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

Tonya
  • 5.0 (4)
  • Entrepreneurship

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.

  1. 5d ago

    How A Third-Generation Photographer Built A Gig-Economy Team

    In this episode of Plan Like a Boss, Tonya Lawson sits down with Lesle Lane, CEO of Studio 13, to talk about what it really takes to scale a creative business without burning out. Lesle is a third-generation photographer who stepped into her family business at a young age and quickly found herself navigating major industry disruption, including the transition from film to digital photography. She shares the story behind investing $200,000 in her first digital camera, modernizing a generational business, and eventually moving from an exhausting solopreneur model to a more flexible team of independent contractors. You’ll hear how Lesle built systems and standard operating procedures, delegated administrative work, and created more space to think strategically about the future of her company. She also explains why 1099 contractors helped her business scale more efficiently, how asking for feedback strengthened her sales process, and why relationships and warm introductions can be more powerful than cold outreach. Lesle also shares lessons from her years as a competitive ice skater, including discipline, resilience, handling rejection, and learning to seek constructive criticism instead of avoiding it. In this episode, you’ll learn: • How to scale a creative business without doing everything yourself • Why systems and delegation can reduce burnout • How independent contractors can create more flexibility • Why feedback is essential for improving your sales process • How mentors and allies outside your industry can help you make better decisions • Why relationships matter more than transactions • How stepping away from technology can create space for better strategic thinking Lesle’s challenge for small business owners is simple: take 30 minutes without technological input. Go for a walk, meditate, practice yoga, or simply give yourself quiet space to think. When you create room for original thought, you create room to lead your business instead of only reacting to it. Connect with Lesle Lane and Studio 13: https://www.studio13online.com/contact/ Subscribe to Plan Like a Boss wherever you listen to podcasts, and share this episode with a fellow entrepreneur who needs more space, better systems, and a smarter way to grow. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  2. Aug 6

    Human-First Marketing in the Age of AI with Jocelynn Flowers

    How do you grow your business with digital marketing and AI without losing the human connection behind your brand? In this episode of Plan Like a Boss, Tonya Lawson sits down with Jocelynn Flowers, founder and CEO of J. Flowers Marketing, to talk about human-first marketing, sustainable productivity, and creating content without burning yourself out. Jocelynn shares how she helps coaches, authors, and service-based business owners simplify their marketing, strengthen their messaging, and build systems that support both their business goals and their lifestyle. She explains how entrepreneurs can use AI and automation intentionally while keeping their own voice, personality, and relationships at the center of their brand. You’ll also hear practical strategies for managing your time and social media as a solopreneur, including Jocelynn’s color-coded calendar system, the importance of firm work boundaries, and why you do not need to post every day to build a strong online presence. In this episode, you’ll learn: • How to use AI without losing your authentic voice • Why human-first marketing creates stronger connections • How to choose one social media platform and stay consistent • Which engagement metrics matter most • How to create sustainable boundaries around your work • Why capturing ideas is often more important than creating on demand • How one idea can become multiple pieces of content • Why showing up before you feel ready can move your business forward Jocelynn’s biggest reminder is simple: you may not have a content creation problem—you may have a content capture problem. Write down your ideas when they come, return to them during your content-planning time, and turn each one into multiple ways to serve your audience. Get 30 days of social media prompts: https://jflowersdigital.com/30-day-social-media-prompts-299556 Connect with Jocelynn Flowers: Website: https://jflowersdigital.com Social Media: @JFlowersMarketing Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  3. Jul 30

    How to Turn Social Media Followers into Paying Customers (Without Chasing Virality)

    Posting consistently but still not seeing meaningful business growth from social media? The problem may not be how often you post. It may be what your content is designed to accomplish. In this episode of Plan Like a Boss, Tonya Lawson sits down with Jamie Coleman, digital marketing strategist and founder of By Jamie Social, to discuss how entrepreneurs and creators can move beyond surface-level metrics and build a social media strategy rooted in clarity, connection, and conversion. Jamie explains why authentic storytelling is outperforming constant selling, how to create content that remains valuable long after it is published, and why viral views do not always translate into loyal followers, leads, or customers. In this episode, you’ll learn:  • Why posting more is not always the answer  • How authentic storytelling builds trust  • The difference between attention and sustainable growth  • The three content categories every entrepreneur needs  • How to create evergreen social media content  • Why your hook, on-screen text, caption, and hashtags should align  • How to use hashtags for content categorization and search  • How to stay top of mind without constantly selling  • How to choose the right platform for your target audience  • What makes LinkedIn content different from TikTok and Instagram Whether you’re a solopreneur, creator, coach, or small-business owner, this conversation will help you create intentional content that supports your long-term business goals—not just your next viral moment. Connect with Jamie Coleman:  https://stan.store/byjamiesocial Chapters 0:00 - Why Social Media Isn’t Converting 2:39 - Authentic Storytelling Drives Growth 5:36 - Best Content Formats Today 9:35 - Authenticity Beats Performance 13:32 - Build Evergreen Content Assets 18:54 - Turn Followers Into Customers 21:57 - Three Essential Content Buckets 24:32 - Best Platform for Your Business 27:01 - LinkedIn Marketing for B2B Subscribe to Plan Like a Boss so you never miss an episode filled with actionable strategies for planning, marketing, and growing your business. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  4. Jul 23

    The Secret Sign That Shows You're Operating Beyond Your Business Capacity

    Somewhere along the way, online business turned into business all the time. How to find Gwen: https://peekadvisory.com/ In this episode, Gwen Taniguchi and Tonya Lawson explore how the shift to constant availability—especially during and after COVID—changed the way entrepreneurs work, communicate, and set boundaries. What once promised more freedom can quickly become an always-on cycle of notifications, expectations, and pressure. They unpack how resentment builds quietly when business begins taking over every part of life, why burnout is often a symptom of deeper boundary problems, and what it takes to create a business that supports your life instead of consuming it. In this episode, you’ll hear: • Why online business can become “business all the time” • How post-COVID work culture changed expectations around availability • The subtle ways resentment develops • Why constant access is not the same as sustainable growth • How to begin creating healthier rhythms and boundaries This conversation is for entrepreneurs, creators, and business owners who want to grow without sacrificing their energy, relationships, or well-being. The goal is not simply to build a successful business. It is to build one you can sustainably live with. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  5. Jul 16

    From Teacher to FinTech Founder: Sarah Potter Jeanneault’s Entrepreneurial Journey

    What does it really look like to use AI in your business without losing the human connection that makes your brand special? In this episode of Plan Like a Boss, Tonya Lawson sits down with Sarah Potter Jeanneault, a growth strategist, published author, FinTech founder, and entrepreneur with two successful exits. Sarah shares her journey from classroom teacher to business owner, corporate executive, and leader in the emerging human-plus-AI workplace. Together, they explore why the future of work is not human versus AI, but human plus AI. Sarah explains how entrepreneurs can use AI to support productivity, content creation, planning, and operations while still protecting their voice, judgment, customer relationships, and authenticity. The conversation also covers the realities of leaving a secure career, navigating the identity shift into entrepreneurship, documenting business systems, and building a company that can operate without everything depending on the founder. In this episode, you’ll learn:  • How to use AI without losing your authentic voice  • Why human connection remains a major competitive advantage  • Where solopreneurs can use AI most effectively  • How to explore entrepreneurship without making an impulsive leap  • Why documented systems make a business easier to grow, delegate, or sell  • What entrepreneurs can learn from teachers about leadership and communication Learn more about ProcedureFlow:  https://procedureflow.com/ Listen to The Why to The Way Podcast:  https://www.whytotheway.com/ Whether you are considering a career change, building a business, or trying to use AI more responsibly, this conversation will help you take your next step with greater clarity and confidence. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  6. Jul 9

    She Built A Company That Doesn't Need Her Anymore - with Jennifer Staats

    What does it really take to grow a business without working 80-hour weeks or becoming the bottleneck in every decision? In this episode of Plan Like a Boss, Tonya Lawson sits down with Jennifer Staats, Chief of Staff at SureSend and founder of Staats Solution, to talk about building the systems, workflows, and team structure every entrepreneur needs in order to scale sustainably. Jennifer shares her journey from real estate to operations, how she built and grew her own virtual operations management company, and the lessons she learned from hiring, delegating, documenting workflows, and eventually stepping back from the day-to-day. If you’re a solopreneur, service provider, real estate professional, or small business owner thinking about hiring a VA, assistant, or team member, this episode will help you avoid common mistakes and prepare your business before you bring someone on. In this conversation, you’ll learn: • Why many VA and assistant relationships fail • What a strong onboarding system actually looks like • Why hiring out of panic can create more problems • How to use checklists, templates, and CRMs to build better systems • How to stop being the bottleneck in your own business • What your business needs before you can step back from daily operations • How to build a business that supports the life you want Jennifer also shares why systems do not have to be complicated, how to start documenting your workflows even if you are still a team of one, and why sustainable growth begins with clarity around your goals, time, and capacity. Connect with Jennifer: Instagram: @JennifertheRealtor SureSend: https://suresend.ai Try SureSend free for 14 days: https://suresend.ai If this episode helped you, be sure to subscribe to Plan Like a Boss and leave a review so more entrepreneurs can learn how to build businesses with more structure, strategy, and freedom. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  7. Jul 2

    7 Ways to Make 7 Figures as a Thought Leader with Aurora Winter

    Learn how to build a thought leadership brand that AI can’t replace. 🔴 Get Aurora Winter’s free hardcover book, Turn Words Into Wealth: ➡️ https://turnwordsintowealth.com ⭐️ Learn more about launching as a thought leader with Aurora Winter ➡️ https://samepagepublishing.com  Connect with us! Instagram: ➡︎ @dr.tonyalawson  TikTok: ➡︎ @dr.tonyalawson  Website: ➡︎ https://tonyalawson.com/search/ Chapters:  0:00 - Meet Aurora Winter  1:32 - Million Dollar Message  5:25 - Storytelling Changes Value  9:42 - AI Branding Warning  12:00 - Four Human Superpowers  15:37 - Use AI Without Losing Voice  20:34 - The 3-Step Thought Leader System  25:18 - $250K Book Strategy  31:32 - Branding Lessons From Icons  36:49 - Best Advice For Entrepreneurs  39:08 - Where To Find Aurora  Connect with Aurora Winter: ➡︎ Free book: https://turnwordsintowealth.com ➡︎ Publishing and thought leadership: https://samepagepublishing.com #ThoughtLeadership #PersonalBranding #AIForEntrepreneurs #BookMarketing #Entrepreneurship In this episode of Plan Like a Boss, Tonya Lawson sits down with Aurora Winter, founder of Same Page Publishing and author of Turn Words Into Wealth, to talk about thought leadership, personal branding, storytelling, and how entrepreneurs can use AI without losing their unique voice. Aurora shares how one seven-word message generated $3 million in one week, why stories can dramatically increase perceived value, and how business owners can become the expert AI quotes instead of the one AI replaces. You’ll also hear her four human superpowers for standing out in the age of AI: story, smile, style, and Socrates. In this episode, you’ll learn:  • How to create a million dollar message  • Why storytelling matters in personal branding  • How to use AI as a tool without sounding generic  • Why books, podcasts, YouTube, and newsletters build authority  • How a short book helped Aurora generate $250,000 in 90 days  • What entrepreneurs can learn from Taylor Swift and Alex Hormozi Our mission here at Plan Like a Boss is to help entrepreneurs, creators, and business owners build smarter visibility systems, grow with strategy, and show up with confidence. Disclaimer: Some links may be affiliate or partner links, which means we may receive a small commission if you choose to purchase through them at no additional cost to you. This content is for educational purposes only. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  8. Jun 25

    He Managed $8 Million in Ads—Here's What Most Businesses Get Wrong

    Wondering if paid ads for small business are worth it? Jeremy Yang breaks down when to start and what to avoid. 🔴 Try Jeremy’s free ad calculators from Digital Goliath ➡️ https://digitalgoliath.com.au/google-ads-management-services/ ⭐️ Ready to build a business that feels calmer, clearer, and more profitable? ➡️ https://freevisibilitycall.com/ =========================== Connect with us! Website: https://tonyalawson.com/search Instagram: @dr.tonyalawson TikTok: @dr.tonyalawson LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/ Chapters 0:00 - Meet Jeremy Yang 0:56 - From Organic to Ads 2:41 - Are You Ready? 4:58 - Meta vs Google Ads 8:19 - Free Ad Calculators 10:40 - Biggest Ad Mistakes 12:01 - Realistic Ad Budgets 17:43 - Start With Video Ads 18:53 - Free vs Paid Offers 24:35 - Cost Per Conversion 34:15 - Connect With Jeremy #PaidAds #MetaAds #GoogleAds #SmallBusinessMarketing #PlanLikeABoss If you’ve been wondering whether paid ads for small business are worth the investment, this conversation with Jeremy Yang of Digital Goliath will help you understand what actually needs to be in place before you start spending money. Jeremy shares why organic marketing can feel painfully slow, when paid advertising can speed up your growth, and why ads should be treated as one pillar of your marketing strategy — not your entire business. In this episode of Plan Like a Boss, we talk about Meta ads vs Google ads, realistic ad spend for solopreneurs and small teams, how to know whether your offer is ready for ads, and why cost per conversion is one of the most important numbers to understand before launching a campaign. Jeremy also explains why face-to-camera video ads are such a powerful tool for coaches, course creators, artists, and service providers who want to stand out online. In this video, you’ll learn: How to know if your business is ready for paid ads The difference between Meta ads and Google ads Why your offer and sales process matter before ad spend What small business owners should budget for ads The one metric Jeremy says makes the ad world go around Why broad targeting and strong creative now matter more than “secret” audience hacks Our mission here at Plan Like a Boss is to help purpose-driven entrepreneurs build businesses with strategy, clarity, and confidence — without burning themselves out. Disclaimer: This podcast is for educational purposes only and does not guarantee specific business, marketing, or financial results. Please do your own research before investing in paid advertising, software, services, or coaching. Some links may be affiliate links, which means we may receive a small commission if you choose to purchase through them at no additional cost to you. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

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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.

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