Entrepreneur Encounter

Entrepreneur Encounter
  • 5.0 (7)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Entrepreneur Encounter is a weekly podcast designed to support creative business owners in developing the soft skills that lead to lasting, values-aligned growth.Hosted by Dana Johnson, founder of a boutique Pinterest marketing agency for wedding pros and creatives, and Sara Lowell, a consultant specializing in business management & team leadership along with podcast management, each episode explores the mindset shifts, communication skills, and leadership habits that empower entrepreneurs to grow sustainably—without the burnout.Through real stories, practical frameworks, and transparent conversations, Dana and Sara offer a behind-the-scenes look at what it really takes to run a purpose-driven business in a constantly changing world.Whether you're building your visibility, managing a team, or simply trying to stay grounded while growing, this podcast is your companion in business and in life.

  1. 19H AGO

    Why Reacting to Business Problems Instead of Analyzing Them Is Keeping You Stuck | EP 35

    Send us Fan Mail It's early morning, you haven't had your coffee yet, and a message comes in that makes your stomach drop. Something went sideways overnight and before you've even opened your laptop, your brain is already spiraling. Whose fault is this? Is it me? Do I need to fix everything right now? Dana knows this feeling intimately. She describes sitting with the weight of a client's stalled Pinterest results before she'd even looked at the account, already absorbing the problem emotionally, already running through a mental checklist of everything that could be wrong, already exhausted before the workday began. That moment of emotional absorption before analysis? It's not a personal flaw. It's one of the most common and quietly costly patterns in entrepreneurship. And this episode is about breaking it. Dana takes an honest look at how entrepreneurs, especially those building solo or with small teams, handle problems when they arise in their business. She talks about why problems feel so personal when you're the one who built the thing, how blame (both outward and inward) keeps you spinning without actually solving anything, and what it actually looks like to shift from reactive to analytical. Drawing from her own client work and research on leadership burnout, Dana walks through a practical toolkit What to Listen for in This Episode: 1. The difference between feeling responsible and feeling personally implicated. Caring about your business is not the same as making every business problem about your worth as a person.  2. Blame is a holding pattern, not a solution. Whether you're pointing the finger outward (at a client, a contractor, the algorithm) or inward (I should have caught this, I knew better), blame keeps you busy without moving you forward.  3. You might be solving the symptom, not the root cause. The Five Whys technique; originally developed by Toyota, is Dana's go-to framework for getting underneath what's actually driving a recurring problem. When you keep asking why, you often find that the real issue isn't the client complaint or the drop in traffic. It's a process gap, a communication breakdown, or a system that was never built to last. If you're the one solving every problem in your business, it might be worth asking: is that a sign of strong leadership or a system that was never designed to work without you?  Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    23 min

  2. APR 10

    Why "We've Always Done It This Way" Is Quietly Killing Your Business Growth | EP 34

    Send us Fan Mail Have you ever followed the same process, made the same decisions, and done things the exact same way, only to feel like something just isn't working anymore? That nagging feeling isn't failure. It's awareness. And it might be the most important signal in your business right now. We dig into how unquestioned assumptions quietly shape the way you run your business and how the phrase "this is how we've always done it" can slowly limit your growth, your team, and your revenue. They break down where these assumptions come from (hint: your early startup days), why they feel like facts even when they're not, and how to challenge outdated thinking without spiraling into self-doubt. What to Listen for in This Episode: Most assumptions don't feel like assumptions, they feel like facts. From how you onboard clients to how you manage your team, defaults can quietly replace intentional decisions.Replace certainty with curiosity. Instead of asking "is this right or wrong," ask "what am I assuming here?" That one question opens the door to real growth.Separate intuition from habit. Not everything that feels natural is intuition — sometimes it's just repetition. Ask yourself: am I choosing this, or just repeating it?Test before you tear it all down. You don't need to burn your SOPs to the ground. Try tweaking one step, one process, or one meeting format and see what shifts.Better thinking doesn't start with certainty, it starts with curiosity. What in your business are you operating on assumption instead of intention?  Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    17 min

  3. APR 3

    Critical Thinking & Problem-Solving Skills Every Small Business Leader Needs | EP 33

    Send us Fan Mail You sat down to finally work on something that actually matters,  the strategy, the vision, the thing that could really move the needle in your business. Then your phone rings. A client has a question. A team member needs a decision. A process broke. And before you know it, the day is gone, you solved twelve problems that weren't on your list, and the one thing you actually needed to think through is still sitting there, waiting. Sound familiar? That moment - that exhausting, draining, "what did I even do today?" feeling — isn't a you problem. It's a pattern problem. And patterns, unlike people, can be changed. We dig into one of the most common and costly struggles in business ownership: why everything keeps landing on your plate and what to do about it. We unpack the difference between reactive problem-solving (putting out fires as fast as they start) and true critical thinking (asking why the fires keep starting in the first place). We walk through a practical three-level filter for deciding what actually deserves your attention, how to build problem-solving capacity in yourself and your team, and how to stop being the bottleneck in your own business — whether you're a solopreneur or leading a growing team. What to Listen for in This Episode: 1. Reactive Problem-Solving vs. Critical Thinking — and Why It Matters Most business owners spend their days solving problems fast. But speed isn't the same as strategy. Reactive problem-solving asks, "What's the fix?" Critical thinking asks, "Why did this happen, and what does it tell me?"  2. The Three-Level Problem Filter Not every problem deserves your energy. We introduce a simple framework for what lands on your plate: what needs your decision right now, what can be delegated or solved with your input, and what doesn't actually need solving at all.  3. Building a Problem-Solving Culture (Even If It's Just You) The goal isn't just to solve today's problems better, it's to build the kind of leader and business that handles problems well over time.  The businesses that thrive aren't the ones with the fewest problems — they're the ones that have built the capacity to think clearly when problems show up. So the real question isn't "how do I fix this?" It's "am I building a business that thinks?" Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    27 min

  4. MAR 27

    The 5 C's Leadership Framework Every Entrepreneur Needs to Build a Team That Thrives | EP 32

    Send us Fan Mail You started your business with a vision, the strategy, the hustle, the late nights figuring out the marketing funnel. But somewhere between onboarding your first client and managing your growing team, a quiet panic set in. Nobody taught you this part. Not the people part. Not the "why is everyone moving in different directions and why does everything feel like a fire to put out" part. You read the books, you followed the gurus, and yet here you are, leading by default instead of by design — and wondering why your best efforts still feel like they're falling just a little short. Sound familiar? You're not alone, and more importantly, you're not without a solution. We break down a five-part leadership framework called the Five C's - Common Purpose, Clear Expectations, Communication and Alignment, Coaching and Collaboration, and Consequences and Results. Designed specifically for small business owners, solopreneurs, and creative entrepreneurs, this framework gives you a practical foundation to lead more intentionally, align your team (no matter the size), and build the kind of trust that sustains growth even when everything around you is shifting. What to Listen for in This Episode: 1. Why "assumed" alignment is silently sabotaging your team. Common Purpose is the C most leaders skip and it's the one that costs them the most. We talk about why having a mission statement on your website is not the same as your team actually living it. When people aren't connected to the why, they start optimizing for the wrong things. And for solopreneurs, getting clear on your purpose isn't just inspirational, it becomes your fastest filter for what to say yes to and what to walk away from. 2. Clarity is not a nicety, it's a leadership responsibility. Unclear expectations are not a people problem, they're a leadership problem. Learn the "what, by when, and what does success look like" framework that removes guesswork, reduces resentment, and sets every person in your world up to actually win. 3. The difference between a manager and a leader lives in this one C. Coaching and Collaboration is where the real transformation happens.It's asking better questions so the people around you learn to think, not just execute.  If accountability without consequences is just hope, what are you actually building and is it strong enough to hold? Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    27 min

  5. MAR 20

    How to Pivot Your Business Without Panicking: A Strategy Guide for Entrepreneurs | EP 31

    Send us Fan Mail You've been building something real. You've put in the hours, made the sacrifices, and shown up even when it was hard. But lately, something feels off - the offer isn't landing the way it used to, the calendar isn't as full, or the direction you were so sure about six months ago has started to feel foggy. You know something needs to shift, but every time you get close to making a move, that little voice in the back of your head pipes up: What if I blow everything up trying to fix it and make it worse? That tension - between knowing change is necessary and being terrified of making the wrong move - is exactly where so many creative entrepreneurs get stuck, spinning their wheels and waiting for a sign that never quite comes. Today, we break down one of the most common and costly experiences in entrepreneurship: the urge to pivot, and the panic that comes with it. We dig into the real difference between thoughtful adaptation and reactive change and why knowing which one you're doing could be the thing that saves your business. We walk through a practical framework for diagnosing what actually needs to shift (spoiler: it's usually not what you think), how to communicate change without creating confusion or chaos, whether you have a team or you're flying solo and how to protect the trust you've worked so hard to build while you're in the middle of a transition. What to Listen for in This Episode: Data over feelings — always. Before you change your offer, your pricing, or your whole business direction, we challenge you to separate facts from feelings. We breaks down how to identify the actual bottleneck in your business, whether it's awareness, conversion, delivery, or retention.  How you communicate change is just as important as the change itself. The case that communicating poorly creates confusion, and confusion creates panic — both in your team and in yourself.  Give the change time to breathe. One of the biggest mistakes entrepreneurs make is abandoning a new strategy before it's had a real chance to work. We remind you that change isn't a light switch, it's more like a course of antibiotics. You have to take every dose, for the full amount of time, before you can honestly evaluate the results. Commit to the whole process before you decide it isn't working. If you're always changing the plan before the plan has had a chance to work, the real question isn't what needs to pivot — it's whether you're wi Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    21 min

  6. MAR 13

    Growth Mindset for Leaders: How Entrepreneurs Build Real Confidence Without Having All the Answers | EP 30

    Send us Fan Mail You're running a business, and people are looking to you for answers. Your team needs direction. A client asks something you didn't see coming. And in that split second, instead of saying "I don't know yet," you feel the pressure to perform certainty because leaders are supposed to have it all figured out, right? Sara knows that pressure firsthand. Five years into building her business, she's still navigating real-time decisions, learning from mistakes, and choosing transparency over performance. And what she's discovered is this: admitting you don't have all the answers isn't what breaks your authority. Pretending you do is. Today, Sara explores what growth mindset actually looks like in leadership, not the inspirational-quote version, but the honest, daily practice of staying curious while building a business in real time. She digs into why entrepreneurs feel pressure to appear certain, what vulnerability and transparency really do for trust, and how modeling a learning mindset can make you a stronger, more credible leader. What to Listen for in This Episode: The myth of knowing everything. Performing confidence instead of building it keeps leaders stuck. Admitting you're still learning isn't a weakness, it's what actually earns long-term trust from your team and clients. What growth mindset looks like in real decisions. It's not constant positivity. It's testing ideas, adjusting when something isn't working, inviting feedback, and staying curious especially when things get uncomfortable. How to lead through uncertainty without losing authority. Authority isn't knowing everything. It's guiding progress. When you model openness to learning, the people around you feel safe to do the same — and that's where real growth happens. Strong leadership isn't about having all the answers. It's about being willing to keep learning, even when people are watching. So where in your business are you putting pressure on yourself to have it all figured out and what might change if you didn't? Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    17 min

  7. MAR 7

    Why Leaders Get Stuck: Overcoming Fear of Change in Business Growth | EP 29

    Send us Fan Mail You built something from nothing, your systems, your team, your entire identity wrapped up in the thing you call your business. And then one day, quietly, something stops fitting. Maybe it's a role on your team, a service you've been offering for years, or the way you've been showing up as a leader. You can see it clearly. You could draw a diagram of exactly what needs to shift. And yet... you don't move. You reorganize your desk. You answer emails. You tell yourself you'll get to it. Sound familiar? That frozen feeling isn't weakness and it isn't laziness. It's something far more human and far more fixable than most people realize. In this episode, we get honest about the emotional side of change that no strategy session ever addresses. We unpack why our brains treat a business pivot the same way they treat a physical threat, why logical clarity and emotional readiness are two completely different things, and why the most self-aware leaders still find themselves stalling, micromanaging, or spinning in busy work instead of taking the one action they already know they need to take. Drawing from our own experiences we walk through what it actually looks like to move through resistance not around it, without beating yourself up along the way. What to Listen for in This Episode: Your nervous system isn't broken; it's doing its job. When change feels threatening, your brain responds the same way it would to physical danger. The freezing, overanalyzing, and micromanaging you experience during a pivot aren't character flaws. They're your nervous system trying to protect you.  Knowing what to do and being ready to do it are not the same thing. You can have the new org chart drafted, the offer revamped, the plan documented and still feel completely frozen. That's because strategy lives in the mind, but resistance lives in the body. What hasn't been processed is the grief; the version of yourself you're leaving behind, the control you're releasing, the identity you've tied to the way things used to be.  Naming your fear takes away its power. Vague fear is loud. Named fear is workable. We share a practical technique of personifying your inner critic — giving your negative self-talk an actual name, separate from who you really are — so you can catch it in the moment, call it out, and make decisions from a grounded place instead of a reactive one.  The next time you catch yourself avoiding the very thing you already know needs t Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    21 min

  8. FEB 27

    Stop Micromanaging: How Entrepreneurs Can Delegate, Build Trust, and Scale Without Burnout | EP 28

    Send us Fan Mail You've poured everything into this business — late nights, early mornings, every decision running through you. You send the follow-up, review the contractor's work, loop yourself into every conversation. But somewhere between checking in for the fourth time and rewriting a message someone else already drafted, a question creeps in: Am I leading this business, or am I suffocating it? That moment is exactly where this conversation begins.  In this episode, we dig into one of the most uncomfortable truths in entrepreneurship: the difference between communicating to lead and communicating to control. Through the story of Marcus — a six-figure consultant who became the biggest bottleneck in his own business — plus real experiences with team management and the fear of stepping into leadership, we explore what actually changes when you set clear expectations and finally let go.  Together, we lay out five practical shifts, from setting expectations upfront to building systems instead of dependencies, that help entrepreneurs stop being the answer to every question and start building something that can actually scale. What to Listen for in This Episode: The difference between growing and scaling and why it matters. What's the difference? Growth means you're doing more. While scaling means your business is doing more without you doing more. This reframe can change how you think about delegation. And where you spend your energy every day.  How to communicate from trust instead of fear. Why the words you use matter less than the why behind them. You have to communicate from a place of clear expectations and trust. Because this allows not only you to thrive but those in your space. Communicating from anxiety and the need to control will create friction. Learning to tell the difference in yourself is the first real step.  The sign you need a system, not another conversation. If you're answering the same question from your team more than twice, that's your signal. Create a template that can be used all the time. Create a process you can send out to your team. Record trainings to your business doesn't have to depend on you every time. You have to lay the foundation to grow.  If your business can't move forward without you, the question worth sitting with isn't how to communicate more, it's whether you've built a business, or just a job you can't leave. Episode Mentioned: 🎧 Support the show Whether you’re looking to grow your visibility through Pinterest Marketing or streamline your Podcast Operations and Team Management, we help business owners and creatives build sustainable systems that work for them, not against them. Want to learn more about how this can work for you and your business, reach out to us! Connect with Entrepreneur Encounter:  Your Free Gift: 20 Min Clarity Map https://entrepreneur-encounter.kit.com/clarity-map    LinkedIn: https://www.linkedin.com/company/entrepreneur-encounter/  Host Sara Lowell:  LinkedIn: https://www.linkedin.com/in/youarerembertllc/ Website: https://www.youarerembertllc.com/ Host Dana Johnson:  LinkedIn: https://www.linkedin.com/in/d-m-johnson/ Website: https://ddvirtualmanagement.com/

    18 min
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5
out of 5
7 Ratings

About

Entrepreneur Encounter is a weekly podcast designed to support creative business owners in developing the soft skills that lead to lasting, values-aligned growth.Hosted by Dana Johnson, founder of a boutique Pinterest marketing agency for wedding pros and creatives, and Sara Lowell, a consultant specializing in business management & team leadership along with podcast management, each episode explores the mindset shifts, communication skills, and leadership habits that empower entrepreneurs to grow sustainably—without the burnout.Through real stories, practical frameworks, and transparent conversations, Dana and Sara offer a behind-the-scenes look at what it really takes to run a purpose-driven business in a constantly changing world.Whether you're building your visibility, managing a team, or simply trying to stay grounded while growing, this podcast is your companion in business and in life.

Information

  • Creator
    Entrepreneur Encounter
  • Years Active
    2023 - 2026
  • Episodes
    148
  • Rating
    Clean
  • Copyright
    © 2026 Entrepreneur Encounter
  • Show Website
    Entrepreneur Encounter