Burned Out in Tech, Can I Retire at 49?

Summary

Episode Overview

Podcast: Jill on Money with Jill Schlesinger
Episode Title: Burned Out in Tech, Can I Retire at 49?
Date: December 24, 2025

In this episode, Jill Schlesinger speaks with John, a longtime tech worker from Boston experiencing burnout as he approaches his 49th birthday. John wonders if he can retire early while maintaining his family’s lifestyle. The conversation dives deep into his finances, options, and emotional readiness for a major life change. Jill, with her hallmark warmth and clarity, breaks down John’s situation and dispenses practical, jargon-free advice for anyone considering their own “great money reset.”

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Key Discussion Points and Insights

1. Setting the Scene: Holiday Rituals and Podcast Announcements

• [01:16–04:18] Jill and her producer Mark banter humorously about Christmas Eve traditions and the Italian “seven fishes.” They briefly discuss updates to the show’s website and subscription offerings—for listeners to interact more with the Jill on Money community.

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2. Introducing John from Boston

• [04:18–05:54]
  • Jill jokes about Boston’s “town” feel compared to New York City.
  • John is hosting Christmas for both immediate and extended family, with a mix of traditional holiday foods and a special Argentinian treat, sandwich de miga.

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3. John’s Dilemma: Burnout and the Retirement Question

• [05:54–06:21]
  • John shares he’s been in the tech industry for 29 years and feels burned out.
  • He asks: “Can I retire ASAP? Or should I wait until my mortgage is paid off?”
  • Jill answers decisively: “No.” (referring to working just because of the mortgage.)

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4. Deep Financial Profile Dive

• [06:21–10:05]
  Jill probes John’s financials in detail:
  • Age: 48, turning 49 soon.
  • Spouse: 43, also recently quit tech in what John describes as a “rage quit.”
  • Children: Three adult kids (29, 24, 20) from a prior marriage, plus a three-year-old with his current spouse.
    • “You did. You are really a glutton. You were all done. Now you got a three year old.” (Jill, 07:17)
  • Income: Over $2 million last year, largely from tech stock grants.
  • Retirement Savings: $1.1 million (traditional), $50k (Roth).
  • Brokerage Account: $4.1 million, fully diversified into ETFs. John didn’t hesitate to “pay the tax” to diversify out of tech company stock.
  • Home: Worth $2.3 million, mortgage of $815k at 5.25% (recent purchase), intended as their “forever home.”
  • Cash: ~$150k in cash.
  • 529 Plan: $30k set aside for the three-year-old’s education.

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5. Expenses and Desired Lifestyle

• [10:14–11:08]
  • With mortgage: about $129k/year for baseline expenses.
  • “Probably another 70” (thousand) for discretionary spending.
  • Jill pushes for $20k/month ($240k/year) as a generous estimate.
  • No pensions expected for either John or his spouse.

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6. Other Responsibilities and Long-Term Considerations

• [11:09–12:52]
  • No outstanding obligations to ex-spouses or adult children.
  • Some potential for needing to help aging parents in the future, but John expects their own assets to cover care.

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7. Is the Money Enough?

• [12:52–14:45]
  • Jill and Mark analyze the numbers:
    • $4.1 million in brokerage could likely provide ~$150k/year safely—but the desired budget is closer to $200k+.
  • "It’s more like that money would generate, like, I would say, like, more like $150k a year, not the $200k a year.” (Jill, 13:28)
  • Mark and Jill discuss options: Work a few more years? Cut spending? Find part-time income?
  • John contemplates giving notice in May, “playing it out” through the year to cash in more stock grants, and then paying off the mortgage.

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8. A Path Forward: Pay Off the Mortgage, Reduce Fixed Expenses

• [14:45–16:36]
  • If John clears the $815k mortgage on schedule, fixed expenses drop to ~$71k/year—a “game changer” in Jill and Mark’s view.
  • Jill: “If that… mortgage is gone… then sure, this probably works.” (Mark, 15:09)
  • Potential vulnerabilities: a bear market could delay things, but John is young, employable, and open to new opportunities.
  • Jill’s concern: “Can you downshift into something else… have fun, enjoy your 3 year old, all that, but you know, you got a lot of time, man.” (Jill, 16:14)
  • Mark jokes: “One month with a three year old, he’s gonna be itching to get back into the work.” (16:14)

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9. Next Chapters and Non-Financial Considerations

• [16:36–17:06]
  • John plans to “lean into the dad thing” and maybe take on pro bono tech work for charities or causes he cares about.
  • Estate planning is complete, as are his parents’.

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10. Managing a Major Life Transition

• [17:06–19:19]
  • John is self-managing investments: “The plan has just been, you know, put it in there and just don’t touch it. And it’s been working fairly well.”
  • Jill’s advice: boost cash reserves before leaving work—ideally one year of living expenses on hand as a cushion during the transition.

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11. Notable Quotes and Key Takeaways

• On Diversification:

  • “I'd rather just pay the taxes, diversify, and hedge my bets a little.” — John (09:05)

• On Career Windfalls:

  • “Sometimes you’re lucky because of the sector you’re in... If John were, you know, an academic...he wouldn’t have this kind of net worth. You’re in a sector that pays really well. You were able to ride the wave and now I think you’re smart enough to realize, hey, this takes something out of me.” — Jill (17:38)

• On Downshifting:

  • “This is like essentially my whole great money reset thesis, which is if you’re gonna change your work, if you’ve got the wealth to do this, you can change your life.” — Jill (17:49)

• On Family and Money:

  • “You have no obligation to your ex anymore, do you?” — Jill (12:14)

• On Lifestyle Inflation:

  • “I know you probably have had, like, your lifestyle has been creeping higher as you're making more money, but you can do this, so it’s exciting for us.” — Jill (19:19)

• On Options and Security:

  • “He is living a life that I think is commensurate with the income that he and his wife have had. And now he's got choices. And what is better than having those choices?” — Jill (19:40)

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Important Timestamps and Segment Highlights

• 05:54 — John introduces himself and shares burnout concerns
• 07:47 — Details on income, investments, and family
• 09:41 — The "forever home" and mortgage specifics
• 10:45 — Details of living expenses and desired lifestyle
• 13:28 — Jill’s calculation on sustainable withdrawal rate from investments
• 14:31 — John’s proposed plan: notice in May, mortgage payoff, reduced expenses
• 15:09 — Mark and Jill green light the revised plan if the mortgage is paid off
• 16:36 — John’s vision for post-retirement life
• 17:38 — Jill’s core takeaway on luck, sector, and readiness for “the great money reset”

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Tone and Final Thoughts

Jill’s tone is practical, supportive, and a little playful. She recognizes the privilege and luck in John’s situation but never diminishes the seriousness of making such a big life decision. There's an undercurrent of empathy for listeners who aren’t “$6 million tech people”—with clear encouragement that understanding your choices is empowering at any level. The episode reinforces Jill’s ongoing message: with good planning, honest assessments, and a bit of luck, you can take control and reset your life and money.

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Suggested for Listeners

If you're wondering if YOU have enough to make a big life change, or how to approach a personal “work reset,” this episode and Jill’s approach are a practical, kind, and refreshingly honest place to start. For personal questions, listeners are invited to visit jillonmoney.com and use the “Contact Us” button to get Jill’s advice.

Transcript

[A]

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[B]

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[A]

Head over to get started.TikTok.com TikTokapps. Welcome to the Jill on Money show. It's Wednesday, December 24th. It's Christmas, Christmas Eve. Do you have a particular Christmas Eve kind of ritual that you go through? Is there some family thing you do? Are you having seven fishes? Mark, you don't even do seven fishes anymore, do you?

[C]

No. God no. I don't have time. I don't have patience. I don't want to clean up the mess. No. I may do a fish or two.

[A]

Okay. You know, one year I was obsessive that I had to get all seven, but I, I have to say I cheated because the way I cheated was that I got. I had like, you know, sort of like the linguine and clam sl and we had this and. But then I decided that I was kind of petering out when I got to four. So I just got like a seafood salad and there are four different fishes in there. That's a cheat, right?

[C]

Big time.

[A]

When you were growing up, was there, was there a seven fishes ritual for your family or not?

[C]

Yeah, my grandma, my grandparents, my grandmother. That was the big Christmas Eve tradition. We went to my grandparents place for Christmas Eve and it was nothing really but seafood.

[A]

Okay. All right, well that's good. I am very excited that we are coming to the end of the year. I'm very excited. I'm already psyched for next year. You know, this is the problem that when you have this little side hustle, which I have, Jill on Money is my side hustle. Obviously, it's outside of my whole CBS News world. But when you have a side hustle and you work with someone like Mark as your partner in crime, you can do all sorts of fun things and experiment and do great stuff. And Mark had a fantastic idea which we are experimenting with for next year, and that is about our subscription service, Jill on Money Live. So when you go onto our website, jillonmoney.com, of course, there's a contact us button. It's in the upper right hand corner. Click that if you've got a question. Write us a note, tell us if you want to come on the air. But as you go down through the website, you'll see Jill on Money Live, that is our subscription service where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content. It all comes in at 45 bucks for 12 months. But Mark said it's another commitment that people have to make. Maybe people just want to buy one webinar at a time, like for some topic they're really into. And so we're going to roll that out next year. I'm so excited that if you want to just purchase one webinar, It'll cost you 15 bucks. Big deal. Mark, what's a movie cost these days to go to an actual movie? What is the price? I haven't gone to a movie in a while.

[C]

Oh, I haven't gone in years. But I can tell you it's definitely more than 15. I would think so.

[A]

You know, I think it's kind of cool that you could get something like that. I don't know, just one at a time. Anyway, movie tickets here in New York City, According to the AI filter, I just went through 23 bucks. 23 bucks in new York City.

[C]

That's insane.

[A]

Anyway, so check it out. It's going to be so much fun. And of course, please, over the holidays, if you have questions, concerns, you just want to escape your family, go play around with the website and give us any sort of ideas. If you want us to cover a particular topic that we have on covered, let us know. I don't know. We're all very open and willing to hear from you guys. Okay, Mark, exciting. Right now we are going to talk to John, who joins us from Boston, which is a lovely town, not a city, John. Because I'm from New York. And so when I got to Boston, I'm like, this isn't really a city. It feels more like an extended village, like a town. Are you from Boston originally?

[D]

I am.

[A]

And do you agree with that? You know, like, that it doesn't feel cityish? Right? I agree.

[D]

It's a tiny little city.

[A]

It's cute. It is cute. Except for the Boston fans. I'm only kidding. That's so mean. Okay, John, what's happening? What are you. Are you excited? Are you cooking for Christmas Eve or Christmas Day?

[D]

We are hosting again, and we do Christmas Eve, we do Christmas Day, and then we do extended family Christmas, believe it or not.

[A]

Get out of here. What is on the menu?

[D]

Pretty much everything. Your traditional hams, turkeys, that kind of stuff. Casseroles.

[A]

Okay. All right. What's your favorite side dish?

[D]

Favorite side dish? Probably something called sandwich de miga, which is.

[A]

What's that?

[D]

It's a sandwich. It looks like a sandwich, but it doesn't taste like a regular sandwich. And it comes from Argentina. It's something that my family does.

[A]

I'm all in. I want a picture of that right now. Okay. What can we do for you, sir?

[D]

Well, I've been in tech for about 29 years, and I think I'm burning out. And so I'm trying to figure out, can I stop, like, asap? Should I keep going until my mortgage is paid off?

[A]

No. See how I answered that already?

[D]

And will I be able to kind of live the lifestyle I would like to live, which is a dramatically crazy lifestyle, but still.

[A]

I know. It's so funny how it sort of creeps up. Very funny. Okay, so, John, how old are you?

[D]

I am. I'll be 49 next year, next July.

[A]

But I'm 38 now. And your spouse?

[D]

Yep, I have a spouse. She's 43. She'll be 44 next year.

[A]

Okay. And is she working also?

[D]

She recently rage quit, so she's, I think, also a tech worker.

[A]

I want to know what that looked like, but we're going to get to that in a second, because I love that idea. The rage quit. You're not supposed to do that, of course. Right? You don't want to burn bridges, but, boy, does that must feel so good in the moment. So, John, you have some kids?

[D]

Yes, I have three that have launched from a first marriage. They're 29, 24, and 20.

[A]

29. Wait a second. 29, 24, and 20. Oh, my God. Okay, that's A lot. And any in the second?

[D]

Yep. I have a three year old son right now.

[A]

Oh, you did. You are really a glutton. You were all done. Now you got a three year old. Oh, how is it the second time around doing the parenting? You're like a grandparent.

[D]

It's a little easier.

[A]

Yeah. Because you're not worried about anything. You're like, it's fine. Right?

[D]

Yeah. He survives everything, so.

[A]

Exactly. Big bounce. Is the 20 year old done with college and all? Like done done?

[D]

Yep, all done.

[A]

Okay, great. So how much are you earning in your 29th year in tech?

[D]

Well, I've had some good fortune on the timing of my original grant, so let's just say it. Because of the timing, it's plus 2 million.

[A]

That is what you are actually earning because you've been headhunted to get to a place where you are right now. I get it. Okay. And you were granted some stock to come over and tech has been on a hot, hot, hot run. And that's kind of amazing. O. So let's get you out of this rat race, truly. I mean, if you're going to make a couple million dollars, let's see how much you have really saved. So let's go and be methodical about this, John. In your retirement account, what do you have?

[D]

Okay, so in just a traditional retirement between my wife and I, we have roughly about 1.1 million.

[A]

Okay, and what about any Roth assets?

[D]

Yep, we have about 50k in Roth.

[A]

Okay, and what about in brokerage?

[D]

4.1 million.

[A]

And is it all in stock or have you sold the stock of the tech companies?

[D]

Oh, it's all been diversified into ETFs.

[A]

Did it bother you to pay the tax or not?

[D]

No, it didn't.

[A]

All right. Isn't it funny? We hear from so many people, they're like, I don't want to pay the tax, these RSUs. But you know, you can't look back like that.

[D]

Right, exactly. I mean, the market goes up and it goes down. So I'd rather just pay the taxes, diversify, and hedge my bets a little.

[A]

Okay, so 4.1 million a brokerage, traditional 1.1, Roth 50. What other assets are out there?

[D]

We have a home that's worth about 2.3 million and it's got a mortgage of 815,000.

[A]

What's the interest rate?

[D]

5.25.

[A]

Oh, it's a new purchase. Ish.

[D]

Yep.

[A]

Okay. Is this your forever home? Like, this is good. You're going to want to stay in there.

[D]

This is the house we'll be in forever.

[A]

Okay. Which is a long time. Any rental property, vacation home, you got a little crash pad on the Vineyard? What do you got going?

[D]

No, we don't have any of those things.

[A]

Okay. Any other assets that we should know about? Do you have a draw full of crypto because you were an early adopter?

[D]

No, we have about 150k in cash assets, but that's okay.

[A]

Okay, you ready for the magic question of all? Oh, wait, before I do that, what about the three year old? Do we have a 529 for the kid?

[D]

Yep, I already have a 529 set up.

[A]

How much is in there?

[D]

It's about 30,000.

[A]

Okay. If you finished up next year like you were done done, you. You have to probably have a long notice, just I'm guessing. But if you are done, what is it? The. What amount of money do we need to produce for you to live your lifestyle?

[D]

I mean, I did some rough math, so actual living expenses if the mortgage stays is about $129,000. Like all our.

[A]

That's it.

[D]

That's our bills.

[A]

Okay.

[D]

We were talking about discretionary spending.

[A]

Yes, yes.

[D]

Probably another 70.

[A]

Good. Okay. All right.

[D]

So it's like 215. 230 total.

[A]

Let's say 20 grand a month. Let's go nuts. Okay. Right. Okay. Now you will not have a pension. Will your wife be entitled to a pension?

[D]

Nope, no pension.

[A]

Okay. Will you do nothing, in other words? You obviously are a young man. You have been able to accumulate a chunk of money here. What about just some other off ramp? Do you think that you'll have some extra income coming in potentially?

[D]

Like, I'm doing some board stuff now. I don't want to have to, but I would likely still tinker here and there in time.

[A]

That's what I would think. And what about your wife? Same thing.

[D]

Probably not.

[A]

She's like, I want to know more about. Oh, fantastic. Maybe she'll become a pilates instructor, which would be great because then you can just, you know, have her teach you. Okay, so 20 grand a month, we leave this traditional account alone for 10 years. Right. And you think that there's no other major new moves that you would make? There's no change. Okay. And what about family? In terms of the. The three launch kids we got from the first marriage? You don't have any. You have no obligation to your ex anymore, do you?

[D]

Nope.

[A]

Okay. And what about parents? Do you guys have parents that you might have to take care of?

[D]

That would be the. Probably the Plan. We have two sets of parents still. My parents, though, do own two homes, one in Florida and one in Boston. So I think the plan would be we would take care of them, but pay for somebody to take care of them in our home with their assets.

[A]

Okay. So not like you'd have to. You would want them to live with you, but you don't have a lot of money that you'd have to shell out. What about her parents?

[D]

I think they're kind of mixed because they never have the conversation. So who knows?

[A]

I love that we're withholding, even though you'll be the one on the hook. Okay, Exactly. So the question is, if next year you give your notice, if we're talking a year from now, is your $4 million enough to actually float your lifestyle? Mark, what's your view on the. He's really a $6 million man, obviously. But what do you think about the situation for John? What do you think he. Do you think he's okay? Yeah.

[C]

I mean, I'm only looking at the brokerage. Cause that's really all that's accessible. I mean, at $20,000 a month.

[A]

No, it's not quite there. It's like. It's more like that money would generate, like. I would say, like, more like 150 grand a year, not the 200 grand a year. But on the other hand, we've kind of rounded up a little bit. Is it possible that instead of, okay, the two choices being that you keep working for just a couple years? It does not a lot. I think it's probably just a couple of years where you just keep socking away some more money in that brokerage account. Keep, as my father used to say, keep milking the cow as long as the cow has milk. Meaning you work for a couple more years, you get more money, you get this stuff. Like, it will help you to have, you know, extra money floating around for this, or are you so miserable that you're like, screw it, I'll just spend less money and I won't. I won't take fancy vacations. I'll just deal with it. Or I will do everything and between, you know, I'll figure out how to, you know, cobble together 100 grand a year of income. What would you think are the. Of those choices, what is most appealing to you?

[D]

I mean, the one that I've been doodling is giving notice by May and then, you know, probably playing it out through the rest of the year. I think that could get rid of the mortgage and drop my fixed bills. Down to 71K.

[A]

Oh, okay. If that. Oh, because you're going to get a big stock Grant.

[C]

Yeah.

[D]

Every three months. I'm essentially cashing out probably about 400,000 after taxes.

[A]

Okay, so what you're. So if you give your notice in May and you get your money by the end of the year and then our expenses are dropping down now, Mark, how do you feel about this? I feel a lot better about that.

[C]

Yeah, yeah. That's a game changer. If the mortgage, if the mortgage is gone, if he can do that, then sure, this probably works.

[A]

And then, so if that's the case, I mean, the only downside, the downside risk is that if you're in some horrible bear market for the company stock, that you won't do it quite as quickly. But I don't know, I feel like you're resilient. You'll. You'll find, you obviously could find a job somewhere if you gave your notice here. And you know, they're like, no, stay for, you know, an extra three months. Like, you know, you could probably top it off. I think this is doable then. If only because that mortgage is big and it's a higher interest rate than, you know, for most. Right. So I think it could work. I am tiny bit concerned about what you're gonna do with yourself, but I'm gonna leave it to you to figure that out. I am. I mean, cause you're young. Cause this is a, you're a young type a human being. So the question is really, can you downshift into something else that would allow you to use your brain, have fun, enjoy your 3 year old, all that, but you know, you got a lot of time, man.

[C]

One month with a three year old, he's gonna be itching to get back into the work.

[A]

Oh God. I don't know about that, but I mean, it is possible. But you would have a lot of options then, wouldn't you, John?

[D]

Yeah, I think, I think that would be my plan is, you know, lean into the dad thing and then probably do some pro bono type tech work for charities or things that we're, we're more passionate about.

[A]

Okay. And then if somebody had to pay you, of course you could get that. Let's see, what else are we not talking about? How about your estate planning? Have you done that?

[D]

Yep, all done.

[A]

Okay.

[D]

And actually just got my parents done too.

[A]

Oh, thank goodness. And is there anything else that you. So you're managing your money yourself, you don't need any help with this, right?

[D]

I am managing it Myself.

[A]

And you feel good?

[D]

Feel pretty good. The plan has just been, you know, put it in there and just don't touch it. And it's been working fairly well.

[A]

Amazing. I like it. I think I'm good. Or Mark, are we going to get hate mail from. From Mr. Tech, the $6 million tech man?

[C]

Oh, we will for sure. Without a doubt. And you know, it's always the same characters, it's always the same names. They all bitch and moan. But you know, I'm not going to and moan over this.

[A]

Yeah, I mean I was at the.

[D]

Broke level before myself. Like 2020, sorry, 2012, I had in, in 401k, we probably had about 300k.

[A]

What?

[D]

But in the bank we probably had about five grand between my wife and I, so.

[A]

Oh my goodness. So listen, I think gang, what like the lesson here is that sometimes you're lucky because of the sector you're in. If John were, you know, an academic, working, you know, working his butt off at BU or Harvard and he's doing, you know, lots of really smart stuff, he wouldn't have this kind of net worth. You're in a sector that pays really well. You were able to ride the wave and now I think you're smart enough to realize, hey, this takes something out of me. In fact, I would say that this is like essentially my whole great money reset thesis, which is if you're gonna change your work, if you've got the wealth to do this, you can change your life. And you know, I always feel bad for the people who are like just grinding it out just cause they don't know what else to do with themselves. So I think this is awesome. We're all, we're, we're, you know, pretty psyched. Except for the fact that you're probably a Patriots fan and a Red Sox fan and a Bruins fan. Besides that, we are psyched for you.

[C]

I was gonna ask him just quickly, is any of that brokerage account in cash?

[D]

In cash in the brokerage account.

[C]

Yeah. I mean, you know, as you, as you think about exiting the workforce, I would think you're going to want to free up some of that money.

[A]

Yeah, I think that. Well, I don't know about that. I think what you could do is you could take your every three months. I think you can, what, you know, sort of slap down a bunch of money on the mortgage and also add to your cash position of your 150 that's in cash right now. I would like you to have at least a year of those expenses in the bank beyond, you know, the actual, like, cash level that you'd feel comfortable with. So my guess is you probably need another 100 grand in cash. But do it along the way when you're paying off the mortgage. Just make sure you got some money in cash available.

[D]

Yeah, that makes sense. That's the plan for February and May.

[A]

Great. I can't believe it. This is awesome. I love it. I know you probably have had, like, your lifestyle has been creeping higher as you're making more money, but you can do this, so it's exciting for us. Hey, gang, you probably don't have $6 million. Okay, I get it. But if you listen to John, you hear that, you know, he's kind of been grinding this out, and he's in a business or a sector where there's a ton of opportunity, and not all of us have that. But he has also squirreled away the money. He doesn't have the big house in Martha's Vineyard or Nantucket. He is living a life that I think is commensurate with the income that he and his wife have had. And now he's got choices. And what is better than having those choices? If you want to understand what choices you might have, I encourage you to go to our website, jillonmoney.com jillonmoney.com and in the upper right hand corner, there is a contact us button. Click that and send us a note. If you want to join us on the show live, all you need to do is go to that little box at the bottom and check it. All right, gang, sign up for the free weekly newsletter comes out every Friday. And of course, just check out all the content that lives on our website. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. And just want to say, as always, it is Christmas Eve, but do this anyway. Just do something nice for someone else today. You know what I've been thinking about is I've been reaching out a lot during this time of year to anyone who has had loss previously in this year. And if this is like your first holiday without that somebody in your life, reach out to those people and tell them you're thinking about them. It means so much. Change your work, change your wealth, change your life. Thank you for listening. And yes, we will be having a Christmas show, so we'll talk to you tomorrow.

[E]

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[F]

What's up? It's Draymond Green. I'm back for my 14th NBA season and my podcast, the Draymond Green show is back too. This season I'm breaking down games, reacting to the biggest NBA stories, and sitting down with teammates, rivals and culture shapers. And trust me, I'm not holding back on the court or on the mic. Two new episodes every week. New segments, big conversations, real basketball talk for the real hoop heads. Listen to and follow the Draymond Green show wherever you get your podcast. We're back. We're better. Let's get it.