Sensemaking with Wolé and Tobi

112: Rethinking Work, Starting With the Job Market

A simple question about today’s job market led us somewhere deeper.
We began by reflecting on what we’re seeing — shifting hiring patterns, oversaturated applications, the quiet disappearance of certain entry-level pathways, and the rise of AI-augmented talent. But as the conversation unfolded, it became clear that the real question wasn’t just about jobs.
It was about work itself.
What makes someone valuable in their work? Is experience still defined by time, or by exposure and context? And as new tools begin to compress the distance between beginner and expert, what happens to the structures we’ve built around expertise, hierarchy, and apprenticeship?
If knowledge can be accelerated, what becomes of judgment? If output can be amplified, what becomes of experience?
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

111: Are We Thinking Clearly About AI?

We’re living through something strange, and nobody really knows how it ends.
In this episode, we try to articulate that feeling — the sense that something massive is happening, billions are being poured in, companies are racing, narratives are hardening… and yet nobody actually knows how this ends.
It feels like we’re inside a chapter that will later get a name.
The “AI Boom.”
The “AI Bubble.”
The “AI Reset.”
We just don’t know which one.
We talk about:
Why so many powerful people sound absolutely certain about the future
What incentives are driving the hype (and who benefits if we believe it)
Whether this is genuine transformation — or another cycle of over-promise
But more importantly, this was a very human conversation about our scepticism and curiosity in all of this.
About choosing to think for yourself instead of joining the hive mind.
About asking what responsibility looks like when you’re building, investing, working, or creating in the middle of something that might reshape everything.
Because sometimes the most important thing isn’t knowing what will happen, but being aware that you’re already living through it.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

110: Bro, When Did Everything Become a Subscription?

Subscriptions used to be simple. A newspaper. A gym. Maybe a DVD club if you were feeling fancy.
Now they’re everywhere: apps, TV, work tools, cars, even things in your house. And somehow none of them feel expensive on their own… until you look at them together.
 
This episode starts with a quiz, but it quickly turns into a bigger conversation about how the subscription model has quietly taken over modern life.
We talk through how and when this shift happened, why entertainment subscriptions dominate so many budgets, and why cancelling things often feels harder than it should. 
Subscriptions are everywhere now — from entertainment to work to things we used to own. But then you step back and realise how quietly that changed everything. And you start wondering if it’s actually better.
We compare our own subscription lists, talk about the “zombie” payments we forgot to cancel, debate ownership vs access, and question whether this model is even sustainable long-term. Plus: which subs are genuinely worth it, which ones feel like scams in disguise, and the simple rules we use to avoid drowning in monthly charges.
If you’ve ever looked at your bank statement and thought, “wait… what am I even paying for?” — this one’s for you.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

109: When Did Raising a Child Become a Luxury?

In this episode, Wole and Tobi try to make sense of a growing tension many people feel but struggle to articulate: why starting a family now feels economically overwhelming.
Sparked by real nursery costs, they unpack how raising children has become increasingly financialised — from childcare and education to housing and work expectations. They explore fertility decline across regions, the mismatch between income growth and family costs, and whether modern economies have quietly made children feel like liabilities rather than a blessing.
This isn’t an episode with neat answers. It’s a conversation about numbers, faith, fear, privilege, necessity, and meaning — and how people navigate parenthood when the system itself feels misaligned.
As always, this is sensemaking in real time.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

108: Is the Culture Moving On Without Us?

In this episode, we explore a conversation around celebrity, accountability, and mental health, using Kanye West’s public apology as a reference point.
We question what public apologies actually mean, how fame complicates responsibility, and why real growth usually happens away from the spotlight. We also touch on how mental health language has become more common, sometimes in helpful ways, but often in ways that blur accountability and reality.  
From there, the conversation widens into culture and the rise of internet-native fame.
We talk about figures like IShowSpeed and what they represent — a new kind of celebrity built on personality, algorithms, and constant visibility.
It’s a reflection on how culture is shifting in real time, how relevance is being redefined, and what it means for people like us trying to stay grounded while the rules keep changing.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

107: Between Point ‘A’ and Whatever’s Next

A wide-ranging conversation on ambition, intuition, entrepreneurship, and the messy reality of building something meaningful.
We talk about career uncertainty, momentum over clarity, the danger of hustle culture, and why sometimes the best progress happens when you stop trying to control everything.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

106: The New Dad in Town

We’ve talked about fatherhood before, but usually in a vague, hypothetical way; looking at what it might look like, what it could require, what kind of men we'd need to become. But this time, it's different.
One of us is now living it 🍼.
So the conversation ended up being less about “being a dad” and more about what changes when life suddenly asks more of you. How your time feels different. How your head feels fuller. How you can be exhausted and grateful at the same time. How you catch yourself thinking, “Oh… this is me now.”
We talk about the small stuff: the moments you don’t post, the quiet guilt, the pride you don’t know where to put, the sense that you’re still yourself but also… not quite. And how strange it is to figure things out while you’re already responsible for something that matters this much.
We did not intend for this to come across as a how-to guide. There’s no big takeaway. Just two friends talking honestly about change, identity, and trying to show up properly, whatever that looks like right now.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

105: Cold Starts and Fresh Hopes

In this intimate New Year catch-up, Wole and Tobi ease into the year with a raw, meandering conversation about returning to routines, grappling with unfinished goals, and adjusting expectations.
They reflect on how difficult it is to start anew—whether in fitness, career, or life—and explore what it means to show up for yourself and others, even when you’re tired, distracted, or unsure.
From gym resolutions to global grief, from personal inertia to the politics of empathy, this episode offers a tender reminder: starting again is hard, but it’s also a brave and beautiful thing.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here:  http://bit.ly/sensemakingvn 

104: What the Diddy Story Forces Us to Confront

Familiarity does strange things to judgment.
It’s surprisingly easy to feel informed about people we’ve never met. Artists, leaders, creators, public figures. When someone has been around long enough, their presence alone can start to feel like understanding.
But being familiar with someone isn’t the same as knowing them.
Using the recent conversation around Sean “Diddy” Combs as a loose reference point, we talk about what happens when new information messes with a picture we already had in our heads. How quickly we settle into stories about people. How slow we are to change them. How much of what we “know” is really just repetition and proximity doing their thing?
We also explore the concept of parasocial attachment, examining why closeness (real or imagined) sometimes softens our judgment and how familiarity often convinces us we’ve figured someone out.
.
.
.
If, while you’re listening, something crosses your mind, or you get that urge to jump into the conversation, we’d love to hear from you! Please send us a quick voice note using here: http://bit.ly/sensemakingvn

103: Are We Falling Out of Love With Social Media?

If you’ve been feeling weird about social media lately, we’d love to hear it. Send us a quick voice note on Speakpipe (http://bit.ly/sensemakingvn).
Now… into the episode:
.
.
Do you ever feel like everything online looks like a movie trailer now? From Instagram reels to indie films - same lighting, same tone, the same “algorithm-approved” format.
In this episode, we talk about the conflict of being people who actually enjoy creating things… but are slowly falling out of love with the platforms we’re supposed to use to share them.
We get into why Instagram has started to feel like junk mail, how marketing your work can quietly breed resentment, and why even modern cinematography — as clean and beautiful as it looks — sometimes feels strangely empty.
We also get into the deeper questions:
Is it still possible to make meaningful work in a world that seems to reward noise?
What does authenticity even look like anymore?
And what happens when your art starts serving the machine, instead of the other way around?
A slow-burning, think-out-loud kind of episode. For the creators, the observers, and everyone in between.
Before you go, remember you can send us a quick voice note on Speakpipe (http://bit.ly/sensemakingvn) and tell us how you feel about social media right now. Are we all experiencing the same quiet fatigue?
 

102: Thinking Out Loud at About AI

You can send us a quick voice note with your thoughts on Speakpipe (http://bit.ly/sensemakingvn).
.
.
.Artificial intelligence has gone from a niche conversation to an unavoidable presence in work, in creativity, in relationships, in how we communicate, and even in how we think. And suddenly, it’s hard to remember a time before “ChatGPT”
But beneath the hype, there’s a deeper struggle: How do we stay human when the tools around us are accelerating faster than our ability to make sense of them?
For some of us, AI feels like magic, the thing that expands what we can build, speeding up work, giving us leverage we’ve never had.
For others, it triggers anxiety, identity questions, shame, and a quiet fear that we’re slowly outsourcing the very things that make us who we are.
In this episode, we sit in the messy middle. We talk about how easy it’s become to hand our thinking over to machines, where the line is between getting help and becoming dependent. Why the internet is filling up with AI-generated slop. And how we risk losing the muscle of thinking if we stop using it.
.
.
.
You can also share your thoughts with us. How is AI showing up in your work and life right now? Send a quick voice note on Speakpipe (http://bit.ly/sensemakingvn), and we’ll weave your thoughts into future conversations.

101: We're Back

After an 18-month break, a rebrand, a move across countries, a wedding, a baby, and a whole lot of growing up, we’re back on the mics - this time as Sensemaking with Wolé and Tobi.
If you’ve been with us for a while, the name probably won’t surprise you as it’s what we’ve always quietly been doing on this show: trying to make sense of a world that feels familiar and unpredictable at the same time.
Work, relationships, cost of living, identity shifts… and now AI headlines, changing definitions of home, and the pressure to choose wisely and stay sane in the middle of it all.
Underneath the life updates, there’s a bigger “wicked problem” we’re trying to make sense of: How do you keep making sense of your life when everything keeps changing - your city, your work, your relationships, the tech you use - and you’re stuck between overthinking and actually doing?
This is what Sensemaking is for.
Formally, it’s the process of giving meaning to experience. Informally, it’s psychological survival - a way of keeping chaos from taking over.
This podcast is our modest attempt to engage in that process: earnestly, imperfectly, and out loud. And this time, it won’t just be our voices.
We want to hear you: your reflections, your questions, your confusions, your hard-won insights. Fewer guests, more community. Because the antidote to isolation is shared attention, and the path forward is rarely walked alone.
If you’ve been with us since 20s Convos or The Yellow Pill, this episode is a welcome-back hug.
If you’re new, this is the perfect place to start.
Welcome to Sensemaking. Let’s bring order to the chaos, one conversation at a time.

S10E20 - The Farewell Episode

After four amazing years and 100+ unforgettable episodes, The Yellow Pill journey comes to an end 💛
It has been an incredible chapter of our lives, & we want to take a moment to express our deepest gratitude to each and every one of you.
Whether you’ve been with us since day one of ‘Instagram Lives’ and 20sConvos or you’ve joined the journey along the way, you have been the heartbeat of our podcast.
Your presence and support have meant the world to us and have been the driving force behind every episode.
Together, we’ve explored 100 burning and meaningful topics that have inspired, challenged, and entertained us. You have no idea how much the conversational exercises on such diverse topics have made us nearer to being Whole. We’ve laughed, we’ve learned, and we’ve grown.
Honestly, it’s been a privilege to have had this shared space that permitted you to witness our thoughts, experiences, and passions each week. Your engagement, comments, and messages have sparked countless conversations and brought our community closer together.
We also want to extend a special thank you to all 60+ guests who have been on this podcast, and whose words and experiences have enriched our podcast over time. We know you are all one text away and we appreciate that. Thank you! 💛
And finally, to you, our listeners, thank you for inviting us into your lives, for lending us your ears, and for being a part of this extraordinary journey. Your support has been the greatest gift of all, and we are endlessly grateful for the memories we’ve shared 💛
This may be the end but it is not goodbye. We hope our paths will cross again in the future, whether it’s through new projects, social media, or chance encounters 😉. Until then, please know that you will always hold a special place in our hearts.
As we bid farewell, we urge everyone to take up our message in the previous episode and believe that your lives have meaning. And with that, have a great 2024!
Thank you for being a part of our podcast family and for making these past four years an unforgettable adventure.
Peace & love,Wolé & Tobi
.
.
.
To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e20
.
.
.
Before you go, here's one more way to still support the podcast for one last time 💛
Leave us a review where you're listening right now! 💫

S10E19 - Why Your Life Has Meaning

To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e19
You can also ask us anything for the TYP Corner on Youtube using this link here - http://bit.ly/typauas10
.
.
.
Season 10, Episode 10, our 100th topic-episodeThis will be the most important episode to emerge from our podcast. There’s a chance it will also be the last.We’re closing the curtain with an episode we believe will be an abiding formula for hope and sustenance. We’re bowing out with a hymn of encouragement.We believe your life has meaning. Despite all the unfathomable and overwhelming chaos that may exist (in reality or perception) on a global, societal, and personal level, we believe your journey is meaningful, we believe you matter.Young adults are rarely taught how to realise that their existence has a justification. And from this podcast seat, convincing one of these truths is the most difficult of tasks.Due to this difficulty, we ended up with a 2-hour episode. But it’s an episode where each sentence, response, and message maturely represents what we’ve learnt in the last 4 years, inside and outside the podcast.We hope this episode helps to confirm that your life has meaning.
.
.
.
Before you go, here are a few ways to support the podcast!
Become a TYP Patreon ♥️ - http://patreon.com/theyellowpillpod
Leave us a review where you're listening right now! 💫
Ask us anything - http://bit.ly/typauas10
Follow us on Instagram (@theyellowpillpod) 📷
Follow us on Twitter(X?) (@yellowpill_pod) 🐦

S10E18 - The Future of TYP II

To listen to this episode in its entirety, join us on Patreon for more exclusive content from Wolé and Tobi! - http://patreon.com/theyellowpillpod
 
To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e18
.
.
.
As the title suggests, this episode serves as a follow-up to our previous "cinematherapy" episode, where we invited all of you to "eavesdrop" on our conversation about the future of the podcast.
In this episode, we make our best effort to address a detailed comment about the original episode and also take the opportunity to share a few more thoughts about what lies ahead for The Yellow Pill.
We hope you enjoy listening to it!
.
.
.
Before you go, here are a few ways to support the podcast!
Become a TYP Patreon ♥️ - http://patreon.com/theyellowpillpod
Leave us a review where you're listening right now! 💫
Ask us anything - http://bit.ly/typauas10
Follow us on Instagram (@theyellowpillpod) 📷
Follow us on Twitter(X?) (@yellowpill_pod) 🐦

S10E17 - PDA on Social Media

To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e17
You can also ask us anything for the TYP Corner on YouTube using this link here - http://bit.ly/typauas10
.
.
.
From the days of Display Pictures (DPs) on Blackberry Messenger to the present day with Instagram and others, many social media users have chosen to share and post about their love lives online.
This activity of public displays of affection (PDA) online is not new, but it is certainly pervasive. With obvious reasons aside, why do we do it? Why do some people share a lot more about their partners and relationships with the world than others?
In this episode, our intention is not to categorize this behaviour as good or bad, right or wrong. After all, to each their own 😉.
For this reason, we focus our discussion on online PDA mostly based on our own experiences. No science, no philosophy, just our personal experiences and approach to online PDA.
.
.
.
Before you go, here are a few ways to support the podcast!
Become a TYP Patreon ♥️ - http://patreon.com/theyellowpillpod
Leave us a review where you're listening right now! 💫
Ask us anything - http://bit.ly/typauas10
Follow us on Instagram (@theyellowpillpod) 📷
Follow us on Twitter(X?) (@yellowpill_pod) 🐦

S10E16 - The Future of TYP

To listen to this episode in its entirety and for more exclusive content from Wolé and Tobi, join us on Patreon! - http://patreon.com/theyellowpillpod
To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e16
.
.
.
With Season 10 nearing its end, we chose to bring one of our off-air conversations into this on-air cinematherapy episode: what does the future hold for this podcast?
While this may or may not sound existential lol, it’s actually a normal behind-the-scenes exercise for us to re-evaluate our podcast, our responsibility, and frankly, ‘why we (continue to) do this’.
We haven’t yet figured out what the future holds, but we hope we can do that together by inviting you into our thoughts.
.
.
.
Before you go, here are a few ways to support the podcast!
Become a TYP Patreon ♥️ - http://patreon.com/theyellowpillpod
Leave us a review where you're listening right now! 💫
Ask us anything - http://bit.ly/typauas10
Follow us on Instagram (@theyellowpillpod) 📷
Follow us on Twitter(X?) (@yellowpill_pod) 🐦

S10E15.9 - Happy New Year!

To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e15-9
You can also ask us anything for the TYP Corner on YouTube using this link here - http://bit.ly/typauas10
.
.
.
What’s in store for you this new year?
Did you make any new resolutions focused on 2024? Goals? Paradigm shifts? Or is it business as usual because the ‘new year change’ is often overstated?In this episode, we exchange our feelings and thoughts about the new year, most of which centre around gratitude, love, health, & money!
.
.
.
Before you go, here are a few ways to support the podcast!
Become a TYP Patreon ♥️ - http://patreon.com/theyellowpillpod
Leave us a review where you're listening right now! 💫
Ask us anything - http://bit.ly/typauas10
Follow us on Instagram (@theyellowpillpod) 📷
Follow us on Twitter(X?) (@yellowpill_pod) 🐦

S10E15.5 - The One About Christmas

To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e15-5
You can also ask us anything for the TYP Corner on Youtube using this link here - http://bit.ly/typauas10
.
.
.
In their usual fashion, Wole and Tobi take a "break" from their regular programming to reflect on Christmas and its significance to them. They discuss their Christmas traditions, or the lack thereof, as well as how their backgrounds and cultures influence the celebration of the season among their families. The conversation also includes Tobi's “recurring complaint” about capitalism and its impact on various aspects of life.
Enjoy the conversation and Merry Christmas!
.
.
.
Before you go, here are a few ways to support the podcast!
Become a TYP Patreon ♥️ - http://patreon.com/theyellowpillpod
Leave us a review where you're listening right now! 💫
Ask us anything - http://bit.ly/typauas10
Follow us on Instagram (@theyellowpillpod) 📷
Follow us on Twitter(X?) (@yellowpill_pod) 🐦

S10E15 - The Death of Hobbies?

To leave a comment at any point during your listen, here's a link you can use - https://bit.ly/typs10e15
You can also ask us anything for the TYP Corner on YouTube using this link here - http://bit.ly/typauas10
.
.
.
What are your hobbies?
Depending on the context, we’ve struggled/cringed at answering this question at some point.
When we talk about hobbies colloquially, we are describing an aspect of a broader idea of ‘serious leisure’.
Hobbies, or serious leisure, have typically been associated with activities undertaken for play or pleasure during free time. But there’s a growing concern that nowadays, everyone’s free time activities always have to be ‘productive’ or ‘profitable’, and therefore we are witnessing the death of hobbies.
We try to tackle this in this episode by answering some of these questions: What is the function of hobbies? How do they differ from leisure? Are hobbies truly dying? What role has capitalism and social media played in modern hobbies? What hobbies are attractive, and why?
By tackling this, we realised that understanding the role of hobbies is of huge importance to our humanity and why hobbies matter!
Not sure if this caption does justice but this was one of our favourite episodes to record so far! 🎤 💛
.
.
.
Before you go, here are a few ways to support the podcast!
Become a TYP Patreon ♥️ - http://patreon.com/theyellowpillpod
Leave us a review where you're listening right now! 💫
Ask us anything - http://bit.ly/typauas10
Follow us on Instagram (@theyellowpillpod) 📷
Follow us on Twitter(X?) (@yellowpill_pod) 🐦