
The Happiest Sad Person Podcast
Eternal optimist who also perpetually worries the world is ending -- you know, normal people stuff.
Episodes
39 episodes
your girl got hacked | the happiest sad person podcast
Episode #39 of The Happiest Sad Person Podcast. Join me, Alessandra, as I explain how on earth I was hacked in the year of our lord, 2024. Yep, you heard that right. I talk about how I'm trying to learn something from this whole experie...
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Episode 39
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20:50

showing up is the first step | the happiest sad person podcast
Episode #38 of The Happiest Sad Person Podcast. Join me, Alessandra, as I open up about my desire not to film today and my futile addiction to perfectionism (always to my own detriment). I also give my own spin on the notion that the gr...
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Episode 38
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27:45

adulthood ain't the bees knees | the happiest sad person podcast
Episode #37 of The Happiest Sad Person Podcast. Join me, Alessandra, as I discuss designing my own hodgepodge syllabus for my life-long education plan (or at least for the foreseeable future). I also muse on the sadness that is adulthoo...
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Episode 37
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52:20

life is one loooong hallway | the happiest sad person podcast
Episode #36 of The Happiest Sad Person Podcast. Join me, Alessandra, as I embrace the unemployed yet somehow constantly busy life of a creative. I also muse on Harrison Butker's commencement speech and how repulsive I find that way of t...
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Episode 36
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32:47

just busy chopping wood & carrying water | the happiest sad person podcast
Episode #35 of The Happiest Sad Person Podcast. Join me, Alessandra, as I discuss being unemployed whilst keeping up my spirits -- and keeping myself busy. I end with an excerpt of my book that connects to the conversation, and I promis...
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Episode 35
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32:43

our modern world limits our experience of love | the happiest sad person podcast
Episode #34 of The Happiest Sad Person Podcast. Join me, Alessandra, as I discuss the limitations of love our modern society has created -- but I tried to end it with some tangible suggestions for actually fixing the problem. My rule to...
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Episode 34
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14:22

depression mode -- what are we all doing here, bro? | the happiest sad person podcast
Episode #33 of The Happiest Sad Person Podcast. this was filmed a month agoJoin me, Alessandra, as I document a bout of depression mode in my life. It is a bit of woe mixed with, hopefully, some optimism at the end. Alway...
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Episode 33
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18:56

i'm trying to get rejected 100 times in 2024 | the happiest sad person podcast
Episode #32 of The Happiest Sad Person Podcast. Join me, Alessandra, as I try to repair my relationship with rejection and seek out getting no's in the wild. It's regular therapy alongside rejection therapy in 2024. As always, e...
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Episode 32
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39:20

my resolutions for 2024 that i'm ACTUALLY going to do | the happiest sad person podcast
Episode #31 of The Happiest Sad Person Podcast. Join me, Alessandra, as I get real with myself and choose actual goals I can actually accomplish in 2024. It *actually" is new year, new me. As always, email suggestions to 11jacob...
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Episode 31
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54:20

microdosing changed my life | the happiest sad person podcast
Episode #30 of The Happiest Sad Person Podcast. Join me, Alessandra, as I do a deep dive on my microdosing journey thus far. It's been a ride, to say the least. :)As always, email suggestions to 11jacobsa@gmail.com.-----...
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Episode 30
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55:30

no one's coming to save you
Episode #29 of The Happiest Sad Person Podcast. Join me, Alessandra, as I discuss the concept of searching, muse about the magic that is serendipity and synchronicity + read a snippet of my book. 'Tis the season of self development and ...
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Episode 29
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37:16

i'm done being somebody else for everybody else | The Happiest Sad Person Podcast 28
Episode #28 of The Happiest Sad Person Podcast. I'm back bb. Join me, Alessandra, as I make my very anticlimactic return, muse about where I've been + have an honest moment or two. It's really good to be back, you guys:)As alway...
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Episode 28
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17:47

CRYING ON CHRISTMAS *emotional* | The Happiest Sad Person Podcast 27
Episode #27 of The Happiest Sad Person Podcast. Join me, Alessandra, as I close out the 2022 season, muse about my relationship with change + whine about people cutting down trees. This episode was definitely more sad than happy, but juxtaposit...
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Episode 27
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27:25

MY DREAM WAS TO BE A NEPOTISM BABY | The Happiest Sad Person Podcast 26
Episode #26 of The Happiest Sad Person Podcast. Join me, Alessandra, as I open with the complaints surrounding my massive hangover, wonder if I will ever get over my imposter syndrome + question if there is such a thing as an ethical bill...
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Episode 26
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28:52

ANOTHER YEAR CLOSER TO DEATH | The Happiest Sad Person Podcast 25
Episode #25 of The Happiest Sad Person Podcast. Join me, Alessandra, as I open with, of course, another ankle update, ruminate on why I hate my birthday + dig into my season of newfound discipline. This Thanksgiving episode, as always, is...
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Episode 25
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29:25

THE NATURE OF HUMAN NATURE | The Happiest Sad Person Podcast 24
Episode #24 of The Happiest Sad Person Podcast. Join me, Alessandra, as I open with another ankle injury update (I swear it connects to the rest of the ep lol), dwell on the influx of terrible tragedies lately + question how the immense p...
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Episode 24
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21:50

**BONUS EPISODE** | INTRO TO SOBER OCTOBER 101 | The Happiest Sad Person Podcast 23
Episode #23 of The Happiest Sad Person Podcast. A little bonus episode introducing my Sober October Challenge. As always, email suggestions at 11jacobsa@gmail.com.Links:Podcast Instagram:
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Episode 23
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23:59

LEGIT DEPRESSION MODE | The Happiest Sad Person Podcast 22
Episode #22 of The Happiest Sad Person Podcast. Join me, Alessandra, as I give another update on my ankle injury, brainstorm about how I can improve my empathy + detail how I ironically find altruism in caring for myself. This episode is ...
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Episode 22
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23:59

MY RIGHT FOOT | The Happiest Sad Person Podcast 21
Join me, Alessandra, as I try to learn a lesson from my current ankle injury, give an update on my latest spin on the 75 Hard(ish) Challenge + pontificate on the fallibility and fragility of the human being. This episode is more Schadenfr...
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Episode 21
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21:13

THE REFRAIN OF BAZ LUHRMANN | The Happiest Sad Person Podcast 20
Join me, Alessandra, as I give an update on my attempt at The Rachel Carson Trail Challenge, introduce a new challenge I'm starting that's inspired by the one and only 75 Hard + I give my own review on the book "4000 Weeks: Time Managemen...
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Episode 20
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33:47

NEW BEGINNINGS & NO SUCH THING AS THE RIGHT TIME | The Happiest Sad Person Podcast 19
I’m back, baby. I know, I know. It’s been a minute. Well, a series of minutes. And I do extend my sincerest apologies.No really, I do.And this ep talks about where I’ve been, or lack thereof. What I’m doing now and what’s on the...
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Episode 19
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17:27

"if it's mentionable, it's manageable..." | The Happiest Sad Person Podcast 18
Join myself, Alessandra "Ali" Jacobs, and a fellow classmate, Allison, while we discuss the qualms we had with our yoga teacher training course, question if life actually is a game + if you can ever truly win and how we will be remembered as hu...
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Episode 18
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1:41:10

**Bonus Episode** | Weight Loss Part 2 | The Happiest Sad Person Podcast 17
After a brief hiatus - my apologies, I needed to clear my head - an update of my brother and I's weight loss challenge. Spoiler alert: It continues. Again, feel free to join in on the endeavor and give some tips in the comments. :)As al...
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Episode 17
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15:43

**Bonus Episode** | Weight Loss Part 1 | The Happiest Sad Person Podcast 16
A little New Year's Eve bonus episode of my brother and I embarking on a weight loss challenge. Feel free to join in on the endeavor and place a bet in the comments on who you think will be victorious:)As always, email suggestions a...
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Episode 16
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26:37

"I don’t get the Target hype..." | The Happiest Sad Person Podcast 15
Join myself, Ali Jacobs, and my brother Nate once again while we discuss the semantics of happiness v. contentment, investigate Nate's disdain for Target, and what exactly you can learn from the magic that is a 9-5 job. Another episode that tou...
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Episode 15
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56:19
