Ex-Tech Reveals The Regrets To Avoid Before Retirement | Retirement Reality

In this episode of Retirement Reality, Louis shares how a mid-year layoff after 32 years in tech became an unexpected doorway to something lighter, calmer, and more intentional. At 57, he is weighing recreational employment against full freedom, noticing how life feels when the inbox goes quiet and mornings are unhurried.

Louis talks travel as a value, not a splurge. First-class seats, suites, and stretch-time together are part of the plan when the plan is built right. He loves scuba and earned his instructor certification, yet he also honors what matters at home: a younger partner who still works and two aging dogs who set the pace. His “opportunity” mindset reframes a layoff into a season to breathe, learn, and choose with purpose.

We also explore the money side without turning it into a spreadsheet show. Louis is candid about concentration in company stock, learning the language of diversification, and discovering tools like NUA for 401(k) company shares. He wants to stay CEO of his money while bringing in an expert as CFO, so the plan funds a life well lived, not just a tax win. After the sudden loss of a friend, he and his partner finished their wills and trust work, proving that clarity is a gift to the people you love.

If you are a high-achiever in your 40s to 60s, maybe recently laid off, wondering whether to jump back in or step into something new, this conversation gives you both inspiration and next steps. You will hear how less stress can feel like new oxygen, why “wait and breathe” beats a knee-jerk job hunt, and how to design travel, work, and wealth around the life you actually want.
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Louis is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known. 

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.

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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.

Transcript

Welcome And Show Purpose

SPEAKER_00 0:00

How are you thinking about that in terms of health and stress at this point?

SPEAKER_01 0:04

So I will be honest. I never did a budget before because money grew on trees from my, you know, my little thought process. And so I never worried about do I can I buy things if I wanted something, I bought it when I was working. But now I was like, oh, I should probably figure out exactly what how much and what am I spending. So I did kind of a budget, but I never really thought of it as stress. But I will tell you, since May, I feel so much lighter. The only difference is I don't have a job. I don't have emails to check that are work related or or you know some deadline looming or something like that.

Meet Lewis And His Pivot

One Word For Retirement: Opportunity

SPEAKER_00 0:42

What I'm doing in this new show, Retirement Reality, is having heartfelt, candid conversations with people who have already retired so you can hear from them what worked well, what didn't, and everything in between. I hope you enjoy. And if you're retired and you want to personally come share your story on a future episode, there's a link right below this in the description of this episode where you can apply to be a guest. Now go enjoy the episode. My guest today spent 32 years at Microsoft and was forced to leave and is now wondering if it was actually a good thing in the end because his stress has decreased. He used to go to the doctor and always just say, hey, my stress levels are zero out of ten. But he didn't know there was a baseline to that, and that he actually expands on that and tells us his favorite travel destinations, what he's spending his time doing now, how he's considering consulting, and how he's managing his age gap with his partner. And he's just such a cool guy. I think you're gonna love this episode. Enjoy. Lewis, thank you for taking the time to join me on the Retirement Reality Show. This is where we get into the non-financial side of retirement. Sometimes finances do come up naturally in conversation, but for those who are looking for, okay, what Roth conversion should I do and what's the healthcare analysis, you will hate this episode because this is a real episode with someone who is actually in limbo a little bit, which we're gonna get to talk about about someone who retired early, we're navigating the health aspect, the stress aspect. So what I actually start with, Lewis, is one question for all of my guests at the beginning, which is if there was one word that you would use to describe retirement so far, what would it be?

SPEAKER_01 2:24

Opportunity.

SPEAKER_00 2:26

Opportunity, I like that. And we were talking even before we started recording that how you're kind of in limbo. Do you mind talking to us a little bit about that?

Recreational Employment Mindset

SPEAKER_01 2:34

I don't. So I'm uh I I don't know what the typical age of your your listener and watcher is for retirement, but I am I was not planning on retiring this year, like 2025. I'm 57, I'll be 58 at the end of the year. Uh and I expect that I'll work until 60 or so, uh, and then I'll retire. Um but I work in tech, and as people probably know, tech is doing uh contraction right now. A lot of companies are doing layoffs. Um and so I was impacted in mid-year, July 12th, uh of this year, uh and laid off. But I and I was fortunate. I 32 years uh at can I say the company at Microsoft was given a reasonably good package uh to leave. So it's not I'm not upset, I and I'm very happy. 32 years at Microsoft is a long career, and I I made a good bit of money doing that, so that's good. Um it puts me in a good financial place to actually decide, well, am I done? Am I really retired now instead of at 60? I can do, I think. I mean, maybe you're the expert, you might tell me later, um, whether I really can, but I think based on everything I've done, I could. So, but I in in transparency, when I post it, just like people do, hey, I I I'm no longer at Microsoft, I've retired, uh, or and or laid off. Um, I had people from a couple of other companies reach out to me. So I have talked to them and we'll see if anything comes of that. Uh, but I will still weigh whether retirement now or semi-retirement, like maybe I'll work, maybe I'll do consulting, maybe I'll do or like I love to travel. I I I I'm a big traveler, and uh maybe I will just spend more time traveling.

Budgeting For The First Time

SPEAKER_00 4:25

Wow, a lot to unpack there. I love we have some big travel fans. To answer your first question, Lewis, the majority of people who listen are 40 to 65. That's the majority of people. We have some people who have significant equity, like I'm sure you have a good amount, going, do I have enough? I mean, I don't know if I'd live my perfect life, but I just I'm done with this company. There's other people that are like, no, I like my company, but there's something happening where maybe I want to go to another company. So there's a wide range. What I want to dive into, and I hope you take this to heart, is that phrase I talk about, recreational employment. Are you working because you want to or because you have to? Because I see this a lot, Lewis, where you go on LinkedIn, I retired, all the coworkers congratulate you. Those that maybe you didn't even think you were that close to go, you were so amazing, we were best friends. You're like, really? Because I wasn't feeling that from you. And then all of a sudden the other companies go, Oh, Lewis, I mean, you know, you've still got years in you. How about you come over to us? We're, you know, growing, and here's how we're gonna add so much value, and maybe some golden handcuffs a little bit. And so, how are you thinking about that in terms of health and stress at this point?

SPEAKER_01 5:33

So I will start with from my own math and doing like for the first time. So I will be honest, I never did a budget before because money grew on trees uh from my you know my little thought process. And so I never worried about do I can I buy things? If I wanted something, I bought it when I was working. But now I was like, oh, I should probably figure out exactly what how much and what am I spending. So I did kind of a budget, and then I looked at what I have, um, and I have made the decision, I don't have to work. If I don't want to work, I do not have to. So that's and and and maybe somebody uh uh can tell me, oh, you're wrong, uh, or you're right. But I mean, even at the lifestyle that I like living in, I will be honest, I when I travel, I'm going first class. When I travel, I'm staying in a suite, you know, I don't do budget travel. Um, and and maybe you might say if you looked at, oh well, yes, but maybe don't eat the caviar or have the you know the the little cheese at crackers or something like that. But we not we're not talking about the specifics of the finances, but I know I don't have to work if I don't want to. But I loved my job, and I still loved tech. And I while I have been enjoying, I will talk, you know how you go to the doctor and uh for a physical once a year, and they ask you this. I always found it stupid. And in the waiting room, they give you the survey where they like circle the answers like how stressed are you, and how much do you drink, and how much do you all that basic stuff. And I've never drank and never smoked, so that was always but and I always said zero for stress. I'm not stressed because I honestly never felt stressed. But I will tell you, since July, um, and actually even up uh because there was a technically July was my last update employed day, but I was no longer working in May because they have a the Warren Act requires a period of time after a layoff where you're still fully employed, um, but not working. And so from about May till now, I haven't actually had a job. Now I've gone on vacation, I've taken you know, even many weeks off at a time. But you always in the back of your mind know that job is there when you come back. And so what's going on? And so that but I never really thought of it as stress. But I will tell you, since May, I feel so much lighter, you know, and I don't I I can only attribute it to the only difference is I don't have a job. I don't have emails to check that are work related or or you know, some deadline booming or something like that. And so honestly, what I thought was not being stressed was just because I'd been working the in the same company for 32 years, and even before that, I was working, you know, 10 years before that, um uh before Microsoft. And so I guess I've just never had a time in my life where I wasn't doing this kind of job. And so the the low-level baseline stress, whatever, maybe it wasn't even low level, just the baseline stress, felt like no stress because I never lived a life without it. And now I have only to be fair, it's only been a few months, but it is significantly different.

Health Shifts And Daily Rhythm

SPEAKER_00 8:57

That is powerful stuff. So, one thing I want to talk about, which I love in terms of just how you travel, there's a phrase I call appetizer planning. When people retire and they're like, Yeah, I can do it, but you know, I'm not getting an appetizer. You don't want to live your retirement that way. If you want to retire and go, I'm getting the suite, I'm going first class, and if I want to stay an extra week, I'm doing it. You know, the budget's not so tight that, oh, why didn't I work one more year? You don't want to be in that spot. And it doesn't sound like you are, which is great. Now, I love the way you're literally saying, I would write zero, I would circle the zero, yet I didn't know that baseline could be different. So, how has that impacted your day-to-day just in terms of health, how you're feeling, things like that?

SPEAKER_01 9:37

I can't describe it other than I feel lighter. I s I I go to bed easier, I sleep easier, uh, I wake up in the morning not like jumping up or right away and like, oh, I gotta get going, going, going. Uh, I'm like, I can have a leisurely wake up and and uh relax. I can spend more time, I have dogs, I can spend more time with my dogs, uh uh, which sounds silly, but it's really nice. Uh and they really appreciate it too. Um, so the number of things that around the house, just things that I have saying, oh, we should do that, and then not doing it because I always had an excuse and now doing it and doing more of it. Not as much as my partner would like, but still uh getting getting more into it.

Boredom Fears And Learning Finances

SPEAKER_00 10:21

So let's let's talk about that because I have a lot of people, most people fall in one of two categories. I'm scared to retire because I don't know what I'm gonna do. And I have a long list of things that once financially I know I'm good to go, I'm hitting the list. Do you find that you're bored? Do you worry about that aspect?

SPEAKER_01 10:38

I so it's only been since really mid-May that I haven't had a job, that I haven't gone to a job. Um uh so it may be too early to say I'm uh I right now, no, I'm not bored. Um partly uh I never worried about finances, as I mentioned, and including retirement, because it just you know, you know, there was a 401k setup, and I money would go in there and I just ignored it, and it just kind of did its thing. Yeah and I never really bothered to learn, well, you know, how should I plan my finances because I didn't need to worry about money. I was unfortunate enough not to have to be in that case. And so the last month and a half I've spent watching your videos, watching other people's videos, trying to absorb as much of all the things that I should probably know. Even if I hire you know the best financial advisors and planners, I don't want someone else to say this is what you need to do, and I just to go blindly yes or no. I want to be able to participate equally in that conversation. Um because at the end of the day, if you're my financial planner and you make a decision for me that bankrupts me, you may feel bad, but it doesn't affect your finances, it affects my finances. So I should be part of that decision for my money and my future.

SPEAKER_00 12:03

You're right. And so, yeah, Lewis, on that, a big thing I love you just said. So many of you are aware, but my parents were burned by multiple advisors. That's why I became an advisor. And my parents always used to say, Look, I am currently making movies. That's what my parents do. And we want to have a CEO of our finances. So that's how they would phrase it when they go to speak to someone. And I used to go, that's interesting, CEO. It's not, you know, it's your money, it's not their money. Like, what do you mean CEO? And they go, well, we believe that we do great work making movies. We believe they should give us great advice. I said, Well, I would love to be six foot five. I'm five foot four, okay? We don't live in fairyland. Like, they have so many clients, how could they do it? And there was a little bit of my parents of, hey, what do you know? Which there was a right to think that. But the way I explain it now is when clients work with us, and every relationship's different, is you stay the CEO. And some people don't like that. They're like, I don't want to know where my money is, I don't want to know where I log in. I say, that's okay, but we will not be working together. Because with us, we are the CFO, and you are the CEO. And you're right. There are times, Lewis, where you may have heard me at one point talk about something called a Roth conversion or harvesting. And I have clients that will come to me and they'll say, Ari, I've already analyzed the conversions and here's what I'm gonna do, and I'm so excited. And I said, But you told me you wanted to travel more with your mom, is that right? They go, that's right, but not to interrupt the conversion strategy. And I'll say, What's the point? The point of this is the sign of a good financial plan is an awesome life. Not being 90 going, I did the best Roth conversion. At the same time, I don't want you mad at me going, well, why didn't we save on taxes when it was a no-brainer? So only you can answer the question of how much you want to travel and what you want it to look like. So I'm glad you're looking at it in that lens. Let's talk a little bit more about that recreational employment. So there's other offers potentially coming in, is what it sounds like. Yeah. If I did not let you take them, which I have no saying, I'm just hypothetical here. If would you go, oh, I think I would be like right now, it's okay, it's only been a few months, but I think the purpose would start to itch. And or would you go, you know, the thought of just having another job and being forced to come in, or even if it's virtual, having forced work feels different than if I was a consultant and I think I'd want to explore that first. Like, where's your mind at today?

Purpose, Consulting, And Flexibility

SPEAKER_01 14:14

Well, so it's interesting. So my partner, there's an age gap. Um, and so they still work. Um uh only two days a week, um, but but still they work, which puts a like oh, well, what if we traveled, you know, every month, you know, a week and a half or at a time. Uh that doesn't work if someone's got to work. Um uh even if it's only two days a week, that that puts a crimp in planning and and scheduling. Um and so there's the oh, I could go down the route of I just travel, but I don't want to travel alone. I want to travel with my partner, and that's not always gonna be possible. The other thing is my job was a passion anyway. I used to joke before I got laid off. I used to joke, I would do this job for free, but it's a good thing they pay me well for. Um uh because I love it. And and that's how I feel. Yeah, and so I feel like, yes, it's been fun. This last couple of months has been a lot of fun diving into YouTube, especially on the financial stuff, but even other stuff, um, uh different travel places to go learn about places I might want to travel that I haven't gone to yet. Uh but I do a lot of like I'm doing a lot of YouTube just keeping up with the tech, the the areas where I was working because I miss it. And so if I didn't go full-time, you know, put the shackles back on, because that's what you know, some of these companies I would be, even if I knew you know what my end time frame was, that time between now and then at a at a full-time job is you know giving myself pretty much a hundred plus percent back to that company. Um the other option is, you know, I could consult, but you know, maybe it's you know, 40 hours a week, but maybe it's 10 hours a week or 10 hours a month. Um I feel like I could do that as well. There's a there's more risk in the if I depended on it, but I don't feel like like my finances require that income um uh to live. I have the money to live. Um but uh you know it it it it it's one of these things of just shifting my mindset from a job is, you know, and I say this tongue in cheek now, knowing that I got laid off after 32 years, but you know, a job is security uh and and and predictability versus consulting isn't, um, because just as easily as I was laid off after 32 years, it's even easier for them to look to stop paying for a consultant. So it's been it's been one of these, but I have thought about it because it does give me the flexibility that says if I want to travel next month, I can say I don't need to go get permission to take a month off. I just don't consult.

SPEAKER_00 17:15

It sounds like it's Lewis time to me. Here's what I'm curious to hear more of. Because we're gonna get into the travel. Everyone loves hearing favorite travel spots where you're looking forward to going, maybe some pro tips. But sometimes I find, Lewis, our partner knows us better than we know ourselves. And the reason I say that, sometimes I'll speak to a partner and they'll say, I'm just not worried. I'm just not stressed, and then I'll say, Well, what does your partner have to say? And they go, They're not telling you that they're staying up. I'm sleeping next to I got the best seat in the house. So I want to know what would your partner say if he was asked, how stressed is Lewis?

SPEAKER_01 17:48

So how stressed is Lewis?

SPEAKER_00 17:51

Or has there been a change in?

SPEAKER_01 17:55

Yeah, he has certainly noticed um a more relaxed version of me. Um but uh my partner's also um uh much more conservative with money than I am. Um so for example, I'm like, no, we're buying first class, and he's like, we don't need first class, or we're getting a sweet, we don't need a sweet house. Let's be honest, he enjoys it and loves it. But he would, if it was up to him and he did the planning, we would be flying coach or staying in the inexpensive place um uh and wouldn't be working until death because you have to. That's just what you've got to do, and that's not where my mind is at.

SPEAKER_00 18:39

Yeah, well, you sound like a good team. And there is a balance there. There's people that reach out that go, I want to retire at 40, and they're on track to run out of money at 75. And there's people that are gonna work till 85 and then go, wow, what was what was worth it here? And I only have my health and time and energy. I like the way um have you ever read Diewood Zero? Have you ever heard of this book before?

SPEAKER_01 19:00

So I haven't read it yet, but my uh uh a good friend who was a boss like three bosses ago at Microsoft actually read that book and was very strongly recommending it. And he he's trying to live his life that way as well.

SPEAKER_00 19:16

Self-explanatory title, but the way I like that he phrases things is you're paying for memories. And how can you look back in your life with all these memories? And flying first class is a great one because if you have the money to do it and you decline it, I'll often ask my clients, I'll say, You better have a good reason for it, because I don't want you mad at me when you're 85 with 10 million bucks going, why didn't you tell me I should have spent more if I was in a spot to do so? Other times we'll say, look, you have trade-offs. You can absolutely fly first class, but it means you're taking X trips instead of you know whatever it is. So in terms of travel, because it sounds like that is a passion of yours, is it a passion of I want to see the world? Do you travel and go for a week and stay at the traditional hotels? Do you do Airbnb? What's your ideal kind of travel style?

Dogs, Long Trips, And Cruises

SPEAKER_01 20:02

So I have a pretty varied idea, depending on where I'm going and what I'm doing. So um I love, for example, scuba diving. Um I'm a big scuba diver. Um uh so much so when I I loved it so much when I first did it that I not only went and got certified to be a diver, but I thought this is great, and I became an instructor. I actually got certified all the way to becoming a dive, uh, a professional uh dive instructor. Where did you do that? Sorry? Where did you do that? So I took the the courses and most of the work here in Seattle. I mean, I live in Seattle area, um, but then my you have to do what's called an instructor exam where Patty, the uh professional dive association, does they they bring uh potential instructors together to take an exam, um both practical and written, and that was in Hawaii. Um but um so I love diving. There is one problem, and I used to uh travel to super exotic places for dive trips, uh like super exotic, like you have to take charter planes to get there because there's no commercial uh aircraft. Um there's one problem with that. I mentioned I like to travel with my partner. Um my partner is afraid of the ocean. Um so we'll we'll run we'll be on top of the ocean in a boat or even on a paddle board, um, paddling, but not in the ocean. Um so it does make dive trips interesting. Um there is one that I've got agreement that he will go with me because I've got a friend who runs a uh very uh world known resort in the Maldives. Um uh the kind of the one you've seen, probably pictures with the giant villas over the water. Um Uh so she runs that and she's like, I will find stuff for him to do. Like we have yoga, we have all this other stuff on the beach, and you can go diving. So that will be the perfect one of my our perfect trips because I can go do diving while he's doing other things.

SPEAKER_00 22:15

That's amazing. I did a similar my mom and dad deal with that in their my dad loves surfing, and we were recently in Indonesia. Similarly, we had to take a charter plane. My mom doesn't want to surf. And so what often happens is they don't go on trips together, which is sad because they want to spend time together. It's just they do have difference in activities, which you are not the first person to not exactly overlap with what your partner enjoys doing. So what I want to explore deeper, if you're willing to share, is when you are traveling, are you booking, hey, this is a month we're taking a trip for? Like does the even that thought, you're probably thinking, well, I just could have never done that with my traditional job. Is the thought, now that you don't have to go back to work, of booking a month something that's realistic? Could your partner do that? Does their position not allow for that?

Concentrated Stock And Diversifying

NUA Strategy And Tax Angle

SPEAKER_01 23:04

So I think they could. The biggest wrinkle right now for a month, because yes, I want to go travel and do that, but I have dogs, and we have someone who comes to the house, and you know, so we don't put them in boarding, the dogs get free room of the house, and then someone comes. But they complain is the best way to describe it when I come back, even from a week and a half of being gone. Um, but then again, they complain when I'm gone an hour from the house. So and my dogs are getting a little older, so uh being gone a month right now um because of the dogs might not be in the cards, but that's it's not because of my unwillingness to it, it's my uh for for being gone a month and traveling a month. It's more about you know making sure I get to maximize the the most amount of time I have left with my dogs, but still go and enjoy stuff. Now as much as I don't like talking about it in a couple of years, as they're getting up in age, if if they're no longer here, um then yeah, the idea like one of the things we love doing is we we like going on cruises. Um and uh there are some most people do the cruise they do a week or whatever that is, maybe maybe it's a week and a half, but there are what they call repositioning cruises where they, you know, a ship is, you know, we live in Seattle, so there's cruise ships that go up to Alaska, but that's only during like three or four months of the year, and then they they don't let the cruise ship just sit there, they have they move it to the Caribbean or somewhere like that, and they have to get the ship from somewhere like Seattle to Florida or wherever it's going out of. And they offer the opportunity to get on the ship and ride along on the requisitioning, and it's usually like 15 days minimum, sometimes even longer. Um, and it's even you can get a really good room at a good price because it's not the the sh the purpose is they're they're moving the ship. They have to do it anyway, but they make a little bit of money or cover their costs. So you get a really good cruise um for and get to see a lot more um and be just okay with the fact that you started in one city, you end up in a completely different city.

SPEAKER_00 25:17

That is a pro tip. I love that. And yeah, never fun to talk about, but appreciate you sharing that, Lewis. Um, if we can switch to the financial side, I don't need account numbers, I don't want to go into those details, but I am curious because a lot of people all see retire off of significant stock, and there's a little hesitancy of well, I don't want one company to dictate whether or not I retire. How do you view that with your financial situation?

Risk, Memory Dividends, And Balance

SPEAKER_01 25:45

So so as you you probably have surmised, and based on the question, a large percentage of my network, not including my house and stuff like that, but a large percentage of my assets are in Microsoft stock. Now, fortunately, Microsoft has been doing relatively well. Um, and at least the the the near-term outlook is still looking positive. Um but I do feel like I should not stay long-term. I'm literally 72% of my assets are in Microsoft, and again, not including the house. Um and that's a lot. Um and um I feel like I need to divest a good chunk of that over the next several years. Obviously, I can't do it all at once, um uh, but uh uh because I don't want a huge capital gains tax. But I do feel like over the next five years I should build a plan that lets me diversify to some other industries, maybe even not just all in tech, uh, even though tech is what I'm most familiar with. You know, I I feel like there are, you know, it's not that it's great for growth, it's not necessarily the best for like long-term income. I've been looking at where I could divest and put it into things that will ensure you know an income stream in retirement so that there's always money coming in. Um and I but I am also looking at how to do this either in a brokerage account, so getting it out of my 401k, um, which the good news is I do have a great option because my 401k is mostly Microsoft stock, which is the company I work for, and I'm over 55. I have uh uh an option that I found out about called NUA, um, which is gonna let me use the cost basis, which surprisingly it's the my cost basis is 10%, less than 10% of the value of the stock.

SPEAKER_00 27:51

Wow.

SPEAKER_01 27:52

So it's so it's a great opportunity for me to not pay any income tax on my, you know, 75% of my 401k is just going to be capital gains instead of when and at time of selling, which for me, I mean, I I'm very fortunate that uh at the time that I was allowed to, because they don't allow you to do it anymore for people that work at Microsoft now, but back in the day, I could invest in the company stock in the 401k, and I just put all my money. I was a big believer, I still am a believer in the company, and so I put all my money back then and just let it sit there. And it just lucky for me, it grew quite a lot.

Wills, Trusts, And Hard Lessons

SPEAKER_00 28:34

You I love the way you explain that, Lewis. Yeah. So for those of you who are going, N-U-A, what did you call me? That's not unrealized appreciation. And for a lot of you who don't have significant company stock, that's just one thing not to worry about. I view part of my role as, hey, yeah, here's important things, and here's things that your neighbor or coworker or friend is going to bring up, and you're gonna go, got it. I'm not letting that take up some headspace. But it is an amazing opportunity, and it's a really cool tool if you use it well. Now, I tell this story a lot. I was already telling you it before we started today, Lewis, but my dad at one point had about 60% of his investable assets, not including his home, similar to you, in Monster Energy, which was one of the best performing stocks. Now, that was all in a brokerage account, which I call a superhero account. And at one point, my dad said, Ari, you know, what do you think I should do? And I could tell if I told him to diversify, he would look down, probably start crying at the thought of it going down because look how well it's done. I said, Dad, I get it. I can already tell when I say the S word, sell, it already has given him bad vibes. But I said, Dad, do you want to spend the rest of your retirement hoping one company does well? And he goes, no, no, no. I said, well then you're thinking about it right. But my dad, if he were, if I were to tell him to sell, it would just crush him. So generally, what makes most sense is how can we, as to your point, over time look at this and be intentional with creating and maybe shifting towards more companies that offer dividends and more income. At the same time, it depends on where it is, if it's in a 401k, if it's in a brokerage account, if it's in an IRA. So no matter where you're having your company stock, or it doesn't have to be company stock, a big game that's done really well for you, you want to make sure you're looking at it on a custom basis. And I tell the story of my dad often because my dad loves to surf. And at one point he was telling me his neck was hurting. And I said, Why do you think that is? He said, I don't know. And when he was saying that, his head was down. I go, Dad, do you think maybe you're looking at the stock often? He goes, Of course. I mean it's really 60% of my portfolio. I go, I think you looking at the stock is actually impacting your surfing, which is interesting because here you are trying to make sure you're enjoying retirement, but you're worried about the stock, you're checking it so often it's impacting what you actually want to do. And that's the predicament of, well, you don't want to sell and give as much money to the IRS, but you also want to make sure that you still get that skin in the game. So one thing I encourage people to remind themselves when they're in your position, Lewis, is hey, guess what? It's fun going to work when you've got more skin in the game. It makes you work harder, it is more enjoyable. But how do we make sure we have enough that if that stock doesn't do well, you're still flying first class, you're still living the life you want to live. So love the way you're looking at that. One question I have for you, Lewis, is specifically just with an age gap. I'll talk to a lot of different partners where there's a 20-year age gap, a 10-year age gap, and it's I want to make sure if something happens to me, they're gonna be okay. But at the same time, I want to make sure that they get interested in finances so that I don't pass away and it's just, hey, good luck. Are those conversations that you have, or how do you navigate that?

Lewis’s Message To The Newly Laid Off

SPEAKER_01 31:45

Yeah, so it's it is interesting. So for the longest time, for actually several years, uh he had been nagging me, you should have a will, you should do this. And it's one of those things that it's like, yeah, yeah, but I don't want to talk about it because or even do it because it makes you think about things like your death. And so and and I I still even though I'm almost 58, I still feel young, like, oh, I I'm immortal, I'm not gonna die. And unfortunately earlier this year, the beginning of this year, I went we went on a trip, a cruise actually, um, with uh a a couple friends and literally a week later we got back and one of them passed away, just unexpectedly, just passed away. And and he was like 34 and young. And it it kind of freaked me out. Um, and to the point where I'm like, oh I need to go get my estate in order to go get a will, an actual will, and all this other stuff because I don't want you know, it literally, if it can happen to someone who's 34, and I know you know logically it can, of course it can happen to anyone, be by a bus or whatever, but when it's that close, um uh it it kind of shocked me into okay, I need to go get so I did it. I went and got, you know, an estate plan done. I had a trust set up with removing assets so that they're in the trust instead of personally so that they can pass easily uh without going through probate. We discussed it. Uh he's doing the same thing, even though he's he my partner is 34, um, so much younger. But he went to the same lawyer to get his estate done as well. Um so uh we're taking care of that, making sure we understand, you know, like what even the more morbid but conversation how do you want the funeral? You know, what would you want your you know and I in my perspective is you know, I I take a very pragmatic approach. The funeral isn't for me. I'm dead, uh, if in this in that scenario. So it's what do you want? Like how do you want to, you know, do this? Uh uh the only thing I I said is, you know, I well I I don't personally like the idea of getting buried, I'd rather be cremated. Um, but again, I'm dead, so I probably don't care too much. Um so it's really meant for who's left behind.

SPEAKER_00 34:27

I'm sorry to hear about your friend. And unfortunately, sometimes it takes that level of action. I wish it didn't, for people to actually go, wow, I'm gonna get it in order. And and this is just the truth where yeah, there's how many things are on all of our to-do lists, so many, but we have to prioritize. And unfortunately, it takes sometimes actions to go, well, I'm gonna do that. And that's just life. So don't take that lightly that you shared that, Lewis. So this has been so fun. I appreciate this conversation. I like to end these episodes by doing something a little fun where I will go silent for the next one to two minutes, and you get to talk to someone who is in your head, it can be younger you, it could be you five years ago, and going, hey, trust me, you're gonna retire, you're gonna be fine, you're gonna enjoy it, you're gonna go to the Maldives. Like you can do, but you can also talk to someone who isn't anything like you, but is probably having similar concerns in terms of, okay, so there's another job offer. I don't know if I should take it. So I know you're not a veteran of 20 years retirement experience, you're just a few months, but I like when you share your perspective. So it's almost as if you're talking to someone who's let's call it five years out from being retired, and they just want to hear from someone who's there, maybe even for a few months, as to what they wish they would have known. So I'm gonna go silent now and give you the floor, Lewis.

Closing And How To Get Help

SPEAKER_01 35:49

Yeah, thanks. Uh I'll start with because it's something I've been thinking about a lot, which is people in my age range, you know, maybe I'll say late 40s to 60, who are in the workforce and unexpectedly find themselves no longer actively working because of layouts, because it is happening um a lot lately. Um and it can feel if you let it, it can feel demoralizing, especially if you immediately turn around and try and go get another job. It's hard. Uh especially nowadays, for all the good and exciting things AI can do, it can also be responsible for getting almost immediate auto-rejections when you submit your resume and stuff like that. I and not so much for me, because I purposely decided I I I said I'm taking the summer off anyway. I'm gonna just not look. I I didn't actively pursue anything. But I people in this unfortunately, I know a lot of people that were affected at the same time that were in my friend group and my network, and they did either because they felt they had to or they did have to financially immediately turn around to find something. And I see I and talk with them about how rough it is out there. And the first thing I would say is in this situation, if you find yourself unexpectedly unemployed or retired early than you expected, take a step back and and breathe. That's I I feel like I've given myself and I really appreciate the time to not feel rushed to do anything. Um no immediate financial decisions about my retirement or going back to work, just kind of breathing and letting it like hit you and and wash over you what it means and what it could mean. Like I said, I use the word opportunity. I'm using the I feel like it's important to think of this as an opportunity to reassess what is important um and what you want to do and what you can do, um uh rather than knee-jerk. I think so many people do knee-jerk reactions um uh even when they don't have to. I feel that's where people make unfortunate mistakes um in choosing a path, either whether it's a financial decision that may or may not be wise, or a job thing. Maybe, maybe, like I said, I feel so much better and I uh now than I did, even though I didn't realize it before. I feel so much lighter and better now that maybe uh uh a less stressful job, even though it didn't feel stressful in the moment, might help me live a healthier and longer life to enjoy it, and that might be better than making you know a few extra bucks now.

SPEAKER_00 38:43

Great advice, Lewis. This has been a pleasure. Thank you so much for coming on the show.

SPEAKER_01 38:48

You're welcome.

SPEAKER_00 38:48

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