How a Date Turned Into a
Client Opportunity

Freelance writer meeting with client

Awhile back, I was on a call with several AWAI Circle of Success Mentors when the topic of getting clients came up.

Someone posed the question, “What’s the weirdest way you ever got a client?”

I immediately responded, “On a date!”

Naturally the group was curious how I pulled that one off, so I told them my story, and now I’m sharing it with you.

To clear up any confusion, I don’t make a habit of going on dates and pitching my business as a solution to a host of marketing problems. Before I went out with this guy, I had no clue if he was a potential client. There are certainly more effective ways to find new clients than blurring the lines between business and pleasure!

So, how did it happen? It started out like any other date. Inevitably we graduated from small talk to discussing what each of us does for a living.

When I tell people I’m a copywriter, they tend to assume I’m either a novelist or someone who helps file for copyright protection, so I’ve become accustomed to explaining what a copywriter does, and how businesses benefit from strong, persuasive copy.

Suffice it to say I got a little passionate about my work, and he was intrigued. We wound up talking about everything from the kinds of copy I write and why to what I hope to achieve by being in business for myself.

Two days after our date, he hired me to write a press release for his startup company, which had just received a million-dollar round of funding from investors.

Passion is essential, in dating and in business.

I would have considered this a one-off, until it happened a second time. Then I noticed the pattern — I was winning these guys over as clients, because I wasn’t in sales mode. I was simply talking about something I love doing. I obsess about finding the right words and expressing concepts clearly, and that shines through when I talk about my business in a setting where there’s no pressure to land a sale.

Luckily for me, both of the guys I dated run their own businesses and understand the value of good writing.

After they expressed interest in my copywriting services, I tried to help out where I could. I offered to give their sites once-overs and suggested minor tweaks that could improve the language of their offerings. This showed my dates my value as a business writer, and ultimately, it led to their hiring me.

I think it worked so well because instead of trying to “win the sale” and convert prospects into clients, I was just telling people about something I love.

I’ve discovered that when I’m in “sales mode,” I talk very differently about my work — almost like I have to speak differently or more “professionally” if I’m trying to pitch.

When you’re trying to impress someone enough to land a contract, any nervousness you might feel has a way of working its way into the conversation. However, when you talk about what you do with genuine passion and conviction, you’re providing true value, not being an obnoxious salesperson who’s just trying to win someone over.

These days I’m a lot more adept at marketing and promoting myself, because I know how to have a conversation vs. seeing it as a pitch. It’s not obvious self-promotion, and you don’t have to have a perfected elevator pitch. Just get good at asking good questions and talking about what you do in a way that highlights your passion and enthusiasm.

You’ve got to embrace your identity as a writer and be comfortable pitching, even off the clock.

By the way … the lesson in all this is NOT how to perfect the art of picking up clients on the dating scene. It’s in recognizing how you talk about yourself and what you do in different situations. I used to have a mental dividing line between “prospects” and “off-limits” — I would make decisions about who needed me and who didn’t, without ever giving them a chance to weigh in on the subject.

Preemptively determining someone is off-limits could mean you miss out on an awesome client with a paying gig. That’s why I don’t consciously separate my business contacts from my personal contacts anymore. Good business connections can come from anywhere — in line at the grocery store, at a local networking event, and yes, even on a date.

Remember, you’re offering a legitimate service to people who need and WANT your help. Get comfortable talking about yourself and your business no matter where you are — you never know when it will pay off.

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Published: December 25, 2024

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