Why Are We Still Doing That? E11 – Why Are We Loyal To Things That Don’t Serve Us?

We’re back with another episode of Why Are We Still Doing That? This week, we’re tackling the topic of quitting’s close cousin: Changing Your Mind.If quitting makes people squirm, changing your mind about a decision seems to send the whole system into a meltdown. We've been trained to treat our decisions as final, even when new, credible information shows up. We’re conditioned to think that being "belligerently resolute" is a virtue, but that is simply choosing to not grow.Here’s the truth: Changing your mind isn’t confusion, it’s clarity. It’s a smart, fluid move that shows you are paying attention. Real progress comes from being open to new information, not from sticking to a fixed stance.In this episode, we dismantle the culture that fears the "flip-flopper" label and make the case for mindful, informed evolution.You’ll hear:Why changing your mind about a decision isn't confusion, it's clarity… And one of the smartest moves you can make.Kent's "mind share" on having an attitude of gratitude for being able to help people, and Caanan's thoughts on end-of-year "best of" lists.How the fear of being called a "flip-flopper" (especially in politics) teaches us that we aren't allowed to evolve, which discourages personal growth.The crucial difference between being flaky and mindfully changing your mind when new information shows up.Why being "belligerently resolute" is not a virtue but is, in fact, an inability to grow.The crucial value of perspective and why an inability to take in new information in any area of your life stops growth.How to apply this fluidity to big life decisions, like a new career track or a move, to avoid a larger long-term disaster.Our recommendation for the psychological thriller After the Hunt, and how it forces you to consider a character's "myriad perspectives".If you’re holding onto a decision or path simply because you think you’re "locked in," this episode is for you. We’re giving you permission to embrace the clarity that comes from changing your mind.Onward and Inward,Caanan and Kent

We’re back with another episode of Why Are We Still Doing That? This week, we’re flipping the script to ask: Why are we still not recycling the things that actually work for us?For a culture obsessed with constant reinvention, there’s a strange, collective pressure to always move on to the next thing, as if new is always better. We're conditioned to believe that you don't get credit for consistency and that true success lies in the next big innovation.The truth is, when a habit, routine, or approach delivers, it deserves another round. It deserves to be recycled and repeated with purpose. That's not boring—that’s how you build momentum, free up mental space, and create the stable foundation needed to support all the exciting changes you do want to make.In this episode, we unpack the social pressure to constantly reinvent and make the case for proudly leaning into what works.You’ll hear:Kent's "mind share" on the vital and necessary conversation around no-contact relationships, especially as the holidays approach, and why you shouldn't confuse real needs with immature behavior.Why "recycling" what works – like your fitness routine, core diet, or schedule – is the secret weapon that frees up the mental space for innovation.The funny paradox of being "The Change Guys" who also crave a deliberate, fulfilling core routine and how that balance fuels our life.The social commodity problem: Why there's no social currency in consistency and how social media performance encourages you to constantly chase the next big thing.A funny travel story about why we finally leaned into "basic" popular destinations (like Italy and Hawaii) and discovered that they are popular for a reason.How this mindset applies to everything from your daily schedule to large-scale infrastructure.Our simple, actionable tip for identifying and leaning into the routines that "fill you up and free you up."If you’re feeling the pressure to blow up the good things in your life just to "shake things up," this episode is your permission to proudly stick with what delivers.Onward + Inward,Kent and Caanan

We’re back with another episode of Why Are We Still Doing That? – and this week, we’re asking a question that comes up every year as the calendar winds down: Why are we still waiting for New Year’s resolutions?For a culture obsessed with grit, commitment, and self-improvement, we have a strange, collective habit of putting off the very things we know would benefit us right now.If you’re serious about making a change, real progress starts the moment you decide it’s worthwhile, not on some arbitrary date determined by the Earth’s orbit. Yet, we let the concept of "New Year, New You" become a massive pressure cooker, leading to analysis paralysis and the fear that if we don't succeed perfectly, we’ve failed (or worse, lied to ourselves).In this episode, we unpack why waiting is just a delay tactic and make the case for a lighter, more fluid, and immediately satisfying approach to change.You’ll hear:Kent's "mind share" on the current national increase in anger and how to choose to be a positive force in the world (hint: it's not toxic positivity).Why waiting for a New Year's resolution is often just a form of procrastination and a tool for delaying change you fear.The damaging idea that if you don't follow through on a plan exactly as you intended, you've lied to yourself – and why that mindset guarantees failure.Why change should be fluid and fun, allowing you to "dabble," iterate, and test-and-learn without committing to a four-year plan.The crucial value of knowing your personality type to determine your most optimal approach to change.A brief musing on the power of upbeat music and a look at our favorite end-of-year books that are heavy on topic but essential reads.If you’re holding onto something you know you want to start, but you’re waiting for January 1st, this episode is for you. We’re giving you permission to stop waiting and start moving.Onward and Inward,Caanan and Kent

We’re back with another episode of Why Are We Still Doing That?—and this week, right before the stress of the holidays hits, we're asking a fundamental question: Why are we staying miserable?We've spent the last few weeks talking about quitting and staying loyal to things that don't serve us , but now it’s time to focus on your absolute non-negotiable right to protect your own peace. We’re done with passive misery and letting external forces dictate our mood and steal our joy.This episode is all about diving into the tools you need to build resilience, choose fulfillment, and finally, confidently say yes to what serves you and no to what doesn't.In this episode, we unpack why we constantly let external forces steal our joy and what happens when you decide to take control of your experience by "curating your life".You'll hear:The damaging effects of the platitudinal old-school message that you "owe" family everything and must "make the holidays work".The concept of curating your life—looking at your time and energy as an art exhibit where you are the selective curator.Tools rooted in positive psychology that help you flourish, including how to re-work your sense of obligation and experience more positive emotions.All that, along with the breaking news that we're claiming the title of "Joyologists" (no, not really) and our suggestion for a worthwhile practice to start this holiday season: a gratitude journal.If you're dreading the holidays, or if you're constantly letting situations or people steal your peace, you'll want to give this listen. We want you to set yourself up for a better holiday season and a better year ahead.Onward & Inward,Caanan and Kent

We’re back with another episode of Why Are We Still Doing That? — and this week, we’re talking about something that makes people squirm, triggers collective pearl-clutching, and guarantees at least one relative whispering, “But what will people think?”We’re talking about quitting.For a culture obsessed with grit, commitment, and “never give up,” quitting has been framed as a moral failing instead of what it often is: a brave, protective, and self-honoring choice. We’re conditioned to push through, stay loyal, and tolerate things that make our lives smaller — even when we know something is no longer healthy or aligned.In this episode, we unpack the real reasons we avoid quitting and what opens up when we finally do.You’ll hear: • The cultural programming that makes quitting feel like failure — and why that script is overdue for a rewrite. • The identity shame loop that keeps people stuck in jobs, relationships, and roles long past their expiration dates. • Why other people panic when you choose yourself — and how your quitting often exposes where they feel trapped. • A pivotal story from Kent’s early career that shaped our entire No Vacation Required philosophy around agency, alignment, and not waiting for permission.All that, along with a brief musing on “cozy season” and something less cozy – ICE using Taylor Swift’s music on TikTok and the surprising silence from her normally hyper-responsive team. Like, what’s going on there?If you’re feeling stuck in something that no longer serves you – or deserves you – you’ll want to give this listen because we’re giving you permission to quit that nonsense.Onward & Inward,Caanan and Kent

We’re back with another episode of Why Are We Still Doing That? — and this week, we’re talking about something we’ve all been conditioned to do: staying loyal to things that no longer serve or deserve us.From jobs that drain us to loyalty programs that stopped rewarding us years ago, we have a knack for sticking around out of habit – or fear. Fear of missing out, fear of change, fear of uncertainty. But that kind of blind loyalty keeps us stuck, limits our options, and quietly steals resources (time, money, energy) we could be using to pursue what actually matters.In this episode, we unpack what’s really behind our tendency to “stay loyal,” even when it’s not serving us — and what it looks like go “free agent.”.You’ll hear:How loyalty programs have diminishing returns and greater demandsHow companies use identity and belonging to keep us tied to systems that don’t have our best interests at heartWhy fear — not commitment — is often the real reason we stay putHow mindfulness and regular “life audits” can help you spot where your loyalty has turned into autopilotAnd in this week’s Mindshare, we’re talking about gratitude — and how small acts of appreciation can cut through cynicism and help build a more empathetic world, especially in tough times.This episode is your reminder that loyalty is beautiful when it’s earned, but limiting when it’s automatic.Choose what (and who) you give your loyalty to — and make sure it’s giving something meaningful back.Onward & Inward,Kent and Caanan

We’re back with another episode of Why Are We Still Doing That? This week, we’re taking on something we’re all guilty of – assuming we know what someone else is thinking instead of just asking.You know what we’re talking about. That reflex to fill in the blanks, interpret a tone, or spin a whole story from a single look. It’s become such a normalized part of communication that we rarely notice when we’re doing it. But all that guessing creates unnecessary drama, blocks real understanding, and keeps us from the very thing we want most: connection.In this episode, we talk about why mind reading persists (and how much of it comes down to fear of rejection, confrontation, or vulnerability).You’ll hear:Why we developed TwoFinder to help people in all kinds of relationships stop assuming and start understanding.How learning about each other’s personalities changed our own relationship – and dramatically reduced the number of chair-related misunderstandings.Why it’s worth asking instead of assuming, even when it feels uncomfortable.And in this week’s Mindshare, we’re talking about off-cycle elections and vote-by-mail, something every citizen in the US should have access to.This episode is your reminder that connection starts with curiosity — and that asking beats assuming every single time.Onward & Inward,Caanan and Kent

We’re back with another episode of Why Are We Still Doing That? This week, we’re taking on something we all do more than we’d like to admit: naysaying.You know what we’re talking about — that knee-jerk reaction to critique, compare, or center ourselves in someone else’s story. It’s become such a common part of the way we engage with the world that we hardly notice it anymore. But it’s bad, literally bad, for our health and it keeps us from connecting, learning, and growing.In this episode, we talk about how naysaying shows up in our own lives (including a very real listener email).You’ll hear:Why habitual naysaying is usually more about fear or insecurity than insightHow to stop centering yourself in every conversation (yes, even in bean soup and chocolate chip cookie recipes)What positive psychology says about breaking the cycle and finding more joyAnd in this week’s Mindshare, we’re talking (briefly, we promise) about the new iPhone 17 Pro and how gorgeous Seattle is in October.This episode is a nudge to notice when we’re slipping into criticism and to remember that encouragement, curiosity, and compassion are better for everyone.Onward & Inward,Kent and Caanan

We’re back with another episode of Why Are We Still Doing That? This time, we’re asking a question that’s surprisingly hard to talk about: Why are we still ashamed of building the life we actually want?In this episode, we get real about what it feels like to live – and publicly own – a life that’s been designed with intention. From our early marathon-training conversations that sparked the No Vacation Required philosophy to the curious reactions we still get when people learn we spend nearly all of our time together, we’re unpacking the cultural conditioning that makes fulfillment feel like something we have to defend.You’ll hear:Why it can feel awkward to admit you’re happyHow social conditioning keeps us apologizing for joy and fulfillment (if it doesn’t keep us from pursuing those things first)What a poolside conversation revealed about how people measure worthPlus, in this week’s Mindshare, we talk about our recent Disneyland trip—what it taught us about nostalgia, value, and why it’s time to rethink what we’re buying into.This episode is all about removing the shame from fulfillment and celebrating the courage it takes to build and broadcast the life you truly want.Onward & Inward,Caanan and Kent

We’re back with another episode of Why Are We Still Doing That? — and this time, we’re asking the question that’s been on our minds lately: Why are we still sitting things out when everything is changing?In this episode, which marks a bit of a relaunch with a whole new format, we take a hard look at how much the world has shifted — politically, culturally, and personally — and explore what it means to really show up right now. From volunteering experiences that reminded us how much good is still happening to a tough decision to leave Substack behind, we talk about what it looks like to live our No Vacation Required philosophy in real time.You’ll hear:Why sitting things out isn’t an option in times of rapid changeHow we decided to step away from Substack — and what that revealed about our valuesHow a commercial we filmed for the State of Washington last year provided the clarity we were seeking nowHow our CHANGE framework helps us (and our clients) navigate uncertain timesPlus, we share the mindset shift that’s helping us — and hopefully you — redefine what it means to build a life you don’t need a break from in a world that’s anything but steady.Onward & Inward,Kent and Caanan