<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd"><channel><title><![CDATA[The Playbook Podcast]]></title><description><![CDATA[Hosted by Dakota Kate Isaacs, brand builder and founder of The Big Sister Playbook, this podcast offers behind-closed-doors conversations with the expanders shaping culture today: founders, creators, healers, and modern leaders whose stories reveal what’s possible. Through intimate interviews and practical frameworks, Dakota helps listeners design lives that feel as good as they look. <br/><br/><a href="https://bigsisterplaybook.substack.com?utm_medium=podcast">bigsisterplaybook.substack.com</a>]]></description><link>https://bigsisterplaybook.substack.com/podcast</link><generator>Substack</generator><lastBuildDate>Sat, 20 Jun 2026 07:33:50 GMT</lastBuildDate><atom:link href="https://api.substack.com/feed/podcast/6154813.rss" rel="self" type="application/rss+xml"/><author><![CDATA[Dakota Kate Isaacs | The Big Sister Playbook ]]></author><copyright><![CDATA[Dakota Kate Isaacs]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[bigsisterplaybook@substack.com]]></webMaster><itunes:new-feed-url>https://api.substack.com/feed/podcast/6154813.rss</itunes:new-feed-url><itunes:author>Dakota Kate Isaacs | The Big Sister Playbook </itunes:author><itunes:subtitle>The big-sister playbook for ambitious women building careers and lives they love. I learned the hard way, and now I’m giving you the shortcuts.</itunes:subtitle><itunes:type>episodic</itunes:type><itunes:owner><itunes:name>Dakota Kate Isaacs | The Big Sister Playbook </itunes:name><itunes:email>bigsisterplaybook@substack.com</itunes:email></itunes:owner><itunes:explicit>No</itunes:explicit><itunes:category text="Education"><itunes:category text="Self-Improvement"/></itunes:category><itunes:category text="Business"><itunes:category text="Careers"/></itunes:category><itunes:image href="https://substackcdn.com/feed/podcast/6154813/dc9b450c9164e1d04825fa6a75597017.jpg"/><item><title><![CDATA[💌 07: The Someday Syndrome]]></title><description><![CDATA[<p><p><em>The Big Sister Playbook</em> drops every Monday. To get on the list for next week, pop your email below 💌 </p></p><p>I had two unread texts on my phone that night.</p><p>The first was the usual <em>Welcome to Canada</em> message, the kind you barely read, reminding you that data rates apply. The second was from a number I knew by heart.</p><p>I had just landed in Toronto for a business trip. The air in the jet bridge was thick with metal and humidity. That faint, recycled scent of rain-soaked tarmac. The fluorescent lights hummed overhead, becoming too bright all of a sudden, almost blurring the words on the screen.</p><p>My eyes scanned the letters — back, back and forth, back and forth — trying to make it make sense. Each reread was a small denial, a desperate attempt to find the part I’d misread. <em>Was this a joke?</em> As if I moved quickly enough, the words might rearrange themselves into saying something that made sense. As if the motion could rewrite them somehow. They didn’t. They just stayed there. </p><p><strong>Final.</strong> </p><p>The nausea came first. That wave that starts in your stomach and rises like an elevator to your throat, the body’s quiet rebellion against what the mind can’t yet process. I read it again. And then again. I felt sick. My mind scrolled through the past decade, searching for proof I hadn’t imagined the whole thing. Then came the hollowness — sudden, all at once — like getting the wind knocked out of you, that helpless gasp where your body forgets how to breathe.</p><p>I used my hand to steady myself against the jet bridge and turned the screen toward my then CEO. He read it, blinked, then grabbed my arm with a look of disbelief and tenderness I’ll never forget.</p><p>“<em>We’re going drinking,</em>” he declared softly — not as a suggestion, but as mercy.</p><p>His response made it real. Now that someone else had seen it, there was no unseeing. I blinked, held my eyes closed for a moment. “<em>Please,</em>” was all I could manage to mutter, an almost silent acquiescence. A plea for what, I wasn’t even sure. A vodka martini, yes. But maybe for the nausea to pass. Maybe for the world to stop spinning. Maybe just to not throw up in front of all these people waiting for their bags.</p><p>Six weeks earlier, he’d called to say he needed space before we got engaged, that he’d call when he was ready to get married. I believed him, in that weary way you believe someone you’ve loved all your life. I rolled my eyes, tossed his house keys in the trash under my desk, told myself I was done. I’d said that before too.</p><p>But standing on the jet bridge at Pearson International that night, I got another call. Not from him, but from reality. A text saying he’d met someone. That he was “conflicted and overwhelmed” about how to tell me he was planning to propose.</p><p>To her.</p><p>The Psychology of Someday</p><p>He was the constant — if I was in a ditch, he’d be the one call. He knew me before I knew myself, and I saw him in ways no one else ever would. That kind of loyalty builds quietly over time. We were stitched together by growing pains and history, by something that always felt bigger than either of us.</p><p>But every time he pulled away, I kept going. </p><p>Because life doesn’t stop just because someone else isn’t ready to live it with you. So forward I went — into my purpose, my work, toward the person I wanted to be. I laughed, I danced on tables, I dated great guys, I learned to show up for myself. I said yes to the ones who actually wanted me, even while part of me still held space for the one who didn’t. </p><p>He always came back. I could never say when, only that he would. But it was the people who stayed that carried me forward, the ones who never had to decide were the ones who always did. <strong>But that’s the thing about life: no one can live it for you.</strong></p><p>Somewhere in the quiet corners of my mind, I kept a small light on for him, a pilot flame I couldn’t quite extinguish. Not that he particularly deserved it, but because I knew what he was capable of. The brilliance. There were glimpses — brief, blinding — of who I knew he could be. The version that appeared in flashes between the leaving. I saw him clearly in those moments, maybe more clearly than he saw himself. Maybe that’s what made it hardest: I loved his potential long after he stopped living up to it.</p><p>It wasn’t just conditioning, it was projection. We don’t treat people as good as they are; we treat them as good as <em>we</em> are. I was loyal to him in ways I never was to myself. I excused bad behavior. It was the ache of believing in someone more than they ever did.</p><p>Psychologists call this <em>future projection bias</em>, the tendency to invest in what someone <em>might</em> become instead of what they consistently show you. It’s how <em>cognitive dissonance</em> settles in: the mind can’t reconcile the two realities so it creates a narrative that makes both feel true.</p><p>It wasn’t hope; it was habit. The chaos became its own kind of comfort — a rhythm my nervous system learned to crave. </p><p>It wasn’t that I couldn’t let go; it was that every return came with a story — the grand gesture, the sweeping promise, the déjà vu of devotion. Each one made me think I could finally exhale, but the relief was always temporary. There was always another “not yet,” another pseudo-intellectual rationale for why timing, or logic, or fear had once again delayed the promise of being chosen.</p><p>The thing about <em>someday</em> is that it’s a trap. It feeds on your empathy, your optimism, your willingness to believe. It’s where your peace gets put on pause, waiting for someone else to be ready.</p><p>The Reframe</p><p>When you love someone who doesn’t choose you fully, the most radical thing in the world you can do is simple: <strong>stop trying to convince them</strong>. </p><p>So I started studying the pattern — not his, but mine. Because that’s who this story is really about. Why I stayed, what I believed, and how I could finally choose differently.</p><p><p>“Someone can be madly in love with you and still not be ready. They can love you in a way you have never been loved and still not join you on the bridge. And whatever their reasons you must leave. Because you never ever have to inspire anyone to meet you on the bridge. You never ever have to convince someone to do the work to be ready. There is more extraordinary love, more love that you have never seen, out here in this wide and wild universe. And there is the love that will be ready.” — <em>Nayyirah Waheed</em></p></p><p>The kind of love that is meant for you doesn’t come with conditions. It doesn’t ask you to wait, disappear to compare options, or reach for you again only after learning the difference between attention and depth. </p><p><strong>It doesn’t shrink your world, it expands it.</strong> It meets you on the bridge, the first time. </p><p>How to Break the Someday Cycle</p><p><strong>1. Stop Time Traveling</strong></p><p>Every time you replay the past or pre-live the future, you abandon the present. The mind loves to live in the <em>what ifs</em>, because they keep the fantasy alive. When you catch yourself imagining how things <em>could</em> be, say quietly:</p><p>“That’s not happening right now.” Then ask: “What <em>is</em> happening right now?”</p><p>Naming the truth interrupts the projection. Reality, even when painful, is where your power lives. Something my mom regularly says is that our thoughts are just that, <em>thoughts</em>. They aren’t reality. </p><p><strong>2. Replace Hope with Data</strong></p><p>When you love someone’s <em>potential</em>, you become a master of selective memory, highlighting the moments that validate the fantasy and excusing the ones that contradict it. To break that loop, switch from emotion to evidence:</p><p>* What have their <em>consistent actions</em> shown you?</p><p>* What happens when you state your needs clearly?</p><p>* Do words and follow-through align?</p><p>Write it down if you need to. Seeing patterns on paper replaces “maybe someday” with measurable truth, and truth is what sets you free. But first it will really piss you off.</p><p><strong>3. Choose the Mirror, Not the Movie</strong></p><p>The movie is the fantasy, the beautiful storyline you’ve been directing in your head for years. The mirror is what’s actually in front of you. Stand in it.</p><p>“Who am I when I’m waiting?”“Who could I be if I stopped?”</p><p>The moment you shift your gaze from how<em> they </em>see you to how <em>you see yourself </em>is how you break the cycle<em>. </em>That’s where “someday” ends, and self-trust begins.</p><p>You are not on this Earth to be someone’s <em>sometime</em>. Not their pause between chapters, not their almost, not their “if only.” You are the whole story — not a subplot, not a placeholder. You’re not the “one day” or the “what if.” You’re the one. You’re the “of course.” You are not meant to be <em>almost</em>, or <em>almost enough. </em><strong>You are not the backup plan. You are the plan.</strong></p><p>If they need space to decide, you already have your answer. If it’s not a hell yes, it’s a no.</p><p>And that’s the only kind of yes worth waiting for.</p><p>As for me? Later that night in Toronto, I got my own proposal — from a man who didn’t hesitate and who never needed convincing. He asked me to run his North American business. Some questions come with rings, others come with raises.</p><p>💌 xo, dk</p><p><strong>P.S.</strong> One text ended a decade of faith… until six months later, when he looked at me and said the words we both knew he eventually would: it should’ve been me. But that’s a story for another time.</p> <br/><br/>Get full access to The Big Sister Playbook by DK at <a href="https://bigsisterplaybook.substack.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">bigsisterplaybook.substack.com/subscribe</a>]]></description><link>https://bigsisterplaybook.substack.com/p/07-the-someday-syndrome</link><guid isPermaLink="false">substack:post:176450616</guid><dc:creator><![CDATA[Dakota Kate Isaacs]]></dc:creator><pubDate>Mon, 20 Oct 2025 13:54:53 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/176450616/cf1bb7e325a71c5a8b8092e5cbe6653e.mp3" length="7577227" type="audio/mpeg"/><itunes:author>Dakota Kate Isaacs</itunes:author><itunes:explicit>No</itunes:explicit><itunes:duration>631</itunes:duration><itunes:image href="https://substackcdn.com/feed/podcast/6154813/post/176450616/fea6673416e045aacc6b1e5631ac3474.jpg"/></item></channel></rss>