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PODCAST

Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs

Plan Like a Boss is your go-to podcast for mastering planning, productivity, and strategy as a solo or small business entrepreneur. Each week, you"ll get practical tips and real-life insights to help you set smart goals, manage your time, and grow a business that actually fits your life.

business entrepreneurship

All Episodes

33:51

The Pitching Playbook: Human Connection in a World of...

Plan Like A Boss | Planning, Productivity, and... ·

2025/09/30

Want to grow your visibility and establish yourself as an authority in your industry? Podcast guesting might just be your most powerful untapped strategy. Kimberly Roy, founder of Pitch With Kim, shares her remarkable journey from a 20-year career in corporate banking to becoming a podcast pitching expert. After using podcasting as a healing outlet during a personal trauma, Kim discovered her passion for helping entrepreneurs amplify their voices through strategic media appearances. The con...

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13:38

From Hidden to Visible: 5 Proven Strategies to Get...

Plan Like A Boss | Planning, Productivity, and... ·

2025/09/23

Have you ever felt like you're shouting into the void with your business? You know your offers could truly transform lives, but somehow, the right people just aren't finding you. The harsh truth is that without strategic visibility, even the most brilliant business will stay stuck in obscurity. Drawing from my own journey that began with a moment of panic when my music teaching career was threatened, I share the exact visibility strategies that not only saved my business but transformed it i...

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8:58

Your Schedule is Broken, Not Your Ambition

Plan Like A Boss | Planning, Productivity, and... ·

2025/09/16

Join My Planning Workshop! Ever found yourself with all the schedule flexibility in the world, yet somehow working longer hours and feeling more stressed than when you had a traditional job? You're not alone, and it's not your fault – it's a common entrepreneur trap that comes from misunderstanding what true time freedom really means. Freedom without structure is just chaos. When I first started my business, I thought working whenever I wanted would be liberating. Instead, I ended up worki...

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11:32

Stop Spreading Yourself Thin: The Smart...

Plan Like A Boss | Planning, Productivity, and... ·

2025/09/09

Join my workshop "Plan Your Quarter with Confidence" on September 20th Visibility is non-negotiable for business success, but you don't need to be everywhere online to be seen by potential clients. Smart entrepreneurs choose platforms strategically, focusing on consistent quality content rather than spreading themselves too thin across multiple channels. • The biggest mistake entrepreneurs make is trying to be everywhere at once, leading to burnout and inconsistency • Inconsistent visibility...

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11:14

From Chaos to Clarity: How Simple Systems Save...

Plan Like A Boss | Planning, Productivity, and... ·

2025/09/02

Systems are containers for your chaos, not complicated software or corporate manuals, but repeatable ways of doing things that free up mental space and reduce overwhelm. They function like bowling bumpers, keeping you on track even when you're not at your best, saving time by preventing reinvention and reducing decision fatigue. • A client and money system tracks leads, manages onboarding, handles invoicing, and organizes contracts • A content and marketing system includes a content calendar...

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8:36

Setting yourself up for success means planning for...

Plan Like A Boss | Planning, Productivity, and... ·

2025/08/26

The signature quarterly planning method revealed in this episode delivers big results without burnout by focusing on planning for your actual capacity, not just your calendar. Setting too many goals splits your time, energy, and focus, resulting in minimal progress that feels unsatisfying and creates a constant feeling of being behind. • Set no more than three goals total for the quarter • Plan around the time you actually have, not the time you wish you had • Create a "future parking lot" t...

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11:21

What Happens When You Disappear from Instagram for...

Plan Like A Boss | Planning, Productivity, and... ·

2025/08/19

I disappeared from Instagram for three months during breast cancer treatment, and nobody even noticed. This unexpected experience taught me valuable lessons about building a sustainable business that doesn't require constant visibility to remain profitable. • Social media is a tool, not a comprehensive business strategy • My business continued running because of searchable content and established systems • During chemotherapy, my capacity dropped to zero, forcing me to simply stop posting • ...

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17:19

Three Priorities, Five Steps, Zero Meltdowns

Plan Like A Boss | Planning, Productivity, and... ·

2025/08/12

I share my detailed weekly planning ritual that keeps my business running smoothly and prevents my brain from melting into a puddle of chaos when juggling content, client work, admin tasks, and life commitments. The Planner I Use: https://amzn.to/3H7Wz9j *This is an affiliate link that helps support the podcast • Weekly planning helps prioritize what matters in both business and life • The ritual starts with reviewing the previous week without judgment, looking at what worked and what did...

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12:32

Planning Like a CEO (Even If You’re a Team of One)

Plan Like A Boss | Planning, Productivity, and... ·

2025/08/06

Grab your seat today - Plan Your Quarter With Confidence We explore how solopreneurs can shift from constant hustle mode to strategic CEO thinking, even when working as a team of one. By implementing three practical CEO planning habits, you can take back control and lead your business instead of letting it run you. • Most solopreneurs lack strategy rather than hustle • Planning like a CEO means creating time to look ahead, using data for decisions, focusing on impact over busyness, and tre...

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10:35

The Truth About Solopreneurship (and Why No One Talks...

Plan Like A Boss | Planning, Productivity, and... ·

2025/08/06

Is solopreneurship really the dream everyone says it is? In this honest and unfiltered first episode of Plan Like a Boss, I’m sharing the truth about what it’s really like to run a business solo—the parts no one posts about on Instagram. From burnout and decision fatigue to the mental load of doing it all yourself, we’re pulling back the curtain on the hidden challenges of solopreneurship. Whether you're a creative entrepreneur, coach, or service provider trying to stay focused without a team...

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30 results

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