Fear of Selling & How to Overcome It

by guest blogger Mckenna Hallett

Does the thought of trying to close a sale of your artwork give you anxiety? Read on.




How do you react when you hear any of these statements or questions?

Group A:

  • I love your art.
  • I love your creativity.
  • I love your style.
  • Your work is so beautiful.
  • You are so talented.

Group B:

  • You are why I came to this event.
  • I have been enjoying your art for years.
  • I bought from you last year.
  • This is the perfect size for my wall (or shelf or table top)
  • I love the way you have it framed.

Group C:

  • Can it be left outdoors year round?
  • Do you have prints?
  • Can this be framed (or unframed)?
  • Do you accept commissions?
  • Do you ship?

Group D:

  • Do you have a website?
  • Do you have a card?

Chances are you need to rethink your responses to all of the above!

There is a sale lurking within every group above. How you react to each scenario will move you closer or farther away from that sale. How you respond can help make the moment where you “ask for the sale” an easy and natural moment. But, Fear of Selling (also known as Fear of Rejection) is keeping you from asking for the sale.

You worry, “What if they say no, what then? What will they think of me? Will they feel that I am a pushy salesperson?” To that last one: if you are afraid of being pushy, I daresay it will be the last thing you will be capable of being. Seriously.

In fact, the opposite is more worrisome. If you are fearful and uncomfortable, your unspoken fear rules your attitude, language choices, and body language. You might appear nervous or disingenuous. Or worse, you will distance yourself to the point that they feel you don’t care about them and feel snubbed as potential collectors. Ouch!

How the Power of Assumption helps overcome Fear of Selling

Think of yourself as a “Decision Counselor” instead of a salesperson. Assume they want to buy something and help them find the right piece. Be like an impartial, but enthusiastically helpful and caring clerk in a shoe store. You are helping them consider a few options and eventually getting them the perfect fitting shoe.

By taking on this very specific role, you remove the sense of obligation from them and let them explore with you. By converting a looker into an explorer, you move them closer to feeling ownership without pressure.

Opportunities you might be missing

Group A:

Nearly every one of those comments can be the start of great engagement by responding, “Thanks! Have you seen my work before?” If it’s a “yes”: Yippee! Find out more! If it’s a “no”: Great! Give them the quick background tour. Keep it to less than 30 seconds and end with a question.

Always let them enlighten you about what they like or what problems they have. The more they are talking, the more they are confiding in you. That makes them feel more trusting. Throughout this process you need to assume they are buying. Then “closing” is just a question: “Would you like this shipped to your home or office?”

Group B:

Replies can be much more direct: “Do you own one of my pieces?” Or, “Are you considering adding to your art collection?” “This is ready to hang, and I ship this size for free.” Think of some more replies to each of these scenarios.

Group C:

There should be no doubt that these questions are from someone who is interested enough that with a bit more information they may deeply consider buying. After they have tried on a “few pair of shoes,” gotten the details, reassurances, and are feeling comfortable, they usually respond very nicely to a little encouragement. “Shall we wrap it up?”

Group D:

Do you have a website or business card? The answer is basically “No.” See this article and learn why you should put your business cards away.

Just remember this: you are creating something that can potentially enrich someone’s life forever. They deserve to own your work and your art deserves to be loved forever. Honor your art by asking for the sale. It’s a win-win. Every time.



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  1. It was great listening to you and Carolyn on the Webinar yesterday and just ordered the guide.

    I am starting to market my art and began by setting up a PayPal account and posted my art on Dailypaintworks and purchased my own Domain name to have on a card and link to purchase. Do you think I should have my own website when this seems to cover what I need for now and continue on with working on my mailing list?

    Also, should I proceed with a blog after my email list or before?

  2. Thanks for listening, Nadia! And for ordering the Artsy Shark Success Guide to Email Marketing for Artists. You are on a great path as you start to market your art! The guide will be a great long-term (and short-term) help with your career.

    LOL… you are going to cringe, but the answer is yes to all: you need a website and you should start to blog and you need to start sending emails asap. Emails are you best method for remaining in your collectors mind. AND only an email gives you that “personal” touch that sends people racing to see your newest work or read your blog or buy your art.

    Dailypaintworks (DPW) is what is known as a “third party” site. Like others in this category, (Etsy would be the supreme example) they can have many hundreds to many thousands of other artists on a site that they control. DPW therefore calls all the shots. They have specific and rigid one-size-must-fit-all templates, absolute rules of engagement, and the ability to dictate and change terms in order for you to remain on the site. You are “just another” page, and you have no persona, no branding. THEY are your brand. It appears that you have one choice? The style of font you use on your gallery page? Hardly branding you, right?

    Meanwhile, they can change anything in a blink, the terms, the costs, or even reformat their entire presentation to the public without warning and without you having any voice. Not saying they will ever do that on DPW, just sayin’….

    Many people (I have personally consulted many) have had a difficult time, standing out in the crowd on these sites. And of course, there are ongoing costs to be on these sites, even if you don’t sell anything. That’s just the way it works and it’s usually a fair and reasonable cost: it just adds up for anyone not selling.

    All that said, I don’t see any reason not to be on sites of this kind if you can justify the costs (make sales) but they will never replace the marketing you can do with your own website, blog, and email program.

    Case in point: I randomly clicked on an artist on DPW and then clicked on her website link. She creates Monotypes. On her website she is able to clarify with a full step-by-step pictorial of the monotype process. Clearly, whatever any artist’s medium, there is much that can be offered in addition to just some art on a site and a bio. If you click on the websites of many of your fellow artists on DPW you will see this demonstrated again and again. They have real worlds to share and none of that can be done on any third party site.

    So I am saying to you and everyone: get that domain name (congrats to you for having that done, Nadia!) and get started on building a site. SIDEBAR: Sorry to say, that DPW is not compliant with the new Google Search rules that hit back on April 21st. DPW will now get little to no SEO rank if someone is searching for art on any mobile device. Anyone reading this can check their own site’s status by going to http://www.google.com/webmasters/tools/mobile-friendly/

    Driving traffic to ANY site takes a lot of work. I question driving traffic to a site that also has many dozens of other peoples art a click away. Drive traffic (via emails) to YOUR site. If you still want to use the convenience of another site to sell from, consider using SquareUp’s Market. It’s free – totally Free to use, beautiful template, shopping cart with low fees (2.75% max) per sale. I have an entire page devoted to this system on my website.

    Your last question: Blogging feels pretty lonely sometimes. No comments make you feel like no one read the post, right? But start blogging! (It helps with SEO, too!) As you continue you grow your email list, you will eventually have people go to your site and read your blog. It’s nice if they have several to look at, right?

    So to end this (blog post! LOL) is to repeat my start: do it all. Do it yesterday! And know that Carolyn and I both have your back. Contact either of us for deeper or more specific marketing and business consultations. You have a distinctive style, Nadia. And a desire to grow in a professional way. We love to help people like YOU!

    Best wishes! And enjoy the E-course!

    (In case you haven’t heard about it yet, here’s the details about the course:

  3. Thank you so much for this generous response and helpful information such as “Square Up’s Market”. I agree totally, I sell more art at a show of my own than say an art fair. I was taking the quick route to get my art out there but will pursue your advise.

    What are the benefits of going with Constant Contact to start my email list rather than MailChimp which I hear is free? I’d like to keep my costs down starting out with marketing and other expenses.

    Thanks again for your help and I look forward to hearing more from you and Carolyn. I did sign up to be on your email list as well 🙂

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