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

When Is The Ideal Time To Hire An Advisor?

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

Ari Taublieb, CFP®, MBA

Real Estate Investing, Stock Investing, Careers, Save On Taxes, Retirement, Business, Personal Finance, Investing, How To Retire, Early Retirement, Retirement Planning, Entrepreneurship

4.7583 Ratings

🗓️ 5 January 2026

⏱️ 16 minutes

🧾️ Download transcript

Summary

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 w...

Transcript

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0:00.0

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.

0:08.1

Not just when should I not hire an advisor, but when should I hire an advisor?

0:11.7

What's the right time? And to me, hiring an advisor is all about timing. It's not just competency and value.

0:19.3

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 going to tell you a story right now that hopefully is going to help you decide when does it make sense for me to hire a financial advisor. I try to do all these stories and fun ways because this actually happens to me. So I'm going to tell you a real life story. Then you'll be the judge to see if this helps you. So I am a soccer player. I love playing soccer to one unhealthy degree. I like to play five nights a week. Should I? No. Any 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?

1:28.4

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 going to have to do one on your left hip so shortly after? And I said, hey, respectfully, doctor, I hear what you're saying,

1:44.9

but this is my call here. It's my body. I know that you think this makes most sense. And if there's

1:49.6

something I'm missing, please tell me. But it sounds like if I just do my right hip first and see how I do,

1:56.5

the downside is I have to come back and get another surgery and maybe the recovery is even worse,

2:01.6

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 the same time. That's why I would do it 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

2:20.0

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 going to bring this back to finances now. My parents were burned by four finance 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 going to, 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 weak recovery. So a 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?

3:42.7

Because if they can have value, great, that's not the sole reason to hire someone.

3:46.7

I spoke to many people who go, I believe that you guys could add value. I've seen the

3:50.6

videos. The tax strategy analysis, the health care management, the insurance, investing, all

3:55.7

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

4:14.5

I otherwise couldn't have known about because I'm not doing it all day, would that make me feel

4:18.5

better about my decision to retire? Many of you are like, yes, that would. Many of you are like,

4:23.0

well, I actually like doing this stuff. I enjoy, I'm listening to a financial podcast for fun right now.

4:29.4

Awesome. You might not be the person that needs an advisor until, and as I say often, my rebalancing story, I had someone who reached out. 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. And I should be on an as needed basis. What if markets fluctuate wildly in a week?

4:47.6

We should rebalance.

4:48.6

What if you have 100% equities? Well, you should rebalance still. What if domestic did really well and international deported? 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 going to want to do in retirement? many people want to 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 advisor. They're already retired and they wish to hired 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.

5:39.8

Yeah, there's more reasons to hire an advisor.

5:41.8

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 worth breath?

...

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