Selling with Confidence as a Creative Entrepreneur - Creative at Heart


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Selling with Confidence as a Creative Entrepreneur


As a creative, you have an advantage over most. You were born with a gift. Whether it’s floral design, calligraphy, event planning, photography, copywriting or even gift design like me, it’s what makes you who you are and the story behind your unique gift is your biggest selling point. Yet, it’s not uncommon for me to hear from creative entrepreneurs that they hate selling. They associate selling with the “ick factor”. They have no problem showing their work on social media or offering items in their online shop but actually selling? Coming up with a sales strategy and implementing it? Well, this feels somehow slimy.

You may be thinking to yourself “I’m a creative so my work sells itself.” Or, “People find me on Instagram so no need to pitch anyone.” But after excelling in a professional medical sales career and now successfully crossing over to creative entrepreneurship, I’m here to emphatically say that the single most important factor in determining the success (or failure) of your business is your ability to sell. A bold statement, I know. But it’s true.

It’s time to transition from viewing sales as sketchy to viewing sales as an essential skill to help best communicate your creative gifts to those who can benefit from what you do. Here’s how…

Selling with Confidence as a Creative Entrepreneur // Creative at Heart #bosslady #confidence

Shift your Mindset

Instead of sales being slimy, what if instead you view it as serving? Think back to time when you’ve gone into a store where you know you need something but you don’t know enough about it to make an educated decision. I’m not talking about sales in terms of making people buy what they don’t need. I’m talking about targeting those who have a need that you can fill, doing an amazing job educating them, and in turn, earning a client who will return to buy more and/or refer you to others because they view you as a problem solver. This is the mindset of selling to serve.

Listen then Solve

What’s the best way to learn about what your customers really want? Listen to them. When you get a potential client on the phone or in person, sometimes one’s first instinct is to talk, talk, talk and dump as many details on them as possible so something is sure to stick and they’ll book with you. But not so fast. People ultimately want to feel important and be heard. The best way to serve your clients is to FULLY understand their pain points and how you can help solve their problems. Always let them speak first and resist your urge to jump in and interrupt. In gaining a better understanding of their needs, you can then better address their concerns and increase the likelihood of them booking with you. You also increase the likelihood that the relationship will be a good fit for both parties.

Master Your Elevator Pitch

I learned a TON in my 11-year career in medical/surgical sales but undoubtedly the most important was the art of the so-called “elevator pitch”. Prior to starting my gifting business, my days were spent in a pretty hard-core sales environment, where my audience was overworked hospital staff and surgeons who rarely had extra minutes to spare. Sometimes the only chance to pitch to them was after being invited into the operating room with a patient asleep on the table and surgery underway. Learning to consolidate my key points into 20-to-30-second spiels was absolutely critical to my success. The same is true for you and your business. Know how to clearly communicate the following and practice it until it becomes second nature.

  1. What you do: “Hi my name is Jamie and I’m the owner & founder of Marigold & Grey, an artisan gifting business specializing in custom gift design for weddings, corporate events and client appreciation”
  2. How you’re different: “Anyone can put pretty things in a box but we believe that execution is as important as aesthetic so our clients are stress-free knowing their gifts will arrive looking beautiful and will arrive on-time in perfect condition”
  3. Why you do it: “We believe that the gift giver deserves the same amazing experience as the one receiving the gift”

Know Your Competition

What differentiates you from your competition? By competition, I don’t mean that you should refer to your competition by name nor should you disparage them in any way when you’re selling. In fact, DON’T do that. (#CommunityOverCompetition is alive and well, my friends!) Instead, know your competition and exactly where your business fits within your market. This will help you articulate how you’re different and what makes your business stand out from the crowd. It also prepares you in case the person follows up with industry-related questions. The last thing you want is to be caught off guard or seem like you operate your business in a vacuum. Not to mention, finding your own niche within a market is a huge determining factor in the success of a business so understanding all that’s out there will help you further niche down and focus.

Own Your Pricing

One of the easiest ways to decrease your revenue and devalue your brand is to immediately cave when potential clients request discounts. It’s normal to have some fear when this happens because the risk saying ‘no’ can lead to the loss of an opportunity for sales. However, consistently discounting is dangerous! It means you’ll be working hard for less money (think: burnout) and your brand’s reputation will take a hit which means you’ll begin to attract clients who only seem to book solely based on price. In my four years of being in business, the few times I’ve allowed clients to talk me out of charging our up-front design fee because I was afraid they wouldn’t book, NOT ONE OF THEM moved forward with the project. I did the design work in good faith and they took it and disappeared. When a prospect inquires about discounting, force yourself to get excited about actually SELLING. Let them know all that goes into your craft and speak with confidence. Let them know that you have experience and are reliable. Let them know that you charge what you charge so you can stay in business and continue offering the level of service that you do. If they’re the right client for you, they will respect you even more for standing your ground and will believe in your brand that much more too. This may sound like it’s easier said than done but I beg you to try it and I think you might be surprised with the results!

Digital Footprint

At the same time as you’re are delivering your message to others via phone, email, Skype or in-person, your entire digital presence should be working hard to sell on your behalf. For example, your social media profiles should have clear, concise messaging so potential clients immediately understand what you do and why you do it. The various types of content you post should have your brand messaging in mind each and every time you post. This is especially true for the copy on your website. If it doesn’t grab someone’s attention immediately and explain how they’ll be better off with your product/service, they’ll click out and chances are they’ll not return. Optimizing your platforms to work on your behalf is the perfect way to multiply your sales efforts beyond what you can accomplish alone. In addition to social media and web copy, this also includes your email signature, inquiry forms, questionnaires, sales landing pages and your blog. I’m sure you use most of these platforms, if not all, but are they really, truly working for you? If not, spend some time clarifying your message (think: elevator pitch) and then make sure that message is consistent across the board.

Pipeline Management

If you’ve ever heard someone say “sales is a game of numbers” well, this is partially true. As small business owners, we put so much emphasis on client experience and our creative process that we often forget about the pipeline of potential clients. In the same way you focus on what happens when a client signs on with you or makes a purchase, have an equally defined process once someone inquires with you. Know exactly what they’ll receive from you the moment they inquire and when they’ll receive it. Decide how much time to allow to pass before you follow up with a potential client who has received info from you but not responded. Then make a decision when to close out their inquiry if they ghost on you completely. Following this process will allow potential clients who inquire to receive information from you much faster which, by the way, is proven to increase close rates! It will also allow you to filter out prospects who are unlikely to ever buy from you so you can nurture those who will. I can’t begin to tell you the number of times I’ve methodically followed up with leads whom I thought would never buy from me yet they’re so appreciative when I follow-up that it prompts them to take the next step. Managing your pipeline is a behind-the-scenes function and not at all glamorous but it really does work.

Think Long Term

View your business as long term and treat your potential customers accordingly. Just because they’re not buying from you now doesn’t mean that they won’t or that they don’t know someone who is the perfect fit for you. Spend that little bit of extra time offering a sentence or two of advice or encouragement even if they’re not going to book with you. Recommend another vendor whom you think would be a better fit for them. Trust me, this goes a long way. They view you as someone they can trust. A source of information. A valued partner. And this is precisely the type of business who people end up buying from the in long run and for the long term. This isn’t necessarily going to yield sales immediately but it’s planting the seeds for long term success.

If you’re feeling overwhelmed, don’t panic. The good news is that anyone can learn to improve their sales foundation but not everyone can learn to be creative. You already have a huge advantage so feel confident in your ability to sell yourself. You’re the very best asset your business has and will ever have.

Jamie Kutchman Wynne is a former medical/surgical sales professional turned creative entrepreneur. She founded the artisan gifting business Marigold & Grey back in 2014 after recognizing the need to fully outsource curated gifts for weddings, corporate events and all of life’s occasions. Her motto? She strongly believes that gift givers deserve the same amazing experience as the ones receiving the gifts. She lives in the DC area with her husband and two rescue pups Lewis & Clarkie and when not designing gifts, she enjoys prop styling, blogging, speaking, and mentoring other small business owners. She’s thankful to run a business where she can flex both her creative mind and business savvy, no longer just one or the other.

Be sure to connect with Jamie here: 

Blog// Website // Shop// Instagram



All images by Lissa Ryan Photography

  1. Juliette says:

    Just… great precious advices ! Thanks a lot 🙂

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