Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
Plan Like a Boss is your go-to podcast for mastering planning, productivity, and strategy as a solo or small business entrepreneur. Each week, you'll get practical tips and real-life insights to help you set smart goals, manage your time, and grow a business that actually fits your life.
Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
Money Shame & Why Creative Entrepreneurs Struggle to Sell
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Why selling feels icky (and how to fix money mindset for creatives) Apply for Group Coaching ➡ https://api.leadconnectorhq.com/widget/form/016RC5MtLNSBM5xH1apa
If selling feels uncomfortable or “icky,” it’s not because you’re bad at sales—it’s because of your money mindset. In this video, we break down why creative entrepreneurs struggle with selling, how internalized money shame holds you back, and the truth about ethical selling. You’ll learn how to shift from avoidance to confidence so you can make more sales, serve more people, and grow your business without feeling pushy or manipulative. If you’re a coach, creative, or service provider, this will completely reframe how you think about selling.
In this video, you'll learn:
• Why selling feels “icky” (and what’s really causing it)
• The difference between manipulation vs ethical selling
• How money mindset affects your income and impact
• A powerful reframe to sell with confidence
• Journal prompts to overcome money shame
Ways to Work with Us
• Apply for Group Coaching - https://api.leadconnectorhq.com/widget/form/016RC5MtLNSBM5xH1apa
• Book a 90 Minute Intensive - https://api.leadconnectorhq.com/widget/form/SEfLO1vIsbgUaxc6TogN
Connect with us!
• Website: https://tonyalawson.com
• Instagram: @dr.tonyalawson
• TikTok: @dr.tonyalawson
Question - Have you ever felt like selling makes you “too much” or uncomfortable? Why?
Chapters:
0:00 Introduction: Selling Feels Icky
1:48 Why Creatives Struggle with Sales
4:15 The Money Mindset Shift
7:06 Manipulation vs Ethical Selling
8:15 How to Sell with Confidence
11:02 Journal Prompts to Rewire Beliefs
#MoneyMindset #SellingWithoutFeelingSalesy #CreativeEntrepreneur
About:
Welcome to Plan Like a Boss! We help creative entrepreneurs build profitable, aligned businesses with smarter strategies and powerful mindset shifts. New episodes weekly to help you grow with clarity and confidence.
DISCLAIMER: This content is for educational and informational purposes only and does not constitute financial, legal, or business advice. Results may vary based on individual effort and circumstances.
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The Money Shame Behind Sales
Fear, Undercharging, And Hidden Costs
Money As A Neutral Tool
Manipulation Vs Ethical Selling
Journal Prompts And Closing Ask
SPEAKER_00Today we're talking about money. But first, I need to confess something. There was a season in my business where I would create something incredible, pour my heart into it, know that it could change someone's life. And then I wouldn't talk about it. Not really. I would post value, I would educate, I would encourage, I would share insights. But when it came time to actually say, here's how you can work with me, I would get kind of weird. Tight in my chest, overthinking the wording, rewriting the email 12 times, softening every single sentence so that I didn't sound salesy. Because somewhere in my mind, selling felt icky. And if you're a coach, service provider, creative, you probably know that feeling. But here is what I've learned selling isn't icky. Avoidance is icky. Welcome back to Plan Like a Boss. I'm your host, Tanya Lawson, entrepreneur of over 20 years. And today we are going to be talking about why most creative entrepreneurs struggle to make sales. And the truth is, most creative entrepreneurs don't struggle with actual selling because they lack skills. They struggle because of an internalized money shame. And we just don't talk about that enough. Let me ask you something. When you first fell in love with what you do, was money part of the story? For most of us, no. We loved the craft, the creativity, the transformation, the impact. And then somewhere along the way, we absorbed this belief. Art shouldn't be about money. And as a classical musician, let me just tell you, the truth is there. If you go to any classical performance and the musicians have just been paid, they quickly peek at their paycheck and put it back. They hide it. They don't talk about how much they were made. They don't share that information because talking about money is dirty. It's bad. And if you're a musician, an educator, a creative, or a coach, you've probably heard some version of the do it for the love. If you're passionate, money doesn't matter, or you shouldn't care about money. And well, I'm also from the South. So I get it double duty because you know it's just not polite to talk about money. And then the Bible verses: it's easier for a camel to go through an eye of a needle than for a rich man to enter into the kingdom of God. Or the love of money is the root of all evil. We have been fed this untruth that money equals bad. Rich people are entitled and gross. And that conditioning that we've been fed, it runs deep and it's subtle. No one says it outright, but it's there. I remember being in environments in graduate school and music school where the most respected people were the ones who sacrificed the most, the ones who worked the longest hours, the ones who charged the least for their services. They gave the most away and they were admired for it. Almost like struggle was proof of integrity. And I internalized that. So when I started building something that could actually make money, I felt tension because making money felt like I was betraying something. Have you ever felt that way? Like if you charge what you're worth, you're somehow less pure. We romanticize the starving artist lifestyle because that's how we've been conditioned. But what no one talks about is the burnout, the resentment, that quiet financial anxiety that wakes you up at 2 a.m. And here's what shifted for me. There is nothing noble about being broke. Let me repeat that. There is nothing spiritual about undercharging for your services. And there is nothing virtuous about making your life harder than it needs to be. Let me be real honest with you here. There was a time when I would send one email a month because I didn't want to bother my audience. I would never directly promote my offers because it just felt icky. I would rarely mention them. I would hope people would just know how to work with me if they wanted to. And then when sales were low, I would say things like, Well, I don't want to be pushy. But if I'm being totally honest, that wasn't integrity. That was fear. I was afraid of being judged. I was afraid of being rejected, of being seen as greedy, being seen as too much. Because if I was constantly talking about my offer, people would think, well, all she wants to do is sell things. But the reality is, people need to see an offer or marketing message seven to 20 times before taking action. And the cost of all of my fear, I was limiting my impact, my ability to help people. Not because my work wasn't good, but because I wouldn't fully stand behind it. That was the real problem. So here is a reframe that changed everything for me. And I think it can change things for you too. Money is neutral. It is Switzerland. It is simply a tool. It's not evil, it's not holy, it's not greedy, it's not selfish. It amplifies who you already are. And having more of it, more money allows you to serve more people, to create better experiences, to invest in support so that you can get even better at helping people. It allows you to be able to offer scholarships. It allows me to be able to offer my live workshops for only$10 because I have margin and it allows you to have rest. It is a privilege to be able to work for free. And you can only give generously when your needs are covered. Because we all have life needs. We have rent or a mortgage to pay. We've got to keep the lights on, keep gas in our cars, keep healthy food on the table. And avoiding money doesn't make you humble, it makes you limited. Now let's clear something up. When people say selling feels icky, what they actually mean is manipulation feels icky. Manipulation is that fake urgency, the overpromising, and you know what I'm talking about. Do this and make seven figures. Guilt tactics. If you really cared about your business, you would invest. Preying on fear and then inflating results. I know one person who claims they make seven figures from a low-ticket download. And I don't know. I've not seen inside their business, but I question how real that is because I could totally make seven figures from a low-ticket download this month. I could create it and I could run$900,000 worth of ads to it. And I could sell a million of them by running$900,000 worth of ads. I just made seven figures, but that's not the truth. That's how much came in, but that doesn't include what went out. And of course, that feels gross. That is not okay. But ethical selling, that is clarity. Ethical selling is just saying, hey, this exists. This is who it's for, and this is what it does. If you want it, here it is. So for example, my group coaching membership I'm building right now. Hey, I have a group coaching membership. It is for creative entrepreneurs who want to feel unstuck in their business. They want to feel less scattered and be able to make more money while putting in fewer hours. If you want it, reach out to me and I will be happy to give you founding member prices because it's not officially open yet. It's still in the building phase. And if you want to come in while it's being built, I'll give you a discounted price for life. That's not pressure, that's permission. Giving people permission to improve themselves because you have the ability to help them. I once worked with someone who told me, I just hate being sold to. And then I asked her, Do you hate being sold to or do you hate being manipulated? Because those are not the same thing. I want you to think about this. Have you ever read a book that changed your life? Or bought a course that unlocked something? Or hired a coach that shifted everything? Were you mad that they sold it to you? Were you like, how dare that book change my life? How dare that course help me unlock something broken in my business? How dare that business coach help me see things a different way to shift my business and make more money? No, of course you didn't. You were grateful that it existed. You were grateful that you spent the money on it. If someone has something that can genuinely help you and they never tell you about it, that's not humility. That's withholding. Here's the hard truth. You cannot scale impact without scaling your income. You cannot serve powerfully while secretly resenting how much you're charging. And you can't change lives quietly. Avoidance, that feels safe. But avoidance also keeps you small. And your work, it deserves better than that. If you truly believe in what you do, if you know it helps people, if you've seen the transformation, then selling is not flea. It's responsible. It's a line, it's leadership. Because clarity is kindness. People cannot buy something that they don't know exist. So this week I'm going to ask you to journal. I want you to journal on this. Where did I learn that money is shameful? Who modeled that discomfort around charging what I'm worth? And what part of me believes that selling makes me bad? After you journal on those, I want you to then ask yourself: what would change in my business if I sold from confidence instead of apology? Now, if this episode is hitting you and you realize you've been avoiding instead of inviting, I want you to know you're not broken. You're conditioned. And that can be unlearned. And if you ever want support in learning how to talk about your offers in a way that feels calm, ethical, and powerful, that's something that I help people with all the time. But whether you work with me or not, I hope this lands. Selling is an icky. Manipulation is icky. Avoidance is costly, and your work is too important to hide. So if this episode hit, I would love it if you would give us a review on your favorite podcast platform of choice. And until next time, keep planning like a boss.