When you’re smart, capable, and still not seeing the traction you want… It’s easy to start second-guessing yourself. That’s where Gabby was when we started coaching. She wanted change, but didn’t know how to make it happen without burning out. Together, we built a plan that matched her pace, strengths, and priorities. The result? Less spinning, more strategy. In her words: “Once I had a plan, it felt lighter. I stopped overthinking every move and started following the process.” Six months later, she had: → Landed a role at a Big Four consulting firm → Negotiated pay aligned with her experience → Built the confidence to communicate her impact with clarity This isn’t about hustle. It’s about knowing your value, and building a process that reflects it.
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Casey Handmer on Cheeky Pint: “One of the mistakes I’ve seen a lot of first-time founders make is they assume that an hour of coaching is as good as an hour of firing. Nothing is worse for your career than sitting in a job failing for you because you don’t have the guts to quit and your manager won’t fire you.” Watch the full conversation: https://lnkd.in/gEUKuJZU.
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The number 1 mistake coaches and consultants make when trying to attract clients is marketing to everyone instead of niching down and communicating a clear transformation. A coach once told me, “𝘐 𝘩𝘦𝘭𝘱 𝘱𝘦𝘰𝘱𝘭𝘦 𝘭𝘪𝘷𝘦 𝘵𝘩𝘦𝘪𝘳 𝘣𝘦𝘴𝘵 𝘭𝘪𝘧𝘦.” I smiled and asked, “Which people?” She paused. That pause said everything. She was passionate and talented, but her message was lost in the noise. Her posts were inspiring, but they didn’t speak to anyone in particular. Her content was being seen, but not converting. We worked together to refine her message. She decided to focus on corporate professionals who felt stuck and wanted to transition into purposeful coaching careers. Within a month, her content shifted from vague inspiration to laser-focused value. Suddenly, her inbox wasn’t empty anymore. People started saying, “𝘐𝘵 𝘧𝘦𝘦𝘭𝘴 𝘭𝘪𝘬𝘦 𝘺𝘰𝘶’𝘳𝘦 𝘵𝘢𝘭𝘬𝘪𝘯𝘨 𝘥𝘪𝘳𝘦𝘤𝘵𝘭𝘺 𝘵𝘰 𝘮𝘦.” That’s the power of clarity. When you speak to everyone, you connect with no one. When you speak to someone, you attract the right ones. So ask yourself 𝙒𝙝𝙤 𝙖𝙧𝙚 𝙮𝙤𝙪 𝙧𝙚𝙖𝙡𝙡𝙮 𝙝𝙚𝙧𝙚 𝙩𝙤 𝙝𝙚𝙡𝙥, 𝙖𝙣𝙙 𝙬𝙝𝙖𝙩 𝙩𝙧𝙖𝙣𝙨𝙛𝙤𝙧𝙢𝙖𝙩𝙞𝙤𝙣 𝙙𝙤 𝙮𝙤𝙪 𝙬𝙖𝙣𝙩 𝙩𝙤 𝙘𝙧𝙚𝙖𝙩𝙚?
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𝐈 𝐭𝐡𝐨𝐮𝐠𝐡𝐭 𝐩𝐚𝐬𝐬𝐢𝐨𝐧 𝐰𝐨𝐮𝐥𝐝 𝐛𝐞 𝐞𝐧𝐨𝐮𝐠𝐡. 𝐈 𝐰𝐚𝐬 𝐰𝐫𝐨𝐧𝐠. A few years ago, I was pouring my heart into coaching — Late nights, endless prep, always giving 100%. But I wasn’t seeing growth. One mentor told me something that stuck forever: “Kapil, passion without structure is just noise.” He was right. I had the passion… but I was missing the pillars. Here’s what I learned (and what I now teach my clients): 👇 1️⃣ A Compelling Vision – You need a North Star. Something that pulls you forward, not just keeps you busy. 2️⃣ Energetic Action – Strategy matters, but energy wins. You can’t build momentum without consistent motion. 3️⃣ 4 Key Relationships – A trusted mentor, supportive family & friends, a growth-minded peer group, and a star team that believes in your mission. 4️⃣ Resilience – Because the journey will test your belief before it rewards your effort. When I aligned these with my passion, things changed fast. Clients grew. My purpose deepened. Momentum returned. Remember, when you combine these four with your Passion, you stop being a dabbler... You become an Executor: someone who finishes what they start and inspires others to move. 💡 Question for you: Which of these 4 do you feel you need to strengthen most right now?
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“I know what to do… so why would I need a coach?” Most of the business founders and leaders I speak with already know exactly what to do. ✅ They’ve built something from nothing. ✅ They’ve made bold decisions. ✅ They’ve taken risks most people never will. On top of that they’re driven, smart and not short on ideas. But here’s the part most people don’t say: Knowing what to do doesn’t mean it’s easy to do! Because… We all get in our own way sometimes. We hesitate. We overthink. We second-guess ourselves. We carry too much, struggle when others around us aren’t up to our speed. And when things feel like they are getting to much, we just try to push through and ignore. That’s why people work with me, not because they’re lost or incapable, but because having someone in your corner gives you space to: → Slow down and get clear. → See things you might not have noticed on your own. → Talk openly in a space where you can actually be honest and feel heard. → Stay grounded when things feel uncertain or chaotic. → Turn clarity into focused action. It’s never about being told what to do, it’s about having someone who actual listens, who supports, encourages and challenges you when required. If this post speaks to you, reach out and let’s talk!
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I’ve sat in rooms where I felt like an imposter. Excellent post by Dr. Heather Maietta - Coach for Career Coaches. Follow her for career growth advice. Those were the rooms that expanded me most. Most of us spend our careers trying to prove we belong. But real growth happens when we barely feel like we do. Being the least knowledgeable person in the room isn’t a deficit. It’s a developmental advantage. It means you’ve stepped beyond your current ceiling. Every field has its own version of the best classroom: For coaches: + supervision groups that challenge your methods. For leaders: + strategy sessions that move faster than your instincts. For professionals: + circles where others have already solved the problems you’re still learning to name. The higher you rise, the fewer of these rooms you’ll naturally find. Which means you have to intentionally seek them out. When everyone around you stretches your thinking, You’re not the weakest link. You’re the fastest learner. When’s the last time you intentionally joined a room that made you feel like a beginner again? ⬇️ _____ ♻️ Share to encourage taking chances at work. ➕ Don’t miss out — follow Dapper Dog now.
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Why you still feel stuck as 🧠ADHD founder and exec. (It’s not what you think.) You’ve probably tried every productivity hack, focus tool, and goal-setting system. -You’ve read the books -Tried the “ultimate” techniques. -Maybe even invested in high-end business coaching programs. -And if you are just a bit like me you even know your Enneagram number. (I'm a 9) Yet, despite all that effort, you’re still spinning your wheels. Here’s the thing that might surprise you: Your frustration isn’t just about: A lack of focus. Poor motivation. Not having the “right” system. The real issue is not about more hacks or tools. 𝗜𝘁’𝘀 𝗮𝗯𝗼𝘂𝘁 𝗔𝗟𝗜𝗚𝗡𝗠𝗘𝗡𝗧. Procrastination? - It’s not just a “focus problem.” It’s an alignment problem with the way your brain works. Clarity? - It’s not something you “find.” It’s something you build by understanding your nervous system, your unique strengths, and the stories you’re still carrying. It’s not about just “pushing through.” It’s about operating from a deep understanding of what lights you up and aligns with your core values and strengths. It’s about the inner work to untangle the narratives holding you back. Stop trying to force yourself into systems that don’t work for you. Start asking: 1. How many of my goals are fueled by “shoulds” instead of what genuinely matters to me? 2. What narratives am I carrying that are driving my actions? The answer isn’t more effort. It’s alignment. And that changes everything. What’s one thing you could realign today?
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Confidence isn’t something you wait for — it’s something you build. This week, Ben and Adam dive into 5 real ways to develop unshakable confidence — no fluff, no hype, just real strategy. You’ll learn: - Why action always comes before confidence - How to build trust in yourself through daily wins - The role of mentors and how to borrow belief - How to flip the fear of failure into fuel for momentum - Why consistency creates identity (and identity drives everything)
Season 2, Episode 43: Self-Belief Is Built, Not Given
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A lot of founders I meet with are lonely. They're exceptional at what they do and it comes at a cost. Friends and family are proud but don't really get it. Their team isn't fully honest with them. It's the same whether they run a boutique firm or a legacy business. Their problem isn't marketing or business development. It's trust. When the business is an extension of your life's work, the lines blur. Personal dilemmas and work problems that keep you up at night are one and the same. Every decision feels personal because it is. Usually, they don't need a coach, consultant, or framework. Just someone to listen. Someone they can trust to think through the big and small things with without judgement or agenda. Someone that will help them see what they're missing when no one else will speak up. Someone that can think with them, not at them. Someone that can keep up and doesn't need to be spoon fed. When the stakes are that high, clarity isn’t optional. It’s the difference between survival and succession.
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When I first started feeling overwhelmed as a law firm owner, I thought something was wrong with me. Maybe I wasn’t cut out for leadership. Maybe I lacked the right skills. Maybe everyone else had it figured out. Then I had a conversation with another female founder that changed everything. “The job of a CEO is to deal with the hard problems, not the easy ones,” she said. “That’s literally what you’re being paid to do.” It hit me like a revelation. The easy decisions never make it to my desk — my team handles those. What lands in my lap are the complex challenges: - The difficult personnel issues - The strategic investment decisions - The ethical gray areas - The cash flow crunches This perspective completely changed how I view being overwhelmed. It’s not a sign of failure. It’s proof that I’m doing my job. Of course, that doesn’t mean I don’t need strategies to manage it. I’ve joined groups of other small firm founders who understand exactly what I’m facing. There’s something powerful about hearing “I’ve been there too” from someone who actually has. And I’ve learned to step away when I need to. Sometimes the best solution isn’t more thinking — it’s less. I’ll play tennis — the focus it requires clears my head. Or I’ll do something simple like organizing my space or folding laundry. Tasks with clear beginnings and ends. Ironically, that’s when the best solutions usually appear. The truth is, building something meaningful will always include moments of overwhelm. The goal isn’t to eliminate them — it’s to change your relationship with them. To understand that the hardest moments aren’t proof of weakness. They’re proof of leadership. If you’re a founder or leader — what helps you manage those “I can’t do this” days?
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Patterns show up fast in coaching rooms. Whether it’s the writer who can’t choose between five ideas, the leader who keeps comparing timelines, or the producer afraid to hand things over. The root is rarely laziness or lack of talent. It’s usually a creative block hiding in plain sight. In this week's Freshly Reframed, our in-house coach, Ismat Abidi, shares five blocks that come up most often in her coaching work, and what they usually signal underneath. Based on real-life stories from over 200 hours of coaching creatives, executives, CEOs, law firm partners, founders and a stereotyped finance bro who want to open a bakery. If one, or a blend of these sounds familiar, you can learn more about how we support headspace blocks through our Coaching framework on our website. #freshlygroundstories #creativecoach #creativebusiness #founderstory #storytelling
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