The SS Crew
The Seeing Sideways Podcast
We're a podcast about regular (ish) people going through the regular highs and lows about life right alongside with you. We '' share tools, resources and relatable stories to help you navigate this maze or mess called... life.
Where to listen?
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Episodes
The GOOD Old Days...? (W/ Special Guest, Trent) 08.07.2026 1:04:18
Why do we use this term? "The good old days?" so damn often? As if the "old" days were the golden years as opposed to the dark dystopian times we live in now? WERE the days of yesterday as good as we remember them? Or is there more nuance to that mindset we all tend to have? Join Kyle, Jessica and special returning guest, Trent as we discuss...well...the good old days? Question...
Betting On YOURSELF (w/ special guest, Joy) 24.06.2026 1:08:44
Joy once again joins Kyle and Jessica this week discussing the risk of betting it all...on yourself. What is it like to quit the corporate world and go after your dreams with no guarantees of success. What is it like to put your full faith in yourself to succeed in what YOU believe in? Joy shares her story and drops the mic SEVERAL times throughout this inspiring discussion on perseverance and fai...
Data Overload and Overwhelm (w/ special guest, Joy) 16.06.2026 59:19
Today we add a new voice to the conversation of the millennial burnout epidemic: our good friend Joy joins us on this episode of the podcast. She adds an enlightening perspective on DATA and how we consume and use data to make decisions or does the overload just make us feel...stuck?
The MILLENNIAL BURNOUT Crisis (Part 2) 09.06.2026 1:01:24
PART DEUX of the epic discussion on the topical...er..topic on why Millennials are feeling the burn and just have had it. But is it just Millennials? What about Gen Z? Is there more going on? Join Kyle and Jessica as they continue their discussion...rant...therapy session on why everyone these days is taking a step back, looking around them and going...what the fuck?
The MILLENNIAL BURNOUT Crisis! (Part 1) 02.06.2026 1:03:03
WE'RE BAAACK! After a bit of a hiatus the SEEING SIDEWAYS PODCAST returns with hosts Kyle and Jessica tackling the current epidemic that seems to be pervasive amongst the Millennial demographic of people being burnt the Hell out and fed up. Why are Millennials feeling the crash? We take a deep dive discussion on the epic return of your favorite podcast about LIFE!
Lets Stop People Pleasing 06.03.2026 1:06:46
The crew is back in this episode which closes an ...arc (?) of sorts to our conversations of self advocacy and boundaries which leads into inevitable issues of ...people pleasing or a preoccupation of pleasing others for the sake of keeping the peace. We break down the pros and cons and why perhaps we need to ease up on keeping everyone else happy but ourselves.
Let the Universe Do its Thing 24.02.2026 29:29
This week....Kyle rolls solo! This week's episode is a brief on-on-one chat with Kyle and himself (and of course you listeners) about the notion of control. And how perhaps we dont need to have such a firm grip on control and the need to be several steps ahead of everything. Perhaps one of the best things about life is just...letting go and letting the universe do its thang! (maybe? Lets disc...
Creating BOUNDARIES!! 18.02.2026 1:28:54
This week we continue our discussion with our special guest and friend Abby and talk about the art of creating boundaries. The hosts all discuss moments in their lives where they have expressed boundaries that were important to them and perhaps they weren't quite honored. This is a discussion about how expressing your needs and boundaries and standing firm on them are some of the BEST things...
Self Advocating...Even When Its Hard 10.02.2026 57:09
On today's episode we are joined by a special guest, our good friend Abby joins us for a discussion on the topic of self advocacy and essentially speaking up for yourself. It can be surprisingly hard to speak up for yourself, speak your needs and speak your truth. The hosts discuss their experiences and struggles with self advocating for themselves and how we can all take steps into being our...
Why Does TIME Flow Faster As Adults?! 04.02.2026 59:08
On today's episode, Kyle Jessica and Rey discuss...time. The enigmatic, intangible thing we all want so desperately to control...but we cant. Or can we?! (we can't) But what we CAN control is our perception of time. Why does Time seem to go by faster the older we get vs when we were young? Let's discuss!
2026 Vs....2016 21.01.2026 1:09:34
Yes...we're doing that thing. Everyone on social media's doing a 10 year retrospective so...why not us?! Kyle, Jessica and Rey take a look back to 2016 and introspect on where they were that year and how the last decade in general has been transformative to each of them in their own unique ways. They also dive into where the WORLD was in 2016 as well. So, sit back, relax as we take a tri...
Finding COMFORT in DISCOMFORT 07.01.2026 56:18
A New Year is often synonymous with growth and growth is often synonymous with discomfort. Because in order to grow we must step into the unknown and embrace the unfamiliar and the uncomfortable. But we HATE that shit, don't we?! Our nervous systems forbid it. In this episode our hosts discuss how we can learn to find comfort in being uncomfortable in order for us to ease into growth.
Looking BACK to Look AHEAD 01.01.2026 1:04:13
HAPPY NEW YEAR everyone! 2026 is here and our hosts reflect on the past year... which ends up becoming a reflection on life as a whole and how our experiences shaped us and how we can use that to have a positive outlook at what lies ahead.
The HOLIDAYS...How do they make you feel...Really? 24.12.2025 56:32
The holidays are upon us and our merry (ish) hosts discuss Christmas and the general holiday warm and fuzzies and what feelings they evoke when this time of the year rolls around. Are we festive? Melancholic? Alcoholic? Grab some milk, cookies and eggnog and relax as our hosts discuss the vibes that holiday season evokes.
Social Media Part 2! 16.12.2025 1:00:57
We've got more shit to say! On this week's episode Reynard joins the discussion on social media, its benefits, its pitfalls and the best way social media can be utilized to enhance your career aspirations!
Social F***ing MEDIA 09.12.2025 1:00:24
Instagram, Tik Tok, Facebook (do people still use Facebook?) etc all inundate our day to day and have become a staple in society. Social media has made the world feel smaller and easier to communicate to one another but is it s gift or a curse? Or Both? In this episode Jessica and Kyle discuss the dangerous pitfalls social media can pull us into and how this modern staple can potentially actually...
The Art of Saying "NO" (Part 2) 02.12.2025 1:01:01
Continuing from Kyle and Reynard's conversation last week, co-host Jessica joins in on the conversation and offers very insightful perspective on the art of setting boundaries and how, in her words, sometimes when we say "yes" we are saying "no" to something else. The three also delve into the origin of why we all tend to be averse to saying the word "no" as a fe...
The Art of Saying "No" (Part 1) 25.11.2025 36:16
The word "no" is an inherent negative term, an inherent term of rejection. But saying "no" is sometimes the healthiest thing we can do for ourselves. And yet we struggle with it especially with the people we care about and as a result we people please to our own detriment. In this episode Kyle and Reynard discuss the word "no" and why we should say "YES" to...
Feeling DISEMPOWERED in The Work Place 04.11.2025 1:07:42
There's nothing more frustrating than wanting to do a good job in your day job but you're constantly being stonewalled by work politics. And when we feel frustrated at work, it bleeds into our personal lives. In this episode Kyle, Jessica and newcomer Trent dive into the feeling of disempowerment in the workplace and the effect it can have on your mental health and how you navigate your...
Working For YOURSELF vs Working for OTHERS 28.10.2025 1:14:05
We all strive for the day where we can tell our bosses to F*** off, right? That day where we can be financially free and independent and don't have to take anybody's BS anymore. But what are the potentials pitfalls that come with working for yourself vs having a stable job working for "the man." (do kids still say that?) On this episode we have a special guest and friend, Trent...
Mourning Your Old Self 21.10.2025 54:05
Life is about change and that often means saying goodbye to the old iteration of your life and the people in it but saying "What up!" to the new version of yourself waiting in the wings. But saying goodbye is always hard in all its forms. In this episode we dive into how to say goodbye to your old self and to allow yourself to feel the feelings that come with it.
The RENT IS TOO DAMN HIGH! 15.10.2025 51:14
With egg prices skyrocketing to legendary heights, Kyle and Reynard tackle the PAINFULLY timely and relatable topic of why the cost of living in 2025 is just beyond ridonculous at this point. Why is that and what, if anything can we do about it?
Fall SUCKS (Or Does it?) 07.10.2025 1:00:41
Fall is upon us and with it comes...mixed feelings. At least from these hosts who are bit tepid on the season. What is it about Fall that evokes these emotions, we dive deep into the meaning of Fall, why it may feel like a comedown after the summertime and why maybe its the most underrated season of them all.
PROGRESS over PERFECTION 30.09.2025 1:04:06
You ever get stuck (well duh that's why you're listening to us, right?) and you realize the reason why you're stuck is because you're so laser focused on getting whatever it is you're stuck on...right. But maybe the key is getting it wrong first, several times. In this episode Kyle. Rey and Jessica discuss why its important to screw up first before you get it "right.&...
TOXICITY in the Workplace! 23.09.2025 55:18
In this episode, Kyle and Jessica welcome the newest co-host to the podcast, Reynard! The trio discuss toxic work environment s and how that puts a toll on our mental health and affects our job productivity. The team also dive deep into different management styles, because, face it, we've all had shitty managers and dissect what management styles work, what doesn't and what provides the...
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