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

Your business can look “successful” on paper and still feel like you’re one bad week away from the kitchen floor. Joe Casabona knows that reality firsthand. He shares how a panic attack during the pandemic forced him to rethink everything, and how building simple, reliable systems helped him save 10 to 15 hours a week so he could actually take time off without the business falling apart.

We walk through the first moves Joe makes when a solopreneur feels buried: start with the beliefs that keep you stuck, then get honest about where your time goes by tracking a real week. From there, Joe breaks down a clear decision tree for automation vs delegation, including the kinds of tasks that are perfect for tools like Zapier or Make and the work that should stay human. If you’ve ever wondered what to automate, what to hand to a VA, or what only you can do, this framework makes the choice easier.

We also get real about AI for solopreneurs. Joe lays out three warning signs of “AI brain rot,” explains why “AI is for tasks, not craft,” and shows how to use large language models without outsourcing your thinking. Expect practical examples for podcast workflows, scheduling, Notion-based planning, and time management, plus a simple “Daily Three” task journaling practice to protect your best hours and reduce overwhelm.

If this helps, subscribe, share the episode with a fellow solopreneur, and leave a quick review. What’s the first task you’re going to automate or delegate this week?

Connect with Joe: https://streamlinedsolopreneur.com/

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Your best marketing might not need louder claims, daily reels, or a harder pitch. It might need one thing: curiosity. I’m joined by copywriter Emily Aborn to unpack how curiosity marketing works, why it feels so much more human than “convince and convert,” and how a small shift in what you say and how you say it can keep the right people reading, listening, and reaching out.

We get practical about content strategy and social media marketing without the overwhelm. Emily shares how to find the sweet spot between too much information and not enough, why jargon quietly kills engagement, and how to use the exact words your clients use so your messaging lands. We also talk platform choice the smart way: define who you serve, then reverse engineer where they already are. If you’ve felt pressured to be everywhere, you’ll love the idea of three-month experiments and letting data, capacity, and real results guide the plan.

From there, we dive into repurposing content and building content clusters so one strong idea can fuel a blog post, email newsletter, LinkedIn post, Instagram content, or a podcast promo without creating 27,000 new things. And because so many of us are building a second act business after a major life transition, we go deeper than tactics into courage, fear tolerance, and the value of grounding and self-soothing when you’re doing the work that matters most.

If you’re ready for marketing that feels clear, honest, and effective, listen now, then subscribe, share this with a friend rebuilding her next chapter, and leave a review so more women can find the show.

Connect with Emily: https://emilyaborn.com/

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A marriage proposal lasts a few seconds, but the planning behind it can be a full blown production. We sit down with Ash Fox, a New York City based proposal planner who started as a freelance photographer and accidentally discovered a niche that kept knocking on her door. What began with photographing one proposal turned into a proposal planning business that helps thousands of couples create an unforgettable “yes” moment with locations, private venues, flowers, decor, musicians, photo and video, and a calm expert guiding every step.

We get into the real mechanics of building a service business when there is no playbook. Ash explains how she used client feedback to shape her offers, why “the niche chose me” is more than a cute phrase, and how she thinks about value, quality, and repeatable results. We also talk about the parts people skip: burnout, the pressure of being the one woman show, and how COVID created a reset that made the old pace impossible to return to.

You will hear exactly how she tested stepping back from being on site by training a lead, building systems, and creating pricing tiers that serve different budgets without sacrificing the look and feel of the experience. If you are a solopreneur trying to validate an idea, her practical advice is simple and sharp: pick a number like 10 customers, test it quickly, collect honest feedback, and iterate.

Subscribe for more founder stories, share this with a friend building a business, and leave a review so more creatives can find the show. What idea are you ready to test on 10 customers?

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✨ Get your free Idea to Income Workbook: https://thesecondactentrepreneur.com/business-idea-validation-workbook

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AI can crank out a website overnight, but it can’t manufacture trust, reputation, or the one thing that makes clients say, “I want to work with you.” That’s why we sit down with Kelly Shukneck, a marketing strategist and thought leadership expert, to get practical about personal branding that actually drives opportunities instead of just adding noise.

Kelly shares her “Authority X Factor” approach for uncovering the unique mix of skills and experience you’ve probably been taking for granted. We talk about her journey from publishing to leading marketing for a fast-growing firm, then building Two Mile High Marketing after a layoff. Along the way, we dig into the real reason talented professionals stay “hidden,” and how to step into visibility without feeling fake, loud, or salesy.

We also unpack Kelly’s three-pillar framework for building a strong thought leadership platform: visibility (show up where your audience already is), credibility (prove you can deliver with stories, results, and case studies), and consistency (create a cadence you can actually sustain). If you’re a solopreneur or service provider juggling client work, we cover planning tactics like overblocking your calendar, batching content, and building a buffer so life disruptions don’t wipe out your momentum.

If you want a clearer message, a stronger LinkedIn and podcast presence, and a personal brand that differentiates you in a crowded market, hit play. Subscribe, share this with a friend who’s trying to get seen, and leave a review so more professionals can find the show.

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🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

Think influencer marketing is only for big brands with massive marketing budgets? Think again.

In this episode of Plan Like a Boss, Tonya Lawson sits down with Sherri Lambert, founder of BabbleBoxx, to talk about how influencer marketing has evolved—and why small businesses and solopreneurs have more opportunities than ever to tap into the power of creators.

Sherri was working in traditional marketing when she recognized the potential of bloggers and digital creators long before “influencer marketing” became the industry it is today. That insight eventually led her to build BabbleBoxx, an influencer marketing agency that helps brands connect with consumers through authentic creator partnerships.

In this conversation, Sherri shares practical advice for businesses that want to experiment with influencer marketing without spending thousands of dollars. She explains why smaller creators can sometimes be more valuable than influencers with massive audiences, how to find potential partners among the people who already love your brand, and the red flags businesses should watch for when working with creators.

They also dive into the changing relationship between influencers, affiliate marketing, AI, and brand partnerships—and why Sherri believes the future of influencer marketing isn't simply about getting someone to post about your product. It's about using creator content strategically across your entire business.

In this episode, you'll learn:

• How influencer marketing evolved from the early blogging era
• Why small businesses don't need huge budgets to work with creators
• How to find influencers who are already fans of your brand
• Why micro and nano influencers can have incredibly valuable audiences
• Red flags to watch for when choosing influencer partnerships
• How affiliate relationships can help businesses test influencer marketing
• Ways to repurpose creator content across social media, email, sales, and more
• How AI can help creators evaluate and negotiate brand partnerships
• Where Sherri believes influencer marketing is headed next

Whether you're a business owner wondering if influencer marketing is worth testing or a creator looking for more brand opportunities, this conversation will help you understand how to build partnerships that make sense for both sides.

Subscribe to Plan Like a Boss for more conversations about entrepreneurship, marketing, business growth, and building a business on your own terms.

Connect with Sherri: https://www.linkedin.com/in/sherri-langburt/

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✨ Get your free Idea to Income Workbook: https://thesecondactentrepreneur.com/business-idea-validation-workbook

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🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

Resumes don’t tell you who someone is when the pressure hits, and that’s where most hiring advice falls apart. We sit down with Renee Hastings, president and CEO of Executive Help Now, to talk about what actually makes a virtual assistant relationship work: values alignment, clear communication, and the courage to delegate before you burn out.

Renee shares her journey from being raised in an Amish community in Wisconsin with an uncompromising work ethic, to supporting C-suite leaders at Fortune 100 and Fortune 500 companies, to building a virtual assistant agency that helps busy founders get their lives back. We dig into the real reasons delegation feels terrifying, fear of losing control, perfectionism, and the worry that mistakes will reflect on you. Then we get practical: what to delegate first (email, calendar, recurring client needs), how to stop expecting your assistant to be a mind reader, and how to onboard well by sharing context, priorities, and introductions to key stakeholders.

If you’re a solopreneur who thinks you can’t afford help, we break down fractional back office support and why even 20 hours a month can create leverage. You’ll leave with a simple reset plan: breathe, do a quick time analysis, write a “never again” list, and use it to start a clear conversation about budget and support. Subscribe, share this with a friend who’s drowning in admin work, and leave a review with the one task you’re finally ready to hand off.

More About Renee: https://executivehelpnow.aflip.in/whatcanavadoforyou.html

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✨ Get your free Idea to Income Workbook: https://thesecondactentrepreneur.com/business-idea-validation-workbook

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Your business can’t keep running on instinct, caffeine, and chaos forever and if you’re feeling that strain right now, this conversation is for you. We sit down with Kenneth Kollasch, a certified business coach, third-generation entrepreneur, former franchise operator, and pastor, to talk about what it actually takes to grow a small business without surrendering your sanity.

We start with the surprising leadership lessons that show up long before you ever hire your first employee: the dinner table mindset of an entrepreneur family, the pressure and possibility that come with it, and how high-level soccer builds humility that most owners don’t learn until much later. Kenneth shares the moment his grandfather asked one simple question that changed everything, turning a near-pro soccer path into a values-driven choice about family, presence, and long-term purpose.

Then we get practical. Kenneth explains why doubling revenue doesn’t have to mean doubling your hours, and why “more volume” is usually the wrong answer when you’re already overwhelmed. We dig into the Small Business Flight Plan approach: diagnosing what’s real (not just what you feel), identifying win points to double down on, and fixing the pain points that quietly wreck marketing, sales, retention, and cash flow. If you’re a solopreneur, running a mom-and-pop shop, or building a small team, you’ll leave with a clearer framework for business systems, sustainable growth, and burnout prevention.

If you got value from this, subscribe, share it with a business owner friend, and leave a review so more people can build companies that support their lives instead of consuming them.

Learn more about Kenneth: https://kennethcoaches.com/free

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✨ Get your free Idea to Income Workbook: https://thesecondactentrepreneur.com/business-idea-validation-workbook

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Your Mac can either be a fancy typewriter or a serious business advantage, and the difference is usually a handful of habits you set up once. We sit down with Damian Schres, the explainer-in-chief at EasyTech and host of the Mac Preneur Podcast, to talk about the practical side of running a lean solopreneur business on Apple gear without chasing every shiny new tool.

We start with Damian’s story: a Fortune 500 engineer who took a slow, careful path into entrepreneurship. Instead of quitting overnight, he spent years running mini-experiments, building confidence, and reducing risk before going full-time. If you’re risk-averse, juggling family priorities, or just tired of “go all in” advice, this conversation offers a more realistic roadmap that still leads to freedom and control.

Then we get into the fun part: Mac productivity, automation, and AI for entrepreneurs. Damian shares why macOS longevity and security can be a win for small business owners, plus the specific workflows that save time daily, like iCloud-synced Text Replacement for instant emails and repeat replies. We also explore templates for Gmail and client docs, and Damian’s AI setup using API-driven tools like Writers Brew, alongside Mac utilities like PopClip, Apple Shortcuts, and Hazel, including an automation that renames screenshots based on the text inside them. The takeaway is simple: build systems that remove friction, and you buy back hours every week.

If you found something you want to try, subscribe, share this with a fellow Mac-using business owner, and leave a review so more solopreneurs can find the show.

Contact Damien: https://macpreneur.com/tips

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In this episode of Plan Like a Boss, Tonya Lawson sits down with business coach and entrepreneur Louis Swart to talk about delegation, productivity, and what it really takes to build a business that doesn’t depend on you for everything.

Louis shares the hard lesson he learned after discovering that his first business had little value because he was the bottleneck. That experience changed the way he approached business—and eventually helped him build a company he could step away from and sell successfully.

You’ll hear Louis break down his simple “2K rule” for calculating what your time is worth, why spending your day on low-value tasks can quietly sabotage your income goals, and how a single post-it note can change the way you decide what deserves your attention.

Tonya and Louis also dig into productive procrastination, the fear of letting go, the importance of focusing on one needle-moving task each day, and how AI can become just another form of shiny-object syndrome when it isn’t tied to a clear business goal.

In this episode, you’ll learn:
• How to identify which tasks are truly worth your time
• Why delegation is essential for building a scalable business
• How to stop treating “busy” as a badge of honor
• A simple way to calculate the hourly value of your work
• How to recognize productive procrastination
• Why focusing on one important task can move your business forward faster
• How to avoid getting distracted by every new AI tool
• One simple exercise you can implement immediately

Ready to get clear on what you should delegate? Visit:
https://clarify.ironbrij.com.au/

If you’re a solopreneur, coach, or small business owner who feels like everything depends on you, this conversation will help you rethink how you spend your time—and what you need to let go of to grow.

Let's Connect:

✨ Get your free Idea to Income Workbook: https://thesecondactentrepreneur.com/business-idea-validation-workbook

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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:

✨ Get your free Idea to Income Workbook: https://thesecondactentrepreneur.com/business-idea-validation-workbook

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📸 Follow me on Insta and TikTok @dr.tonyalawson

🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/