This Is Not Going Well

Summary

Armstrong & Getty On Demand – "This Is Not Going Well" (July 27, 2026)

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Episode Overview

In this episode, Armstrong & Getty explore the theme of mishaps and underwhelming performances, both in professional sports and in personal adventures. The title, “This Is Not Going Well,” serves as a motif for discussions about the much-maligned WNBA All-Star Game and the harrowing tale of a solo sailor's near-disastrous journey. The hosts inject humor, personal anecdotes, and thoughtful analysis as they dissect why some things—whether league sports or ambitious excursions—just don’t play out as gloriously as people imagine.

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Key Discussion Points & Insights

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1. The WNBA All-Star Game: Entertainment or Embarrassment?

[01:15–05:44]

• Setup: The hosts discuss the WNBA All-Star Game, describing it as a showcase that, in theory, should highlight the league’s best talents for fans, much like other sports leagues ([01:15]).

  • A: “I saw wild action and the skills on display and the greatest, you know, going at each other. It's fun.” ([01:48])
  • D: Describes a social media reel compiling “the worst moments of the game,” emphasizing a string of missed layups and lackluster plays ([01:57–02:35]).
  • A: Points out that while the reel is “slightly unfair,” as it only captures the worst moments, “there were a lot of it-looks-like-me-out-there-at-my-current-age plays.” ([02:40])

• Critical Analysis: The segment transitions from snark to a nuanced critique.

  • A: “I really want to be fair on this topic... as the father of a couple of girls who took part in sports, and a guy who coached girls sports... Here's the disconnect.” ([03:24])
  • Argues that athletics serve many purposes—exercise, teamwork, skill development, scholarships—but at the professional level, “it’s popular entertainment.”
  • A: “But stop pretending that the WNBA is great entertainment. And the only reason it's not huge like the NBA is because of sexism or, or racism or anti-lesbian phobia or whatever. It's just not great entertainment. So stop it, Stop pretending it is.” ([05:29])

• Notable Quotes:

  • A: “To say that a sport, say the WNBA is not very good entertainment isn't to denigrate anything like below that on the totem pole. It's still great in a hundred different ways. But don’t pretend it's great entertainment. It's not.” ([03:24–05:29])
  • D: “That was quite a collection of really awful plays.” ([03:21])

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2. Solo Sailing Disaster: When Dreams Meet Reality

[07:20–14:33]

• Host Fascination: One host admits to a fleeting obsession with the notion of solo circumnavigation.

  • D: “I was obsessed for a cup of coffee with the idea of sailing around the world alone.” ([07:20])
  • Read books, watched documentaries—until recalling his own intense motion sickness ([07:53]).

• The ‘This Is Not Going Well’ Story: The tale of Kai Sato, a California man who attempted a solo round-the-world sail, but quickly found himself stranded after his mast broke.

  • “[His] mast snapped... He ran out of gas on the motor and his phone died, leaving him floating hopelessly outside of shipping lanes...” ([08:35–09:23])
  • Resorting to licking condensation for water and eating raw squid and “other fish that ended up on his deck.” ([09:29])
  • D: “He said he cried for days and gave up on the idea of ever being rescued.” ([09:42])
  • A: Joke: “Good to have goals. That was his plan. And by the way, stop crying. You’re wasting your body fluids.” ([09:55])

• Desperation Turns to Survival:

  • After five days of despair, Sato’s survival instinct kicks in: makeshift repairs using PVC pipes and kayak paddles ([10:15]).
  • A shift in wind brings him into shipping lanes, where he’s rescued by a container ship ([10:29]).
  • D: “Just based on the picture and some of the things he said, he might not be the most normal person.” ([11:34])

• Notable Quotes:

  • A: “Holy crap, my mast broke. How do I erect some sort of sail—I think would be my first thought.” ([11:52])
  • A: “I don't have the balls to sail solo across, like, a golf course water hazard. So again, I'm not trying to be the hard ass, I just. I'm a little flabbergasted.” ([12:29])

• Reflections on Sailing:

  • The hosts reflect on the realities of sailing versus the common romanticized image.
  • D: “It's way harder than it looks. Tremendous amount of work to do and, and there's nothing relaxing about it at all.” ([13:55])
  • Discuss basic sailing lessons, constant labor, and how challenging it is “to feel the wind” ([15:29]).
  • A: “Made me appreciate people who have that skill... That's not some sort of pleasure. It's, it's like hard work, constant work to do that.” ([16:17])

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3. Sailing Pop Culture and Perceptions

[16:31–18:07]

• Discussion of famous sailing-themed songs and artists—Jimmy Buffett, Kenny Chesney, Christopher Cross, and Lionel Richie.

  • A: “Who writes sailing-related songs. There are a few notable ones.” ([16:36])
  • D: “Jimmy Buffett... Christopher Cross... Crosby, Stills and Nash.” ([16:41–16:55])

• Jokes and continued lampooning of the fantasy of relaxing, wind-at-your-back sailing:

  • D: “Yeah, it's got a different vibe than its reality. I feel like for most people who have never done it.” ([17:04])
  • Imagining drinks and squid-eating as part of the experience.

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Memorable Moments & Quotes

• On the WNBA All-Star Game:
  • “Stop pretending that the WNBA is great entertainment... it's just not great entertainment.” — A ([05:29])
• On Survival at Sea:
  • “He survived on the squid and some other kind of fish that ended up on his deck. They just fly out of the water and land on your deck, I guess.” — D ([13:05])
  • “You got to make sure that is it the boom or whatever doesn’t crack you in the back of the head and into the water.” — A ([14:37])
• Humor about Fantasy vs. Reality:
  • “Did you go with the sailor suit like a little boy in wartime or did you go with the Ted Baxter and Caddyshack blue blazer and captain’s hat?” — A ([14:57])
  • “As a highly skilled golfer, I think I’d be decent at that because we like try to figure out the wind every single shot. But you all almost never get blasted in the head if you wait too long.” — A ([16:03])

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Important Timestamps

• [01:15] – WNBA All-Star Game discussion begins
• [03:24] – Broader perspective on the role of sports in society
• [05:29] – Direct comments on WNBA entertainment value
• [07:20] – Sailing solo story introduction
• [09:29] – Details of dire survival efforts at sea
• [10:15] – Turning point: Sato starts to improvise
• [13:55] – Reflections on the challenges of sailing
• [16:36] – Pop culture sailing songs
• [17:04] – Reflection on the fantasy of sailing

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Summary in Armstrong & Getty’s Tone

With their trademark blend of humor and candor, Armstrong & Getty deliver a reality check: whether you’re watching a hyped-up sports exhibition or dreaming of solitary heroism on the sea, things often “just aren’t that great.” The WNBA All-Star Game may have flopped as entertainment, but that’s not an attack on women’s sports—just an honest assessment. Meanwhile, those who romanticize daring solo adventures rarely grasp the grit (and, sometimes, the raw squid diets) required when “this is not going well” is your daily refrain. In the end, the episode is a witty meditation on expectation versus reality, with a side of 1980s yacht rock.

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Transcript

[A]

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[B]

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[D]

It's one more thing Armstrong and Getty One more thing. Before we get to the this is not going well story of the day. So the wnba, that's the Women's National Basketball association, had their All Star game over the weekend in which you take the best players in your entire league and have them play against each other as kind of an exhibition for the fans. We've all seen this sort of thing in other sports.

[A]

I saw wild action and the skills on display and the greatest, you know, going at each other. It's fun.

[D]

Somebody put together a reel of the worst moments of the game. The visual probably is more important than the audio. The audio sounds like this. Five seconds left in the third. Copper's jump.

[A]

Unable to hit that one. Young can't flip it in Malanga.

[E]

No.

[A]

Howard takes it right back. What a pass from Neca Asia.

[D]

Wilson can't finish it. The lots and lots of missed layups in which the ball never got above the rim.

[A]

I realized that they air balls from 12ft and I realized somebody picked out

[D]

the worst moments from the game, which is slightly unfair. I mean, if you put together the highlights, the best moments. I'm sure there were some, but I was amazed looking at that how many just like it's me out there at my current age plays. There were in that game.

[A]

Did you see that?

[D]

I did.

[A]

It was embarrassing. It was terrible. It was, it was not very good basketball, which, you know, to your point, is kind of misleading because often the WNBA or high level college women's basketball is very good basketball. Yeah, it's, it's nowhere near men's basketball, but it's very good basketball.

[D]

Man, that was quite a collection of really awful plays.

[A]

Yeah, yeah. You know, I was thinking about this a lot because I really want to be fair on this topic. You know, it's easy to just be snide and you know, cynical about it, but as the father of a couple of girls who took port, took part in sports, various levels, and a guy who coached girls sports, which was an experience I absolutely loved and I am staunchly like enthusiastically in favor of girl sports. Here's, here's the disconnect. Sports, or if you want to sound European sport, is a lot of different things on different levels. It's exercise, it's fun, it's learning a skill, it's learning about teamwork, it's playing at a high level, perhaps it's getting a scholarship. Maybe at the very, very highest level it's popular entertainment. But to say that a sport, say the WNBA is not very good entertainment isn't to denigrate anything like below that on the totem pole. It's still great in a hundred different ways. But don't pretend it's great entertainment. It's not. I'll give you a perfect example. I love baseball. The game of baseball, the sport of baseball. I, up until recently was a big major league baseball fan. Nobody goes to college baseball games until you get to like the college World Series and the elite are trying to win national championships and go head to head. You got an average college baseball game, even some fairly good programs on a Tuesday afternoon. There are fewer people there than like a good wing dinger of a high school basketball game. Sure, people just don't go. It's just for whatever reason, people don't perceive it as great entertainment. I'm a baseball freak, so I do, I go to games. But I would never ever denigrate what those baseball players are doing or why they're doing it or their skills or whatever. But stop pretending that the WNBA is great entertainment. And the only reason it's not huge like the NBA is because of sexism or, or racism or anti lesbian phobia or whatever. It's just not great entertainment. So stop it, Stop pretending it is

[B]

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[F]

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[A]

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[D]

Different topic as I teased. What did I say? This is not going very well. Or something like this. I was obsessed for a cup of coffee with the idea of sailing around the world alone.

[A]

Oh, really? Yeah, I've been fascinated by the idea. I know I'm not the guy to do it.

[D]

I read books about it, watch documentaries about it, looked into the skills that would be they would take and the best routes. I was really into the idea for a while.

[A]

Were you just fascinated by the idea of it or did you think I would at least like to consider this?

[D]

I'm not sure I understand the question.

[A]

Well, I'm fascinated by the idea of getting away with a murder. What it would take.

[D]

Oh, no, I was actually. Yeah. No, I was actually interested in like doing it someday.

[A]

Okay. Yeah.

[D]

The thing that turned me off of it is when I realized how bad my motion sickness is, I just thought, I can't. I can't do it for that reason. So I had. I just abandoned it completely. I'd be. I'd be miserable.

[A]

You know what? I have a. I have a question. I'll go ahead and do it in Thumb style while you're talking.

[D]

Okay, so a guy attempted to do it the other day. It happens now and then and, and it's, it's kind of entertaining. But a guy tried to do it solo. California man took off from Catalina island, which is a big island just off of Los Angeles, and headed out toward Hawaii. And a couple of weeks into his journey around the world, 39 year old Kai Sato. The mast snapped on his sailboat. That would be a bad feeling. The mass, very bad feeling the mask snapped into. He ran out of gas on the motor and his phone died, lifting him, leaving him floating hopelessly outside of shipping lanes and little hope of coming across a boat.

[A]

On the other hand, Kai, you still got your health. No mask, no gas, no radio. Oh well.

[D]

He was licking condensation in the morning to try to stay alive because that was the only water he had. Eating squid that would land on his boat by accident.

[C]

Raw.

[D]

He said he cried for days and gave up on the idea of ever being rescued. His goal was to try to get his motor going long enough that he could suffocate himself and kill himself.

[A]

Good to have goals. That was his plan. And by the way, stop crying. You're wasting your body fluids. Of course, I've never faced death on the Pacific.

[D]

I'm not sure that was like. I don't know if he sat there and decided, should I cry or not cry? Yeah, I think I'll cry.

[A]

Or maybe he drank his own tears

[D]

anyway. And I think this is kind of interesting about the human spirit. After five days of crying and thinking five days is a long time to bob around in the water licking condensation in the morning.

[A]

Right after five days, squids.

[D]

He snapped into action and began to make shift repairs to the boat with PVC pipes and kayak paddles. Paddles. He was hoping to be seen. And he was he the wind change or something. He ended up in a shipping lane, rescued by a passing container ship that were on the way to the Hawaiian Islands. And he got rescued.

[A]

Well, I don't, I don't want to be a knee jerk armchair hard guy. It reminds me of the kind of guy who looks at a beautiful woman, says she's not good looking. I wouldn't do her. Yeah, you weren't. You won't do anybody. You're not given the opportunity. That's up sad and pathetic backward boast and you're embarrassing yourself. I've always hated that. So for me to say it took you five days to think, all right, what do I have at hand Here to craft any sort of sale. I've got to admit, I'm a little intrigued by that.

[D]

Yeah. Just based on the picture and some of the things he said, he might not be the most normal person.

[A]

A bit of a condensation liquor if you ask me, you know, you don't even know what I'm saying.

[D]

Oh, he's a squid eater if I've ever seen one.

[A]

Yeah, yeah. Holy crap, my mast broke. How do I erect some sort of sail? I think would be my first thought.

[D]

No, his first thought was, can I get the motor going enough to suffocate myself?

[A]

And then after five days, a weep and thought, wait a minute, a mast is a long stick. I got some long, straight things around here. Let me think. Yeah. I wonder if he's a bit touched. They used to say back in the day.

[D]

Yeah, I suppose anybody who sets off to sail around the world alone is possibly a little abnormal.

[A]

I don't have the balls to sail solo across, like a golf course water hazard. So I'm again, I'm not trying to be the hard ass. I just. I'm a little flabbergasted. I like calamari, which is squid. I like sushi. I have no problem with raw fish. You get fluid and nutrition. So how does squid accidentally end up on your deck? Do they just leap in the air a lot?

[D]

I don't know. I thought that was kind of interesting, too. He survived on the squid and some other kind of fish that ended up on his deck. They just fly out of the water and land on your deck, I guess.

[A]

Wow, that's handy.

[D]

Yeah, it is. Better luck next time there. Kai says he's gonna try it again.

[A]

I wish sailing was a skill I had learned. I've got a guy, actually, a train, my trainer, my personal trainer. You're thinking, get your money back, dude. If you look at me, he has been into sailing since he was a little kid, and his kids are into sailing now. And you start on a little boat. Well, you start with help, but then you start on a little boat that you can control. And as you get bigger, your boat gets bigger. And they have regattas and races and stuff. I remember that.

[D]

I took lessons last year and.

[A]

Oh, that's right.

[D]

Yeah. How'd that go? It's way harder than it looks. Way harder. Tremendous amount of work to do and. And there's nothing relaxing about it at all. It's constant challenge of figuring because the wind is shifting every second. I didn't realize there's that much work to sail but it is constantly swinging it that way, that way, raise it, lower it, loosen it up, tighten it up, just never ending to keep going at all. And I don't know, I just, I had this vision of sailing to where there was a fair amount of kickback in there, you know, let the wind take you. But.

[A]

Glass of champagne?

[D]

Yeah, there's practically none of that.

[A]

And you got to make sure that is it the boom or whatever doesn't like blast you in the head and into the water.

[D]

Yeah, yeah, yeah, yeah. Constantly got to worry about that thing swinging back and cracking in the back of the head. But it's a tremendous amount of work. And I took the classes for a couple of days and got some certificate of as a beginning sailor. And I'm not going to try it again. I just thought it's not for me.

[A]

Did you go with the sailor suit like a little boy in wartime or did you go with the Ted Baxter and Caddyshack blue blazer and captain's hat?

[D]

I, I wore clothes to keep me from getting sunburned. But I remember there was woman, one woman that showed up to the sailing lesson. She did not last very long dressed like it was.

[A]

She was dressed in kind of a

[D]

sailor outfit and she was all excited about it, I think because I think a lot of people like her and me kind of have this vision of,

[A]

oh, I'm in a boat and where

[D]

you have to put the sail up and the wind takes you and it's

[A]

just, we're hanging out on the boat.

[D]

There's no, it's non stop trying to figure out where the wind's coming from and you have to like get used to feeling it on the back of your head or your face and. And then automatically your arms adjusting the sails to where you're feeling the wind coming from. And I never got, I mean I only tried it for hours. But getting that talent to where you can feel the wind on your neck, side of your face, kind of half front of your face, side of your face, you know exactly where it is. And tacking appropriately is a skill that would. Yeah, you'd want to start it as

[A]

a kid, as a highly skilled golfer. I think I'd be decent at that because we like try to figure out the wind every single shot. But you all almost never get blasted in the head if you're, you know, if you wait too long.

[D]

Yeah. Made me appreciate people who have that skill or you know, go out to San Francisco Bay and, and realize when I look out there that's not some Sort of pleasure. It's. It's like hard work, constant work to do that.

[A]

Yeah, yeah. Hear, hear. All right. Favorite musical artist.

[B]

Who.

[A]

Who. Who writes sailing related songs. There are a few notable ones.

[D]

Well, I gotta go. Jimmy Buffett.

[A]

Jimmy Buffett. Kenny Chesney, his musical cousin.

[D]

Friend of the.

[B]

Give me both.

[D]

Chris Cross.

[A]

Christopher Cross.

[D]

Not far down Paradise. At least it's not for me.

[A]

Crosby, Stills and Nash.

[D]

Oh, that's a good.

[A]

All three of them big into sailing. A bunch of different sailing songs. Yeah. Google it.

[D]

Yeah, Again, it's. It's got. It's got a different vibe than its reality. I feel like for most people who have never done it.

[A]

Lionel Richie, Sail on.

[C]

Right.

[A]

My favorite Lionel Richie song.

[D]

Is that one of those constant work and getting hit in the head with a big beam?

[A]

Yeah. I picture like the wind's blowing that way. So you set the sail and you just get pushed along by the wind.

[D]

You have a drink, look around.

[A]

Sure, sure. Eat a squid or two. Whatever book.

[D]

Get thirsty, you lick a little condensation. Joe, didn't you get kind of close to this on Lake Tahoe one time? You guys got out there.

[A]

Well, that was motor boating. Not literally motor.

[C]

Not.

[A]

Yes, yes, it was terrible. But, you know, we were powered by a gasoline engine. As a matter of fact, you know, Sticks is another one.

[D]

Come sail away.

[A]

Anyway, that's not actually.

[D]

Anyway, okay.

[A]

They served a soul some stranded squid and headed for the sky.

[D]

I'm licking the bow.

[A]

Beautiful.

[D]

Well, I guess that's it.

[B]

One last thing before you go. You know that feeling when feedback notes and data are coming in from every direction? ChatGPT work can make sense of it all, turning scattered inputs into ready to review work. With your permission, work in ChatGPT can gather context from apps and files, summarize incoming messages, rebuild decks, and help finalize high quality documents for your team or clients. Stay in control as you move from a goal to polished. Work faster with ChatGPT work. Download the ChatGPT desktop app today and take on your most ambitious work.

[E]

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