From Corporate Sales to Handmade Business Owner: How I Learned to Sell With Confidence

Switching from a 9-to-5 sales job to running a creative handmade business might seem like stepping from one world into another. For many creative entrepreneurs, the thought of leaving behind a predictable paycheck to pursue your artistic passion is equal parts exhilarating and terrifying. 

But here’s the truth that no one really talks about at first: the skills you’ve gathered in your previous jobs – no matter what they were – are more valuable than you think. 

I spent 16 years working in sales before I took the leap to go full-time with my creative business. In fact I ran my creative business for three years alongside my corporate sales job before I went full time. And I have zero regrets. 

Because those 16 years provided me with tools and insights that are still the backbone of how I run my business today. They taught me how to not only sell a product but also communicate, connect, and build something meaningful. 

No matter where you are in your handmade business journey, here are the biggest lessons I brought with me from those 16 years in sales that transformed how I sell my handmade goods with confidence. 

1. Rejection Doesn’t Mean You’re Not Good Enough

Rejection is part of life in sales. It’s unavoidable. People say no, stop mid-conversation, or walk away. Learning not to take it personally was one of the hardest but most valuable lessons I gained. 

When you step into a creative business, rejection often looks different, but it’s still there. Maybe you launch a new product and don’t get the sales you hoped for. Or you pitch your handmade items to a store and never hear back. 

Thanks to my years in sales, I’ve developed resilience. When something doesn’t work as planned, I don’t panic. I look at the numbers, ask whether my offer needs tweaking, and keep moving forward. Rejection isn’t the end; it’s just feedback. 

2. Asking for the Sale Isn’t Pushy – It’s Necessary 

If there’s one universal struggle among creative entrepreneurs, it’s this fear of appearing “too salesy.” Sound familiar? 

What I learned in sales, though, is that asking for the sale is not pushy; it’s clarity. If you don’t make it crystal clear what you’re offering, how it helps, and how someone can buy it, they simply won’t take action. 

I now approach selling in my handmade business just like I did when I worked sales. I confidently say, “Here’s what I’ve made, here’s how it can make your life better, and here’s how you can own it.” 

Over time, asking for the sale becomes natural, and trust me, your audience will thank you for making it easy. 

3. Understanding Value Turns Browsers into Buyers 

It’s easy to think that having a great product is enough to attract sales, but that’s only part of the equation. People don’t just want to know what your handmade item is–whether it’s a scarf, mug, or painting. They want to know what it does. 

Sales taught me how to translate product features into benefits. For example, is your scarf made from eco-friendly wool? That’s great, but more importantly, how will it feel on a cold winter morning? Once I began to frame my product descriptions around benefits rather than features, buyers connected with my offerings in a whole new way. 

4. Listening to Customers Changes Everything 

One of the most valuable skills I built in my sales career was learning how to really listen. Early on, I thought successful selling meant having all the answers. But over time, I learned that the best salespeople are the best listeners. 

By asking thoughtful questions and staying curious, I learned how to uncover what people truly cared about. Now in my creative business, listening is central to my strategy. Whether it’s feedback about a product, a customer explaining their needs, or reading between the lines of an Instagram DM, listening has made me a better problem-solver, creator, and entrepreneur. 

The Foundation Built in Sales Helped Me Thrive 

I’ll always be grateful for the foundation working in sales gave me. Those years gave me the confidence to show up even when I felt nervous and the tools to recover when things didn’t go my way. They taught me how to craft clearer messaging, communicate value, and stay open—even when feedback wasn’t what I wanted to hear. 

I know many seasoned business owners feel like they should have “started earlier” or that their experiences in other fields somehow don’t count. But if you’re building a handmade business, I can promise you this: the skills from your past jobs are worth more than you think. 

Your Past Experiences Are Your Superpower 

Maybe you worked in retail, food service, healthcare, education, or some other field. Whatever your background, you’ve got tools, resilience, and lessons you might not even realize yet. 

That experience may just make you the kind of creative entrepreneur who can tackle rejection, connect authentically, and confidently ask for the sale. 

Think back to a job you’ve had before starting your handmade business. What’s one skill or lesson you’ve carried with you? 

I’d love to hear your story! Join my email list and message—I’m all ears.