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. 4D AGO

    Why Your Clients Keep Misunderstanding You (And It's Not Their Fault) | EP 39

    Send us Fan Mail You did everything right. You sent the proposal, followed up with a recap, laid out the timeline — and somehow your client came back asking for something that was never on the table. If you've been there, you know the feeling: a mix of frustration, confusion, and that quiet dread of having to address it without damaging the relationship.  For entrepreneurs, client miscommunication isn't just uncomfortable,  it's one of the most common drivers of scope creep, resentment, and burnout. And here's the part that's hard to hear: most of the time, it's not the client's fault. In this episode, you'll hear why client misunderstandings keep happening even when you think you've been clear and more importantly, the specific language shifts you can start making right now to stop the cycle. From the "curse of knowledge" that makes you skip over critical details, to the sneaky patterns that quietly burn down client relationships What to listen for in this episode: Communicate from your client's starting point, not just your expertise. You're communicating from inside your business — you know your process, your industry standards, and what your terms mean. Your client is hearing your words through the filter of their own assumptions, so the small undefined spaces you leave behind are exactly where scope creep takes root.Use specific numbers and details instead of vague scope language. Words like "a few," "as needed," and "regular check-ins" feel concrete when you write them, but they mean completely different things to different people. Instead of "two rounds of revisions," try "two rounds of revisions where each round is defined as one list of feedback submitted within five business days.Pause and confirm understanding during conversations, not just at the end. Asking "does that make sense?" at the end of an onboarding call tells you nothing, your client will say yes because they're excited to work with you, even if they only retained 40% of what you said. Instead, pause throughout the conversation and ask, "what's your understanding of how this process works?" so you can catch the gap before it becomes a problem.(03:08) The Curse of Knowledge and Client Assumptions  (05:49) Identifying Communication Patterns  (09:05) Practical Language Shifts for Clarity  (11:56) Establishing Boundaries and Expectations (15:06) Building Stronger Client Relationships  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/

    19 min

  2. MAY 8

    Why Solving the Same Problems Over and Over Again Is a Leadership Red Flag | EP 38

    Send us Fan Mail Something goes sideways in your business and within seconds, your brain is already racing. Whose fault is this? How do you fix it right now? You know that spiral intimately. Maybe it’s the moment a client messages you saying results have completely stalled, and before you’ve even had your coffee, you’re already deep in your own head, running through every possible cause and absorbing the problem emotionally before you’ve even opened the account. That mental weight, that reflexive panic or blame, is something almost every entrepreneur experiences. And it’s also exactly what keeps you solving the wrong things.  In this episode, you’ll hear the real skill of business problem solving. Not moving fast. Not finding fault. But solving the right thing at the right level. You’ll learn why problems feel so personal when you’re a solopreneur, how emotional absorption clouds your judgment, and why reactive decision-making causes the same problems to cycle back again and again.  Using research-backed frameworks like the Five Whys technique, developed by Toyota and widely used in root cause analysis today, alongside real-world agency examples, you’ll walk through a practical, step-by-step shift from blame to analysis and from treating symptoms to uncovering the actual source of the problem.  What to Listen for in This Episode Why do we absorb problems emotionally, and what is it actually costing you? When you’re a solopreneur, every problem can feel tied to your identity. You may know the difference between being responsible for something and feeling personally implicated by it, but closing that gap is where clearer thinking begins. How do you move from blame to root cause analysis? Blame, whether directed outward or inward, can feel productive, but it’s often just a holding pattern dressed up as action. Instead of staying stuck in emotional conclusions like “my launch failed,” you’ll learn how to describe problems in clear, factual termsHow do you stop being the only one solving problems on your team? If every issue eventually lands back on your desk, that’s a signal worth paying attention to. (03:14) Understanding Communication  (06:03) Clarifying Roles and Responsibilities  (08:53) Choosing the Right Tools  (11:52) The Importance of Boundaries  (14:47) Creating Structure for Sustainable Collaboration  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

  3. MAY 1

    Why Feeling Like a Fraud Is Actually a Sign You're Growing | EP 37

    Send us Fan Mail You landed the client. You got the opportunity. Someone called you an expert and instead of feeling proud, your stomach dropped. That quiet voice that whispers you're about to get found out is a common experience entrepreneurs face, and yet most people suffer through it in silence. You’ll hear the moment she landed her first client  and, instead of celebrating, spent an entire week convinced she was going to disappoint them. It's a feeling many creative business owners know all too well and it usually shows up not when things are going wrong, but when things are finally going right. We’re unpacking imposter syndrome from a different angle -  not as a problem to fix, but as a signal worth understanding. We break down what imposter syndrome actually is versus what most people assume it means, why it tends to intensify as your business grows, and how the discomfort of self-doubt is often a marker of a growth mindset at work. With practical tools and a perspective shift that sticks, this episode is a reminder that confidence doesn't arrive before the action, it comes from it. What to Listen for in This Episode Imposter syndrome isn't evidence you're unqualified — it's evidence you care. The internal belief that you're less capable than others perceive you to be tends to live in people with high standards and self-awareness. People who aren't growing don't feel like imposters. That discomfort is your comfort zone marking its edge, not a stop sign.Build an evidence file. When the imposter voice gets loud, it works with selective memory. Keeping a running log of wins, client feedback, and moments where you showed up and delivered gives you something real to look back on. Not for ego — for accuracy.Separate the feeling from the fact. "I feel like I don't know enough" is a feeling. "I have no experience in this specific area" is a fact. They require completely different responses. Auditing the facts almost always reveals the feeling doesn't hold up.Thought to sit with: If you felt completely comfortable every time you took a new step in your business — were you actually taking a new step? The stretch is supposed to feel like a stretch. What if the doubt isn't a warning to slow down, but a signal that you're finally moving in the right direction? 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/

    10 min

  4. APR 24

    From Resentful to Intentional: How to Set Boundaries Without Blowing Up Your Relationships | EP 36

    Send us Fan Mail You're on a call. Someone asks for a favor, a rush turnaround, a scope addition you didn't plan for. And even as the word "yes" is leaving your mouth — you already know. You didn't want to say it. You were already stretched. But the discomfort of disappointing them felt heavier than the cost of overextending yourself. Again. For a lot of creative entrepreneurs and solopreneurs, that moment happens quietly, repeatedly, and often feels like just being a good business owner. Being flexible. Being client-focused. But underneath it, something is running the show that has nothing to do with generosity — and everything to do with self-protection. We dig into the hidden cost of over-commitment and why people-pleasing in business is one of the most underdiagnosed sources of entrepreneurial burnout. We share real, personal stories — from long-term client relationships gone sideways, to networking partnerships that quietly drained them dry — and unpack why saying yes to everyone is often the loudest possible no to your own time, energy, boundaries, and sense of self.  What to Listen for in This Episode 1. People-pleasing isn't about caring — it's about managing discomfort. The moment Dana reframes people-pleasing not as generosity but as self-protection in disguise is one that will stop a lot of listeners in their tracks. If you've ever confused your accommodating nature with your values, this one is for you — and it's the insight that makes everything else in the episode click. 2. The cost of over-commitment goes far beyond your calendar. Time is the obvious loss. But we get specific about the costs most solopreneurs don't put a number on: resentment that leaks into your work, foggy decision-making when you're always in reaction mode, and the slow erosion of knowing what you actually want. When your default is yes, you eventually outsource your own instincts to everyone else's needs. 3. Your "no" needs language — not just intention. Knowing you should say no and knowing how to say it are two very different things. We offer real phrases you can use immediately — for scope creep, for rushed timelines, for favors you can't afford — that are clear, kind, and relationship-preserving. Because a good client relationship can absorb a no. A fragile one couldn't have survived long anyway. Your value is not your usefulness. You built this business — you don't have to keep earning your place in it. 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/

    25 min

  5. APR 17

    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

  6. 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

  7. 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

  8. 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
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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
    152
  • Rating
    Clean
  • Copyright
    © 2026 Entrepreneur Encounter
  • Show Website
    Entrepreneur Encounter