My sister and I sometimes worked as housekeepers when we worked our way around the country for six months in 1996. We’d approach bed and breakfast managers to see if we could get spring-cleaning gigs to help the overworked staff.

While we were waiting for the manager, we’d look around the lobby or the office, hoping to spot signs of need: dust bunnies, drink rings, dead leaves on tired plants. We’d be so brave in our planning, deciding we’d pitch our services to the manager by boldly drawing a finger across a shelf, holding up the dusty finger and proclaiming, “See? You need us!”

Yeah. It never happened that way. The manager would come in, and we’d be cheery and polite. I inevitably held my dusty finger behind my back. Sometimes we got jobs. Sometimes we didn’t. But we rarely mustered the courage to be so brazen.

I’m still in the same boat, I think. Yesterday I got a flyer from a local gym. The slick, expensive door hanger advertised “Personal Trainging.” Yep. “Trainging.” I am looking for a gym, so I thought “Trade out?” I could help them with their copy (their website was very attractive and rife with typos), and I could get a gym membership for free.

So I called, and the saleslady immediately wanted me to come in, of course. She was looking for ways to give me discounts. Was I a teacher? A government employee?

“I’m a freelance copywriter,” I said. And then I took a breath. “And that was another thing I wanted to talk to you about…. No offense at all, but I just read your flyer….” I trailed off, and she jumped in.

“Oh, I JUST heard the owners talking about how they really had to step up their promotions and get them to a different level! I TOTALLY need your card,” said the saleslady, who obviously spent a few years on a pep squad.

The moral? I should always be brave enough to ask. If a business is not interested, all that will happen is that I’ll hear “no, thanks.” And that I can handle.