, some of you are like, well, I hate the lines at Disneyland. Okay, imagine it's fast past Disneyland. This is what it should feel like. It's like, oh, I'm gonna see how much I can spend this year and how much I'm gonna save on taxes. I'm gonna be asked real questions about what matters most to me. It's not the traditional, what happened to my parents of, all right, Mr. and Mrs. Smith. So here's some numbers and spreadsheets, and they have colors. So, you know, hopefully you like those. And you see how some go up and down? Yeah, great. You're like, hey, you're trying to put me to sleep. Like, this is not helpful. So hopefully it feels different. And many of you that fill out our MPS survey, our net promoter score, we have currently a net promoter score of 92. So if you're familiar with net promoter score at all, okay, how likely are people to recommend Root Financial? You can of course go to our Google reviews and Yelp reviews, but at the end of the day, it's a feeling. So I recommend if it's ever been of interest, beginning of the year, go ahead and reach out to us at rootfinancial.com. And there's a little button in the top right that says CF4 fit. You can click on that, answer a few questions, and then speak to an advisor about how we might be able to help, or maybe we can't help, and we'll tell you it makes sense in the future, or not at all, for whatever reason. I just believe in being honest and transparent. I hope you guys are off to a great start of the year. Thank you as always for listening to this show because I do all of this for you, and without you, I would just be doing a weird TED talk to this camera. So thank you guys and see you next time.

SPEAKER_00:

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.