The Skill That Built My Business Had Nothing to Do With Design.
If you’re a freelancer or solopreneur who dreads getting on a sales call, you’re not alone. Most creative business owners are great at the work and uncomfortable with the selling. This post isn’t about becoming a pushy salesperson. It’s about one specific shift in how you run discovery calls that changed everything for me — and why listening is the most underrated sales skill any freelancer can build.
When I left my job and started my own business, I made a list of the skills I was bringing with me.
Design. Marketing. Twenty years of experience. These felt like the obvious ones. The skills I was building a business around.
What I didn’t think much about was sales.
Not the pushy kind. Not the cold-calling kind. The real kind. Being able to talk to someone, understand what they need, earn their trust, and help them make a decision.
That skill saved my business more times than any design tool ever did.
What My Sales Background Actually Gave Me
I spent years in sales before I ever started freelancing. That time gave me two things I now think every solo business owner needs.
The first is resilience. In sales, most pitches don’t land. You talk to ten people and maybe two say yes. You learn not to take the no personally. You learn that a no today doesn’t mean no forever. That mindset kept me going through three months of pitching on Upwork with zero results. It kept me going after getting ghosted on my first project. It kept me going when I just wanted to stop.
The second is what I call a hunter mentality. Knowing how to go find work instead of waiting for it to show up. A lot of solopreneurs struggle with this. Most people start a creative business because they love the work, not because they love selling. But at some point, passion alone is not enough. You have to go find the clients.
The Anxiety Nobody Talks About
If you have never worked in sales and you run your own business, there is a specific kind of worry that comes with it. You don’t know how to get in front of people. You jump on a call with a potential client and freeze up. You don’t know what to say without feeling pushy.
I have seen talented people lose clients not because their work was bad, but because they didn’t know how to handle that conversation. They froze. They over-explained. They tried too hard to prove themselves.
A sales call is not a test you have to pass. It is a conversation with a purpose. The sooner you see it that way, the better those conversations go.
What I Got Wrong Before I Got It Right
Most solopreneurs starting out don’t have a sales background. And that gap is bigger than most people think. You can be great at what you do. Your offer can be exactly what someone needs. But if you don’t know how to walk them through a conversation and into a decision, none of that matters.
When the rejection comes, the doubt starts. Is my work not good enough? Is my price too high? Am I in the wrong business? Most of the time, the problem is simpler. The sales process just isn’t working.
I made my own version of this mistake. I came from a hard sales background. Five years of it. And in my first two years of business, I did what I had been trained to do. I pitched. I pushed. I talked through everything I was offering before I even knew what the person in front of me actually needed.
In my third year, something changed.
I stopped talking so much and started asking questions. What are you trying to solve? What have you already tried? What does success look like for you? And then, only once I understood what they needed, I would talk about how I could help.
That one change made my sales calls completely different.
A good discovery call is not a presentation. It is a conversation where you listen more than you talk. The goal is not to impress anyone. It is to understand what they need. When someone feels truly heard, saying yes becomes much easier for them.
Most people skip this. They start selling before they have earned the right to be heard. That is the most common mistake I see. And it is one of the easiest to fix.
Sales is not about being pushy. It is about being ready, being present, and making the person across from you feel like they are in good hands. That is a skill anyone can build.
Shawn
Working With a Web Designer Who Also Knows How to Sell
One of the things my clients notice early in our process is that the first call doesn’t feel like a sales call. It feels like a real conversation about their business. That’s not an accident. It’s the result of years spent in sales roles learning that the best way to earn a client’s trust is to listen before you pitch.
If you’re a small business owner in New York or beyond looking for a Squarespace web designer who brings strategy and sales experience to every project, I’d love to have that conversation. Reach out through the contact page.
