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

Ready to Retire? Here's How to Tell Your Company │ Root Talks

• Ari Taublieb, CFP®, MBA • Episode 255

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In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career.

Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, and a powerful reframe: every “yes” to more work is a “no” to your time, your family, your dreams.

Hear more stories from the Root Community here:  https://www.skool.com/rootcollective/what-was-your-experience-when-you-told-your-employer-you-were-retiring 

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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 1:

The Root Collective is our free community where you can go and learn from other people in a similar stage of life to you. It's one thing to hear from James or myself hey, you should go retire early. Hey, you should consider this strategy. It's different when someone else is saying, hey, I'm 54. I want to retire early. It's healthcare that's bothering me. It's oh my gosh, how am I going to fulfill my time? But today's episode is a special one. I alluded to it two weeks ago, but it's about actually how do you quit. We're talking about logistically how do I tell my boss or myself if you're running your own business, hey, I'm going to walk away. And this was prompted by a post in the Root Collective. And that is how we select what we're going to talk about.

Speaker 1:

And this comes from Eric, who says what was your experience when you told your employer you were retiring? He writes a lot of awesome stuff. Here I'm going to summarize it. And he says here I'm going to give my employer two months notice so they can find a replacement. I know they're going to try to talk me out of it. They're going to make promises, they're going to throw more money. I will certainly be professional and thank them for the opportunity, but more money is not what I'm looking for. I need to start valuing my time over money. So start valuing time over money. I don't know how old Eric is, but the first thing I'm seeing is was that not happening before? Why now? These are thoughts that go into our heads. He further goes on to say I was curious if others here, who may have retired, experienced these things, and how did you deal with it? So that's what we're going to be talking about today.

Speaker 2:

Let's do it and I there's. There's kind of three main categories that I think through. The first is obviously the financial side. Like, don't go say you're going to retire if you don't have that dialed in. The big things I look at is do you have income to replace your paycheck Obviously the paycheck's going away Do you have insurance coverage that will see you through and that you'll maintain the right health insurance coverage? Have you made the appropriate changes to your investments? And do you have a tax strategy to minimize whatever your tax liability might be when you start lifting off your investment? So that's obviously step one. But I think Eric I've got to assume has gone through those steps.

Speaker 2:

It's more of the call it, the emotional side or the fear side, or what do you do when you feel like you're letting people down side of this I got so many thoughts. If people I was fired from my last job, I was asked to resign and I think that one thing that people don't realize or maybe we fail to think of we are so replaceable as employees we feel like I mean I had a good relationship with my last firm. I had a great relationship with my boss and with the owner. I employees, we feel like I mean, I had a good relationship with my last firm. I had a great relationship with my boss and with the owner. I thought I was going to be there forever and then, literally in a span of 24 hours, that was gone, and so it kind of got me to think of I feel like I've given so much to this organization and I'm just effectively forced out on a dime like that. And I think that a lot of people have that experience of this extreme loyalty to a company, which is great. I think you should have loyalty to your company. I think that you should do great work, but you should never.

Speaker 2:

You know, people talk about work being like family. Hopefully, it feels like that in some ways, but work is never going to be family. Family is going to be this group that, for better or worse, they're with you through it. Work's not that Like you hope. That work is a place where you can have an amazing life, you can have amazing friendships, you can do incredible work for people. It's not a family. There are some standards that you have to hit to continue to be part of that, and I think that that goes both ways. We feel this extreme loyalty to work. But sometimes, especially in the corporate world, you see this all the time. How many times do you go on LinkedIn and you see all these people from a certain company. I gave my all to this company. I worked weekends for this company, I sacrificed everything for this company. Then layoffs and I was asked to join a Zoom meeting with 300 other people and we were told our positions are gone.

Speaker 2:

And it's that sense of of course we don't properly, I think, view our relationship with work in the right context. Have that loyalty, have that duty of care, have those things that you do, but let's never forget that we're replaceable and so we have to have that same mindset of is work still giving us what we need? But I think the biggest thing for Eric here is anything you say yes to by default, you are saying no to something else. So by you not retiring, by you saying yes to the money, by you saying yes to it doesn't sound like it's about that. Maybe it's yes because you don't want to let them down. Just keep in mind that every single time you do that, you are saying no to your freedom. You are saying what did you say Time? You are saying no to your fill in the blank that you want to do. Are you okay with that? And then be honest with yourself, because I think we would say, no, I'm not okay with that. But then we would justify six more months, then we would justify one more year, then we would justify I'll stay on until they find my replacement.

Speaker 2:

And this isn't to say you should just drop out cold turkey. Yes, if your company has been good to you, if you've got a great relationship, don't just leave them high and dry, but set a very real end point for this. I am going to do this. Here's a time I can commit, here's what I'm going to do. And then do it and recognize that these conversations are not always. It's a breakup.

Speaker 2:

We're growing fast here at Root and we are onboarding great advisors. They're very excited to join Root. They're also nervous to tell their current firm, hey, we're leaving. They've got great relationships. They're not trying to leave somewhere, they're trying to come to Root. And that's hard. And so I think that it's what's on the other side of that hard conversation is what you have to keep in mind and what's on the other side of that conversation whether it's joining a great firm that you're really excited to join, whether it's retirement and being able to do what you want to do. That hard conversation doesn't get easier because you push it off, and so just recognizing the fact that you continuing to say yes to more work is you say no to whatever you could have been doing with that time instead.

Speaker 1:

I'm going to read some of these responses in just a moment, because the question was what was your experience when you told your employer you were retiring? And the amazing thing about this community is you guys went and told them and there's over. It looks like 30 to 40 responses in here and there are people just like you going and I'm reading a few of them. Now I plan to retire in 10 years. I've already begun to imagine the conversation might be like 10 years out. He says, like you, I expect pushback, more money thrown, even a possibly more advantageous work schedule. Very curious for an update in your story as it will help me. So this is someone who's 10 years out thinking about that conversation and is nervous. But to your point, james, valuing time, the only non-renewable currency, is he thinking of hey, I have to work 10 more years because I couldn't imagine having that conversation in like five years, because that would just I mean, my manager loves me so much and there's just no way that's possible. So the reason I'm going to go through this in just a moment I'll probably do this near the end of today's episode but the thing that I want all of you to be aware of when we're talking about planning. I will joke in my videos and I will say I'm the meanest financial advisor. I promise I'm not mean, I'm very transparent.

Speaker 1:

But my dad used to say I'm the meanest dad there is. And I used to say, dad, it's not fair, why isn't I wasn't picked on this team, and he'd say life's not fair. That coach didn't pick you, and I'd say it's not fair, why aren't you as fast as them? He goes, it's not fair. And he used to say it's not fair and it's, to be honest, out of your control. So the earlier you learn that, the better. Now, did I like hearing that early on? No, but he used to say one thing that I still think about today Choose your heart. It's hard to go, break up Might be harder to live in that. So is there a story or something that comes to mind, james, from either something you've spoken to a client about who really couldn't leave, then finally did and went oh my gosh, my life's so different. Or in your personal life where you went look, this really was hard, but I realized this would be harder personal life where you went.

Speaker 2:

Look, this really was hard, but I realized this would be harder Tons of things. I don't know why this story comes to mind and this might not connect, so apologies and we'll edit this out of. This story Sounds completely ridiculous. I was at this was right after high school ended and a friend invited me out to their, their river place I think it was Lake Havasu, and they had the jet skis and the fun stuff. And we went out there and I had never ridden one before and I was like, oh, this is so fun, this is so cool.

Speaker 2:

And we were a bunch of, I mean, we were 18. We were dumb and we were just riding those. And I remember I had a friend riding the back and I was trying to do you know the back of it. And I did that as other friends. I did not realize we're going really quickly behind us. So I was going full speed, I whipped it around, threw him off, thought it was so funny. And then the water subsides, the spray kind of clears, and I see my other friend coming right at me and thankfully I had about a split second to jump off and I jumped off but those water skis collided and it was a pretty direct hit, like they kind of hit the side and then creamed off and I messed up this jet ski and no one was hurt, everyone was good.

Speaker 2:

But I just remember feeling this like pit in my stomach of I've got to go tell my friend's dad that I just crashed her jet ski. This isn't mine. They're so gracious, they invited me on this trip. I've never been here Like this is a group of friends. They come every summer. I'm like the new kid into this thing and I just got on as fast as I could and gunned it back to the house and I just went right up and told him and I think I, I just I don't remember. I think my mind was just, you know, you're 18. You're so nervous, this is your friend's dad. I just blacked out. I don't know what happened, but I remember after that my friend who I threw off was like wow, that was really amazing. You just like went and said it. You just went and did the hard thing. And in that moment I kind of realized, yeah, what else would you do? What else would you do? Why prolong the inevitable? And what you start to realize is there's a difference between hard and suffering. Like to me, the conversation was hard, but the anticipation of it, that's where the suffering is. The suffering is the sense of I've got to do it. It's weighing on me. Is there anything else I can do? And you relate that to every other aspect of life, of I've got to have this difficult conversation. Can I respond to emails instead? Can I reschedule it? And that's where the suffering is is in the prolonging of the inevitable. Do the hard, not the suffering.

Speaker 2:

I think that there's a saying that says hard choices easy life, easy choices hard life. And it's that same sense. If you want life to go well, if you want to live life, easy choices, hard life. And it's that same sense. If you want life to go well, if you want to live life on your terms, make those hard decisions. Short-term pain for that long-term gain. If you want a hard life, continually make the easy decision, continually put off the things that you know you should do.

Speaker 2:

There's a famous book, bronnie Ware. I don't know if it's a book, but she wrote like the five regrets of the dying. She's this Australian hospice nurse and she got the chance to interview I don't know how many people, but tons and tons and tons of people who were on their deathbed about. What are your five biggest regrets? And one of the top five regrets was too much time spent at work. People who felt like they had to give their all to their employer. And what they realized in retrospect is I never actually lived my own life. I always felt like I was trying to please someone else or give to someone else or do something. That was time Again. A yes to that means a no to something else. That was no that I had to say to my family because of that. That was no that I had to say to myself, to my health, to whatever.

Speaker 2:

And sometimes we get on this, this jag, I feel like, where it seems like work is bad and retirement is good. That's not the case. Like, I think work in its purest form is amazing. We, we both love what we get to do with work. We have a lot of clients love what they get to do with work. So this is not a get out of work as fast as you can, but it's a have that honest conversation with yourself of is this contributing to your version of the life that you want to live, yes or no? And if the answer is no. Have that difficult conversation. Obviously, have the financial plan in place, have a financial advisor review that do work through it with you, but then have the ability to have that conversation.

Speaker 2:

And one more thing I'll say on this is understand why you're having that conversation, because sometimes it's not as binary, it's not as black and white of either continue working and I'm miserable or I'm retired and I love it. Why do you want to retire? I, lots of people, just I, just I can't stand the commute, I can't stand all the travel that I have to do. I get okay. Well, maybe you go like that's one of the cards you have, is you go to this and if they want to negotiate, your negotiation card is okay, I I'll stay, but I'm not doing any more travel, I'm not commuting to the office. I'm not.

Speaker 2:

For so many people now they actually get the parts of work that they love and they carve out what they don't love. So when you're preparing to have this conversation, to leave work, go and do it with the understanding of what are you actually trying to get away from? Is it actually the work itself? Is it the team you're on? Is it the department you're in? Is it the commute. Is it the? You fill in the blank. Is there a way of holding on to what you do love? Hopefully there's something that you do love. Maybe there's not Meaning. Do you want a full exit, a full breakup? If so, be firm. Say no to work so you can say yes to everything else. If not understand what those things are, so that it's either ranking your priorities. Best case scenario is I keep working with no commute. Second, best is I retire fully. Third, best is I keep staying in the same thing that I've been doing and nothing changes. So just having a deep understanding of why are you making the decision that you're making.

Speaker 1:

The jet ski story is incredible, perfectly relates, by the way. I was thinking what are you going to do Now? When you were saying it, I was thinking I know you, you're going to go up and tell him. But look, I didn't know if a part of you was going to go up and strategize and go. Oh my God, how should I tell him? Should I? Should I describe that it was my fault and I don't want to be at blame? I really want to still come here. Were you thinking about, oh my gosh, how is he going to react? Because I want to make sure I get invited back? Did you and there's a legit question before a few other things I want to make sure we get through in today's quick episode. Did you worry about oh my gosh, will I be invited back? Were you thinking that? Or did you think I'm gunning it to get to the doc, to go up there and tell him right away?

Speaker 2:

I, I. It was just that maybe now this was what, how, 18 to 30, 17 years ago, 18 so heart, I. I don't remember. And I do remember, almost like that flood of adrenaline of you don't even remember what you said. It was just a I I crashed, I'll pay for it, I'll, but I didn't know some paper.

Speaker 2:

I think I was working a minimum wage smoothie king job at the time, so I would have figured it out, but it was just the sense of I don't want this nagging feeling, this dread hanging over me. So, instead of avoiding it and having that existential dread go with you everywhere, it's yeah, I, I. It was a good lesson. I'm learning everywhere. It's yeah, I, I. It was a good lesson in learning that dealing with things head on, even if you don't have a perfect strategy. I think that's the right thing.

Speaker 2:

Like I've had conversations with team like how to let a team member go in the past where it's like can I'm rehearsing this? What am I going to say? How do you do it? But at the end of the day, it's just like, hey, you just send them the message and say can we chat? You have a hard conversation with a spouse or friend or whatever you rehearse it, how is this going to go At the end of the day? Yes, prepare to an extent, but you just need to do it, and it's just the message that needs to be said.

Speaker 2:

And we spend so much time obsessing over the little what-ifs and how do we do it? That's that avoidance behavior coming out. It doesn't actually matter, it's just us going through that, because that's easier to try to role play a different way or try to you know, see what other what if? Scenario might happen. It's easier to try to distract yourself with that than just to address the issue head on, which the issue is. You got to let someone down. You're saying I'm going to retire, I'm going to. You got to let your boss down, or at least you feel that way. For all you know, they might have your replacement ready. For all you know, there might be someone else who's doing a great job that they can't wait to fill your position. For all you know, they don't appreciate you as much as you appreciate them. So keep that in mind and just make sure that you're having the conversation and don't worry about hitting it perfectly as much as just making sure that message is heard and that you're staying firm with what the non-negotiables for you are.

Speaker 1:

I think you're dead on and I think it's powerful for everyone to hear hey, it's normal, we are not perfect. No one expects you to be. I have a quick story that I'll tell because it helped a client. If it helps anyone else, that's why we do this, but I'm going to go through responses at the end. I've not forgotten, because a lot of you are wondering yes, how did other people deal with it? It's one thing to hear what you and James have to say on here, but I want to hear with other people, because I'm about to tell you about people who said 30 years with same company, I gave my employer X amount of months. Here's how it went down.

Speaker 1:

So there was a time where I was speaking to a couple and they wanted to quit, but they didn't want to do nothing. They wanted to quit and then do something else more meaningful, and we did pros and cons and I helped them with it and part of my job as an advisor, as I see it, is, could I tell them go do pros and cons when I'm offline? Of course I could, but it's me being there, it's the accountability. I was with them and we're going through it and I was seeing they would say pro yep, this is awesome. More time, con. Not enough money. Is it worth it? I'm worth more than 80,000 a year. I could tell it really wasn't helping. They were writing it down, but I could really tell that wasn't the issue. So I said pause and they said really, I'm starting to. I think we're gaining traction here I go look, you could be right. I don't think we and you found a job that paid way less, but you enjoyed it more. Once again, you don't have to tell them you quit, you're gone. You start your new job Tuesday. What do you do? And all I cared about was the speed of the response. And they said I do it. And they looked at me and I went that's all I needed to know. We can keep pros and conning all you want. You do not want to work here any longer.

Speaker 1:

And you were saying before am I worth 80,000 a year? I feel like I give more value than that. You just said you would do something else if it paid less, if you enjoyed it more. So now this conversation is about what do we want to do? And it made them start writing really fast. I'd actually love to volunteer with pets. You know what, even Ari, if it turns out, they don't pay me anything. If my plan, let me do it, I would just do that. I go, okay. Well, that's very different from you. Are not valuing yourself at 80,000. And that's because of a question. So the value of what James talks about in the Root Ready show, which we talked about a few weeks ago, is how do you, as an advisor, know when to ask the right questions, know when to shut the heck up and let someone keep exploring because they're thinking, and that's really our role. So, with that being said, I'm going to just tell you guys a few responses here so you can see all of this. We're going to actually put the thread to this in the description. So if you want to read all 40 plus responses, you can. I'm not going to obviously go through all of them, but just a few to finish out.

Speaker 1:

Someone here, john Hawkins, says I gave my employer six months. I worked for the company for almost 30 years. The CEO and I are close, worked out really well for transitioning all of my responsibilities, but I got a few calls after I left to clarify things. But because we did such a good job transitioning in two phases. It was seamless. Phase one was we're helping people taking over my accounts, attended calls and I led the discussions. In phase two, I had them leading discussions and I found this decreased my anxiety. But it wasn't perfect. I was available to help but I actually found I gave more time than I wanted to.

Speaker 1:

The reason I find that an interesting response is here's someone who quit. His responsibility is to retire and enjoy his life now, but he's still kind of working Now. Maybe he enjoys that and he actually wants to do that. We don't know. But don't be the person that's just going to offer, just to be nice. Yep, I'm going to help train the next six months or a year and now all of a sudden you feel like you're being taken advantage of. So that's the first one. The other story I want to say here. This comes from Tommy C, who we quote a lot. He says I was prepared to say no when I turned in my paperwork. I had a great relationship. If they offer me more money to stay one more year, my prepared response was I just love this, so why didn't you offer me more before today? And I don't I? I there's a little bit of attitude I can kind of feel, but there was some resentment I can kind of. But it's kind of cool, right it's, it's cool.

Speaker 2:

Yeah, and it's I like it. I don't know the context, but there is that sense of like you talk when someone's about to leave or someone's about. Then you offer more. It's like, well, why did? Why didn't you come with your best and final first? If they're committing all they are to you, why don't you commit all you are to them, or at least on equal ground?

Speaker 1:

And yeah, I like it, it's, it's, I like it too. Last thing here is he says be prepared. And I think this is a really helpful piece. Some colleagues will congratulate you, some will be indifferent, some will avoid you like the plague. It's a real eye opener to see which category some of your colleagues fall into. And don't get it twisted. You will need people in retirement. It's not as fun alone. So I like the way he was saying don't get it twisted, you're going to still want people, you're going to want to communicate. So it's not like, hey, I'm just out of here, I'm under retirement. It's hey, what do I? And if you find someone's really nice to you all the time at work, but the minute you say you're retiring, they're like well, you're not of value to me anymore. Well, that's telling.

Speaker 2:

Yeah, the final thing there's so often you hear this of the company doesn't value you as much as you value them. And it's, oh well, not my situation. Like you don't understand the relationship I have with my boss, with my company, my role. That was me. Like I remember, like I I never wanted to start a company before route, I'd never thought I would, I thought I was going to be at my last company forever. And I remember even thinking like I don't even know how I could say to my boss like I'm leaving, like I feel like they've been so good to me, I've learned so much here, yada, yada.

Speaker 2:

And then, within a matter of 24 hours, one day I was asked to resign and it was like this big wake-up call of oh, maybe the company never really does feel like that the same way to me as I do to them, that the same way to me as I do to them. And and this isn't to say that it should be this purely transactional relationship between work and between the people that work there Like hopefully there is something special there. I would like to think at root, we have a lot of loyalty and want to make sure that this is a place that people could stay for a long time and it would not be that transactional relationship. But there, there, it does need to be that gut check of. We always think we're different in a lot of ways, our circumstance is different. I can't tell them I'm retiring because of how much that would hurt.

Speaker 2:

Maybe, true, but going back to you, continuing to say yes if you're in a position where you should retire and need to retire and want to move on to different things, continuing to say yes to work is saying no to the things that you actually want to do, which is the first point. But then, number two, that feeling might not actually be mutual, and I say that because sometimes that's the thing that's keeping people going, because they feel like there's this thing that they would never do that to me. So how could I retire from them? How quickly would you be replaced if you left, is a question I would ask, and the answer is probably as soon as they possibly could, which would not be that long. So it's a difficult thing to do. It is a breakup. You are breaking up with them, but at some point along the way you need to do that to make sure you can do what you're actually trying to do with the rest of your life.

Speaker 1:

It's true. So just a super happy episode today, guys. Hope you enjoyed this and we will be back in a few weeks. More fun topics Once again. Go to the Root Collective. That is where you can go if you want to really comment about anything, and that's how we're choosing what we discuss. Additionally, if you are thinking, hey, honestly, I know I need to break up, it's mainly the financial side. How do I even know where to begin? We help clients with everything, so that's from. Hey, here's how we would have that conversation to financially, are you in a spot to make it happen? This is what we love to do. So go to rootfinancialcom. In the upper right. You'll see a button that says see if you're a fit, and you can click that to get started.

Speaker 2:

Awesome. Thank you everyone for watching and we will see you next time. See ya, thank you.