EPISODE 034 | APPLE PODCASTS | SPOTIFY

In this episode, we’re looking at a topic that I know will resonate with most small business owners: the fear of selling and putting yourself out there. It's a common challenge, whether you're stepping onto a stage, hitting 'post' on social media, or launching a new product.

Understanding this fear is the first step towards tackling it, and that's exactly what we're going to look at today. We'll understand why this fear affects so many of us and I’ll share practical strategies to overcome it. I'll also be sharing some of my own experiences along with insights from experts who have turned their initial fears into success.

Understanding the Fear of Selling

Let’s start by digging into the fear of selling—it’s such a common feeling, and I honestly don’t think it matters whether you are at the beginning of establishing your business or many years in, most of us face this fear, and it isn't just about the act of selling; it’s about the vulnerability that comes with putting yourself and your ideas out there for the world to see and to potentially judge.

Why does selling make us feel so uncomfortable? First, let’s talk about why it’s shared by so many of us. I think perhaps it’s because the process of selling is often equated with rejection. The possibility of hearing a 'no' can feel like a direct critique of not just your product but of your entire effort and vision. Establishing and growing a business is hugely personal, and it’s especially intense for entrepreneurs who are deeply connected to their products and services—it's like offering a piece of yourself to others.

so where does this fear manifest?

Let’s first specifically look at social media: For many of us, putting our work and ourselves out on social media can be daunting. There's a fear of not getting enough likes, comments, or worse, receiving negative feedback. When I first started posting about my products, my posts were met with silence. It took time to learn that social media is far less about instant approval and much, much more about building connections, developing a sense of community and providing value over time. If you see social media as a window to your business, it’s effectively a handshake, where you shouldn’t really be selling. It offers a great way to welcome your target audience into your world and once they get to know you, you can build a level of trust, really before you start actively selling. For me, seeing social media in this way, it definitely began to take the pressure away a little, and helped me to share a little more of myself.

Then there’s public speaking and live demonstrations —whether it’s presenting your business at a local networking event or in front of a larger audience. This is perhaps everyone’s greatest fear. It is pretty unusual for people to love public speaking. It comes with the fear of forgetting your lines or not being able to answer a tough question, the idea that you might freeze in front of so many people. Actually just saying that makes me feel intensely nervous!  Oh my goodness, I remember my first big event so clearly, I’ll tell you a little about this later in the episode.

Live virtual events, Q&As and masterclasses, these very much expose you to real-time judgement. It's live, uneditable. The fear that you won't be able to demonstrate your expertise effectively under pressure is very real. The first time I presented in front of a camera and then hosted live Q&As, I was genuinely terrified I’d lose my train of thought or that the technology would fail me.

And then, simply selling your brand and your offerings, creating and writing pitches, meeting customers for the first time, researching and cold calling people as potential clients, putting yourself out there and selling what you do. This is perhaps one of the most direct forms of exposure and vulnerability. It's one thing to manage an online persona or handle a scripted and relatively planned situation, but engaging directly with potential clients or customers—where the immediate response is unpredictable—can heighten the sense of risk and personal exposure. 

Whether it's during consultations, meetings, cold calling over the phone, at trade shows, industry conferences or networking events, each opportunity to pitch your business is also an opportunity for rejection, which can feel incredibly personal.

In each of these scenarios, the fear is rooted in vulnerability—the sense that you are exposing yourself to potential criticism and failure in a very public way. But each interaction also offers a valuable opportunity to learn and improve.

I’ve been fully there in every possible scenario and I have felt those fears and challenges deeply. I have had plenty of rejections, I have though also managed to find ways to break through the fear, and I’m far from a natural and comfortable sales person. Thankfully I have found ways to sell in a very non salesy way. And I absolutely understand how you might be feeling. I fully relate and absolutely empathise. And the great news, you can become the most natural spokesperson for your brand and offerings, and I’m excited to share some of my learning and methods with you.

Personal Stories

I would love to share some real-life examples from my own experience of being scared to sell and how I found solutions on different platforms. Each platform has its unique challenges, but also, uniquely rewarding moments that have contributed immensely to my growth and the success of my business.

Social Media: When I first started using social media, it felt like the world’s eyes were on me, and I know that sounds ridiculous as I also had next to no followers, so it was also an impossibility, but it still felt pretty intense. I remember the first time I posted about a new product; I kept refreshing the page, hoping no one would criticise or judge, and then next for the likes and comments. Initially, the engagement was minimal, and it was pretty disheartening. But over time, I learned that social media wasn't really there for advertising; it was a platform for starting conversations and building relationships. I started sharing behind-the-scenes content, my process, and my day-to-day challenges, which completely humanised my brand and made it more relatable.

Gradually, I built a community that wasn’t just interested in buying what I was selling but was invested in the brand I was creating. I took time to share stories, to understand what would be interesting, helpful and inspiring to look at and read, and I adapted and evolved as I began to learn what my target audience really wanted. And it went both ways, in sharing the right type of content, I was able to have really meaningful conversations, and answer questions. I love helping, I think most of us do, so I was only too happy to share methods I’d learnt and things I’d figured out. It was hugely rewarding, and in return, I was steadily growing our brand’s audience. It wasn't until I saw social media as this positive way to connect with my audience, that it began to work positively and I began to enjoy it.

I was being mic'd up behind stage, ready to go and I think from the outside I miraculously looked quite calm and steady, but the nerves inside were intense.

The fear of public speaking is often about more than just speaking; it’s about being judged. I was worried about forgetting what I had planned to say, stumbling over my words, or not being able to answer a question. To overcome this, I practised relentlessly in front of friends, and when the day came, although I was still nervous, I felt prepared. I knew my subject, I knew exactly what I was going to do and say, and I began to feel less nervous about the questions that might be asked. And on the day, the reception was much, much warmer than I had anticipated, and the questions from the audience showed genuine interest, which boosted my confidence.

Also though luckily, I was creating a large flower design on stage. It was my comfort zone. I felt relaxed about doing this and the design itself provided an imaginary protective barrier, and it gave me an easy point of focus, and I knew that if I forgot what I was saying, I could quickly switch to something about the design. And I started to enjoy it. It was actually quite fun, which I never in a million years thought I would ever say.

When we launched our first online masterclasses in 2018, this brought a very different kind of fear. Unlike live demonstrations where the interaction is transient, videos stay online and can be viewed over and over again. My first few attempts were absolutely stiff and very unnatural, and I also had the pressure of an entire studio team in front of me. I was definitely overly conscious of the camera. I was trying to make everything perfect, which ironically made the videos feel less engaging. With time, I realised that our audience valued authenticity over perfection. I started to relax and let my enjoyment for what I was doing come through. And rather than scripting everything, I simply spoke as I was thinking, sharing what came to me naturally, which made a huge difference in both the viewer engagement and feedback, and how easily our students were able to learn and apply the methods to their own work.

The transition to online masterclasses was definitely initially intimidating, I think mostly because it combined several fears: public speaking, live interaction, and technical challenges. I remember my first Live Q&A so well. I was full of anxiety about the content delivery and the technology aspect—what if the connection dropped, or if I couldn’t engage the audience effectively? So for this, I prepared and prepared. We asked all the questions up front and I took plenty of time to really know exactly how I would answer them, to make sure I could really help and not waste anyone‘s time. I did a few dry runs, we made sure we knew the technology inside out, and I prepared interactive elements at the end, to make sure I kept our audience engaged.

And then with direct selling, I’ve had a huge amount of experience and my goodness, it has been filled with plenty of rejections and nos. I was relatively shy as a teenager, but I started to come out of my shell when I first worked during school and then university years. My first job, after babysitting, was in a local coffee shop and then whilst at uni, in bars and restaurants.

I loved these roles, particularly the latter ones. I loved making cocktails, the creative side and serving customers. I really enjoyed welcoming the customers and helping them to enjoy the evening as much as possible, and although I wasn’t directly selling, the direct interaction with customers - understanding what they needed and coming up with solutions when they didn’t like something - I found it hugely rewarding and helpful for later work. My first office based roles were pure sales, I was working in recruitment and then latterly in strategic search. And I was of course terrible to start with, but I found my own way. I remember when I was struggling with a certain pitch, an incredible boss took me aside and kindly suggested that I was just myself. To take inspiration from others around me, but find my own voice.

And then when it came to selling my own brand and offerings, this was a whole other challenge, filled with complexities and fear. The shift though came when I realised that I wasn’t actually selling something, instead I was providing a genuine solution that my target audience needed. I knew I could make a difference and once I began to see it this way, my confidence grew and grew in front of my potential clients. I looked at clients instead as people I would love to work with, more as collaborators rather than the company and client relationship.

Of course, there were still plenty of nerve wracking moments, particularly when I was approaching Selfridges & Co, ahead of securing our in-store concession (which incidentally took me two years and many, many no’s), all the editorial publications from Conde Naste House and Garden to American Vogue and my clients including Hermes, Chanel and Dior. Each time I carefully considered what I could really do for them, how could my offerings and services really solve a problem and meet a specific need they had, and how could I make their lives easier in this area?

Each of these experiences taught me something so important about selling and putting myself out there—it’s less about the fear of rejection and more about the opportunity to connect, engage, build trust and provide solutions, to help and support others, with incredible offerings.

Embracing vulnerability, being prepared, and learning from each interaction have been key to turning these feelings of fear and potential judgement into powerful strategies and methods, which have in time become relatively natural, for growing my business.

Strategies to Overcome Selling Fears

OK, let’s now look at some strategies to help you. Overcoming the fear of selling definitely doesn't happen overnight, but it is entirely possible to find a way to happily and calmly promote what you do, in a very genuine and down to earth way, that feels entirely natural and far from uncomfortable. It requires a mix of understanding, preparation, and gradual exposure. I’d love to share a few ways that I've found incredibly effective, and I believe they can help anyone become more confident in selling their products and services.

I think the very first and most important step is to know your target audience deeply.

Understanding who you are selling to can significantly reduce anxiety. This involves more than just knowing their age or demographic details; it's about understanding their needs, pain points, and buying behaviours. When you tailor your approach to meet your audience's specific expectations and concerns, the selling process becomes much, much more of a conversation and less of a pitch. This not only makes the process feel more natural but also more effective. If you would love to understand more about identifying your target audience, listen to episode 033, where I also share a helpful guide that you can download.

Next, one of the most powerful tools in overcoming fear is simply knowledge. The more you know, the more you really understand what your brand is absolutely about, what it is you stand for, your purposes, your clear vision and in turn the offerings you supply, and how they deeply fulfil a need, the more confident you'll feel discussing it all with others. This means diving deep into your product's features, benefits, and potential drawbacks. And when I say drawbacks, this includes the potential objections you might come up against. Take time to think what they might be. What will your target audience question or not quite understand and really understand how you will approach these potential questions and objections.

Like any skill, selling gets easier the more you do it. Start by practising your natural solution focussed pitch in a low-stakes environment. This could be with friends, family, or colleagues who can provide honest feedback. As you become more comfortable, you can move on to more challenging scenarios. The key is to build up your confidence gradually without overwhelming yourself.

After every selling opportunity, ask for feedback. This can come from the person you were selling to or from a third party observing the interaction. Constructive criticism is invaluable as it provides insights not only into what you’re doing well but also into what can be improved. Use this feedback to refine your approach continuously.

And if the idea of selling still feels overwhelming, start small. You don’t have to jump into a major sales pitch or a high-stakes meeting right away. Begin with smaller, less intimidating selling situations. This might be a casual conversation at a network event or a soft pitch to a new social media audience. Each small step will build your confidence and prepare you for bigger challenges.

Selling doesn’t have to be—and shouldn't be—about pushing a product onto someone. Instead, think of it as sharing something you genuinely believe in. When you’re true to yourself and your brand, your passion and belief in your product will shine through. This authenticity resonates with potential customers and makes the selling process more natural and less forced. It turns the dynamic from seller-versus-buyer into a conversation between two parties looking for a mutual benefit.

Being authentic means aligning your selling methods with your personal and brand values. It means being honest about what your product can and cannot do and interacting with potential customers as you would with a friend. This approach not only builds trust but also fosters a deeper connection with your audience. People are more likely to buy from someone they trust and who they believe has their best interests at heart.

By using some of these strategies, you can transform the fear of selling from a previous barrier into something that feels natural and comfortable. And when you face aspects that make you feel nervous, I don’t think of the goal as being something you’re looking to eliminate entirely but instead to learn to manage it effectively so that it doesn't stop you from reaching what you know deep down you can achieve.

Expert Tips & Tools

If you would like to look into this subject further, there are a few books that you might find hugely helpful:

“To Sell is Human” by Daniel H. Pink, which offers a fresh look, in which Daniel suggests that selling is a universal human activity, not just a profession. In his book, he proposes that regardless of our career or role, we all engage in non-sales selling—persuading, influencing, and convincing others in ways that don't involve making a purchase. Throughout the book he offers practical exercises and tools to improve your selling, such as how to pitch better, how to improvise, and how to serve others more effectively. It’s a thoughtful and practical guide that combines social science, anecdotes, and practical exercises, with a focus on effective and ethical methods.

Then, "Influence: The Psychology of Persuasion" by Robert Cialdini looks at the six universal principles of persuasion, backed by research and real-world examples that reveal why people say "yes" and how these insights can be ethically applied to influence others. The book is highly practical, offering strategies for enhancing persuasive abilities. It not only explains the psychological reasons behind people's actions but also provides actionable advice on how to apply these findings effectively and responsibly.

There are also helpful Customer Relationship Management tools like Salesforce, HubSpot, and Zoho CRM which can help you manage customer relationships more effectively, and they also neatly provide insights into customer behaviour and ways to help you improve follow-up strategies.

Conclusion

Let’s do a quick recap, we discussed why the fear of selling is such a common challenge. It’s about more than just the fear of rejection—it's about the vulnerability of putting your passion and creativity on the line. I shared some of my own experiences and we looked at practical strategies that can help. From understanding your product deeply to knowing your audience and the importance of authenticity, to help make selling a more natural and engaging experience.

Now, I'd love to hear from you! What are your biggest fears about selling? Have you tried any techniques that changed your approach? I’d love to hear stories and experiences, and if you have any questions. You can send me an email to news@philippacraddock.com and contact me via Instagram.

Philippa x