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Lessons I’ve learned from landing clients on first dates (Guest Post)

Call it “inadvertent self-promotion”…

Men With Pens recently ran a guest post about dating rules you can apply to client prospecting. Considering I’ve inadvertently won over a commercial writing client while on a first date, I found the post pretty funny.

This has actually happened to me not once, but twice.

Dating your clients?
To clear up any confusion, I don’t make it a habit to go on a date and pitch my freelance copywriting business as a solution to a host of marketing problems. Before we went out, I had no clue if this guy 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 a typical dinner date. Inevitably we graduated from small talk to discussing what each of us does for a living.

People 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. We discussed everything from what 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.

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 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 commercial freelancing business in a setting where there’s no pressure to land a sale.

Luckily for me, each of the guys I dated runs his own business and understands 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 led to them hiring me.

Instead of trying to convert prospects into clients, I’m just telling people about something I love. In a nutshell, I’ve become more adept at marketing myself because I no longer see it as obnoxious self-promotion.

Be comfortable pitching, even off the clock.
The lesson in all this is NOT how to perfect the art of picking up clients on the dating scene. It’s in realizing how you talk about yourself to others in different situations.

I don’t consciously separate my business contacts from my personal contacts anymore. I’ve discovered that mindset forces you to mentally divide people into prospects and off-limits. Pre-emptively determining someone is off-limits could mean you miss out on an awesome client with a paying gig.

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.

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

Have you landed a client in an unexpected place?

Has the ‘share-don’t-sell’ approach worked for you as a way to close new clients?

Do you keep your eyes peeled for situations like this, or stick with more traditional methods?

Put another way, do you draw distinct lines between the professional and personal sides of your life?


Angie Colee is a freelance copywriter and branding expert. She loves good food, comedy shows, and the power of words. She is also considering trademarking her awesomely red hair. For more marketing and branding tips, please check out the blog at coleecreative.com. And if you’re ever in the San Francisco bay area, look her up. Coffee is her lifeblood.

Want to be a guest blogger on TWFW Blog? I welcome your contribution to the Well-Fed writing community! Check out the guidelines here.